Ethinylestradiol - Knowledge

8405: 8657: 8195: 8423: 2765:. Unopposed estrogens like EE have carcinogenic effects in the endometrium and progestogens protect against these effects, but dimethisterone is a relatively weak progestogen and was unable to adequately antagonize the endometrial carcinogenic effects of EE, in turn resulting in the increased risk of endometrial cancer. COCs containing dimethisterone have since been discontinued (with more potent progestogens used instead) and doses of EE in COCs in general have been dramatically reduced, abrogating the risk. In turn, most studies of modern COCs have found a decreased risk of endometrial cancer. 13968:

was able to show that 90% of the folliculin taken up in the blood of the vena portae is inactivated in the liver. Neither KAUFMANN (1933, 1935), RAUSCHER (1939, 1942) nor HERRNBERGER (1941) succeeded in bringing a castration endometrium into proliferation using large doses of orally administered preparations of estrone or estradiol. Other results are reported by NEUSTAEDTER (1939), LAUTERWEIN (1940) and FERIN (1941); they succeeded in converting an atrophic castration endometrium into an unambiguous proliferation mucosa with 120–300 oestradiol or with 380 oestrone.

647: 624: 40: 8290:, which is the minimum dosage of diethylstilbestrol required to consistently suppress testosterone levels into the castrate range. The ovulation-inhibiting dose of EE by itself and not in combination with a progestin in women is 100 μg/day. However, it has been found to be about 75 to 90% effective at inhibiting ovulation at a dosage of 20 μg/day and about 97 or 98% effective at a dosage of 50 μg/day. In another study, ovulation occurred in 25.2% with an EE dose of 50 μg/day. 8258:. Due to the marked increase in SHBG levels, free testosterone levels become very low during treatment with EE-containing birth control pills. In men, a study found that treatment with a relatively low dosage of 20 μg/day EE for five weeks increased circulating SHBG levels by 150% and, due to the accompanying decrease in free testosterone levels, increased total circulating levels of testosterone by 50% (via upregulation of gonadal testosterone production due to reduced 8294:

by a dosage of 30 μg/day EE. However, other clinical studies have found that 20 μg/day EE increased testosterone levels by 50% in men (as described above) and that dosages of 32 μg/day and 42 μg/day EE suppressed FSH levels in men but did not significantly affect LH levels. A stronger suppression of testosterone levels was observed in men following daily treatment with a combined oral contraceptive containing 50 μg ethinylestradiol and 0.5 mg

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50 μg oral EE in terms of effects on liver protein synthesis, such as stimulation of hepatic SHBG production. As such, parenteral EE, which bypasses the first pass through the liver that occurs with oral EE, has been found to have a 5-fold lower impact on liver protein synthesis by weight than oral EE. In contrast to EE as well as to oral estradiol, transdermal estradiol shows few or no effects on liver protein synthesis at typical menopausal dosages.

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approximately 100-fold increased oral potency of EE relative to estradiol. In accordance with the high interindividual variability in the oral bioavailability of EE, there is a large degree of interindividual variation in EE levels. A dosage of EE of 50 μg/day has been found to achieve a wide range of circulating EE levels of about 100 to 2,000 pg/mL. Taking EE in combination with a high-

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these events, the dose of EE was greatly reduced, and is now always less than 50 μg. These lower doses have a significantly reduced risk of VTE with no loss of contraceptive effectiveness. Gerstman et al. (1991) found that COCs containing more than 50 μg EE had 1.7-fold and COCs containing 50 μg EE 1.5-fold the risk of VTE of COCs containing less than 50 μg. A 2014

1053:. Studies have found that estrogen replacement helps improve these symptoms when compared to a placebo. Other common menopause symptoms, such as vaginal dryness (which can cause pain during sexual intercourse), vaginal itching, and depressed mood, can benefit from HRT. In addition to treatment of menopausal symptoms, EE has been used as a component of 13419:

with respect to increases in SHBG, whereas conjugated estrogens were 3.2-fold more potent, DES was 28.4-fold more potent, and ethinyl estradiol was 600-fold more potent. With respect to decreased FSH, conjugated estrogens were 1.4-fold, DES was 3.8-fold, and ethinyl estradiol was 80 to 200-fold more potent than was piperazine estrone sulfate.

2749:, as well as greater risk of other liver complications. At one time, EE-containing birth control pills were estimated to be responsible for 84% of all drug-related and histologically verified liver damage. However, these risks now are reduced with modern lower-dose EE-containing birth control pills, with contain 35 μg/day EE or less. 13967:

There is no doubt that the conversion of the endometrium with injections of both synthetic and native estrogenic hormone preparations succeeds, but the opinion whether native, orally administered preparations can produce a proliferation mucosa changes with different authors. PEDERSEN-BJERGAARD (1939)

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are 40 pg/mL following the first dose and 80 pg/mL after three weeks of administration. These maximal concentrations of estradiol are in the same range as the concentrations of EE that are produced by an oral dose of EE that is 100 times lower by weight, which is in accordance with the

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Lower dosages of EE also have significant antigonadotropic effects. A "very low" dosage of 15 μg/day EE has been described as the "borderline" amount required for suppression of LH and testosterone levels in men, and a study found that LH and testosterone levels were "reliably" suppressed in men

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Unlike the case of estradiol, in which there is a rapid rise in its levels and which remain elevated in a plateau-like curve for many hours, levels of EE fall rapidly after peaking. This is thought to be because estrone and estrone sulfate can be reversibly converted back into estradiol and serve as

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derivatives have only a weak effect on CBG levels. COCs may increase CBG levels by 100 to 150%. A dosage of 5 μg/day EE has been found to increase TBG levels by 40%, while a dosage of 20 μg/day EE increased them by 60%. Progestins that are progesterone derivatives do not affect TBG levels,

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Birth control pills containing EE have been found in women to reduce total testosterone levels by 30% on average, to increase circulating SHBG levels by about 3-fold on average (but variable depending on progestin, range 1.5- to 5-fold increase), and to reduce free testosterone concentrations by 60%

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review found that COCs containing 50 μg EE with levonorgestrel had 2.1- to 2.3-fold the risk of COCs containing 30 μg or 20 μg EE with levonorgestrel, respectively. COCs containing 20 μg EE are likewise associated with a significantly lower risk of cardiovascular events than COCs

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Modern COCs contain 10 to 35 μg EE, but typically 20, 30, or 35 μg. The initial formulations of COCs that were introduced in the 1960s contained 100 to 150 μg EE. However, it was soon found that EE is associated with increased risk of VTE and that the risk is dose-dependent. Following

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routes over the oral route does not result in EE having proportional hepatic actions relative to non-hepatic actions. However, the potency of EE on liver protein synthesis is in any case reduced with parenteral administration. A dosage of 10 μg/day vaginal EE has been found to be equivalent to

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EE at 5 μg/day has been found to increase SHBG levels by 100% in postmenopausal women, while a dosage of 20 μg/day EE increased them by 200%. Androgens decrease hepatic SHBG production, and have been found to oppose the effects of EE on SHBG levels. This is of particular relevance when it

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Because of its disproportionate effects on liver protein synthesis and associated cardiovascular risks, synthetic estrogens like EE and diethylstilbestrol are no longer used in menopausal hormone therapy. They are also being replaced by parenteral forms of estradiol like polyestradiol phosphate and

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and markedly increases the 2-hydroxylation of estradiol) and EE. This suggests that estradiol and EE are metabolized by different cytochrome P450 enzymes. There is, however, an increased risk of cardiovascular complications with smoking and EE, similarly to the case of smoking and other estrogens.

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likewise have been found to increase SHBG levels by 2.5-fold and 3.5-fold, respectively. Birth control pills containing high doses of ethinylestradiol (>50 μg) can increase SHBG levels by 5- to 10-fold, which is similar to the increase that occurs during pregnancy. Conversely, increases in

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The amount of EE in COCs has reduced over the years. Previously, COCs contained high doses of EE of as much as 100 μg/day. Doses of more than 50 μg EE are considered high-dose, doses of 30 and 35 μg EE are considered low-dose, and doses of 10 to 25 μg EE are considered very low

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The relative potency of several estrogens has been assayed by determination of effects on plasma FSH, a measure of the systemic effect, and by increases in SHBG, CBG, and angiotensinogen, all of which indicate the hepatic effect. Piperazine estrone sulfate and micronized estradiol were equipotent

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Ethinyl oestradiol 0,05mg cpr 0,05 mg ethinylestradiol (G03CA01) (FR) Ethinylestradiol tablets 50 mcg Ethinylestradiol (G03CA01) (RUS) Ethinylestradiol 25μg (Jenapharm) Dragees: Ethinylestradiol 25μg (G03CA01) (DE) Ethinylestradiol pch 0,002mg cpr 0,002 mg ethinylestradiol (FR) Ethinylestradiolum

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of EE similarly to estradiol, although to a lesser extent. The contribution of enterohepatic recirculation to total circulating EE levels appears to be 12 to 20% or less, and is not observed consistently. A secondary peak in EE levels 10 to 14 hours after administration can often be observed

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in comparison. This is particularly so in the case of combined estrogen and progestogen therapy (as in COCs or menopausal HRT), as progestogens induce the expression of 17β-HSD in the endometrium. The reduced vaginal bleeding and spotting with EE is one of the main reasons that it is used in COCs

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of the C17β position of EE by 17β-HSD, and for this reason, EE is not inactivated in these tissues and has much stronger relative estrogenic activity in them. This is the mechanism of the disproportionately strong effects of EE on hepatic protein production, which results in a greatly increased

2721:(LFTs) are normally found in about 1% of women not on birth control pills or taking lower-dose EE-containing birth control pills, this increases to more than 10% of women taking birth control pills containing 50 μg/day EE or more. With birth control pills containing 50 μg/day EE, 8871:

involved in its metabolism, and this may also play a role in the increased potency of EE relative to estradiol. Indeed, EE is said to have a marked effect on hepatic metabolism, and this is one of the reasons, among others, that natural estrogens like estradiol may be preferable. A 2-fold

2166: 2717:. However, the incidence and severity of cholestatic hepatotoxicity appear to be much greater with EE than with estradiol, which is thought to be due to the reactive C17α ethynyl substitution in EE as well as its greatly reduced susceptibility to hepatic metabolism. Whereas abnormal 8285:

is 50 to 100 μg/day. This high dosage is associated with a high incidence of VTE, particularly in those over the age of 40 years, and it has been said that it should not be used. The dosage of EE used in the treatment of prostate cancer in men is 150 to 1,000 μg/day

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have the same or even higher risk of VTE than COCs. Pregnancy is associated with about a 4.3-fold increase in risk of VTE. It has been estimated that at least 300 to 400 healthy young women die each year in the United States due to VTE caused by EE-containing birth control pills.

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values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of

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that remains in use for menopausal hormone therapy. EE was previously available by itself under brand names like Estinyl and Lynoral in the form of 0.002, 0.01, 0.02, 0.025, 0.05, 0.1, 0.5, and 1.0 mg (2, 10, 20, 25, 50, 100, 500, and 1000 μg) tablets.

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among others, although most or all of these formulations are now discontinued. It is marketed under a very large number of brand names throughout the world in combination with progestins for use as an oral contraceptive. In addition, EE is marketed in the

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of EE in the literature was 13.1 to 27.0 hours. Another review reported an elimination half-life of EE of 10 to 20 hours. However, the elimination half-life of EE has also been reported by other sources to be as short as 7 hours and as long as 36 hours.

2152: 8367:, a progestin with relatively high androgenicity, decreases SHBG levels by 50%; 30 μg/day EE and 0.25 mg/day levonorgestrel has no effect on SHBG levels; 30 μg/day EE and 0.15 mg/day levonorgestrel increases SHBG levels by 30%; and 8386:

A dosage of 10 μg/day EE has been found to increase CBG levels by 50%, while a dosage of 20 μg/day EE increased them by 100%. Progestins that are progesterone derivatives have no effect on CBG levels, while androgenic progestins like the

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for 9 days. However, investigation revealed that the progestin was the more important component responsible for the suppression in testosterone levels. In accordance, the progestin component of COCs is primarily responsible for inhibition of

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Low-dose COCs contain <50 μg of estrogen and are the primary choice for oral contraception. COCs containing ≥50 μg of estrogen should no longer be routinely used for contraception. The estrogen component of COCs can cause breast fullness and

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Ethinyl estradiol is a synthetic and comparatively potent estrogen. As a result of the alkylation in 17-C position it is not a substrate for 17β dehydrogenase, an enzyme which transforms natural estradiol-17β to the less potent estrone in target

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EE levels after a single 50 μg dose by intravenous injection are several times higher than levels of EE after a single 50 mg dose given orally. Besides the difference in levels, the course of elimination is similar for the two routes.

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American Medical Association. Dept. of Drugs, Council on Drugs (American Medical Association), American Society for Clinical Pharmacology and Therapeutics (1 February 1977). "Estrogens, Progestagens, Oral Contraceptives, and Ovulatory Agents".

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Meyer et al. found that ethinyl estradiol was 75 to 100 times more potent than conjugated estrogen on the basis of the doses required to lower testosterone to the adult female range, 0.1 mg of the former and 7.5 to 10 mg of the latter being

6419: 8820:. Hydroxylation of EE at the C4, C6α, and C16β positions into 4-, 6α-, and 16β-hydroxy-EE has also been reported, but appears to contribute to its metabolism to only a small extent. 2- and 4-methoxy-EE are also formed via transformation by 15459:

Inhoffen HH, Hohlweg W (1938). "Neue per os-wirksame weibliche Keimdrüsenhormon-Derivate: 17-Aethinyl-oestradiol und Pregnen-in-on-3-ol-17 (New female glandular derivatives active per os: 17α-ethynyl-estradiol and pregnen-in-on-3-ol-17)".

8266:). The stimulation of hepatic SHBG production by EE is far stronger than with other estrogens like estradiol, owing to the high resistance of EE to inactivation in the liver and hence its disproportionate effects in this part of the body. 8800:

by its C17α ethynyl group, is not metabolized or inactivated by 17β-HSD, and this is the primary factor responsible for the dramatically increased potency of oral EE relative to oral estradiol. EE is also not metabolized into estradiol.

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Rowan JP, Simon JA, Speroff L, Ellman H (June 2006). "Effects of low-dose norethindrone acetate plus ethinyl estradiol (0.5 mg/2.5 microg) in women with postmenopausal symptoms: updated analysis of three randomized, controlled trials".

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Boyd RA, Zegarac EA, Eldon MA (January 2003). "The effect of food on the bioavailability of norethindrone and ethinyl estradiol from norethindrone acetate/ethinyl estradiol tablets intended for continuous hormone replacement therapy".

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In addition, the therapeutic effect of ethinyl estradiol in established disease was demonstrated to require expression of GPER but not ERα, and was associated with the production of the anti-inflammatory cytokine IL-10 (Yates et al.,

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levels at a dose as low as 2.5 μg/day. EE affects several hepatic proteins at a dosage as low as 5 μg/day. At doses above 20 μg/day, the incremental effects of EE on liver protein synthesis become continuously smaller.

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Following a recommendation by its Fertility and Maternal Health Drugs Advisory Committee, the Food and Drug Administration (FDA) recently ordered the removal from the market of all oral contraceptives with contents greater than 50

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Changes in levels of estrogen-sensitive proteins after treatment with oral estradiol or oral ethinylestradiol in postmenopausal women. FSH is a pituitary protein and represents general/systemic estrogenic effect, while SHBG and

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due to an increased risk of VTE. EE use in breastfeeding women who are at least 21 days postpartum should be discussed with a provider and include information on the advantages, disadvantages, and alternatives for using EE.

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in postmenopausal women, EE concentrations have been found to reach a maximum of 50 pg/mL within an average of 1.5 hours. Following the first dose, mean levels of EE in general further increase by about 50% until

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on average (range 40 to 80%). Birth control pills containing high doses of EE can increase SHBG levels in women by as much as 5- to 10-fold. This is similar to the 5- to 10-fold increase in SHBG levels that occurs during

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Ponnatapura J, Kielar A, Burke LM, Lockhart ME, Abualruz AR, Tappouni R, et al. (July 2019). "Hepatic complications of oral contraceptive pills and estrogen on MRI: Controversies and update - Adenoma and beyond".

3210:(piperazine estrone sulfate), which has similar potency to micronized estradiol, in terms of systemic estrogenic potency. In contrast, the potencies of EE and natural estrogens are similar when they are administered 11620:

Oral contraceptive formulations containing greater than 50 ug ethinyl estradiol were removed from the United States market in 1989, and currently marketed formulations generally contain between 20 and 35 μg ethinyl

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Progestins, which are often used in combination with EE, are also known to inhibit cytochrome P450 enzymes, and this may contribute to drug interactions with EE-containing contraceptives as well. Examples include

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EE2 has about 100 times the potency of an equivalent weight of conjugated equine estrogen or estrone sulfate for stimulating synthesis of hepatic proteins. EE2 is about 1.7 times as potent as the same weight of

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have a dramatically higher risk of VTE with EE-containing contraception than women without thrombophilia. Depending on the condition, risk of VTE can be increased 5- to 50-fold relative to non-use in such women.

2599:. Diethylstilbestrol has been associated with an up to 35% risk of cardiovascular toxicity and death and a 15% incidence of VTE in men treated with it for prostate cancer. EE has a to some degree lower risk of 14502:

Stahl F, Schnorr D, Bär CM, Fröhlich G, Dörner G (1989). "Suppression of plasma androgen levels with a combination therapy of depot-estrogen (Turisteron) and Dexamethasone in patients with prostatic cancer".

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Further research showed that the therapeutic effect of ethynylestradiol in established EAE was mediated via GPER, but not via ERα, and possibly involved production of the anti-inflammatory cytokine Il‑10.115

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Ottosson UB, Carlström K, Johansson BG, von Schoultz B (1986). "Estrogen induction of liver proteins and high-density lipoprotein cholesterol: comparison between estradiol valerate and ethinyl estradiol".

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Mattison DR, Karyakina N, Goodman M, LaKind JS (September 2014). "Pharmaco- and toxicokinetics of selected exogenous and endogenous estrogens: a review of the data and identification of knowledge gaps".

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2056:. For comparison, the absolute risk of VTE is generally estimated as 1 to 5 per 10,000 woman–years for non-use, 5 to 20 per 10,000 woman–years for pregnancy, and 40 to 65 per 10,000 woman–years for the 10802:

tablet 0,05mg ethinylestradiol 0,05 mg (G03CA01) (NL) Etifollin tab 0,5mg (Nycomed pharma a/s) ethinylestradiol (L02AA03) (NO) Etifollin tab 50mcg (Nycomed pharma a/s) ethinylestradiol (G03CA01) (NO)

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Escande A, Pillon A, Servant N, Cravedi JP, Larrea F, Muhn P, et al. (May 2006). "Evaluation of ligand selectivity using reporter cell lines stably expressing estrogen receptor alpha or beta".

1026:, to prevent pregnancy after sex. EE in its birth control formulation is not only used to prevent pregnancy, but can also be used to treat absence of menstruation, symptoms during menstruation, and 3228: 10565:

Thibaut F, De La Barra F, Gordon H, Cosyns P, Bradford JM (June 2010). "The World Federation of Societies of Biological Psychiatry (WFSBP) guidelines for the biological treatment of paraphilias".

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has been observed with high-dosage polyestradiol phosphate. In any case, these estrogens are considered to be much safer than oral synthetic estrogens like EE and diethylstilbestrol. In addition,

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von Schoultz B, Carlström K, Collste L, Eriksson A, Henriksson P, Pousette A, et al. (1989). "Estrogen therapy and liver function--metabolic effects of oral and parenteral administration".

710: 8788:(EE sulfate), and levels of EE sulfate in circulation are between 6- and 22-fold higher than those of EE. For comparison, with oral administration of 2 mg micronized estradiol, levels of 8691:. Although relatively low, the oral bioavailability of EE is considerably higher than that of micronized estradiol (5%). Following a single 20 μg dose of EE in combination with 2 mg 2741:

can be observed in half of women on birth control pills with 50 μg/day EE. EE-containing birth control pills have also been associated with a 25- to 50-fold increase in the risk of rare

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The binding affinity of EE2 for the estrogen receptor is similar to that of estradiol. During daily intake, the EE2 levels increase up to a steady state which is reached after about 1 week.

8396:, a moderately androgenic progestin, have been found to increase TBG levels by 50 to 70%, while the combination of 30 μg/day EE and 150 μg/day desogestrel increased them by 100%. 8286:(0.15–1.0 mg/day). A dosage of EE of 50 μg twice daily (100 μg/day total) has been found to suppress testosterone levels in men to an equivalent extent as 3 mg/day oral 2603:

complications than does diethylstilbestrol when used in the treatment of prostate cancer in men. However, both EE and diethylstilbestrol nonetheless have highly disproportionate effects on

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Pugeat MM, Dunn JF, Nisula BC (July 1981). "Transport of steroid hormones: interaction of 70 drugs with testosterone-binding globulin and corticosteroid-binding globulin in human plasma".

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EE was developed in the 1930s and was introduced for medical use in 1943. The medication started being used in birth control pills in the 1960s. Ethinylestradiol is found in almost all

944:. These differences make EE more favorable for use in birth control pills than estradiol, though also result in an increased risk of blood clots and certain other rare adverse effects. 17091: 17086: 11730:

Odlind V, Milsom I, Persson I, Victor A (June 2002). "Can changes in sex hormone binding globulin predict the risk of venous thromboembolism with combined oral contraceptive pills?".

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once every 4 weeks alone; 2) the combination of intramuscular injection of 80 mg polyestradiol phosphate once every 4 weeks plus 150 μg/day oral ethinylestradiol; 3) orchiectomy only.

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for the ERα and ERβ, respectively. In another study, it was found to possess 194% and 151% of the affinity of estradiol for the ERα and ERβ, respectively. EE also appears to act as a

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Jacobi GH, Altwein JE, Kurth KH, Basting R, Hohenfellner R (June 1980). "Treatment of advanced prostatic cancer with parenteral cyproterone acetate: a phase III randomised trial".

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Mashchak CA, Lobo RA, Dozono-Takano R, Eggena P, Nakamura RM, Brenner PF, et al. (November 1982). "Comparison of pharmacodynamic properties of various estrogen formulations".

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and VTE risk with estrogen therapy, although this topic has been debated. SHBG levels with birth control pills containing different progestins are increased by 1.5 to 2-fold with

20315: 8752:. Unlike estradiol, which binds with high affinity to SHBG, EE has very low affinity for this protein, about 2% of that of estradiol, and hence does not bind to it importantly. 8277:

therapy, including with EE, is able to suppress testosterone levels in men by around 95%, or into the castrate/female range. The dosage of EE required for use as a component of

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Stanczyk FZ, Archer DF, Bhavnani BR (June 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment".

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Turo R, Smolski M, Esler R, Kujawa ML, Bromage SJ, Oakley N, et al. (February 2014). "Diethylstilboestrol for the treatment of prostate cancer: past, present and future".

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Stanczyk FZ, Archer DF, Bhavnani BR (June 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment".

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are reached; steady-state is reached after one week of daily administration. For comparison, the mean peak levels of estradiol achieved with 2 mg micronized estradiol or

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Bancroft J, Tennent G, Loucas K, Cass J (September 1974). "The control of deviant sexual behaviour by drugs. I. Behavioural changes following oestrogens and anti-androgens".

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Bastianelli C, Farris M, Rosato E, Brosens I, Benagiano G (November 2018). "Pharmacodynamics of combined estrogen-progestin oral contraceptives 3. Inhibition of ovulation".

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Zhang H, Cui D, Wang B, Han YH, Balimane P, Yang Z, et al. (2007). "Pharmacokinetic drug interactions involving 17alpha-ethinylestradiol: a new look at an old drug".

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Gerstman BB, Piper JM, Tomita DK, Ferguson WJ, Stadel BV, Lundin FE (January 1991). "Oral contraceptive estrogen dose and the risk of deep venous thromboembolic disease".

10669: 3107:, which are CYP3A4 and CYP2C19 inhibitors. In addition, these progestins are known to progressively inhibit the metabolism of and increase concentrations of EE itself. 2737:(GGT) decreases by 30%. However, the values usually remain in the normal range. In addition to abnormal LFTs, pathological changes in partial liver functions and liver 2082:

containing 30 or 40 μg EE. However, discontinuation of COCs is more common with doses of EE from 10 to 20 μg due to problematic changes in bleeding patterns.

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The synthetic estrogen, ethinyl estradiol, more commonly used in oral contraceptives, has a biological activity 100 times that of the native and conjugated substances.

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Goldzieher JW, Pena A, Chenault CB, Woutersz TB (July 1975). "Comparative studies of the ethynyl estrogens used in oral contraceptives. II. Antiovulatory potency".

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Pfeifer S, Butts S, Dumesic D, Fossum G, Gracia C, La Barbera A, et al. (Practice Committee of the American Society for Reproductive Medicine) (January 2017).

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a hormonally inert reservoir for estradiol, whereas the EE sulfate reservoir for EE is much smaller in comparison. In any case, due to the formation of EE sulfate,

19204: 18544: 2638:-like long-lasting prodrug of EE, is used in the treatment of prostate cancer, and is said to have a considerably better profile of cardiovascular safety than EE. 1431:

The severity of side effects can vary based on the dose and administration route of EE. General side effects of EE are the same as for other estrogens and include

8404: 8375:, a progestin with relatively weak androgenicity than levonorgestrel, increases SHBG levels by 200%, while the combination of 35 μg/day EE and 2 mg/day 19406: 15259:

The Climacteric in Perspective: Proceedings of the Fourth International Congress on the Menopause, held at Lake Buena Vista, Florida, October 28–November 2, 1984

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Park BJ, Kidd K (August 2005). "Effects of the synthetic estrogen ethinylestradiol on early life stages of mink frogs and green frogs in the wild and in situ".

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Stanczyk FZ, Grimes DA (September 2008). "Sex hormone-binding globulin: not a surrogate marker for venous thromboembolism in women using oral contraceptives".

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Plu-Bureau G, Maitrot-Mantelet L, Hugon-Rodin J, Canonico M (February 2013). "Hormonal contraceptives and venous thromboembolism: an epidemiological update".

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Wang B, Sanchez RI, Franklin RB, Evans DC, Huskey SE (November 2004). "The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol".

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Kottmeier HL (1947). "Ueber blutungen in der menopause: Speziell der klinischen bedeutung eines endometriums mit zeichen hormonaler beeinflussung: Part I".

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of 16.5 hours and 10.2 hours, respectively. It has been suggested that this phenomenon could represent a "protection mechanism" of males against

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instead of estradiol, in spite of its potentially inferior safety profile (related to its adverse effects on hepatic protein synthesis and VTE incidence).

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Shearer RJ, Hendry WF, Sommerville IF, Fergusson JD (December 1973). "Plasma testosterone: an accurate monitor of hormone treatment in prostatic cancer".

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activity, increases SHBG levels by 400%. As such, the type and dosage of progestin contained in COCs potently moderates the effects of EE on SHBG levels.

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is considered that many progestins used in COCs have varying degrees of weak androgenic activity. A combination of 20 μg/day EE and 0.25 mg/day

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dose. Today, COCs generally contain 10 to 50 μg EE. The higher doses of EE were discontinued due to a high risk of VTE and cardiovascular problems.

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InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1

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IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, World Health Organization, International Agency for Research on Cancer (2007).

8470:(uterus), EE is relatively more active than estradiol in the endometrium and, for this reason, is associated with a significantly lower incidence of 2575:

When used orally at high dosages, for instance as a form of high-dose estrogen therapy in men with prostate cancer and in women with breast cancer,

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of EE, such that EE may have greater oral potency in women than in men. A study found that a combination of 60 μg/day EE and 0.25 mg/day

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serves to inactivate estradiol and effectively suppress its potency in these tissues by reversibly converting it into the far less potent estrogen

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S. Monfardini, K. Brunner, D. Crowther, S. Eckhardt, D. Olive, S. Tanneberger, A. Veronesi, J.M.A. Whitehouse, R. Wittes, eds. (6 December 2012).

3071:. It has been found to increase the clearance of and reduce the concentrations of a variety of drugs known to be glucuronidated. Examples include 19356: 18936: 18928: 11952:

Stege R, Carlström K, Collste L, Eriksson A, Henriksson P, Pousette A (1988). "Single drug polyestradiol phosphate therapy in prostatic cancer".

1122:. In addition, there is a single preparation (brand name FemHRT) containing very low doses of EE (2.5 and 5 μg) plus a progestin in an oral 14007:

Martinez-Manautou J, Rudel HW (1966). "Antiovulatory Activity of Several Synthetic and Natural Estrogens". In Robert Benjamin Greenblatt (ed.).

19446: 18511: 12591:

Perarnau JM, Bacq Y (August 2008). "Hepatic vascular involvement related to pregnancy, oral contraceptives, and estrogen replacement therapy".

8656: 137:

Ethynylestradiol; Ethinyl estradiol; Ethinyl oestradiol; EE; EE2; 17α-Ethynylestradiol; 17α-Ethynylestra-1,3,5(10)-triene-3,17β-diol; NSC-10973

19616: 19421: 19271: 19266: 18764: 18759: 18754: 18624: 10338: 7026: 142: 14989:

Trémollieres F (February 2012). "" [Oral combined contraception: is there any difference between ethinyl-estradiol and estradiol?].

14058: 13045:"GPR30, but not estrogen receptor-alpha, is crucial in the treatment of experimental autoimmune encephalomyelitis by oral ethinyl estradiol" 9499:

Fotherby K (August 1996). "Bioavailability of orally administered sex steroids used in oral contraception and hormone replacement therapy".

20265: 19230: 19150: 18947: 18249: 18033: 8278: 734: 17736: 1499:

therapy with 200 μg/day oral EE for more than three months, gynecomastia occurred in 98% and decreased libido occurred in 42 to 73%.

951:

forms of birth control pills and is nearly the exclusive estrogen used for this purpose, making it one of the most widely used estrogens.

19757: 19636: 19516: 19022: 19017: 18789: 18714: 8263: 20240: 19937: 19877: 18997: 18992: 18839: 18834: 17186: 17016: 16985: 16567: 12496:

Giannitrapani L, Soresi M, La Spada E, Cervello M, D'Alessandro N, Montalto G (November 2006). "Sex hormones and risk of liver tumor".

14654:

Bingel AS, Benoit PS (February 1973). "Oral contraceptives: therapeutics versus adverse reactions, with an outlook for the future I".

20025: 19631: 19546: 19332: 19165: 19160: 18844: 18679: 18634: 17983: 16024: 12996:"International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators" 8458:(which has approximately 4% of the estrogenic activity of estradiol). In contrast to estradiol, the 17α-ethynyl group of EE prevents 8198:

Testosterone levels with no treatment and with various estrogens in men with prostate cancer. Determinations were made with an early

7577: 2692: 10426:"The British Menopause Society & Women's Health Concern 2016 recommendations on hormone replacement therapy in menopausal women" 9339:

Ethinylestradiol is marketed throughout the world. It is marketed exclusively or almost exclusively in combination with progestins.

8371:

COCs containing EE and levonorgestrel increase SHBG levels by 100 to 150%. The combination of 30 μg/day EE and 150 μg/day

8194: 19687: 19002: 18910: 18905: 18895: 18809: 18734: 17746: 14946:

Polderman KH, Gooren LJ, van der Veen EA (October 1995). "Effects of gonadal androgens and oestrogens on adrenal androgen levels".

14800:

Martinez-Manautou J, Rudel HW (1966). "Antiovulatory Activity of Several Synthetic and Natural Estrogens". In Greenblatt RB (ed.).

1111:

EE is available in combination with a progestin in a vast number of COCs. It is also available in combination with progestins as a

8828:

by its ethynyl group at C17α. The ethynylation of EE is largely irreversible, and so EE is not metabolized into estradiol, unlike

18849: 3172:

effects through activation of the ERα. As a contraceptive, EE acts in concert with a progestin to inhibit the mid-cycle surge in

8273:

and are able to suppress the secretion of LH and FSH from the pituitary gland and by extension gonadal testosterone production.

20431: 18525: 16558: 8338:. These effects are mediated by its estrogenic activity. The medication dose-dependently increases circulating levels of SHBG, 1221: 8422: 3883: 19327: 17009: 16975: 16942: 15895: 15860: 15830: 15802: 15748: 15715: 15580: 15443: 15267: 15189: 15067: 15040: 14925: 14844: 14811: 14700: 14589: 14562: 14193: 14041: 13991: 13763: 13660: 13633: 13596: 13569: 13542: 13411: 13380: 13349: 13316: 13286: 13259: 12677: 12650: 12398: 12363: 12315: 12285: 12212: 11857: 11613: 11583: 11552: 11484: 11301: 11271: 11241: 11214: 11086: 11016: 10896: 10866: 10825: 10794: 10740: 10713: 10681: 10183: 10146: 10081: 10028: 9964: 9862: 9827: 9575: 9548: 9382: 8311:. Studies in women have found that 50 μg/day EE suppresses LH and FSH levels both by about 70% in postmenopausal women. 2253: 15637:"Schering Corp. et al.; Withdrawal of Approval of 92 New Drug Applications and 49 Abbreviated New Drug Applications. Notice" 10764:. U.S. Department of Health and Human Services, Public Health Service, Food and Drug Administration, Bureau of Drugs. 1980. 9445:"An overview of the development of combined oral contraceptives containing estradiol: focus on estradiol valerate/dienogest" 8768:, only 1% of an oral dose of an EE appears in the circulation as EE itself. During first-pass metabolism, EE is extensively 779: 19322: 17818: 17296: 16980: 16381: 16017: 13504:

Lauritzen C (June 1977). "" [Estrogen therapy in practice. 3. Estrogen preparations and combination preparations].

9043:

EE was the first orally active synthetic estrogen and was described in 1938 by Hans Herloff Inhoffen and Walter Hohlweg of

8958: 8322:

levels by 27 to 48% in transgender women. This may additionally contribute to suppression of androgen levels by estrogens.

7570: 3011:. As a result, it can affect the metabolism and concentrations of many other drugs. Examples of known interactions include 2931:). Conversely, inhibitors of CYP3A4 and other cytochrome P450 enzymes may increase circulating levels of EE. An example is 2516: 14279:"The effect of combined oral contraception on testosterone levels in healthy women: a systematic review and meta-analysis" 19056: 14211:"Preclinical characterization of a novel diphenyl benzamide selective ERα agonist for hormone therapy in prostate cancer" 11605:

Multigenerational Reproductive Toxicology Study of Ethinyl Estradiol (CAS No. 57636) in SpragueDawley Rats (Feed Studies)

9178: 3161: 2946: 2538: 13871:

Ryden AB (1950). "Natural and synthetic oestrogenic substances; their relative effectiveness when administered orally".

8558: 8447: 8392:

while progestins with androgenic activity may decrease TBG levels. A combination of 30 μg/day EE and 1 mg/day

998:

was the 276th most commonly prescribed medication in the US, with more than 800,000 prescriptions; the combination with

17281: 17276: 9028: 9024: 8687:

of EE is 45% on average, with a wide range of 20% to 74% (though most commonly between 38 and 48%) that is due to high

8318:

at high concentrations. One study found that treatment with a high dosage of 100 μg/day EE suppressed circulating

15890:. Springer Science & Business Media. pp. 4, 10, 15, 165, 247–248, 276–291, 363–408, 424, 514, 540, 543, 581. 9822:. Springer Science & Business Media. pp. 4, 10, 15, 165, 247–248, 276–291, 363–408, 424, 514, 540, 543, 581. 17329: 16767: 16096: 15905:

Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration".

14733: 9680:

Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration".

9104: 8478:

EE has been found to have disproportionate effects on liver protein synthesis and VTE risk regardless of whether the

754: 8935: 2658: 19390: 17345: 16959: 16771: 16108: 15848: 948: 20165: 17900: 17466: 16413: 16182: 20441: 20436: 18480: 9538: 8796:

are 4- to 6-fold and 200-fold higher than those of estradiol, respectively. In contrast to estradiol, EE, due to

8339: 7960: 7135: 7004: 6512: 2466: 2456: 2335: 377: 249: 17540: 17508: 16258: 16234: 14326:Özcan Ö, den Elzen WP, Hillebrand JJ, den Heijer M, van Loendersloot LL, Fischer J, et al. (January 2024). 10360: 9160:

but was eventually changed. In addition, a space is often included in the name of EE such that it is written as

19847: 17731: 16492: 8881: 8769: 1830: 15867:

ETHINYL ESTRADIOL U.S.P. (Esteed®, Estinyl®, Lynoral®, Menolyn®, Novestrol®, Palonyl®, Spanestrin®, Ylestrol®)

472: 9203: 8922:

at the C17α position. The 17α-ethynylation of estradiol to create EE is analogous to the 17α-substitution of

8222:, which decreases free and thus bioactive concentrations of testosterone in the blood; and by 2) suppressing 2530: 2506: 2476: 15318:

Backeljauw P, Klein K (March 2019). "Sex hormone replacement therapy for individuals with Turner syndrome".

14716:

Elger W (1972). "Physiology and pharmacology of female reproduction under the aspect of fertility control".

20456: 20446: 20357: 19317: 17631: 16876: 16509: 16263: 15632: 11875:"Clinical opinion: the biologic and pharmacologic principles of estrogen therapy for symptomatic menopause" 10048: 9995: 9059:

under the brand name Estinyl. The FDA withdrew approval of Estinyl effective 4 June 2004 at the request of

9052: 8821: 8793: 8581: 8239: 8215: 7787: 7505: 7273: 7125: 7086: 6991: 6636: 6502: 3908: 3177: 2542: 2486: 2093: 2040:-containing birth control pills, and 10 to 15 per 10,000 women for birth control pills containing EE and a 1019: 642: 523: 293: 19081: 17191: 17166: 12945:"Exploration of dimensions of estrogen potency: parsing ligand binding and coactivator binding affinities" 12342:. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Berlin Heidelberg. pp. 363–407. 11571: 6172: 6147: 3858: 2709:, appear to be responsible for the cholestasis. Very high concentrations of estradiol, via its metabolite 19892: 19586: 19379: 19337: 17579: 16990: 16880: 11914:

Goodman MP (February 2012). "Are all estrogens created equal? A review of oral vs. transdermal therapy".

8842: 8824:

of 2- and 4-hydroxy-EE. Unlike the case of estradiol, 16α-hydroxylation does not occur with EE, owing to

8688: 2808:

in female fish and feminized male fish such that they produced a protein associated with egg maturation,

2757:

The high doses of EE that were used in early COCs were associated with a significantly increased risk of

2045: 1767: 1684: 1664: 603: 8872:

accumulation in EE levels with an EE-containing COC has been observed following 1 year of therapy.

20411: 20406: 20401: 20371: 17584: 16280: 9318: 9165: 9113: 8976: 8725: 8697: 8343: 6978: 6492: 3165: 2631: 2615: 2496: 2381: 2205: 2129: 2065: 2041: 1749: 1440: 1403: 1270: 1119: 1112: 1054: 1034: 855: 19667: 19662: 15210:

Orme ML, Back DJ, Breckenridge AM (1983). "Clinical pharmacokinetics of oral contraceptive steroids".

10255: 10088:

In 1964, ethinyl estradiol was introduced as an alternative to mestranol as the estrogenic component,

8314:

In addition to its antigonadotropic effects, EE can significantly suppress androgen production by the

2881:

of enzymes such as CYP3A4 can decrease circulating concentrations of EE. Examples of inducers include

2848: 592: 18639: 18549: 17771: 16092: 15852:

American Hospital Formulary Service: A Two-volume Collection of Drug Monographs and Other Information

14328:"The effect of hormonal contraceptive therapy on clinical laboratory parameters: a literature review" 11206:

Hormones and Atherosclerosis: Proceedings of the Conference Held in Brighton, Utah, March 11-14, 1958

10452: 10205: 8923: 6935: 6922: 6444: 6197: 5847: 3271: 3265: 2813: 2734: 2545: 1095:

EE or any estrogen alone is contraindicated for women who have a uterus due to the increased risk of

20150: 19697: 19536: 10280: 10230: 3958: 2945:

the sulfation of EE, with pretreatment of 1,000 mg of paracetamol significantly increasing the

2548:

was not included, but is known to be associated with no additional risk relative to estrogen alone.

20275: 20190: 19200: 18962: 18875: 18500: 18193: 17726: 17721: 17621: 16287: 15887:

Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen

14581:

Textbook of Prostate Cancer: Pathology, Diagnosis and Treatment: Pathology, Diagnosis and Treatment

13676:

Lauritzen CH (January 1976). "The female climacteric syndrome: significance, problems, treatment".

11233:

Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen

9819:

Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen

8785: 8554: 7106: 4984: 2950: 2812:, as well as early-stage eggs. In amphibians, exposure to EE can reduce hatching success and alter 2746: 2722: 2714: 2553: 2409: 2287: 2263: 1897: 1860: 1811: 1274: 1231: 1100: 1006:

was the 277th most commonly prescribed medication in the US, with more than 800,000 prescriptions;

820: 619: 329: 10330: 10305: 2650:

At the lower dosages that are now used in birth control pills, EE has been associated rarely with

2060:

period. Modern COCs are associated with about a 2- to 4-fold higher risk of VTE than non-use. The

936:

when taken by mouth, and shows relatively increased effects in certain parts of the body like the

18488: 18398: 18023: 18013: 17948: 17476: 17246: 16947: 16452: 16430: 16214: 16210: 15462: 11757:

Raps M, Helmerhorst F, Fleischer K, Thomassen S, Rosendaal F, Rosing J, et al. (June 2012).

10673:

Combined Estrogen-progestogen Contraceptives and Combined Estrogen-progestogen Menopausal Therapy

9067: 8862: 8517: 8479: 8435: 8427: 8335: 8331: 7155: 6965: 6482: 3833: 3149: 3141: 2797: 2611: 2604: 2142: 2078: 2061: 2003: 1716: 1673: 1224:(e.g. older age, smoking, diabetes, hypertension, low HDL, high LDL, or high triglyceride levels) 174: 124: 17286: 17261: 17201: 17196: 10730: 9405:

Goldzieher JW, Brody SA (December 1990). "Pharmacokinetics of ethinyl estradiol and mestranol".

8900:

EE, also known as 17α-ethynylestradiol or as 17α-ethynylestra-1,3,5(10)-triene-3,17β-diol, is a

7550:. Liver = Ratio of liver estrogenic effects to general/systemic estrogenic effects (hot flashes/ 4161: 4136: 20421: 19837: 19466: 18456: 18008: 17488: 17413: 17408: 17361: 16447: 16224: 16177: 15572: 15433: 14552: 13906:

Ryden AB (1951). "The effectiveness of natural and synthetic oestrogenic substances in women".

13199:

Quaynor SD, Stradtman EW, Kim HG, Shen Y, Chorich LP, Schreihofer DA, et al. (July 2013).

11542: 10886: 10703: 9322: 9131: 8915: 8745: 8729: 8692: 8673: 8607: 8577: 8499: 8410: 7662: 7637: 7162: 6948: 6524: 4484: 3308: 3157: 3145: 2957:(vitamin C) and EE, although the significance of the interaction has been regarded as dubious. 2942: 2446: 2424: 2419: 2405: 2386: 2315: 2215: 2138: 2011: 1595: 1565: 1557: 1472: 1299: 1273:, it is widely considered that COCs containing EE should be avoided in women with a history of 1244: 1215: 1156: 1062: 921: 867: 816: 283: 190: 17216: 15792: 15257: 15179: 15030: 14690: 14579: 13981: 13650: 13613: 13586: 13370: 13276: 13249: 12698:

Kidd KA, Blanchfield PJ, Mills KH, Palace VP, Evans RE, Lazorchak JM, et al. (May 2007).

12640: 12425:

Kuhl H (December 1990). "" [Ovulation inhibitors: the significance of estrogen dose].

12388: 12305: 12275: 12202: 11847: 11573: 11474: 11291: 11261: 11231: 11204: 11079:

Gynäkologische Endokrinologie und Fortpflanzungsmedizin: Band 1: Gynäkologische Endokrinologie

11074: 11006: 10856: 10784: 10671: 10136: 10071: 10018: 9817: 9372: 928:

estrogen, and differs from it in various ways. Compared to estradiol, EE is more resistant to

20426: 18729: 18554: 18492: 18018: 17562: 17525: 17513: 17381: 16864: 16248: 16242: 16172: 16142: 16052: 16040: 15057: 14915: 14827:

Herr F, Revesz C, Manson AJ, Jewell JB (1970). "Biological Properties of Estrogen Sulfates".

14183: 14024:

Herr F, Revesz C, Manson AJ, Jewell JB (1970). "Biological Properties of Estrogen Sulfates".

13559: 13532: 13339: 12667: 12149:"Androgen Deprivation Therapy and the Re-emergence of Parenteral Estrogen in Prostate Cancer" 11759:"Sex hormone-binding globulin as a marker for the thrombotic risk of hormonal contraceptives" 11603: 11572:

Committee on the Relationship Between Oral Contraceptives and BreastCancer (1 January 1991).

10815: 9852: 9152: 9122: 9020: 8833: 8541: 6926: 6918: 6472: 6439: 3383: 3257: 3211: 3203: 3121: 2960:

In contrast to estradiol, it is unlikely that there is a pharmacokinetic interaction between

2710: 2592: 2174:

Risk of venous thromboembolism (VTE) with hormone therapy and birth control (QResearch/CPRD)

1887: 1869: 1731: 1708: 1649: 1626: 1618: 1603: 1584: 1160: 1050: 894: 797: 572: 463: 202: 19682: 19672: 17291: 17266: 17241: 17226: 17161: 17101: 17096: 15849:

American Society of Hospital Pharmacists. Committee on Pharmacy and Pharmaceuticals (1983).

15777: 15564: 14375:

Yang LP, Plosker GL (October 2012). "Nomegestrol acetate/estradiol: in oral contraception".

6347: 6322: 4111: 4086: 3708: 152: 20020: 19992: 19982: 19601: 18149: 17806: 17545: 17451: 17393: 17171: 16872: 16369: 16317: 16253: 16229: 16202: 16167: 16152: 15471: 14209:

Coss CC, Jones A, Parke DN, Narayanan R, Barrett CM, Kearbey JD, et al. (March 2012).

12711: 12505: 9004: 8789: 8455: 8010: 7812: 7737: 7310: 7236: 7199: 6664: 6608: 4186: 3983: 3358: 3333: 3199: 3198:

Orally, EE is on the order of 100 times as potent by weight as natural estrogens like

3125: 2836: 2777: 2738: 2435: 2311: 2234: 1995: 1785: 1775: 1757: 1492: 1172: 532: 338: 19677: 17231: 17106: 17081: 13711:

Lauritzen C (1975). "The Female Climacteric Syndrome: Significance, Problems, Treatment".

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populations. Chronic exposure to low levels of EE over seven years led to the collapse of

512: 8: 19822: 19722: 19646: 19348: 19210: 19125: 18189: 17973: 17830: 17796: 17606: 17306: 16924: 16868: 16792: 16686: 16518: 16198: 16194: 16127: 10957: 10933: 10912: 9304: 8964: 8911: 8749: 8681: 8621: 8601: 8376: 8223: 7518: 7096: 5009: 4909: 3808: 3173: 2718: 2451: 2210: 2192: 2133: 2125: 2069: 1955: 1697: 1237: 1140: 1115: 995: 917: 824: 801: 418: 289: 182: 20016: 17221: 15955: 15475: 12715: 12509: 11819: 9918: 958:

was the 52nd most commonly prescribed medication in the United States, with more than 12

646: 623: 427: 20295: 20050: 19851: 19382: 19292: 19076: 18957: 18539: 18153: 17813: 17471: 17388: 17333: 17176: 17136: 17126: 17066: 17035: 16376: 16322: 16206: 16190: 16147: 16100: 15997: 15930: 15487: 15394: 15343: 15235: 15157: 15108: 14971: 14959: 14854: 14782: 14636: 14528: 14484: 14434: 14400: 14357: 14303: 14278: 14106: 13848: 13823: 13225: 13200: 13172: 13147: 13120: 13095: 13071: 13044: 13020: 12995: 12971: 12944: 12890: 12830: 12787: 12734: 12699: 12616: 12573: 12529: 12450: 12351: 12173: 12148: 12116: 12029: 11977: 11891: 11874: 11788: 11700: 11675: 11441: 11416: 11180: 11155: 11131: 11106: 11048: 10633: 10590: 10498: 10471: 9705: 9469: 9444: 9235: 8946: 8901: 8816:. This is mainly by 2-hydroxylation into 2-hydroxy-EE, which is catalyzed primarily by 8701: 8388: 8304: 8287: 8274: 7935: 7712: 7687: 7484: 7480: 7419: 7066: 6886: 6580: 6552: 6122: 5334: 4334: 4211: 3933: 3583: 3558: 3533: 3508: 3129: 2758: 2742: 2669: 2584: 2576: 2015: 2007: 1999: 1803: 1793: 1739: 1513: 1496: 1484: 1464: 1295: 1198: 1176: 1096: 1038: 914: 887: 875: 847: 18880: 17156: 15636: 3202:

and conjugated estrogens, which is largely due to substantially greater resistance to

1459:. The estrogen component of oral contraceptives, which is almost always EE, can cause 20416: 20000: 19707: 18890: 18664: 18113: 17121: 17116: 17043: 17032: 16884: 16697: 16547: 16238: 16186: 16061: 15989: 15959: 15922: 15891: 15856: 15826: 15798: 15744: 15711: 15680: 15613: 15576: 15565: 15545: 15510: 15439: 15386: 15335: 15300: 15263: 15227: 15223: 15185: 15149: 15100: 15063: 15036: 15006: 14963: 14921: 14891: 14887: 14840: 14807: 14774: 14739: 14729: 14696: 14671: 14628: 14585: 14558: 14520: 14476: 14459:

Gunnarsson PO, Norlén BJ (1988). "Clinical pharmacology of polyestradiol phosphate".

14438: 14392: 14388: 14361: 14349: 14308: 14259: 14232: 14189: 14159: 14134: 14110: 14070: 14037: 13987: 13958: 13923: 13888: 13853: 13804: 13769: 13759: 13728: 13693: 13656: 13629: 13592: 13565: 13538: 13513: 13486: 13482: 13451: 13447: 13407: 13376: 13345: 13312: 13282: 13255: 13230: 13201:"Delayed puberty and estrogen resistance in a woman with estrogen receptor α variant" 13177: 13125: 13076: 13025: 12976: 12925: 12882: 12878: 12822: 12779: 12739: 12673: 12646: 12620: 12608: 12577: 12565: 12521: 12475: 12442: 12394: 12369: 12359: 12311: 12281: 12256: 12208: 12178: 12108: 12070: 12021: 11969: 11965: 11931: 11896: 11853: 11823: 11780: 11775: 11758: 11739: 11705: 11656: 11651: 11634: 11609: 11579: 11548: 11523: 11480: 11446: 11397: 11357: 11352: 11336:"Combined hormonal contraception and the risk of venous thromboembolism: a guideline" 11335: 11297: 11267: 11237: 11210: 11185: 11136: 11082: 11052: 11012: 10967:. Vol. 65, no. 3. Centers for Disease Control and Prevention. 29 July 2016. 10943:. Vol. 65, no. 4. Centers for Disease Control and Prevention. 29 July 2016. 10922:. Vol. 65, no. 4. Centers for Disease Control and Prevention. 29 July 2016. 10892: 10862: 10831: 10821: 10790: 10765: 10736: 10709: 10677: 10625: 10582: 10547: 10503: 10406: 10142: 10117: 10077: 10024: 9960: 9922: 9858: 9823: 9697: 9571: 9544: 9516: 9512: 9474: 9422: 9418: 9378: 8988: 8813: 8724:

in women and men resulted in peak levels of EE of 495 pg/mL and 251 pg/mL,

8669: 8509: 8282: 8259: 7762: 6952: 6939: 6462: 6452: 5997: 4459: 3783: 3137: 1917: 1460: 1432: 1192: 1144: 1123: 1058: 906: 902: 843: 828: 166: 17271: 16001: 15934: 15491: 15398: 15347: 15239: 15161: 15112: 14786: 14532: 14488: 14404: 12894: 12834: 12791: 12454: 12120: 12033: 11981: 11792: 11107:"Trends in the content and use of oral contraceptives in the United States, 1964-88" 11105:

Gerstman BB, Gross TP, Kennedy DL, Bennett RC, Tomita DK, Stadel BV (January 1991).

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The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies

8210:

in both women and men. It mediates its antiandrogenic effects by 1) stimulating the

2610:

In contrast to oral synthetic estrogens like EE and diethylstilbestrol, high-dosage

20451: 20285: 20005: 19887: 19817: 19702: 19692: 19456: 18609: 17321: 17206: 17146: 17141: 17131: 17111: 17071: 16759: 16747: 16359: 16088: 15981: 15951: 15914: 15736: 15703: 15676: 15672: 15644: 15605: 15537: 15479: 15378: 15327: 15292: 15219: 15141: 15092: 14998: 14975: 14955: 14883: 14832: 14766: 14721: 14720:. Ergebnisse der Physiologie Reviews of Physiology. Vol. 67. pp. 69–168. 14663: 14640: 14618: 14512: 14468: 14430: 14384: 14339: 14298: 14290: 14277:

Zimmerman Y, Eijkemans MJ, Coelingh Bennink HJ, Blankenstein MA, Fauser BC (2014).

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Early COCs contained 40 to 100 μg/day EE and 50 to 150 μg/day mestranol.

8942: 8846: 8825: 8797: 8717: 8471: 8319: 8270: 8199: 8060: 6376: 6097: 5972: 5947: 4434: 3758: 3733: 3683: 3658: 3633: 3608: 3483: 3181: 3169: 2976: 2665: 2097: 1209: 1003: 808:. In the past, EE was widely used for various indications such as the treatment of 659: 265: 232: 222: 57: 17251: 15083:

Sitruk-Ware R, Nath A (June 2011). "Metabolic effects of contraceptive steroids".

14770: 13787:

Scott WW, Menon M, Walsh PC (April 1980). "Hormonal Therapy of Prostatic Cancer".

10175: 9991: 9536: 6434:

Relative affinities of estrogens for steroid hormone receptors and blood proteins

1508:

Beneficial and adverse effects of ethinylestradiol-containing birth control pills

20385: 19962: 19857: 19737: 18699: 18432: 18306: 17938: 17885: 17840: 17641: 16843: 16779: 16467: 16420: 16297: 15985: 15885: 15850: 15820: 15707: 15382: 15002: 14801: 14623: 14606: 14008: 13800: 13625: 13401: 13306: 12347: 12235:"Estradiol for the mitigation of adverse effects of androgen deprivation therapy" 12104: 10759: 9956: 9565: 9460: 9174: 9056: 8996: 8865: 8829: 8773: 8684: 8624: 8355: 8351: 8308: 8231: 8085: 7910: 7492: 7347: 7145: 7076: 6830: 6072: 5434: 4759: 4309: 3064: 2980: 2965: 2866: 2776:

contains various estrogens, including EE, that are not completely broken down by

2623: 1688: 1164: 1139:

EE should be avoided in individuals with a history of or known susceptibility to

1077: 1073: 933: 925: 452: 306: 273: 39: 22: 18410: 18406: 18384: 15740: 14836: 14033: 13755: 12469: 11676:"20 μg versus >20 μg estrogen combined oral contraceptives for contraception" 11156:"20 μg versus >20 μg estrogen combined oral contraceptives for contraception" 5534: 5509: 5459: 1061:. However, it is no longer commonly used nor recommended for this purpose, with 20310: 20230: 20100: 19957: 19812: 19777: 19436: 19170: 18932: 18804: 18233: 17953: 17925: 17917: 17756: 17661: 17651: 17596: 17591: 17493: 17311: 17211: 17001: 16953: 16816: 16804: 16437: 16119: 15609: 12704:

Proceedings of the National Academy of Sciences of the United States of America

11393: 10113: 9288: 9216: 9008: 9000: 8931: 8721: 8393: 8364: 7000: 6987: 6398:

proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ).

6222: 5872: 3195:

EE is a long-acting estrogen, with a nuclear retention of about 24 hours.

3059:. One of the most notable interactions is that EE strongly increases levels of 3004: 2932: 2882: 2878: 2817: 2816:. Exposure to hormones can change frogs' gonadal development even though it is 2793: 2762: 2654: 2619: 2600: 2588: 2105: 2037: 1840: 1821: 1518: 1411: 1407: 1250:

Except when being used to treat it, EE should be avoided in women with current

1180: 1152: 971: 955: 16009: 15918: 15096: 14276: 13954: 13724: 13689: 13163: 13148:"Estrogen biology: new insights into GPER function and clinical opportunities" 12921: 12561: 12164: 10835: 10578: 9693: 9331:

in oral hormone replacement therapy for the treatment of menopausal symptoms.

6297: 4959: 2010:. EE carries a greater risk of blood clot formation and VTE than does natural 2002:(PE). Estrogens are known to increase the risk of VTE due to their effects on 20395: 20250: 20125: 20010: 19972: 19867: 19832: 19767: 19566: 19526: 19426: 18784: 18619: 18594: 18374: 18292: 18125: 18103: 17958: 17835: 17567: 17418: 17376: 16403: 15145: 14163: 13962: 13773: 13732: 13469:

Lauritzen C (September 1990). "Clinical use of oestrogens and progestogens".

12373: 12355: 11432: 11379: 10813: 10442: 10425: 8919: 8809: 8315: 7547: 6961: 6247: 4008: 3458: 3433: 2954: 2902: 2898: 2626:

in men with prostate cancer. However, significantly increased cardiovascular

2086: 2033: 2029: 1879: 1545: 1530: 1278: 1258: 1251: 1081: 1023: 1015: 990:

was the 227th most commonly prescribed medication in the US, with more than 2

982:

was the 198th most commonly prescribed medication in the US, with more than 2

974:

was the 144th most commonly prescribed medication in the US, with more than 4

721: 635: 14472: 14294: 13111: 13061: 12961: 12724: 12517: 12017: 10761:

Approved Prescription Drug Products with Therapeutic Equivalence Evaluations

10488: 966:

was the 76th most commonly prescribed medication in the US, with more than 8

20335: 20305: 20280: 20235: 20180: 20175: 20160: 20155: 20145: 20140: 20065: 19967: 19947: 19932: 19927: 19922: 19907: 19802: 19792: 19621: 19561: 19496: 19491: 19486: 19481: 19461: 19451: 18952: 18924: 18900: 18769: 18694: 18604: 18599: 18589: 18392: 18358: 18348: 18344: 18279: 18273: 18205: 17701: 17691: 17666: 17530: 17483: 17337: 17325: 16826: 16763: 16702: 16631: 16626: 16621: 16616: 16596: 16591: 16538: 16505: 16485: 16479: 16475: 16334: 16329: 16123: 16104: 16044: 15993: 15963: 15926: 15684: 15617: 15390: 15339: 15153: 15104: 15010: 14778: 14718:

Reviews of Physiology Biochemistry and Experimental Pharmacology, Volume 67

14667: 14632: 14516: 14396: 14353: 14344: 14327: 14312: 14263: 14236: 14154: 14074: 13927: 13919: 13892: 13884: 13857: 13839: 13808: 13234: 13181: 13129: 13080: 13029: 12980: 12929: 12886: 12826: 12818: 12783: 12743: 12612: 12604: 12569: 12525: 12479: 12438: 12260: 12182: 12112: 11935: 11900: 11827: 11784: 11743: 11709: 11660: 11527: 11450: 11417:"Systematic Review of Hormonal Contraception and Risk of Venous Thrombosis" 11401: 11361: 11189: 10769: 10586: 10551: 10507: 10410: 10121: 9926: 9701: 9478: 9308: 9100: 9019:

analogues of EE with significant although weak estrogenic activity include

8733: 8466:

On the other hand, due to the loss of inactivation of EE by 17β-HSD in the

8463:

magnitude of effect on VTE and cardiovascular risks relative to estradiol.

8380: 8347: 8307:

was found to suppress FSH secretion in men to an extent sufficient to stop

8211: 8207: 7551: 5790: 4809: 4734: 4709: 3104: 3052: 2894: 2809: 2580: 2117: 2053: 1641: 1476: 1468: 1203: 1089: 1069: 1046: 999: 979: 963: 883: 871: 863: 832: 227: 217: 15549: 15514: 15320:

American Journal of Medical Genetics. Part C, Seminars in Medical Genetics

15304: 15231: 14967: 14895: 14743: 14675: 14524: 14480: 14442: 14114: 13490: 13455: 13216: 13011: 12446: 12074: 12025: 11973: 11927: 11140: 11056: 10629: 10621: 9520: 9426: 8346:(TBG), and also affects a broad range of other liver proteins. EE affects 20320: 20290: 20270: 20220: 20095: 20090: 20075: 20045: 19872: 19827: 19787: 19782: 19732: 19727: 19712: 19551: 19511: 19416: 19297: 19225: 19190: 19185: 19145: 19115: 19101: 19091: 19086: 18915: 18859: 18854: 18749: 18744: 18724: 18674: 18649: 18644: 18569: 18559: 18476: 18472: 18468: 18460: 18450: 18446: 18414: 18402: 18388: 18380: 18320: 18253: 18197: 18169: 18003: 17978: 17850: 17751: 17626: 17550: 17520: 17371: 17351: 17301: 17255: 17151: 16860: 16833: 16812: 16808: 16800: 16785: 16775: 16727: 16666: 16661: 16611: 16499: 16442: 16268: 16218: 16137: 16078: 15331: 15296: 14227: 14210: 13697: 13517: 11122: 10747:

ETHINYL ESTRADIOL: TABLET; ORAL: ESTINYL: SCHERING: 0.02MG; 0.05MG; 0.5MG

9060: 9044: 9032: 8992: 8927: 8926:

to make testosterone derivatives such as 17α-ethynylated progestins like

8781: 8467: 8372: 7115: 7056: 6974: 6720: 5762: 5734: 5659: 5634: 5609: 5484: 5384: 5259: 4884: 4859: 4534: 3408: 3207: 3100: 3088: 3076: 3040: 3020: 2938: 2913: 2781: 2681: 2651: 2109: 2101: 2049: 1576: 1480: 1456: 1148: 1042: 1037:. The main reason for using HRT in menopausal women is to relieve common 839: 186: 160: 15541: 12251: 12234: 10524:

Coelingh Bennink HJ, Verhoeven C, Dutman AE, Thijssen J (January 2017).

2835:

in those experimentally exposed to EE than those not exposed to EE, and

2607:, which is thought to be responsible for their cardiovascular toxicity. 2064:

of EE does not appear to influence VTE risk, as EE/progestin-containing

2036:

of VTE is 2 per 10,000 women for non-use, 8 per 10,000 women for EE and

2018:

differences between the two compounds and different susceptibilities to

492: 20300: 20260: 20205: 20195: 20135: 20120: 20105: 20085: 20060: 20055: 20035: 20030: 19987: 19977: 19942: 19917: 19897: 19862: 19841: 19797: 19772: 19556: 19521: 19506: 19501: 19470: 19431: 19411: 19240: 19220: 19195: 19042: 18987: 18942: 18920: 18829: 18824: 18794: 18779: 18774: 18739: 18629: 18584: 18564: 18442: 18436: 18340: 18328: 18288: 18269: 18245: 18229: 18139: 18135: 18109: 18095: 18048: 18043: 18038: 18028: 17998: 17968: 17963: 17943: 17880: 17801: 17781: 17766: 17761: 17706: 17656: 17557: 17498: 17431: 17426: 17403: 17341: 17316: 16909: 16850: 16732: 16717: 16676: 16651: 16641: 16636: 16606: 16581: 16425: 16391: 16364: 16354: 16349: 16339: 16312: 16307: 16162: 16157: 15630: 15483: 14725: 12943:

Jeyakumar M, Carlson KE, Gunther JR, Katzenellenbogen JA (April 2011).

12942: 10888:

Koda-Kimble and Young's Applied Therapeutics: The Clinical Use of Drugs

10523: 10046: 9293: 9016: 9012: 8995:

at the C17α position exist. Examples include the estradiol derivatives

8972: 8858: 8805: 8709:

meal has been found to significantly decrease its peak concentrations.

8483: 8295: 7985: 7885: 6748: 6387: 5922: 5897: 5684: 5409: 5309: 5284: 5159: 5059: 4784: 4684: 4659: 4634: 4609: 4559: 4409: 4384: 3206:. It is specifically in the range of 80 to 200 times as potent as 3072: 3060: 3056: 3048: 3036: 3032: 2928: 2920: 2909: 2773: 2761:

in certain preparations, for instance those containing the progestogen

2730: 2726: 2684: 2635: 2370: 2188: 2057: 2022: 1987: 1969: 1940: 1906: 1262: 987: 929: 879: 686: 503: 323: 197: 17741: 17236: 14250:

Rich P (January 2008). "Hormonal contraceptives for acne management".

12775: 12700:"Collapse of a fish population after exposure to a synthetic estrogen" 12066: 12051: 11547:. Lippincott Williams & Wilkins. pp. 1024, 1027, 1035, 2153. 11518: 11501: 10361:"Drospirenone; EthinylEstradiol; Levomefolate - Drug Usage Statistics" 4934: 20225: 20215: 20210: 20200: 20185: 20170: 20115: 20070: 20040: 19902: 19882: 19807: 19747: 19742: 19611: 19541: 19531: 19476: 19235: 19215: 19155: 19135: 18977: 18814: 18689: 18684: 18669: 18654: 18614: 18496: 18464: 18422: 18370: 18366: 18362: 18352: 18332: 18316: 18265: 18241: 18237: 18225: 18217: 18213: 18173: 18161: 18145: 18131: 18121: 18117: 18073: 17933: 17907: 17895: 17870: 17860: 17845: 17825: 17776: 17676: 17671: 17646: 17636: 17601: 17461: 17436: 17398: 17356: 16837: 16820: 16796: 16737: 16712: 16646: 16601: 16408: 16396: 16386: 16302: 16292: 16115: 15794:

Concise Dictionary of Pharmacological Agents: Properties and Synonyms

13558:

Göretzlehner G, Lauritzen C, Römer T, Rossmanith W (1 January 2012).

11382:

Best Practice & Research. Clinical Endocrinology & Metabolism

10073:

Hormonal Regulation of the Menstrual Cycle: The Evolution of Concepts

9246:

EE has been marketed as a standalone oral drug under the brand names

9151:(all having the same pronunciation), and the latter was formerly its 9074: 8980: 8968: 8854: 8777: 8761: 8459: 8368: 8300: 8255: 8247: 8238:. Birth control pills that contain EE are useful in the treatment of 8227: 8035: 7860: 7472: 6858: 6802: 5584: 5359: 5184: 5109: 4584: 4509: 4359: 4284: 4259: 4061: 3218: 3189: 3185: 3153: 3096: 3080: 3068: 3044: 3024: 3012: 2917: 2890: 2886: 2825: 2805: 2789: 2706: 2703: 2627: 2618:

estradiol have not been found to increase the risk of cardiovascular

2534: 2121: 2113: 1452: 1282: 1085: 910: 809: 805: 438: 351: 146: 17181: 15698:

Beller FK, Knörr K, Lauritzen C, Wynn RM (1974). "Family Planning".

13557: 13096:"The G-protein-coupled estrogen receptor GPER in health and disease" 12003: 10934:"U.S. Selected Practice Recommendations for Contraceptive Use, 2016" 10913:"U.S. Selected Practice Recommendations for Contraceptive Use, 2016" 5034: 20130: 20110: 20080: 19952: 19912: 19762: 19752: 19626: 19106: 19096: 18799: 18659: 18579: 18574: 18507: 18324: 18261: 18257: 18221: 18209: 18181: 18177: 18165: 18157: 18087: 17875: 17865: 17711: 17696: 17681: 17616: 17611: 17456: 17366: 16919: 16854: 16755: 16586: 16131: 16084: 12495: 12307:

Diseases of the Gallbladder and Bile Ducts: Diagnosis and Treatment

10526:"The use of high-dose estrogens for the treatment of breast cancer" 9313: 8938: 6382: 6272: 5234: 4834: 3084: 3028: 3016: 2924: 2854: 2829: 2677: 2673: 2661: 2359: 1925: 1849: 1444: 1436: 851: 552: 483: 30: 16568: 14325: 12468:

Shreenath AP, Kahloon A (January 2022). "Hepatocellular Adenoma".

2145:

therapy has been found to increase SHBG levels by about 1.5-fold.

709: 20340: 20325: 20255: 19717: 19441: 19261: 19007: 18819: 18719: 18709: 18704: 18484: 18428: 18418: 18310: 18185: 17993: 17988: 17890: 17855: 17786: 17686: 17535: 17503: 17441: 16904: 16457: 15032:

Treatment of the Postmenopausal Woman: Basic and Clinical Aspects

14092: 11756: 11674:

Gallo MF, Nanda K, Grimes DA, Lopez LM, Schulz KF (August 2013).

11154:

Gallo MF, Nanda K, Grimes DA, Lopez LM, Schulz KF (August 2013).

8984: 8907: 8904: 8661: 6692: 5559: 5134: 5084: 4036: 3215: 3214:, due to the bypassing of first-pass metabolism. Relative to its 3133: 2996: 2961: 2832: 2801: 2695: 1720: 1653: 1630: 1607: 1540: 1525: 898: 812: 11502:"Use of Hormone Replacement in Females with Endocrine Disorders" 10786:

European Drug Index: European Drug Registrations, Fourth Edition

9077:, in 1964, and shortly thereafter superseded mestranol in COCs. 8303:

in women. A combination of 20 μg/day EE and 10 mg/day

2096:(SHBG) levels indicate hepatic estrogenic exposure and may be a 19180: 19175: 19032: 18296: 18284: 18099: 18068: 18063: 18058: 17791: 17446: 15596:

Djerassi C (January 2006). "Chemical birth of the pill. 1992".

14059:"Suppression of ovulation by trip-anisyl chloroethylene (TACE)" 13433: 13341:

The Handbook of Contraception: A Guide for Practical Management

10958:"U.S. Medical Eligibility Criteria for Contraceptive Use, 2016" 10281:"Ethinyl Estradiol ; Etonogestrel - Drug Usage Statistics" 9854:

Translational Toxicology: Defining a New Therapeutic Discipline

9327: 9299: 9048: 8868: 8817: 8451: 8443: 8176:

In divided doses, 3x/day; irregular and atypical proliferation.

5709: 3008: 3000: 2992: 2988: 2984: 2968: 2874: 2870: 2688: 2596: 1488: 1448: 941: 859: 583: 315: 18526: 16559: 15970: 15367: 14873: 14756: 14142:

International Journal of Endocrinology and Metabolic Disorders

12546: 10564: 8959:

List of estrogens § 17α-Substituted estradiol derivatives

8728:

of EE of 6.216 pg/mL/hour and 2.850 pg/mL/hour, and

8189: 6395: 6391: 3301: 3296: 3291: 3286: 2935:, which is a potent and highly selective inhibitor of CYP3A4. 1072:

in women, prevent osteoporosis in women, and has been used as

111: 19256: 19130: 19012: 18982: 18201: 18083: 17912: 14578:

Denis LJ, Griffiths K, Kaisary AV, Murphy GP (1 March 1999).

13824:"Hormonal Treatment of Transgender Women with Oral Estradiol" 11951: 11849:

Male Hypogonadism: Basic, Clinical and Therapeutic Principles

11011:. Elsevier. pp. 177, 219, 223, 224, 230, 232, 239, 242. 10807: 10306:"Ethinyl Estradiol ; Norgestrel - Drug Usage Statistics" 9537:

Facts and Comparisons (Firm), Ovid Technologies, Inc (2005).

8889: 8885: 8765: 8672:

containing a single oral dose of 20 μg EE and 2 mg

8604: 8482:

is oral, transdermal, or vaginal, indicating that the use of

8439: 8426:

SHBG levels in men with 1) intramuscular injection of 320 mg

8235: 8219: 5209: 2906: 2019: 937: 700: 563: 361: 356: 311: 15528:

Petrow V (December 1970). "The contraceptive progestagens".

608: 66: 19276: 19057: 18967: 18336: 18091: 14945: 14577: 13620:. Springer Science & Business Media. pp. 309–332. 13403:

Cancer Chemotherapy and Biotherapy: Principles and Practice

12907: 11104: 11034: 10256:"Ethinyl Estradiol; Levonorgestrel - Drug Usage Statistics" 9442: 8418:

are hepatic proteins and represent liver estrogenic effect.

8243: 7464:

Values are ratios, with estradiol as standard (i.e., 1.0).

5818: 3251:

Affinities of estrogen receptor ligands for the ERα and ERβ

3180:(FSH) via its antigonadotropic effects, thereby inhibiting 2821: 2785: 2699: 2642:

transdermal estradiol in the treatment of prostate cancer.

1991: 1027: 543: 105: 96: 84: 63: 19378: 13551: 12697: 10840:

Ethinyloestradiol (Lynoral, 0.05-mg, 0.1-mg, 1-mg tablets)

10206:"Ethinyl Estradiol; Norethindrone - Drug Usage Statistics" 10053:"Approval history: Estinyl (ethinyl estradiol) NDA 005292" 9567:

USP DI 2003: Drug Information for Healthcare Professionals

8748:

of EE is 97 to 98%, and it is bound almost exclusively to

2141:, especially when used parenterally. High-dose parenteral 19111: 15173: 15171: 14909: 14907: 14905: 14420: 13678:

Acta Obstetricia Et Gynecologica Scandinavica. Supplement

13618:

Ovarian Function and its Disorders: Diagnosis and Therapy

12147:

Phillips I, Shah SI, Duong T, Abel P, Langley RE (2014).

11729: 11333: 10665: 10663: 10661: 10607: 10231:"Ethinyl Estradiol; Norgestimate - Drug Usage Statistics" 9105: 8706: 8665: 3221:, EE is about 1.7 times as potent by weight orally. 3148:. In one study, EE was found to have 233% and 38% of the 75: 69: 19391: 15797:. Springer Science & Business Media. pp. 115–. 15697: 15262:. Springer Science & Business Media. pp. 395–. 13614:"Hormonal Treatment of Disorders of the Menstrual Cycle" 13375:. Springer Science & Business Media. pp. 177–. 12804: 12645:. Springer Science & Business Media. pp. 291–. 12390:

Endogenous Toxins: Diet, Genetics, Disease and Treatment

12280:. Springer Science & Business Media. pp. 260–. 11841: 11839: 11837: 11415:

Keenan L, Kerr T, Duane M, Van Gundy K (November 2018).

11414: 10728: 10141:. Springer Science & Business Media. pp. 112–. 10076:. Springer Science & Business Media. pp. 185–. 9811: 9809: 9807: 9805: 9803: 9801: 9799: 9797: 9795: 9793: 9791: 9789: 9787: 9785: 9783: 9781: 9779: 9777: 9775: 9773: 9771: 9769: 9767: 9765: 9763: 9761: 9759: 9757: 9755: 9753: 9751: 9749: 9747: 9745: 9743: 9741: 9739: 8559: 3063:, a substrate of CYP2B6 and CYP2C19. EE may also induce 1014:

There are many uses for EE. It is most commonly used as

14920:. Springer Science & Business Media. pp. 84–. 14501: 14208: 14181: 13344:. Springer Science & Business Media. pp. 23–. 13198: 12672:. Springer Science & Business Media. pp. 11–. 11544:

Principles and Practice of Endocrinology and Metabolism

10880: 10878: 10820:. Springer Science & Business Media. pp. 78–. 10705:

Principles and Practice of Endocrinology and Metabolism

10387: 10331:"Ethinyl Estradiol; Ethynodiol - Drug Usage Statistics" 9737: 9735: 9733: 9731: 9729: 9727: 9725: 9723: 9721: 9719: 8136:

Dosages are given in milligrams unless otherwise noted.

7539: 7136: 7005: 6513: 2949:

levels of EE (by 22%) and decreasing the AUC levels of

405:)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6 17427:

Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)

16844: 16827: 16493: 16486: 15941: 15251: 15249: 15168: 14902: 14829:

Chemical and Biological Aspects of Steroid Conjugation

14826: 14799: 14750: 14177: 14175: 14173: 14026:

Chemical and Biological Aspects of Steroid Conjugation

14023: 14006: 12232: 12090: 11236:. Springer Science & Business Media. p. 390. 11223: 11008:

Meyler's Side Effects of Endocrine and Metabolic Drugs

10885:

Alldredge BK, Corelli RL, Ernst ME (1 February 2012).

10658: 9947:

Shellenberger TE (1986). "Pharmacology of estrogens".

9904: 9179: 7610: 2713:, are also implicated in cholestasis, for instance in 1467:. In males, EE has additional side effects, including 1240:

with positive (or unknown) antiphospholipid antibodies

20369: 15663:

Cantor EB (September 1956). "A survey of estrogens".

15428: 13268: 13042: 12299: 12297: 12146: 11834: 11673: 11153: 10891:. Lippincott Williams & Wilkins. pp. 1072–. 10884: 10424:

Hamoda H, Panay N, Arya R, Savvas M (December 2016).

10423: 10100:

Evans G, Sutton EL (May 2015). "Oral contraception".

9204: 8325: 7630: 87: 81: 72: 60: 16510: 16431:

Methestrol dipropionate (promethestrol dipropionate)

15842: 15731:

Haller J (1968). "Die antikonzeptionelle Therapie".

15426: 15424: 15422: 15420: 15418: 15416: 15414: 15412: 15410: 15408: 15285:

The Journal of Clinical Endocrinology and Metabolism

15209: 14682: 14546: 14544: 14542: 14056: 13821: 13584: 13254:. Lippincott Williams & Wilkins. pp. 708–. 13192: 13043:

Yates MA, Li Y, Chlebeck PJ, Offner H (April 2010).

12380: 11068: 11066: 10875: 9942: 9940: 9938: 9936: 9716: 8582: 8234:, which decreases production of testosterone by the 7620: 7615: 7535: 7506: 7501: 7126: 7087: 6992: 6503: 294: 102: 93: 90: 78: 15438:. Taylor & Francis. January 2000. p. 412. 15246: 14571: 14182:Nieschlag E, Behre HM, Nieschlag S (26 July 2012). 14170: 13973: 10732:

Approved Drug Products with Therapeutic Evaluations

10708:. Lippincott Williams & Wilkins. p. 1027. 10128: 2953:(EE sulfate) in women. The same has been found for 471: 99: 16573:Tooltip selective estrogen receptor downregulators 15255: 14803:Ovulation: Stimulation, Suppression, and Detection 14688: 14010:Ovulation: Stimulation, Suppression, and Detection 13979: 13524: 13300: 13298: 12993: 12294: 12196: 12194: 12192: 11468: 11466: 11464: 11462: 11460: 10170: 10168: 10166: 10164: 10162: 10160: 10158: 9846: 9844: 9842: 9443:Fruzzetti F, Trémollieres F, Bitzer J (May 2012). 9166: 9114: 7605: 6979: 6493: 3124:similarly to natural estrogens like estradiol and 15883: 15405: 15177: 14913: 14539: 14057:Duncan CJ, Kistner RW, Mansell H (October 1956). 13652:Praktische Gynäkologie: für Studierende und Ärzte 13585:Knörr K, Beller FK, Lauritzen C (17 April 2013). 13393: 13274: 12659: 12267: 11845: 11229: 11063: 10676:. World Health Organization. pp. 157, 433–. 10065: 10063: 9933: 9815: 9570:. Thomson Micromedex. pp. 1253, 1258, 1266. 9164:(as well as variations thereof), and this is its 7625: 20393: 17031: 15691: 15435:Index Nominum 2000: International Drug Directory 15363: 15361: 15359: 15357: 15282: 15130: 15126: 15124: 15122: 14820: 14793: 14458: 13642: 13605: 13578: 13241: 12634: 12632: 12630: 12467: 12386: 12233:Russell N, Cheung A, Grossmann M (August 2017). 11565: 10519: 10517: 9900: 9898: 9896: 9894: 9073:EE was first used in COCs, as an alternative to 8832:. A review found that the range of the reported 8716:There may be gender-specific differences in the 8434:EE shows strong and disproportionate effects on 7527: 7107: 2587:are associated with fairly high rates of severe 2326:Conjugated estrogens/medroxyprogesterone acetate 862:among others. In men, EE can additionally cause 451: 16397:Mestilbol (diethylstilbestrol monomethyl ether) 16039: 15825:. Publishing Sciences Group. pp. 540–572. 15784: 15571:. Hoboken, NJ: John Wiley & Sons. pp. 15458: 15317: 15205: 15203: 15201: 15082: 14941: 14939: 14937: 14689:Rietbrock N, Staib AH, Loew D (11 March 2013). 14604: 14550: 14454: 14452: 14416: 14414: 14088: 14086: 14084: 14017: 14000: 13980:Rietbrock N, Staib AH, Loew D (11 March 2013). 13786: 13429: 13427: 13295: 13145: 13093: 12864: 12860: 12858: 12856: 12854: 12852: 12850: 12848: 12846: 12844: 12491: 12489: 12228: 12226: 12224: 12189: 12142: 12140: 12138: 12136: 12134: 12132: 12130: 12086: 12084: 11725: 11723: 11721: 11719: 11499: 11457: 11375: 11373: 11371: 11329: 11327: 11325: 11323: 11321: 11319: 11317: 11315: 11313: 11000: 10998: 10996: 10994: 10817:Manual of Adult and Paediatric Medical Oncology 10465: 10463: 10383: 10381: 10155: 10134: 10042: 10040: 10016: 9892: 9890: 9888: 9886: 9884: 9882: 9880: 9878: 9876: 9874: 9839: 9675: 9673: 9671: 9669: 9667: 9665: 9663: 9661: 9659: 9657: 9655: 9653: 9651: 9649: 9647: 9645: 9643: 9641: 9639: 9637: 9635: 9633: 9631: 9629: 9627: 9625: 9623: 9621: 9619: 9617: 9615: 9613: 9611: 9609: 9607: 9540:Drug Facts and Comparisons 2005: Pocket Version 9532: 9530: 9404: 6966: 6483: 2853:Estrogens like EE are relatively safe in acute 426: 18531:Tooltip Selective estrogen receptor modulators 17886:Furostilbestrol (diethylstilbestrol difuroate) 17247:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 16564:Tooltip selective estrogen receptor modulators 15589: 15452: 15085:Reviews in Endocrine & Metabolic Disorders 14598: 14185:Testosterone: Action, Deficiency, Substitution 14128: 14126: 14124: 13934: 13704: 13362: 13333: 13331: 13304: 13251:Modern Pharmacology with Clinical Applications 12420: 12418: 12416: 12414: 12412: 12410: 12303: 12047: 12045: 12043: 11999: 11997: 11995: 11993: 11991: 11947: 11945: 11805: 11408: 11100: 11098: 11030: 11028: 10992: 10990: 10988: 10986: 10984: 10982: 10980: 10978: 10976: 10974: 10850: 10848: 10060: 9605: 9603: 9601: 9599: 9597: 9595: 9593: 9591: 9589: 9587: 9438: 9436: 9132: 8411: 2344: >0.625 mg/day 19364: 17077:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 17017: 16387:Dimestrol (diethylstilbestrol dimethyl ether) 16025: 15772: 15770: 15768: 15766: 15764: 15762: 15760: 15656: 15624: 15598:American Journal of Obstetrics and Gynecology 15556: 15354: 15311: 15256:Notelovitz M, van Keep PA (6 December 2012). 15119: 15076: 14982: 14876:American Journal of Obstetrics and Gynecology 14368: 14319: 14270: 14243: 14202: 14050: 13943:Acta Obstetricia et Gynecologica Scandinavica 13899: 13815: 13780: 13713:Acta Obstetricia et Gynecologica Scandinavica 13530: 13436:American Journal of Obstetrics and Gynecology 12665: 12627: 12273: 11732:Acta Obstetricia et Gynecologica Scandinavica 11255: 11253: 11072: 10697: 10695: 10693: 10514: 9946: 9557: 9494: 9492: 9490: 9488: 9407:American Journal of Obstetrics and Gynecology 9400: 9398: 9396: 9394: 9226:The name of the drug is often abbreviated as 9153: 9123: 8804:Aside from sulfate conjugation, EE is mainly 8491:Comparison of estradiol and ethinylestradiol 8399: 8350:levels at a dose as low as 1 μg/day and 7578: 7034: 6927: 6473: 6420: 3236: 2839:showed much lower rates of hatching success. 2241: >0.625 mg/day 2160: 1285:, and familial defects in biliary excretion. 1188:Prolonged immobilization due to major surgery 17187:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 15855:. American Society of Hospital Pharmacists. 15521: 15498: 15276: 15198: 15024: 15022: 15020: 14988: 14934: 14867: 14859:: CS1 maint: DOI inactive as of July 2024 ( 14653: 14647: 14557:. Elsevier Health Sciences. pp. 2282–. 14495: 14449: 14411: 14188:. Cambridge University Press. pp. 62–. 14081: 13561:Praktische Hormontherapie in der Gynäkologie 13462: 13424: 13406:. Lippincott-Raven Publishers. p. 186. 13399: 13247: 13139: 13087: 13036: 12987: 12936: 12901: 12841: 12590: 12584: 12540: 12486: 12461: 12221: 12127: 12081: 11907: 11866: 11799: 11750: 11716: 11667: 11626: 11493: 11368: 11310: 11285: 11283: 10654:. American Cancer Society. 13 February 2015. 10652:"Menopausal Hormone Therapy and Cancer Risk" 10558: 10460: 10378: 10093: 10037: 9986: 9984: 9982: 9980: 9871: 9850: 9527: 8934:(17α-ethynyl-19-nortestosterone) as well as 2345: 2340: 994:million prescriptions; the combination with 986:million prescriptions; the combination with 978:million prescriptions; the combination with 970:million prescriptions; the combination with 19647: 19062:Tooltip G protein-coupled estrogen receptor 17881:Fosfestrol (diethylstilbestrol diphosphate) 16519: 16392:Fosfestrol (diethylstilbestrol diphosphate) 15884:Oettel M, Schillinger E (6 December 2012). 15724: 15049: 14914:Margioris AN, Chrousos GP (20 April 2001). 14554:Endocrinology - E-Book: Adult and Pediatric 14374: 14121: 13739: 13669: 13648: 13611: 13497: 13328: 13311:. Williams & Wilkins. p. 132,134. 12407: 12333: 12331: 12329: 12327: 12200: 12040: 11988: 11942: 11846:Winters SJ, Huhtaniemi IT (25 April 2017). 11680:The Cochrane Database of Systematic Reviews 11632: 11534: 11479:. Elsevier Health Sciences. pp. 388–. 11472: 11230:Oettel M, Schillinger E (6 December 2012). 11160:The Cochrane Database of Systematic Reviews 11095: 11073:Runnebaum B, Rabe T, eds. (17 April 2013). 11025: 10971: 10861:. Elsevier Health Sciences. pp. 865–. 10845: 10601: 10099: 9816:Oettel M, Schillinger E (6 December 2012). 9584: 9433: 8780:into the hormonally inert ethinylestradiol 8250:by virtue of their antiandrogenic effects. 8190:Antiandrogenic and antigonadotropic effects 7519: 7514: 7097: 2745:and a 3- to 6-fold increase in the risk of 2339: ≤0.625 mg/day 2193: 257:In general: ℞ (Prescription only) 108: 19698:Allopregnanedione (5α-dihydroprogesterone) 19371: 19357: 18024:Triphenylmethylethylene (triphenylpropene) 17348:, many others; via estrogenic metabolites) 17272:17α-Epiestriol (16α-hydroxy-17α-estradiol) 17024: 17010: 16032: 16018: 15790: 15757: 15184:. Oxford University Press. pp. 272–. 14709: 14605:Scott WW, Menon M, Walsh PC (April 1980). 13864: 12498:Annals of the New York Academy of Sciences 11872: 11476:Clinical Reproductive Medicine and Surgery 11250: 11196: 10952: 10950: 10776: 10690: 10567:The World Journal of Biological Psychiatry 10472:"Hormone therapy for transgender patients" 10135:Shoupe D, Haseltine FP (6 December 2012). 10069: 9563: 9485: 9391: 9366: 9364: 9362: 9360: 9358: 9356: 9354: 9352: 9015:(17α-ethynylestriol 3-cyclopentyl ether). 8987:of EE, while the latter one is not. A few 7585: 7571: 7476: 7067: 7041: 7027: 6427: 6413: 3243: 3229: 2296: >1 mg/day 2272: >1 mg/day 2239: ≤0.625 mg/day 2167: 2153: 1254:due to a possible worsening of prognosis. 1084:in women. It has also been used to reduce 645: 622: 511: 17044: 16548: 16313:Prasterone (dehydroepiandrosterone; DHEA) 16062: 15035:. Academic Press. pp. 177, 770–771. 15017: 14622: 14343: 14302: 14226: 14153: 13940: 13847: 13822:Leinung MC, Feustel PJ, Joseph J (2018). 13710: 13675: 13503: 13468: 13368: 13224: 13171: 13119: 13070: 13060: 13019: 12970: 12960: 12733: 12723: 12638: 12338:Kuhl H (1999). "Hormonal Contraception". 12250: 12172: 11890: 11774: 11699: 11650: 11517: 11440: 11351: 11280: 11179: 11130: 10722: 10541: 10497: 10487: 10453:1983/d96e4479-2ccc-44c3-963c-d3918b1e325b 10451: 10441: 9977: 9468: 9110:Tooltip International Nonproprietary Name 8760:Due to high first-pass metabolism in the 8510: 8160: 8158: 8156: 6953: 6940: 6463: 6453: 3168:, similarly to estradiol. Estrogens have 2780:. The input of artificial estrogens into 2222: >1 mg/day 1398:= Relative to low-dose (not to non-use). 531: 19396:Tooltip Constitutive androstane receptor 16269:Estropipate (piperazine estrone sulfate) 15811: 15595: 14991:Gynécologie, Obstétrique & Fertilité 13750:. Kliniktaschenbücher. pp. 59–124. 13746:Kopera H (1991). "Hormone der Gonaden". 13372:Sexual Behavior: Problems and Management 12994:Prossnitz ER, Arterburn JB (July 2015). 12761: 12666:Surwit EA, Alberts D (6 December 2012). 12393:. John Wiley & Sons. pp. 302–. 12324: 12310:. John Wiley & Sons. pp. 363–. 10789:(4 ed.). CRC Press. pp. 457–. 9498: 8655: 8564:Tooltip 17β-hydroxysteroid dehydrogenase 8421: 8403: 8334:, even at low dosages and regardless of 8202:(RIA). Source was Shearer et al. (1973). 8193: 7546:= Increase in the serum levels of these 3128:(Premarin) and synthetic estrogens like 2672:progestins. Cholestasis can manifest as 2570: 962:million prescriptions; the version with 878:. Rare but serious side effects include 15563:Sneader W (2005). "Hormone analogues". 15562: 15062:. John Wiley & Sons. pp. 79–. 14692:Klinische Pharmakologie: Arzneitherapie 14551:Jameson JL, De Groot LJ (18 May 2010). 14505:Experimental and Clinical Endocrinology 13983:Klinische Pharmakologie: Arzneitherapie 13655:. Walter de Gruyter. pp. 598–599. 13531:Wolf AS, Schneider HP (12 March 2013). 12304:Clavien PA, Baillie J (15 April 2008). 12055:Gynecologic and Obstetric Investigation 11913: 11635:"Hormonal contraception and thrombosis" 11004: 10947: 10926: 10854: 10644: 10070:Gruhn JG, Kazer RR (11 November 2013). 10010: 9992:"Drugs@FDA: FDA Approved Drug Products" 9349: 9063:, which had discontinued marketing it. 8983:(11β-methoxy-EE). The former three are 8172: 8170: 8146: 8144: 8142: 7543: 7493: 7488: 7146: 7141:Tooltip Corticosteroid-binding globulin 7077: 7010:Tooltip Corticosteroid-binding globulin 6518:Tooltip Corticosteroid binding globulin 2291: ≤1 mg/day 2267: ≤1 mg/day 726:182 to 184 °C (360 to 363 °F) 618: 491: 165: 20394: 20151:Pregnanedione (5β-dihydroprogesterone) 19537:Pregnanedione (5β-dihydroprogesterone) 15791:Morton IK, Hall JM (6 December 2012). 15730: 15662: 15527: 15504: 15055: 14759:Expert Review of Clinical Pharmacology 14607:"Hormonal Therapy of Prostatic Cancer" 14132: 13745: 13337: 13094:Prossnitz ER, Barton M (August 2011). 12764:Environmental Toxicology and Chemistry 11540: 11263:Principles of Gender-Specific Medicine 11259: 11202: 10782: 10701: 10023:. John Wiley & Sons. p. 482. 9851:Hughes CL, Waters MD (23 March 2016). 9543:. Facts and Comparisons. p. 121. 9184:Tooltip Dénomination Commune Française 9083: 8153: 7600:Dosage for specific uses (mg usually) 2220: ≤1 mg/day 1227:Age ≥35 and smoking ≥15 cigarettes/day 1222:atherosclerotic cardiovascular disease 636: 19352: 17005: 16013: 14715: 13905: 13870: 13591:. Springer-Verlag. pp. 212–213. 12757: 12755: 12753: 12693: 12691: 12689: 12642:Pathology of the Female Genital Tract 12277:Molecular Pathogenesis of Cholestasis 11954:American Journal of Clinical Oncology 11763:Journal of Thrombosis and Haemostasis 11596: 11578:. National Academies. pp. 143–. 11575:Oral Contraceptives and Breast Cancer 11289: 11081:. Springer-Verlag. pp. 411–512. 10469: 9284: 9209:Tooltip Denominazione Comune Italiana 7599: 7596: 7154: 7144: 7134: 7124: 7105: 7095: 7085: 7075: 7065: 7055: 7048:Relative oral potencies of estrogens 2849:Estrogen (medication) § Overdose 2768: 2254:Estradiol/medroxyprogesterone acetate 1546: 1531: 1320: 1103:with an estrogen mitigates the risk. 591: 571: 151: 16515:Tooltip follicle-stimulating hormone 15904: 15028: 14249: 13534:Östrogene in Diagnostik und Therapie 13152:Molecular and Cellular Endocrinology 12424: 12337: 11266:. Academic Press. pp. 225–234. 10341:from the original on 18 January 2024 10186:from the original on 15 January 2024 10102:The Medical Clinics of North America 9679: 9370: 9055:(FDA) in June 1943, and marketed by 8587:Tooltip Sex hormone-binding globulin 8167: 8139: 7511:Tooltip follicle-stimulating hormone 7131:Tooltip Sex hormone-binding globulin 7092:Tooltip Follicle-stimulating hormone 6997:Tooltip sex hormone-binding globulin 6508:Tooltip Sex hormone-binding globulin 2533:(2015, 2019) based on data from the 2517:Ethinylestradiol/cyproterone acetate 2393: >50 μg/day 1502: 1402:In birth control pills containing a 1134: 299:Tooltip sex hormone-binding globulin 231: 221: 15956:10.1016/j.contraception.2012.12.011 13564:. Walter de Gruyter. pp. 44–. 13305:Gomel V, Munro MG, Rowe TC (1990). 13205:The New England Journal of Medicine 13146:Prossnitz ER, Barton M (May 2014). 12949:The Journal of Biological Chemistry 11820:10.1016/j.contraception.2008.04.004 11209:. Elsevier Science. pp. 411–. 10735:. DIANE Publishing. p. 3-122. 10476:Translational Andrology and Urology 9919:10.1016/j.contraception.2012.12.011 9066:EE was never introduced for use by 8646: 8264:hypothalamic–pituitary–gonadal axis 7531: 7468: 7116: 7057: 3162:G protein-coupled estrogen receptor 3115: 2539:Clinical Practice Research Datalink 800:medication which is used widely in 551: 442: 13: 16920:Androvax (androstenedione albumin) 15876: 14960:10.1111/j.1365-2265.1995.tb02611.x 14695:. Springer-Verlag. pp. 426–. 14656:Journal of Pharmaceutical Sciences 14435:10.1111/j.1464-410x.1980.tb02961.x 14107:10.1111/j.1464-410x.1973.tb12238.x 13986:. Springer-Verlag. pp. 426–. 12750: 12686: 11608:. DIANE Publishing. pp. 27–. 11049:10.1093/oxfordjournals.aje.a115799 9171:Tooltip United States Pharmacopeia 9119:Tooltip United States Adopted Name 8326:Effects on liver protein synthesis 6984:Tooltip mineralocorticoid receptor 6498:Tooltip Mineralocorticoid receptor 2941:(acetaminophen) has been found to 1106: 742:Oc1cc4c(cc1)3CC2((CC2(C#C)O)3CC4)C 14: 20468: 18423:taleranol (teranol, β-zearalanol) 17338:metandienone (methandrostenolone) 16986:Progestogens and antiprogestogens 15178:Dodick D, Silberstein SD (2016). 13537:. Springer-Verlag. pp. 78–. 11111:American Journal of Public Health 10858:Comprehensive Hypertension E-Book 10729:DIANE Publishing Company (1995). 10610:The British Journal of Psychiatry 3132:. It binds to and activates both 2752: 2391: ≤50 μg/day 2297: 2292: 2273: 2268: 409:-cyclopentaphenanthrene-4,17-diol 20379: 19333:Progesterone receptor modulators 19087:Afimoxifene (4-hydroxytamoxifen) 17969:Prinaberel (ERB-041, WAY-202041) 16382:Diethylstilbestrol esters/ethers 16377:Diethylstilbestrol (stilbestrol) 15224:10.2165/00003088-198308020-00001 15134:Journal of Clinical Pharmacology 14806:. Lippincott. pp. 243–253. 14389:10.2165/11208180-000000000-00000 13748:Hormonelle Therapie für die Frau 13369:McConaghy N (21 November 2013). 13308:Gynecology: a practical approach 13275:Allahbadia G, Agrawal R (2007). 12879:10.2165/00003088-200746020-00003 12639:Blaustein A (11 November 2013). 12427:Geburtshilfe und Frauenheilkunde 12153:Oncology & Hematology Review 11966:10.1097/00000421-198801102-00024 11776:10.1111/j.1538-7836.2012.04720.x 11652:10.1016/j.fertnstert.2016.08.039 11353:10.1016/j.fertnstert.2016.09.027 11037:American Journal of Epidemiology 10855:Lip GY, Hall JE (28 June 2007). 9173:name. The generic name of EE in 9088: 9023:(17α-ethynyl-5-androstenediol), 8448:17β-hydroxysteroid dehydrogenase 8130: 8118: 7112:Tooltip High-density lipoprotein 2964:(which potently induces certain 2137:SHBG levels are much lower with 2014:, which is thought to be due to 1261:women who are less than 21 days 670: 56: 38: 29: 19030:Coregulator-binding modulators: 17297:17β-Methyl-17α-dihydroequilenin 14013:. Lippincott. pp. 243–253. 13616:. In Horsky J, Presl J (eds.). 12807:Drug Metabolism and Disposition 12798: 12093:Scandinavian Journal of Urology 11852:. Humana Press. pp. 307–. 11633:Sitruk-Ware R (November 2016). 11506:Hormone Research in Paediatrics 11147: 11005:Aronson JK (21 February 2009). 10905: 10543:10.1016/j.maturitas.2016.10.010 10417: 10403:10.1016/j.clinthera.2006.06.013 10353: 10323: 10298: 10273: 10248: 10223: 10198: 10017:Fischer J, Ganellin CR (2006). 9334: 9035:(17α-methyl-5-androstenediol). 8979:(EE 3-isopropylsulfonate), and 8739: 8340:corticosteroid-binding globulin 6971:Tooltip glucocorticoid receptor 6488:Tooltip Glucocorticoid receptor 3110: 2860: 2778:wastewater treatment procedures 2645: 2467:Ethinylestradiol/levonorgestrel 2457:Ethinylestradiol/norethisterone 2336:Conjugated estrogens/norgestrel 1288: 1151:), due to an increased risk of 1009: 767:Key:BFPYWIDHMRZLRN-SLHNCBLASA-N 19703:Allopregnanolone (brexanolone) 17861:Erteberel (SERBA-1, LY-500307) 16925:Ovandrotone albumin (Fecundin) 16111:) (via estrogenic metabolites) 15974:Critical Reviews in Toxicology 15778:"Ethinylestradiol - Drugs.com" 15677:10.1080/00325481.1956.11691266 15371:Critical Reviews in Toxicology 12340:Estrogens and Antiestrogens II 12204:Holland-Frei Cancer Medicine 8 11692:10.1002/14651858.CD003989.pub5 11172:10.1002/14651858.CD003989.pub5 9949:The Climacteric in Perspective 9857:. Humana Press. pp. 73–. 9241: 9139:. It has also been spelled as 9137:Tooltip Japanese Accepted Name 9003:(17α-ethylestradiol), and the 8930:(17α-ethynyltestosterone) and 8875: 8416:Tooltip pregnancy zone protein 2725:(ALT) levels increase by 50%, 1981: 1831:Erythema nodosum et multiforme 1065:having largely superseded it. 954:In 2021, the combination with 676: 664: 1: 20432:Hormonal antineoplastic drugs 20358:Receptor/signaling modulators 20316:Tropanyl 3,5-dimethulbenzoate 20166:Pregnenolone 16α-carbonitrile 19318:Receptor/signaling modulators 17282:17α-Ethynyl-3β-androstanediol 17277:17α-Ethynyl-3α-androstanediol 15056:Shoupe D (10 February 2011). 14771:10.1080/17512433.2018.1536544 13248:Craig CR, Stitzel RE (2004). 13100:Nature Reviews. Endocrinology 12387:O'Brien PJ, Bruce WR (2010). 12274:Trauner M, Jansen PJ (2004). 11260:Legato MJ (29 October 2009). 10020:Analogue-based Drug Discovery 9564:Micromedex (1 January 2003). 9342: 9158:Tooltip British Approved Name 9128:Tooltip British Approved Name 9029:17α-ethynyl-3α-androstanediol 9025:17α-ethynyl-3β-androstanediol 8857:formation of a very reactive 8755: 8651: 8472:vaginal bleeding and spotting 8240:androgen-dependent conditions 6932:Tooltip progesterone receptor 6478:Tooltip Progesterone receptor 3884:Estradiol 3-gluc. 17β-sulfate 3188:and hence the possibility of 3164:(GPER) (affinity unknown), a 2865:EE is metabolized by certain 2507:Ethinylestradiol/drospirenone 2477:Ethinylestradiol/norgestimate 1257:EE should also be avoided in 1068:EE can also be used to treat 19328:Androgen receptor modulators 17632:Lynestrenol phenylpropionate 16976:Estrogen receptor modulators 16877:hydroxyprogesterone caproate 15986:10.3109/10408444.2014.930813 15708:10.1007/978-1-4615-7128-5_17 15633:Food and Drug Administration 15383:10.3109/10408444.2014.930813 15003:10.1016/j.gyobfe.2011.10.009 14888:10.1016/0002-9378(75)90061-7 14624:10.1002/cncr.1980.45.s7.1929 14584:. CRC Press. pp. 297–. 13801:10.1002/cncr.1980.45.s7.1929 13626:10.1007/978-94-009-8195-9_11 13483:10.1016/0378-5122(90)90004-P 13448:10.1016/0002-9378(82)90218-6 13400:Chabner B, Longo DL (1996). 13338:Shoupe D (7 November 2007). 12348:10.1007/978-3-642-60107-1_18 12201:Hong WK, Holland JK (2010). 12105:10.3109/21681805.2013.861508 11203:Pincus G (22 October 2013). 10049:Food and Drug Administration 9996:Food and Drug Administration 9957:10.1007/978-94-009-4145-8_36 9513:10.1016/0010-7824(96)00136-9 9461:10.3109/09513590.2012.662547 9419:10.1016/0002-9378(90)90550-Q 9053:Food and Drug Administration 9051:. It was approved by the US 8952: 8895: 8822:catechol O-methyltransferase 8668:meal following ingestion of 8216:sex hormone-binding globulin 7592:Potencies of oral estrogens 3178:follicle-stimulating hormone 2487:Ethinylestradiol/desogestrel 2094:Sex hormone-binding globulin 1294:Dose of ethinylestradiol in 1167:. This includes women with: 1020:combined oral contraceptives 7: 19893:Dodecylbenzenesulfonic acid 19652:Tooltip Pregnane X receptor 19380:Xenobiotic-sensing receptor 19323:Estrogens and antiestrogens 18973:Oxabicycloheptene sulfonate 18660:Etacstil (GW-5638, DPC-974) 17836:Doisynoestrol (fenocycline) 17580:Ethinylestradiol 3-benzoate 17092:3β,5α-Dihydrolevonorgestrel 17087:3α,5α-Dihydrolevonorgestrel 16981:Androgens and antiandrogens 16917:Androstenedione immunogens: 16881:medroxyprogesterone acetate 16524:Tooltip luteinizing hormone 16404:Doisynoestrol (fenocycline) 15741:10.1007/978-3-642-99941-3_8 14837:10.1007/978-3-642-49793-3_8 14034:10.1007/978-3-642-49793-3_8 13756:10.1007/978-3-642-95670-6_6 12207:. PMPH-USA. pp. 753–. 11873:Notelovitz M (March 2006). 11473:Falcone T, Hurd WW (2007). 10965:Recommendations and Reports 10941:Recommendations and Reports 10920:Recommendations and Reports 9449:Gynecological Endocrinology 9377:. Springer. pp. 522–. 9371:Elks J (14 November 2014). 8967:of EE exist. These include 8843:enterohepatic recirculation 8726:area-under-the-curve levels 8698:steady-state concentrations 8689:interindividual variability 8438:relative to estradiol. The 7524:Tooltip luteinizing hormone 7102:Tooltip Luteinizing hormone 6445:Relative binding affinities 4166:6,8-Didehydro-17α-estradiol 4141:6,8-Didehydro-17β-estradiol 3272:Absolute binding affinities 3266:Relative binding affinities 2842: 2591:complications such as VTE, 2531:Nested case–control studies 2198:Tooltip confidence interval 2130:Contraceptive vaginal rings 2066:contraceptive vaginal rings 2046:fourth-generation progestin 1768:Benign breast fibroadenomas 1685:Pelvic inflammatory disease 1665:Pelvic inflammatory disease 10: 20473: 19040:Noncompetitive inhibitors: 18665:Ethamoxytriphetol (MER-25) 17826:Dimestrol (dianisylhexene) 17585:Ethinylestradiol sulfonate 16902:Mixed mechanism of action: 16674:Noncompetitive inhibitors: 16426:Methestrol (promethestrol) 16281:Ethinylestradiol sulfonate 15610:10.1016/j.ajog.2005.06.010 15509:. New York: Random House. 14423:British Journal of Urology 14095:British Journal of Urology 13612:Horský J, Presl J (1981). 12550:Magnetic Resonance Imaging 11500:Christin-Maitre S (2017). 11394:10.1016/j.beem.2012.11.002 10470:Unger CA (December 2016). 10114:10.1016/j.mcna.2015.01.004 9321:, and in combination with 9319:contraceptive vaginal ring 9038: 8999:(17α-methylestradiol) and 8977:ethinylestradiol sulfonate 8975:(EE 3-cyclopentyl ether), 8956: 8949:(17α-methyltestosterone). 8400:Differences from estradiol 8379:, a progestin with potent 8344:thyroxine-binding globulin 8206:EE is a potent functional 7638:Estradiol (non-micronized) 7455: 7072:Tooltip Vaginal epithelium 3166:membrane estrogen receptor 2846: 2698:and consequent changes in 2687:of EE, via effects on the 2632:ethinylestradiol sulfonate 2497:Ethinylestradiol/gestodene 2209: 2206:Menopausal hormone therapy 2204: 1750:Fibrocystic breast disease 1404:first-generation progestin 1370:10.0 in 10,000 woman-years 1271:cholestatic hepatotoxicity 1220:Multiple risk factors for 1120:contraceptive vaginal ring 1055:feminizing hormone therapy 1035:menopausal hormone therapy 654:Chemical and physical data 20349: 19645: 19389: 19310: 19285: 19249: 19082:7β-Hydroxyepiandrosterone 19069: 19055: 18868: 18640:Desmethylchlorotrianisene 18521: 17819:Diethylstilbestrol esters 17772:Bisdehydrodoisynolic acid 17192:11β-Chloromethylestradiol 17167:7β-Hydroxyepiandrosterone 17056: 17049:Tooltip Estrogen receptor 17042: 16937: 16894: 16746: 16685: 16659:Exclusively antagonistic: 16553:Tooltip Estrogen receptor 16546: 16537: 16466: 16067:Tooltip Estrogen receptor 16060: 16051: 15919:10.1080/13697130500148875 15567:Drug discovery: a history 15212:Clinical Pharmacokinetics 15097:10.1007/s11154-011-9182-4 14063:Obstetrics and Gynecology 13955:10.3109/00016344709154486 13725:10.3109/00016347509156433 13690:10.3109/00016347509156433 13281:. Anshan. pp. 257–. 13278:Polycystic Ovary Syndrome 13164:10.1016/j.mce.2014.02.002 12922:10.1016/j.bcp.2006.02.002 12867:Clinical Pharmacokinetics 12593:Seminars in Liver Disease 12562:10.1016/j.mri.2019.04.010 12165:10.17925/ohr.2014.10.1.42 11916:Journal of Women's Health 11290:Stein PD (5 April 2016). 10579:10.3109/15622971003671628 9694:10.1080/13697130500148875 9011:(17α-ethynylestriol) and 8637: 8515:Tooltip Estrogen receptor 8330:EE has marked effects on 8109: 8084: 8059: 8034: 8009: 7984: 7959: 7934: 7909: 7884: 7859: 7836: 7811: 7786: 7761: 7736: 7711: 7686: 7661: 7636: 7629: 7624: 7619: 7614: 7609: 7604: 6958:Tooltip estrogen receptor 6945:Tooltip androgen receptor 6913: 6468:Tooltip Androgen receptor 6458:Tooltip Estrogen receptor 6443: 6438: 6371: 6173:Ethinyl-3β-androstanediol 6148:Ethinyl-3α-androstanediol 5902:19-Nortestosterone; 19-NT 4939:16α-Lactone-17β-estradiol 4539:4-Hydroxytamoxifen; 4-OHT 4364:Dihydrodiethylstilbestrol 4191:8,9-Dehydro-17β-estradiol 3859:Estradiol 17β-glucuronide 3813:Estradiol 3,17β-disulfate 3713:16α-OH-E1; 17-Ketoestriol 3488:16β-Hydroxy-17α-estradiol 3463:16α-Hydroxy-17α-estradiol 3438:16β-Hydroxy-17β-estradiol 3280: 3270: 3264: 3261: 3256: 2735:gamma-glutamyltransferase 2554:Statistically significant 2525: 2450: 2445: 2418: 2380: 1964: 1517: 1512: 1394: 1387:5.8 in 10,000 woman-years 1353:7.0 in 10,000 woman-years 1344:Intermediate (50 μg) 1336:4.2 in 10,000 woman-years 821:hormone-sensitive cancers 775: 750: 730: 720: 698: 685: 658: 653: 634: 602: 582: 562: 542: 522: 502: 482: 462: 437: 417: 373: 368: 350: 337: 322: 305: 282: 272: 264: 248: 243: 208: 196: 173: 159: 141: 133: 123: 51: 46: 37: 28: 20276:Testosterone isocaproate 20191:Reverse triiodothyronine 19146:Fulvestrant (ICI-182780) 18963:Methylpiperidinopyrazole 18916:Fulvestrant (ICI-182780) 18399:Resorcylic acid lactones 17622:Hydroxyestrone diacetate 17558:Etamestrol (eptamestrol) 16288:Hydroxyestrone diacetate 16215:estradiol ester mixtures 15146:10.1177/0091270002239706 14839:(inactive 1 July 2024). 14135:"Hirsutism, What to do?" 13588:Lehrbuch der Gynäkologie 13506:Fortschritte Der Medizin 12910:Biochemical Pharmacology 12239:Endocrine-Related Cancer 11433:10.1177/0024363918816683 11296:. Wiley. pp. 187–. 10443:10.1177/2053369116680501 10430:Post Reproductive Health 8786:ethinylestradiol sulfate 8150:Dosed every 2 to 3 weeks 5317:0.0054 (<0.001–0.01) 4985:Methylpiperidinopyrazole 4789:Deaminohydroxytoremifene 4314:17α-Methyl-17β-estradiol 3938:EB; Estradiol 3-benzoate 3788:E2S; Estradiol 3-sulfate 3388:E4; 15α,16α-Di-OH-17β-E2 2951:ethinylestradiol sulfate 2747:hepatocellular carcinoma 2723:alanine aminotransferase 2715:cholestasis of pregnancy 2288:Estradiol/norethisterone 2264:Estradiol/dydrogesterone 2124:, and 4- to 5-fold with 1898:Low bone mineral density 1812:Hepatocellular carcinoma 1674:Cerebrovascular diseases 1275:cholestasis of pregnancy 1232:cerebrovascular accident 330:Ethinylestradiol sulfate 153:International Drug Names 19668:17α-Hydroxyprogesterone 19663:17α-Hydroxypregnenolone 18457:Synthetic xenoestrogens 18014:Triphenylchloroethylene 17949:Methestrol dipropionate 17477:Polyestradiol phosphate 16453:Triphenylchloroethylene 16211:polyestradiol phosphate 15029:Lobo RA (5 June 2007). 14473:10.1002/pros.2990130405 13112:10.1038/nrendo.2011.122 13062:10.1186/1471-2172-11-20 13000:Pharmacological Reviews 12962:10.1074/jbc.M110.205112 12725:10.1073/pnas.0609568104 12518:10.1196/annals.1386.044 12018:10.1002/pros.2990140410 11639:Fertility and Sterility 11340:Fertility and Sterility 10783:Muller (19 June 1998). 10489:10.21037/tau.2016.09.04 9068:intramuscular injection 8480:route of administration 8436:liver protein synthesis 8428:polyestradiol phosphate 8336:route of administration 8332:liver protein synthesis 7498:Tooltip urinary calcium 7151:Tooltip Angiotensinogen 7082:Tooltip Urinary calcium 6302:7α-Methylnorethisterone 6230:0.085 (0.0015–<0.1) 5930:0.038 (<0.001–0.04) 4564:4-Chlorotamoxifen; 4-CT 4289:RU-2858; 11β-Methoxy-EE 4116:7-Dehydro-17α-estradiol 4091:7-Dehydro-17β-estradiol 3834:Estradiol 3-glucuronide 2612:polyestradiol phosphate 2605:liver protein synthesis 2143:polyestradiol phosphate 2062:route of administration 1861:Benign follicular cysts 1717:Subarachnoidal bleeding 1619:Intermenstrual bleeding 1566:Cardiovascular diseases 1495:). In men who received 1214:Current and history of 932:, has greatly improved 817:gynecological disorders 20442:Human drug metabolites 20437:Hormonal contraception 18550:4'-Hydroxynorendoxifen 18545:2-Phenylbenzothiophene 18419:zeranol (α-zearalanol) 18122:phlorizin (phloridzin) 18009:Triphenylbromoethylene 17908:ICI-85966 (Stilbostat) 17489:Estramustine phosphate 17362:Bolandiol dipropionate 16448:Triphenylbromoethylene 16225:Estramustine phosphate 15735:. pp. 1125–1178. 14948:Clinical Endocrinology 14668:10.1002/jps.2600620202 14617:(Suppl 7): 1929–1936. 14517:10.1055/s-0029-1210905 14345:10.1515/cclm-2023-0384 14155:10.16966/2380-548X.140 13920:10.1530/acta.0.0080175 13885:10.1530/acta.0.0040121 13840:10.1089/trgh.2017.0035 13795:(Suppl 7): 1929–1936. 13649:Pschyrembel W (1968). 12819:10.1124/dmd.104.000182 12605:10.1055/s-0028-1085099 12439:10.1055/s-2008-1026392 11960:(Suppl 2): S101–S103. 9323:norethisterone acetate 9307:, in combination with 9291:under the brand names 8746:plasma protein binding 8734:environmental estrogen 8730:elimination half-lives 8693:norethisterone acetate 8677: 8674:norethisterone acetate 8431: 8419: 8203: 8112:Sources and footnotes: 7663:Estradiol (micronized) 6277:7α-Methylnorethynodrel 6227:NET; 17α-Ethynyl-19-NT 6127:17α-Methyltestosterone 5923:Dehydroepiandrosterone 5880:0.01 (<0.001–0.05) 5877:DHT; 5α-Androstanolone 5801:0.01 (<0.001–0.02) 5039:8β-Vinyl-17β-estradiol 4964:16α-Iodo-17β-estradiol 4764:6720-CDRI; NNC-460,020 4485:Triphenylbromoethylene 4239:EE; 17α-Ethynyl-17β-E2 3988:Estrone 3-methyl ether 3959:Estradiol 17β-benzoate 3913:E1S; Estrone 3-sulfate 2583:estrogens like EE and 2541:(CPRD) databases. (2) 2447:Combined birth control 2316:estradiol/drospirenone 2116:, 3.5- to 4-fold with 2108:, 2.5- to 4-fold with 1596:Irregular menstruation 1587:(heart attack) (total) 1558:Iron-deficiency anemia 1471:(breast development), 1300:venous thromboembolism 1245:valvular heart disease 1216:ischemic heart disease 1157:venous thromboembolism 827:but is also used as a 823:. It is usually taken 19407:6,7-Dimethylesculetin 18730:Miproxifene phosphate 18555:27-Hydroxycholesterol 18019:Triphenyliodoethylene 17563:Ethinylandrostenediol 17526:Estrogenic substances 17514:Polyestriol phosphate 17382:Cloxestradiol acetate 16865:chlormadinone acetate 16249:Estrogenic substances 16243:polyestriol phosphate 16143:Cloxestradiol acetate 15665:Postgraduate Medicine 14295:10.1093/humupd/dmt038 13217:10.1056/NEJMoa1303611 13012:10.1124/pr.114.009712 11928:10.1089/jwh.2011.2839 11421:The Linacre Quarterly 10622:10.1192/bjp.125.3.310 10391:Clinical Therapeutics 10176:"The Top 300 of 2021" 9413:(6 Pt 2): 2114–2119. 9325:under the brand name 9311:under the brand name 9021:ethinylandrostenediol 8971:(EE 3-methyl ether), 8863:irreversibly inhibits 8834:elimination half-life 8659: 8542:Elimination half-life 8425: 8407: 8197: 7471:= Clinical relief of 7458:Sources and footnotes 3204:first-pass metabolism 3003:, and is possibly an 2943:competitively inhibit 2711:estradiol glucuronide 2593:myocardial infarction 2571:Cardiovascular issues 2134:contraceptive patches 2070:contraceptive patches 1888:Irritant agent eczema 1870:Photosensitive eczema 1776:Gall-bladder diseases 1732:Benign breast disease 1709:Trichomonas vaginitis 1650:Myocardial infarction 1627:Myocardial infarction 1604:Myocardial infarction 1585:Myocardial infarction 1551:Tooltip Relative risk 1536:Tooltip Relative risk 1361:High (>50 μg) 1307:Ethinylestradiol dose 1195:with vascular disease 1161:myocardial infarction 1022:(COC), also known as 19994:Hypericum perforatum 19983:Hetacillin potassium 18044:WAY-204688 (SIM-688) 17856:ERB-196 (WAY-202196) 17807:Dienestrol diacetate 17546:Estrone methyl ether 17452:Esterified estrogens 17394:Conjugated estrogens 17287:17β-Dihydroequilenin 17262:17α-Dihydroequilenin 17202:15α-Hydroxyestradiol 17197:11β-Methoxyestradiol 17172:8,9-Dehydroestradiol 16873:gestonorone caproate 16687:Aromatase inhibitors 16370:Dienestrol diacetate 16318:Prasterone enanthate 16203:estradiol undecylate 16168:Esterified estrogens 16153:Conjugated estrogens 15822:AMA drug evaluations 15702:. pp. 189–213. 15635:(FDA) (5 May 2004). 15332:10.1002/ajmg.c.31685 15297:10.1210/jcem-53-1-69 14831:. pp. 368–408. 14228:10.1210/en.2011-1608 14028:. pp. 368–408. 13908:Acta Endocrinologica 13873:Acta Endocrinologica 11123:10.2105/ajph.81.1.90 9951:. pp. 393–410. 9287:in combination with 9103:of the drug and its 8920:ethynyl substitution 8450:(17β-HSD), and this 8262:by androgens on the 8011:Dienestrol diacetate 7813:Conjugated estrogens 7311:Conjugated estrogens 6390:estradiol and human 6252:5(10)-Norethisterone 6177:17α-Ethynyl-3β-adiol 6152:17α-Ethynyl-3α-adiol 5064:ERB-041; WAY-202,041 4162:17α-Dihydroequilenin 4137:17β-Dihydroequilenin 4066:6,8-Didehydroestrone 3984:Estrone methyl ether 3338:E1; 17-Ketoestradiol 3200:micronized estradiol 3126:conjugated estrogens 2869:isoforms, including 2719:liver function tests 2668:and 17α-ethynylated 2436:Conjugated estrogens 2312:Estradiol/norgestrel 2235:Conjugated estrogens 1996:deep vein thrombosis 1956:Chlamydia infections 1786:Rheumatoid arthritis 1758:Deep vein thromboses 1493:erectile dysfunction 1327:Low (<50 μg) 1173:deep vein thrombosis 888:cancer of the uterus 804:in combination with 20457:Synthetic estrogens 20447:Prolactin releasers 19823:Cyproterone acetate 19723:Amlodipine besylate 19211:Propylpyrazoletriol 19126:Diarylpropionitrile 17974:Propylpyrazoletriol 17831:Dimethylstilbestrol 17797:Diarylpropionitrile 17607:Etynodiol diacetate 17307:Abiraterone acetate 17217:16α-Fluoroestradiol 16869:cyproterone acetate 16768:testosterone esters 16199:estradiol enanthate 16195:estradiol cypionate 16128:etynodiol diacetate 16097:testosterone esters 15542:10.1021/cr60268a004 15476:1938NW.....26...96I 15463:Naturwissenschaften 12955:(15): 12971–12982. 12716:2007PNAS..104.8897K 12510:2006NYASA1089..228G 12252:10.1530/ERC-17-0153 9305:contraceptive patch 9084:Society and culture 8845:is involved in the 8492: 8377:cyproterone acetate 8224:luteinizing hormone 7593: 7121:Tooltip Cholesterol 7062:Tooltip Hot flashes 7049: 6988:dihydrotestosterone 6435: 6402:See template page. 6202:P4; 4-Pregnenedione 6002:A4; Androstenedione 5873:Dihydrotestosterone 5855:<0.0001–<0.01 5852:T; 4-Androstenolone 5670:0.135 (0.002–4.23) 5667:0.0315 (0.008–1.0) 5270:0.6225 (0.010–1.2) 5245:0.7865 (0.04–17.1) 5114:SERBA-1; LY-500,307 5010:Diarylpropionitrile 4910:Propylpyrazoletriol 3809:Estradiol disulfate 3253: 3174:luteinizing hormone 3067:and possibly alter 2983:enzymes, including 2814:gonadal development 2784:ecosystems affects 2743:benign liver tumors 2634:(EES), an oral but 2175: 2126:cyproterone acetate 2032:estimated that the 2008:coagulation factors 1794:Benign liver tumors 1698:Cerebral thromboses 1509: 1303: 1296:birth control pills 1238:lupus erythematosus 1179:(PE) not receiving 1116:contraceptive patch 1033:EE is also used as 802:birth control pills 25: 16:Estrogen medication 20296:Thonzonium bromide 20051:Methylprednisolone 19852:prasterone sulfate 19293:Diethylstilbestrol 19077:2-Methoxyestradiol 19008:TAS-108 (SR-16234) 18958:Methylepitiostanol 18896:EM-800 (SCH-57050) 18820:TAS-108 (SR-16234) 18540:2-Phenylbenzofuran 18154:8-prenylnaringenin 17814:Diethylstilbestrol 17472:Lipoidal estradiol 17447:ERA-63 (ORG-37663) 17389:Conjugated estriol 17334:methyltestosterone 17292:17β-Dihydroequilin 17267:17α-Dihydroequilin 17242:16β-Hydroxyestrone 17227:16α-Hydroxyestrone 17177:8,9-Dehydroestrone 17162:7α-Methylestradiol 17137:4-Methoxyestradiol 17127:4-Hydroxyestradiol 17102:3β-Hydroxytibolone 17097:3α-Hydroxytibolone 17067:2-Hydroxyestradiol 16964:Never to phase III 16799:releasers) (e.g., 16710:Second-generation: 16323:Prasterone sulfate 16207:estradiol valerate 16191:estradiol benzoate 16148:Conjugated estriol 16101:methyltestosterone 15837:Ethinyl Estradiol 15505:Maisel AQ (1965). 15484:10.1007/BF01681040 14726:10.1007/BFb0036328 14258:(1 Suppl): 13–18. 14133:Ekback MP (2017). 13828:Transgender Health 12669:Endometrial Cancer 11541:Becker KL (2001). 11293:Pulmonary Embolism 10702:Becker KL (2001). 9236:medical literature 9221:ethinylestradiolum 8947:methyltestosterone 8814:catechol estrogens 8702:estradiol valerate 8678: 8490: 8432: 8420: 8389:19-nortestosterone 8305:methyltestosterone 8288:diethylstilbestrol 8275:High-dose estrogen 8204: 7936:Diethylstilbestrol 7713:Estradiol benzoate 7688:Estradiol valerate 7566: 7485:vaginal epithelium 7420:Diethylstilbestrol 7022: 6887:Diethylstilbestrol 6581:Estradiol valerate 6553:Estradiol benzoate 6408: 6348:3β-Hydroxytibolone 6323:3α-Hydroxytibolone 6123:Methyltestosterone 6102:5β-Androstanedione 6077:5α-Androstanedione 5952:A5; Androstenediol 5692:<0.001–<0.01 5335:8-Prenylnaringenin 5292:0.07 (0.029–0.10) 5267:0.04 (0.022–0.15) 5242:0.07 (0.0018–9.3) 5192:0.445 (0.0012–16) 5170:64.125 (0.41–185) 5167:9.225 (0.0117–94) 4895:21.65 (2.05–40.5) 4389:Dehydrostilbestrol 4345:219.63 (61.2–295) 4335:Diethylstilbestrol 4216:8,9-Dehydroestrone 4112:17α-Dihydroequilin 4087:17β-Dihydroequilin 3934:Estradiol benzoate 3709:16α-Hydroxyestrone 3584:4-Methoxyestradiol 3559:4-Hydroxyestradiol 3534:2-Methoxyestradiol 3509:2-Hydroxyestradiol 3322:0.115 (0.04–0.24) 3224: 3130:diethylstilbestrol 2796:populations in an 2769:Ecological Effects 2759:endometrial cancer 2670:19-nortestosterone 2585:diethylstilbestrol 2521:4.27 (3.57–5.11)* 2511:4.12 (3.43–4.96)* 2501:3.64 (3.00–4.43)* 2491:4.28 (3.66–5.01)* 2481:2.53 (2.17–2.96)* 2471:2.38 (2.18–2.59)* 2461:2.56 (2.15–3.06)* 2376:1.49 (1.24–1.79)* 2354:2.38 (1.99–2.85)* 2330:2.10 (1.92–2.31)* 2306:1.84 (1.69–2.00)* 2258:1.44 (1.09–1.89)* 2248:1.71 (1.51–1.93)* 2229:1.35 (1.18–1.55)* 2148: 2000:pulmonary embolism 1804:Endometrial cancer 1740:Pulmonary embolism 1514:Beneficial effects 1507: 1497:high-dose estrogen 1485:sexual dysfunction 1293: 1199:Migraine with aura 1177:pulmonary embolism 1097:endometrial cancer 1039:vasomotor symptoms 909:of estrogens like 903:estrogen receptors 876:sexual dysfunction 864:breast development 292:; is not bound to 21: 20412:Antigonadotropins 20407:Ethynyl compounds 20402:CYP1A2 inhibitors 20367: 20366: 20001:Indinavir sulfate 19708:Alpha-Lipoic acid 19683:Δ-Androstenedione 19673:Δ-Androstenedione 19346: 19345: 19338:List of estrogens 19306: 19305: 19051: 19050: 18891:Cytestrol acetate 18114:isoliquiritigenin 18056:Unknown/unsorted: 17742:β-LGND2 (GTx-878) 17322:Anabolic steroids 17232:16α-Iodoestradiol 17122:4-Fluoroestradiol 17117:4-Androstenedione 17107:3β-Androstanediol 17082:3α-Androstanediol 17033:Estrogen receptor 16999: 16998: 16991:List of estrogens 16933: 16932: 16885:megestrol acetate 16772:nandrolone esters 16760:anabolic steroids 16748:Antigonadotropins 16725:Third-generation: 16698:Aminoglutethimide 16695:First-generation: 16533: 16532: 16239:estriol succinate 16187:estradiol acetate 16109:nandrolone esters 16089:anabolic steroids 15913:(Suppl 1): 3–63. 15897:978-3-642-60107-1 15862:978-0-930530-02-0 15832:978-0-88416-175-2 15804:978-94-011-4439-1 15750:978-3-642-99942-0 15717:978-0-387-90087-2 15582:978-0-471-89980-8 15507:The Hormone Quest 15445:978-3-88763-075-1 15269:978-94-009-4145-8 15191:978-0-19-979361-7 15069:978-1-4443-4263-5 15042:978-0-08-055309-2 14927:978-1-59259-101-5 14917:Adrenal Disorders 14846:978-3-642-49506-9 14813:978-0-397-59010-0 14765:(11): 1085–1098. 14702:978-3-642-57636-2 14591:978-1-85317-422-3 14564:978-1-4557-1126-0 14383:(14): 1917–1928. 14332:Clin Chem Lab Med 14283:Hum Reprod Update 14195:978-1-107-01290-5 14043:978-3-642-49506-9 13993:978-3-642-57636-2 13765:978-3-540-54554-5 13662:978-3-11-150424-7 13635:978-94-009-8195-9 13598:978-3-662-00942-0 13571:978-3-11-024568-4 13544:978-3-642-75101-1 13413:978-0-397-51418-2 13382:978-1-4899-1133-9 13351:978-1-59745-150-5 13318:978-0-683-03631-2 13288:978-1-904798-74-3 13261:978-0-7817-3762-3 12916:(10): 1459–1469. 12813:(11): 1209–1212. 12776:10.1897/04-227R.1 12710:(21): 8897–8901. 12679:978-1-4613-0867-6 12652:978-1-4757-1767-9 12400:978-3-527-32363-0 12365:978-3-642-64261-6 12317:978-0-470-98697-4 12287:978-0-306-48240-3 12214:978-1-60795-014-1 12067:10.1159/000298914 11859:978-3-319-53298-1 11615:978-1-4379-4231-6 11585:978-0-309-04493-6 11554:978-0-7817-1750-2 11519:10.1159/000457125 11486:978-0-323-03309-1 11303:978-1-119-03909-9 11273:978-0-08-092150-1 11243:978-3-642-60107-1 11216:978-1-4832-7064-7 11088:978-3-662-07635-4 11018:978-0-08-093292-7 10898:978-1-60913-713-7 10868:978-0-323-07067-6 10827:978-3-642-82489-0 10796:978-3-7692-2114-5 10742:978-0-7881-0405-3 10715:978-0-7817-1750-2 10683:978-92-832-1291-1 10148:978-1-4612-2730-4 10083:978-1-4899-3496-3 10030:978-3-527-60749-5 9966:978-94-010-8339-3 9864:978-3-319-27449-2 9829:978-3-642-60107-1 9688:(Suppl 1): 3–63. 9577:978-1-56363-429-1 9550:978-1-57439-179-4 9384:978-1-4757-2085-3 9162:ethinyl estradiol 9149:ethinyloestradiol 9145:ethynyloestradiol 8991:of EE with other 8943:anabolic steroids 8644: 8643: 8530:Nuclear retention 8504:Ethinylestradiol 8283:transgender women 8281:for preoperative 8271:antigonadotropins 8260:negative feedback 8187: 8186: 7837:Ethinylestradiol 7763:Estriol succinate 7564: 7563: 7517:= Suppression of 7504:= Suppression of 7020: 7019: 6406: 6405: 6048:3β-Androstanediol 6023:3α-Androstanediol 5998:4-Androstenedione 5620:9.45 (2.43–31.5) 5320:0.15 (0.11–0.33) 5295:2.2 (0.002–3.00) 5220:0.85 (0.10–2.85) 4867:63.5 (3.70–97.7) 4460:Triphenylethylene 4342:129.5 (89.1–468) 4264:EE 3-methyl ether 4242:120.9 (68.8–480) 3784:Estradiol sulfate 3363:E3; 16α-OH-17β-E2 3350:1.75 (0.35–9.24) 3347:0.445 (0.3–1.01) 3325:0.15 (0.10–2.08) 3313:E2; 17β-Estradiol 3138:estrogen receptor 2798:experimental lake 2666:anabolic steroids 2568: 2567: 2441:1.04 (0.76–1.43) 2430:0.84 (0.73–0.97) 2414:0.88 (0.73–1.01) 2400:1.05 (0.88–1.24) 2365:1.02 (0.90–1.15) 2352:1.53 (1.36–1.72)* 2350:1.73 (1.57–1.91)* 2320:1.42 (1.00–2.03) 2304:1.38 (1.23–1.56)* 2302:1.68 (1.57–1.80)* 2282:1.34 (0.94–1.90) 2246:1.40 (1.28–1.53)* 2244:1.49 (1.39–1.60)* 2227:1.22 (1.09–1.37)* 2225:1.27 (1.16–1.39)* 1979: 1978: 1918:Ectopic pregnancy 1503:Long-term effects 1461:breast tenderness 1433:breast tenderness 1429: 1428: 1193:diabetes mellitus 1155:problems such as 1145:venous thrombosis 1135:Contraindications 1059:transgender women 907:biological target 844:breast tenderness 787: 786: 711:Interactive image 604:CompTox Dashboard 20464: 20384: 20383: 20382: 20375: 20286:Thiamylal sodium 20021:γ-linolenic acid 20017:α-Linolenic acid 20015:Linolenic acid: 20006:Lasalocid sodium 19996:(St John's wort) 19888:Docusate calcium 19818:Cyclophosphamide 19693:Allopregnanediol 19678:Δ-Androstenediol 19653: 19649: 19607:Ethinylestradiol 19457:Cyclophosphamide 19397: 19393: 19373: 19366: 19359: 19350: 19349: 19205:2,2',5'-PCB-4-OH 19141:Ethinylestradiol 19067: 19066: 19063: 19059: 18800:Rimostil (P-081) 18610:Chlorotrianisene 18532: 18528: 18307:Metalloestrogens 18086:-related (e.g., 17901:Hexestrol esters 17575:Ethinylestradiol 17467:Estradiol esters 17222:16α-Hydroxy-DHEA 17207:16-Ketoestradiol 17147:5-Androstenediol 17142:4-Methoxyestrone 17132:4-Hydroxyestrone 17112:4-Androstenediol 17072:2-Hydroxyestrone 17054: 17053: 17050: 17046: 17026: 17019: 17012: 17003: 17002: 16846: 16829: 16574: 16570: 16565: 16561: 16554: 16550: 16544: 16543: 16525: 16521: 16516: 16512: 16495: 16488: 16468:Progonadotropins 16414:Hexestrol esters 16360:Chlorotrianisene 16276:Ethinylestradiol 16183:Estradiol esters 16068: 16064: 16058: 16057: 16034: 16027: 16020: 16011: 16010: 16005: 15967: 15938: 15901: 15870: 15869: 15846: 15840: 15839: 15815: 15809: 15808: 15788: 15782: 15781: 15774: 15755: 15754: 15728: 15722: 15721: 15695: 15689: 15688: 15660: 15654: 15653: 15645:Federal Register 15641: 15628: 15622: 15621: 15593: 15587: 15586: 15570: 15560: 15554: 15553: 15530:Chemical Reviews 15525: 15519: 15518: 15502: 15496: 15495: 15456: 15450: 15449: 15430: 15403: 15402: 15365: 15352: 15351: 15315: 15309: 15308: 15280: 15274: 15273: 15253: 15244: 15243: 15207: 15196: 15195: 15175: 15166: 15165: 15128: 15117: 15116: 15080: 15074: 15073: 15053: 15047: 15046: 15026: 15015: 15014: 14986: 14980: 14979: 14943: 14932: 14931: 14911: 14900: 14899: 14871: 14865: 14864: 14858: 14850: 14824: 14818: 14817: 14797: 14791: 14790: 14754: 14748: 14747: 14713: 14707: 14706: 14686: 14680: 14679: 14651: 14645: 14644: 14626: 14602: 14596: 14595: 14575: 14569: 14568: 14548: 14537: 14536: 14499: 14493: 14492: 14456: 14447: 14446: 14418: 14409: 14408: 14372: 14366: 14365: 14347: 14323: 14317: 14316: 14306: 14274: 14268: 14267: 14247: 14241: 14240: 14230: 14221:(3): 1070–1081. 14206: 14200: 14199: 14179: 14168: 14167: 14157: 14139: 14130: 14119: 14118: 14090: 14079: 14078: 14054: 14048: 14047: 14021: 14015: 14014: 14004: 13998: 13997: 13977: 13971: 13970: 13938: 13932: 13931: 13903: 13897: 13896: 13868: 13862: 13861: 13851: 13819: 13813: 13812: 13784: 13778: 13777: 13743: 13737: 13736: 13708: 13702: 13701: 13673: 13667: 13666: 13646: 13640: 13639: 13609: 13603: 13602: 13582: 13576: 13575: 13555: 13549: 13548: 13528: 13522: 13521: 13501: 13495: 13494: 13466: 13460: 13459: 13431: 13422: 13421: 13397: 13391: 13390: 13366: 13360: 13359: 13335: 13326: 13325: 13302: 13293: 13292: 13272: 13266: 13265: 13245: 13239: 13238: 13228: 13196: 13190: 13189: 13175: 13143: 13137: 13136: 13123: 13091: 13085: 13084: 13074: 13064: 13040: 13034: 13033: 13023: 12991: 12985: 12984: 12974: 12964: 12940: 12934: 12933: 12905: 12899: 12898: 12862: 12839: 12838: 12802: 12796: 12795: 12770:(8): 2027–2036. 12759: 12748: 12747: 12737: 12727: 12695: 12684: 12683: 12663: 12657: 12656: 12636: 12625: 12624: 12588: 12582: 12581: 12544: 12538: 12537: 12493: 12484: 12483: 12465: 12459: 12458: 12422: 12405: 12404: 12384: 12378: 12377: 12335: 12322: 12321: 12301: 12292: 12291: 12271: 12265: 12264: 12254: 12245:(8): R297–R313. 12230: 12219: 12218: 12198: 12187: 12186: 12176: 12144: 12125: 12124: 12088: 12079: 12078: 12049: 12038: 12037: 12001: 11986: 11985: 11949: 11940: 11939: 11911: 11905: 11904: 11894: 11870: 11864: 11863: 11843: 11832: 11831: 11803: 11797: 11796: 11778: 11754: 11748: 11747: 11727: 11714: 11713: 11703: 11671: 11665: 11664: 11654: 11645:(6): 1289–1294. 11630: 11624: 11623: 11600: 11594: 11593: 11569: 11563: 11562: 11538: 11532: 11531: 11521: 11497: 11491: 11490: 11470: 11455: 11454: 11444: 11412: 11406: 11405: 11377: 11366: 11365: 11355: 11331: 11308: 11307: 11287: 11278: 11277: 11257: 11248: 11247: 11227: 11221: 11220: 11200: 11194: 11193: 11183: 11151: 11145: 11144: 11134: 11102: 11093: 11092: 11070: 11061: 11060: 11032: 11023: 11022: 11002: 10969: 10968: 10962: 10954: 10945: 10944: 10938: 10930: 10924: 10923: 10917: 10909: 10903: 10902: 10882: 10873: 10872: 10852: 10843: 10842: 10811: 10805: 10804: 10780: 10774: 10773: 10756: 10750: 10749: 10726: 10720: 10719: 10699: 10688: 10687: 10667: 10656: 10655: 10648: 10642: 10641: 10616:(586): 310–315. 10605: 10599: 10598: 10562: 10556: 10555: 10545: 10521: 10512: 10511: 10501: 10491: 10467: 10458: 10457: 10455: 10445: 10421: 10415: 10414: 10385: 10376: 10375: 10373: 10371: 10357: 10351: 10350: 10348: 10346: 10327: 10321: 10320: 10318: 10316: 10302: 10296: 10295: 10293: 10291: 10277: 10271: 10270: 10268: 10266: 10252: 10246: 10245: 10243: 10241: 10227: 10221: 10220: 10218: 10216: 10202: 10196: 10195: 10193: 10191: 10172: 10153: 10152: 10132: 10126: 10125: 10097: 10091: 10090: 10067: 10058: 10056: 10044: 10035: 10034: 10014: 10008: 10007: 10005: 10003: 9988: 9975: 9974: 9944: 9931: 9930: 9902: 9869: 9868: 9848: 9837: 9836: 9813: 9714: 9713: 9677: 9582: 9581: 9561: 9555: 9554: 9534: 9525: 9524: 9496: 9483: 9482: 9472: 9440: 9431: 9430: 9402: 9389: 9388: 9368: 9286: 9213:etinilestradiolo 9210: 9206: 9188:éthinylestradiol 9185: 9181: 9172: 9168: 9159: 9155: 9141:ethynylestradiol 9138: 9134: 9129: 9125: 9120: 9116: 9111: 9107: 9094:Ethinylestradiol 8847:pharmacokinetics 8830:estradiol esters 8826:steric hindrance 8798:steric hindrance 8718:pharmacokinetics 8660:EE levels while 8647:Pharmacokinetics 8588: 8584: 8565: 8561: 8516: 8512: 8493: 8489: 8417: 8413: 8320:adrenal androgen 8200:radioimmunoassay 8177: 8174: 8165: 8162: 8151: 8148: 8137: 8134: 8122: 8061:Chlorotrianisene 7961:DES dipropionate 7632: 7627: 7622: 7617: 7612: 7607: 7594: 7587: 7580: 7573: 7565: 7545: 7541: 7537: 7533: 7529: 7525: 7521: 7516: 7512: 7508: 7503: 7499: 7495: 7490: 7478: 7470: 7384:Ethinylestradiol 7157: 7152: 7148: 7142: 7138: 7132: 7128: 7122: 7118: 7113: 7109: 7103: 7099: 7093: 7089: 7083: 7079: 7073: 7069: 7063: 7059: 7050: 7043: 7036: 7029: 7021: 7011: 7007: 6998: 6994: 6985: 6981: 6972: 6968: 6959: 6955: 6946: 6942: 6933: 6929: 6776:Ethinylestradiol 6519: 6515: 6509: 6505: 6499: 6495: 6489: 6485: 6479: 6475: 6469: 6465: 6459: 6455: 6436: 6429: 6422: 6415: 6407: 6377:Binding affinity 6098:Etiocholanedione 5973:4-Androstenediol 5948:5-Androstenediol 5927:DHEA; Prasterone 5492:<0.001–0.0032 5467:<0.001–0.0875 5195:33.42 (0.86–87) 4542:100.1 (1.7–257) 4435:Chlorotrianisene 4339:DES; Stilbestrol 4236:Ethinylestradiol 4041:7-Dehydroestrone 3759:4-Methoxyestriol 3734:2-Hydroxyestriol 3684:4-Methoxyestrone 3659:4-Hydroxyestrone 3634:2-Methoxyestrone 3609:2-Hydroxyestrone 3484:16,17-Epiestriol 3441:7.795 (4.94–63) 3372:0.45 (0.35–1.4) 3366:12.65 (4.03–56) 3254: 3252: 3245: 3238: 3231: 3223: 3182:folliculogenesis 3170:antigonadotropic 3116:Pharmacodynamics 2564:: See template. 2398:0.94 (0.85–1.03) 2396:0.96 (0.88–1.04) 2347: 2342: 2299: 2294: 2280:1.12 (0.90–1.40) 2278:1.18 (0.98–1.42) 2275: 2270: 2199: 2195: 2176: 2169: 2162: 2155: 2147: 2098:surrogate marker 1943:(6 years of use) 1863:(high-dose COCs) 1552: 1548: 1537: 1533: 1510: 1506: 1322: 1310:No. of VTE cases 1304: 1292: 1210:Vascular disease 1004:levomefolic acid 993: 985: 977: 969: 961: 790:Ethinylestradiol 783: 782: 713: 693: 678: 672: 666: 649: 638: 627: 626: 612: 610: 595: 575: 555: 535: 515: 495: 475: 455: 445: 444: 430: 342: 300: 296: 235: 225: 169: 155: 118: 117: 114: 113: 110: 107: 104: 101: 98: 95: 92: 89: 86: 83: 80: 77: 74: 71: 68: 65: 62: 42: 33: 26: 24: 23:Ethinylestradiol 20: 20472: 20471: 20467: 20466: 20465: 20463: 20462: 20461: 20392: 20391: 20390: 20380: 20378: 20370: 20368: 20363: 20345: 20246:Suberoylanilide 19963:Fluorometholone 19858:Dibunate sodium 19738:Aurothioglucose 19651: 19641: 19577:3,17β-Estradiol 19395: 19385: 19377: 19347: 19342: 19302: 19281: 19245: 19061: 19047: 18881:7β-Hydroxy-DHEA 18864: 18700:Levormeloxifene 18530: 18523: 18517: 18433:deoxymiroestrol 18301:-hinokiresinol) 17939:Methallenestril 17841:Doisynolic acid 17642:Methylestradiol 17157:7α-Hydroxy-DHEA 17048: 17038: 17030: 17000: 16995: 16969: 16954:Clinical trials 16929: 16890: 16789: 16780:fluoxymesterone 16742: 16681: 16572: 16563: 16556: 16552: 16529: 16523: 16514: 16462: 16421:Methallenestril 16298:Methylestradiol 16264:Estrone sulfate 16066: 16047: 16038: 16008: 15898: 15879: 15877:Further reading 15874: 15873: 15863: 15847: 15843: 15833: 15816: 15812: 15805: 15789: 15785: 15776: 15775: 15758: 15751: 15729: 15725: 15718: 15696: 15692: 15661: 15657: 15652:(87): 25124–30. 15639: 15629: 15625: 15594: 15590: 15583: 15561: 15557: 15526: 15522: 15503: 15499: 15457: 15453: 15446: 15432: 15431: 15406: 15366: 15355: 15316: 15312: 15281: 15277: 15270: 15254: 15247: 15208: 15199: 15192: 15176: 15169: 15129: 15120: 15081: 15077: 15070: 15054: 15050: 15043: 15027: 15018: 14987: 14983: 14944: 14935: 14928: 14912: 14903: 14872: 14868: 14852: 14851: 14847: 14825: 14821: 14814: 14798: 14794: 14755: 14751: 14736: 14714: 14710: 14703: 14687: 14683: 14652: 14648: 14603: 14599: 14592: 14576: 14572: 14565: 14549: 14540: 14500: 14496: 14457: 14450: 14419: 14412: 14373: 14369: 14324: 14320: 14275: 14271: 14248: 14244: 14207: 14203: 14196: 14180: 14171: 14137: 14131: 14122: 14091: 14082: 14055: 14051: 14044: 14022: 14018: 14005: 14001: 13994: 13978: 13974: 13939: 13935: 13904: 13900: 13869: 13865: 13820: 13816: 13785: 13781: 13766: 13744: 13740: 13709: 13705: 13674: 13670: 13663: 13647: 13643: 13636: 13610: 13606: 13599: 13583: 13579: 13572: 13556: 13552: 13545: 13529: 13525: 13512:(21): 1388–92. 13502: 13498: 13467: 13463: 13432: 13425: 13414: 13398: 13394: 13383: 13367: 13363: 13352: 13336: 13329: 13319: 13303: 13296: 13289: 13273: 13269: 13262: 13246: 13242: 13197: 13193: 13144: 13140: 13106:(12): 715–726. 13092: 13088: 13041: 13037: 12992: 12988: 12941: 12937: 12906: 12902: 12863: 12842: 12803: 12799: 12760: 12751: 12696: 12687: 12680: 12664: 12660: 12653: 12637: 12628: 12589: 12585: 12545: 12541: 12494: 12487: 12471:Hepatic Adenoma 12466: 12462: 12433:(12): 910–922. 12423: 12408: 12401: 12385: 12381: 12366: 12336: 12325: 12318: 12302: 12295: 12288: 12272: 12268: 12231: 12222: 12215: 12199: 12190: 12145: 12128: 12089: 12082: 12050: 12041: 12002: 11989: 11950: 11943: 11912: 11908: 11871: 11867: 11860: 11844: 11835: 11804: 11800: 11755: 11751: 11728: 11717: 11686:(8): CD003989. 11672: 11668: 11631: 11627: 11616: 11602: 11601: 11597: 11586: 11570: 11566: 11555: 11539: 11535: 11498: 11494: 11487: 11471: 11458: 11413: 11409: 11378: 11369: 11332: 11311: 11304: 11288: 11281: 11274: 11258: 11251: 11244: 11228: 11224: 11217: 11201: 11197: 11166:(8): CD003989. 11152: 11148: 11103: 11096: 11089: 11075:"Kontrazeption" 11071: 11064: 11033: 11026: 11019: 11003: 10972: 10960: 10956: 10955: 10948: 10936: 10932: 10931: 10927: 10915: 10911: 10910: 10906: 10899: 10883: 10876: 10869: 10853: 10846: 10828: 10812: 10808: 10797: 10781: 10777: 10758: 10757: 10753: 10743: 10727: 10723: 10716: 10700: 10691: 10684: 10668: 10659: 10650: 10649: 10645: 10606: 10602: 10563: 10559: 10522: 10515: 10468: 10461: 10422: 10418: 10386: 10379: 10369: 10367: 10359: 10358: 10354: 10344: 10342: 10329: 10328: 10324: 10314: 10312: 10304: 10303: 10299: 10289: 10287: 10279: 10278: 10274: 10264: 10262: 10254: 10253: 10249: 10239: 10237: 10229: 10228: 10224: 10214: 10212: 10204: 10203: 10199: 10189: 10187: 10174: 10173: 10156: 10149: 10133: 10129: 10098: 10094: 10084: 10068: 10061: 10057:search: Estinyl 10045: 10038: 10031: 10015: 10011: 10001: 9999: 9990: 9989: 9978: 9967: 9945: 9934: 9903: 9872: 9865: 9849: 9840: 9830: 9814: 9717: 9678: 9585: 9578: 9562: 9558: 9551: 9535: 9528: 9497: 9486: 9441: 9434: 9403: 9392: 9385: 9369: 9350: 9345: 9337: 9244: 9208: 9196:etinilestradiol 9183: 9170: 9157: 9136: 9127: 9118: 9109: 9091: 9086: 9041: 8997:methylestradiol 8961: 8955: 8898: 8888:and 38% in the 8878: 8866:cytochrome P450 8794:estrone sulfate 8774:glucuronidation 8758: 8742: 8685:bioavailability 8664:or with a high- 8654: 8649: 8586: 8563: 8514: 8442:as well as the 8415: 8402: 8356:HDL cholesterol 8328: 8309:spermatogenesis 8279:hormone therapy 8232:pituitary gland 8192: 8183: 8182: 8181: 8180: 8175: 8168: 8163: 8154: 8149: 8140: 8135: 8131: 8126: 8125: 8119: 8113: 8086:Methallenestril 7911:Methylestradiol 7788:Estrone sulfate 7591: 7560: 7559: 7523: 7510: 7497: 7459: 7348:Equilin sulfate 7274:Estrone sulfate 7150: 7140: 7130: 7120: 7111: 7101: 7091: 7081: 7071: 7061: 7047: 7009: 6996: 6983: 6970: 6957: 6944: 6931: 6831:Methylestradiol 6637:Estrone sulfate 6517: 6507: 6497: 6487: 6477: 6467: 6457: 6433: 6355:1.6 (0.75–1.9) 6330:2.5 (1.06–5.0) 6280:0.5 (0.45–2.0) 6233:0.1 (0.01–0.3) 6208:<0.001–0.010 6073:Androstanedione 5858:<0.002–0.040 5617:7.68 (2.04–28) 5542:0.6 (0.032–13) 5470:<0.001–0.016 5435:Deoxymiroestrol 5004:ERα antagonist 4917:49 (10.0–89.1) 4892:43.5 (9.4–325) 4760:Levormeloxifene 4670:5.34 (0.54–16) 4614:F-6066; Sexovid 4592:25 (19.2–37.2) 4548:2.3 (0.1–3.61) 4410:Benzestrol (B2) 4367:153.6 (31–302) 4310:Methylestradiol 4245:44.4 (2.0–144) 3909:Estrone sulfate 3641:<0.001–<1 3466:55.45 (29–103) 3375:0.7 (0.63–0.7) 3369:26 (14.0–44.6) 3341:16.39 (0.7–60) 3277: 3250: 3249: 3184:and preventing 3160:agonist of the 3118: 3113: 3065:glucuronidation 2981:cytochrome P450 2975:EE is known to 2966:cytochrome P450 2883:anticonvulsants 2867:cytochrome P450 2863: 2851: 2845: 2802:Ontario, Canada 2771: 2755: 2648: 2624:thromboembolism 2573: 2399: 2397: 2392: 2390: 2353: 2351: 2343: 2338: 2305: 2303: 2295: 2290: 2281: 2279: 2271: 2266: 2247: 2245: 2240: 2238: 2228: 2226: 2221: 2219: 2197: 2173: 2004:liver synthesis 1994:, and includes 1984: 1900:(later in life) 1689:hospitalization 1550: 1535: 1519:Adverse effects 1505: 1487:(e.g., reduced 1441:fluid retention 1291: 1269:Due to risk of 1165:ischemic stroke 1137: 1109: 1107:Available forms 1078:prostate cancer 1074:palliative care 1012: 991: 983: 975: 967: 959: 934:bioavailability 856:fluid retention 778: 776: 771: 768: 763: 758: 757: 746: 743: 738: 737: 716: 691: 681: 675: 669: 630: 606: 598: 578: 558: 538: 518: 498: 478: 458: 441: 433: 413: 410: 381: 380: 360: 340: 332: 298: 284:Protein binding 274:Bioavailability 266:Pharmacokinetic 260: 239: 176: 59: 55: 17: 12: 11: 5: 20470: 20460: 20459: 20454: 20449: 20444: 20439: 20434: 20429: 20424: 20419: 20414: 20409: 20404: 20389: 20388: 20365: 20364: 20362: 20361: 20354: 20350: 20347: 20346: 20344: 20343: 20338: 20329: 20328: 20323: 20318: 20313: 20311:Troleandomycin 20308: 20303: 20298: 20293: 20288: 20283: 20278: 20273: 20268: 20263: 20258: 20253: 20248: 20243: 20238: 20233: 20231:Spironolactone 20228: 20223: 20218: 20213: 20208: 20203: 20198: 20193: 20188: 20183: 20178: 20173: 20168: 20163: 20158: 20153: 20148: 20143: 20138: 20133: 20128: 20123: 20118: 20113: 20108: 20103: 20101:Norelgestromin 20098: 20093: 20088: 20083: 20078: 20073: 20068: 20063: 20058: 20053: 20048: 20043: 20038: 20033: 20028: 20023: 20013: 20008: 20003: 19998: 19990: 19985: 19980: 19975: 19970: 19965: 19960: 19958:Flucloxacillin 19955: 19950: 19945: 19940: 19935: 19930: 19925: 19920: 19915: 19910: 19905: 19900: 19895: 19890: 19885: 19880: 19875: 19870: 19865: 19860: 19855: 19845: 19835: 19830: 19825: 19820: 19815: 19813:Corticosterone 19810: 19805: 19800: 19795: 19790: 19785: 19780: 19778:Chlorpromazine 19775: 19770: 19765: 19760: 19755: 19750: 19745: 19740: 19735: 19730: 19725: 19720: 19715: 19710: 19705: 19700: 19695: 19690: 19685: 19680: 19675: 19670: 19665: 19656: 19654: 19643: 19642: 19640: 19639: 19634: 19629: 19624: 19619: 19614: 19609: 19604: 19599: 19597:17-Androstanol 19594: 19592:3β-Androstanol 19589: 19587:3α-Androstenol 19584: 19582:3α-Androstanol 19579: 19570: 19569: 19564: 19559: 19554: 19549: 19544: 19539: 19534: 19529: 19524: 19519: 19514: 19509: 19504: 19499: 19494: 19489: 19484: 19479: 19474: 19464: 19459: 19454: 19449: 19444: 19439: 19437:Chlorpromazine 19434: 19429: 19424: 19419: 19414: 19409: 19400: 19398: 19387: 19386: 19376: 19375: 19368: 19361: 19353: 19344: 19343: 19341: 19340: 19335: 19330: 19325: 19320: 19315: 19311: 19308: 19307: 19304: 19303: 19301: 19300: 19295: 19289: 19287: 19283: 19282: 19280: 19279: 19274: 19269: 19264: 19259: 19253: 19251: 19247: 19246: 19244: 19243: 19238: 19233: 19228: 19223: 19218: 19213: 19208: 19198: 19193: 19188: 19183: 19178: 19173: 19171:Hydroxytyrosol 19168: 19163: 19158: 19153: 19148: 19143: 19138: 19133: 19128: 19123: 19109: 19104: 19099: 19094: 19089: 19084: 19079: 19073: 19071: 19064: 19053: 19052: 19049: 19048: 19046: 19045: 19036: 19035: 19026: 19025: 19020: 19015: 19010: 19005: 19000: 18995: 18990: 18985: 18980: 18975: 18970: 18965: 18960: 18955: 18950: 18945: 18940: 18918: 18913: 18908: 18903: 18898: 18893: 18888: 18886:Chloroindazole 18883: 18878: 18872: 18870: 18866: 18865: 18863: 18862: 18857: 18852: 18847: 18842: 18837: 18832: 18827: 18822: 18817: 18812: 18807: 18805:Spironolactone 18802: 18797: 18792: 18787: 18782: 18777: 18772: 18767: 18762: 18757: 18752: 18747: 18742: 18737: 18732: 18727: 18722: 18717: 18712: 18707: 18702: 18697: 18692: 18687: 18682: 18677: 18672: 18667: 18662: 18657: 18652: 18647: 18642: 18637: 18632: 18627: 18622: 18617: 18612: 18607: 18602: 18597: 18592: 18587: 18582: 18577: 18572: 18567: 18562: 18557: 18552: 18547: 18542: 18536: 18534: 18519: 18518: 18516: 18515: 18506:Others (e.g., 18504: 18454: 18440: 18426: 18396: 18378: 18356: 18314: 18304: 18282: 18277: 18234:liquiritigenin 18143: 18129: 18107: 18081:Xenoestrogens: 18077: 18076: 18071: 18066: 18061: 18052: 18051: 18046: 18041: 18036: 18031: 18026: 18021: 18016: 18011: 18006: 18001: 17996: 17991: 17986: 17981: 17976: 17971: 17966: 17961: 17956: 17954:Paroxypropione 17951: 17946: 17941: 17936: 17931: 17923: 17915: 17910: 17905: 17904: 17903: 17893: 17888: 17883: 17878: 17873: 17868: 17866:Estrobin (DBE) 17863: 17858: 17853: 17848: 17843: 17838: 17833: 17828: 17823: 17822: 17821: 17811: 17810: 17809: 17799: 17794: 17789: 17784: 17779: 17774: 17769: 17764: 17759: 17757:Allenolic acid 17754: 17749: 17744: 17739: 17734: 17729: 17724: 17715: 17714: 17709: 17704: 17699: 17694: 17689: 17684: 17679: 17674: 17669: 17664: 17662:Norethisterone 17659: 17654: 17652:Mytatrienediol 17649: 17644: 17639: 17634: 17629: 17624: 17619: 17614: 17609: 17604: 17599: 17597:Ethylestradiol 17594: 17592:Ethinylestriol 17589: 17588: 17587: 17582: 17572: 17571: 17570: 17560: 17555: 17554: 17553: 17548: 17543: 17541:Estrone esters 17533: 17528: 17523: 17518: 17517: 17516: 17511: 17509:Estriol esters 17501: 17496: 17494:Estrapronicate 17491: 17486: 17481: 17480: 17479: 17474: 17469: 17459: 17454: 17449: 17444: 17439: 17434: 17429: 17424: 17416: 17411: 17406: 17401: 17396: 17391: 17386: 17385: 17384: 17374: 17369: 17364: 17359: 17354: 17349: 17319: 17314: 17312:Alestramustine 17309: 17304: 17299: 17294: 17289: 17284: 17279: 17274: 17269: 17264: 17259: 17249: 17244: 17239: 17234: 17229: 17224: 17219: 17214: 17212:16-Ketoestrone 17209: 17204: 17199: 17194: 17189: 17184: 17179: 17174: 17169: 17164: 17159: 17154: 17149: 17144: 17139: 17134: 17129: 17124: 17119: 17114: 17109: 17104: 17099: 17094: 17089: 17084: 17079: 17074: 17069: 17060: 17058: 17051: 17040: 17039: 17029: 17028: 17021: 17014: 17006: 16997: 16996: 16994: 16993: 16988: 16983: 16978: 16973: 16968: 16967: 16966: 16965: 16962: 16951: 16945: 16939: 16938: 16935: 16934: 16931: 16930: 16928: 16927: 16922: 16913: 16912: 16907: 16898: 16896: 16892: 16891: 16889: 16888: 16858: 16841: 16824: 16817:chlorpromazine 16805:metoclopramide 16787: 16783: 16752: 16750: 16744: 16743: 16741: 16740: 16735: 16730: 16721: 16720: 16715: 16706: 16705: 16700: 16691: 16689: 16683: 16682: 16680: 16679: 16670: 16669: 16664: 16655: 16654: 16649: 16644: 16639: 16634: 16629: 16624: 16619: 16614: 16609: 16604: 16599: 16594: 16589: 16584: 16578: 16576: 16541: 16535: 16534: 16531: 16530: 16528: 16527: 16503: 16483: 16472: 16470: 16464: 16463: 16461: 16460: 16455: 16450: 16445: 16440: 16438:Paroxypropione 16435: 16434: 16433: 16423: 16418: 16417: 16416: 16406: 16401: 16400: 16399: 16394: 16389: 16379: 16374: 16373: 16372: 16362: 16357: 16352: 16343: 16342: 16337: 16332: 16327: 16326: 16325: 16320: 16310: 16305: 16300: 16295: 16290: 16285: 16284: 16283: 16273: 16272: 16271: 16266: 16259:Estrone esters 16256: 16251: 16246: 16235:Estriol esters 16232: 16227: 16222: 16180: 16175: 16170: 16165: 16160: 16155: 16150: 16145: 16140: 16135: 16120:norethisterone 16112: 16081: 16072: 16070: 16055: 16049: 16048: 16037: 16036: 16029: 16022: 16014: 16007: 16006: 15980:(8): 696–724. 15968: 15950:(6): 706–727. 15939: 15902: 15896: 15880: 15878: 15875: 15872: 15871: 15861: 15841: 15831: 15810: 15803: 15783: 15756: 15749: 15723: 15716: 15690: 15671:(3): 224–231. 15655: 15623: 15604:(1): 290–298. 15588: 15581: 15555: 15536:(6): 713–726. 15520: 15497: 15451: 15444: 15404: 15377:(8): 696–724. 15353: 15310: 15275: 15268: 15245: 15197: 15190: 15167: 15118: 15075: 15068: 15048: 15041: 15016: 14997:(2): 109–115. 14981: 14954:(4): 415–421. 14933: 14926: 14901: 14882:(5): 619–624. 14866: 14845: 14819: 14812: 14792: 14749: 14734: 14708: 14701: 14681: 14662:(2): 179–200. 14646: 14597: 14590: 14570: 14563: 14538: 14511:(3): 239–243. 14494: 14467:(4): 299–304. 14448: 14429:(3): 208–215. 14410: 14367: 14318: 14269: 14242: 14201: 14194: 14169: 14120: 14101:(6): 668–677. 14080: 14069:(4): 399–407. 14049: 14042: 14016: 13999: 13992: 13972: 13933: 13898: 13863: 13814: 13779: 13764: 13738: 13719:(s51): 48–61. 13703: 13668: 13661: 13641: 13634: 13604: 13597: 13577: 13570: 13550: 13543: 13523: 13496: 13477:(3): 199–214. 13461: 13442:(5): 511–518. 13423: 13412: 13392: 13381: 13361: 13350: 13327: 13317: 13294: 13287: 13267: 13260: 13240: 13211:(2): 164–171. 13191: 13158:(1–2): 71–83. 13138: 13086: 13049:BMC Immunology 13035: 13006:(3): 505–540. 12986: 12935: 12900: 12873:(2): 133–157. 12840: 12797: 12749: 12685: 12678: 12658: 12651: 12626: 12599:(3): 315–327. 12583: 12539: 12504:(1): 228–236. 12485: 12474:. StatPearls. 12460: 12406: 12399: 12379: 12364: 12323: 12316: 12293: 12286: 12266: 12220: 12213: 12188: 12126: 12080: 12061:(4): 198–205. 12039: 12012:(4): 389–395. 11987: 11941: 11922:(2): 161–169. 11906: 11865: 11858: 11833: 11814:(3): 201–203. 11798: 11769:(6): 992–997. 11749: 11738:(6): 482–490. 11715: 11666: 11625: 11614: 11595: 11584: 11564: 11553: 11533: 11512:(4): 215–223. 11492: 11485: 11456: 11427:(4): 470–477. 11407: 11367: 11309: 11302: 11279: 11272: 11249: 11242: 11222: 11215: 11195: 11146: 11094: 11087: 11062: 11024: 11017: 10970: 10946: 10925: 10904: 10897: 10874: 10867: 10844: 10826: 10806: 10795: 10775: 10751: 10741: 10721: 10714: 10689: 10682: 10657: 10643: 10600: 10573:(4): 604–655. 10557: 10513: 10482:(6): 877–884. 10459: 10436:(4): 165–183. 10416: 10397:(6): 921–932. 10377: 10352: 10322: 10297: 10272: 10247: 10222: 10197: 10154: 10147: 10127: 10108:(3): 479–503. 10092: 10082: 10059: 10051:(FDA) (2007). 10036: 10029: 10009: 9976: 9965: 9932: 9913:(6): 706–727. 9870: 9863: 9838: 9828: 9715: 9583: 9576: 9556: 9549: 9526: 9484: 9455:(5): 400–408. 9432: 9390: 9383: 9347: 9346: 9344: 9341: 9336: 9333: 9289:norelgestromin 9243: 9240: 9090: 9087: 9085: 9082: 9040: 9037: 9009:ethinylestriol 9001:ethylestradiol 8954: 8951: 8932:norethisterone 8897: 8894: 8877: 8874: 8853:EE, following 8850:with oral EE. 8757: 8754: 8741: 8738: 8722:levonorgestrel 8653: 8650: 8648: 8645: 8642: 8641: 8635: 8634: 8631: 8628: 8617: 8616: 8613: 8610: 8597: 8596: 8593: 8590: 8574: 8573: 8570: 8567: 8551: 8550: 8547: 8544: 8538: 8537: 8534: 8531: 8527: 8526: 8523: 8520: 8506: 8505: 8502: 8497: 8401: 8398: 8394:norethisterone 8381:antiandrogenic 8365:levonorgestrel 8327: 8324: 8316:adrenal glands 8269:Estrogens are 8218:(SHBG) in the 8191: 8188: 8185: 8184: 8179: 8178: 8166: 8152: 8138: 8128: 8127: 8124: 8123: 8116: 8115: 8114: 8111: 8110: 8107: 8106: 8103: 8100: 8097: 8094: 8091: 8088: 8082: 8081: 8078: 8075: 8072: 8069: 8066: 8063: 8057: 8056: 8053: 8050: 8047: 8044: 8041: 8038: 8032: 8031: 8028: 8025: 8022: 8019: 8016: 8013: 8007: 8006: 8003: 8000: 7997: 7994: 7991: 7988: 7982: 7981: 7978: 7975: 7972: 7969: 7966: 7963: 7957: 7956: 7953: 7950: 7947: 7944: 7941: 7938: 7932: 7931: 7928: 7925: 7922: 7919: 7916: 7913: 7907: 7906: 7903: 7900: 7897: 7894: 7891: 7888: 7882: 7881: 7878: 7875: 7872: 7869: 7866: 7863: 7857: 7856: 7853: 7850: 7847: 7844: 7841: 7838: 7834: 7833: 7830: 7827: 7824: 7821: 7818: 7815: 7809: 7808: 7805: 7802: 7799: 7796: 7793: 7790: 7784: 7783: 7780: 7777: 7774: 7771: 7768: 7765: 7759: 7758: 7755: 7752: 7749: 7746: 7743: 7740: 7734: 7733: 7730: 7727: 7724: 7721: 7718: 7715: 7709: 7708: 7705: 7702: 7699: 7696: 7693: 7690: 7684: 7683: 7680: 7677: 7674: 7671: 7668: 7665: 7659: 7658: 7655: 7652: 7649: 7646: 7643: 7640: 7634: 7633: 7628: 7623: 7618: 7613: 7608: 7602: 7601: 7598: 7590: 7589: 7582: 7575: 7567: 7562: 7561: 7548:liver proteins 7491:= Decrease in 7466:Abbreviations: 7460: 7457: 7456: 7453: 7452: 7449: 7446: 7443: 7440: 7437: 7434: 7431: 7428: 7425: 7422: 7416: 7415: 7412: 7409: 7406: 7403: 7400: 7397: 7394: 7391: 7388: 7385: 7381: 7380: 7377: 7374: 7371: 7368: 7365: 7362: 7359: 7356: 7353: 7350: 7344: 7343: 7340: 7337: 7334: 7331: 7328: 7325: 7322: 7319: 7316: 7313: 7307: 7306: 7303: 7300: 7297: 7294: 7291: 7288: 7285: 7282: 7279: 7276: 7270: 7269: 7266: 7263: 7260: 7257: 7254: 7251: 7248: 7245: 7242: 7239: 7233: 7232: 7229: 7226: 7223: 7220: 7217: 7214: 7211: 7208: 7205: 7202: 7196: 7195: 7192: 7189: 7186: 7183: 7180: 7177: 7174: 7171: 7168: 7165: 7159: 7158: 7153: 7143: 7133: 7123: 7104: 7094: 7084: 7074: 7064: 7054: 7046: 7045: 7038: 7031: 7023: 7018: 7017: 7016:See template. 6911: 6910: 6907: 6904: 6901: 6898: 6895: 6892: 6889: 6883: 6882: 6879: 6876: 6873: 6870: 6867: 6864: 6861: 6855: 6854: 6851: 6848: 6845: 6842: 6839: 6836: 6833: 6827: 6826: 6823: 6820: 6817: 6814: 6811: 6808: 6805: 6799: 6798: 6795: 6792: 6789: 6786: 6783: 6780: 6777: 6773: 6772: 6769: 6766: 6763: 6760: 6757: 6754: 6751: 6745: 6744: 6741: 6738: 6735: 6732: 6729: 6726: 6723: 6717: 6716: 6713: 6710: 6707: 6704: 6701: 6698: 6695: 6689: 6688: 6685: 6682: 6679: 6676: 6673: 6670: 6667: 6661: 6660: 6657: 6654: 6651: 6648: 6645: 6642: 6639: 6633: 6632: 6629: 6626: 6623: 6620: 6617: 6614: 6611: 6605: 6604: 6601: 6598: 6595: 6592: 6589: 6586: 6583: 6577: 6576: 6573: 6570: 6567: 6564: 6561: 6558: 6555: 6549: 6548: 6545: 6542: 6539: 6536: 6533: 6530: 6527: 6521: 6520: 6510: 6500: 6490: 6480: 6470: 6460: 6449: 6448: 6442: 6432: 6431: 6424: 6417: 6409: 6404: 6403: 6369: 6368: 6365: 6362: 6359: 6356: 6353: 6350: 6344: 6343: 6340: 6337: 6334: 6331: 6328: 6325: 6319: 6318: 6315: 6312: 6309: 6306: 6303: 6300: 6294: 6293: 6290: 6287: 6284: 6281: 6278: 6275: 6269: 6268: 6265: 6262: 6259: 6256: 6255:0.5 (0.3–0.7) 6253: 6250: 6244: 6243: 6240: 6237: 6234: 6231: 6228: 6225: 6223:Norethisterone 6219: 6218: 6215: 6212: 6209: 6206: 6203: 6200: 6194: 6193: 6190: 6187: 6184: 6181: 6178: 6175: 6169: 6168: 6165: 6162: 6159: 6156: 6153: 6150: 6144: 6143: 6140: 6137: 6134: 6131: 6128: 6125: 6119: 6118: 6115: 6112: 6109: 6106: 6103: 6100: 6094: 6093: 6090: 6087: 6084: 6081: 6078: 6075: 6069: 6068: 6065: 6062: 6059: 6056: 6053: 6050: 6044: 6043: 6040: 6037: 6034: 6031: 6028: 6025: 6019: 6018: 6015: 6012: 6009: 6006: 6003: 6000: 5994: 5993: 5990: 5987: 5984: 5981: 5978: 5975: 5969: 5968: 5965: 5962: 5959: 5956: 5953: 5950: 5944: 5943: 5940: 5937: 5934: 5931: 5928: 5925: 5919: 5918: 5915: 5912: 5909: 5906: 5903: 5900: 5894: 5893: 5890: 5887: 5884: 5881: 5878: 5875: 5869: 5868: 5865: 5862: 5859: 5856: 5853: 5850: 5844: 5843: 5840: 5837: 5834: 5831: 5828: 5823:Hydroxychlor; 5821: 5815: 5814: 5811: 5808: 5805: 5802: 5799: 5798:-Dimethoxy-DDT 5793: 5787: 5786: 5783: 5780: 5777: 5774: 5771: 5768: 5759: 5758: 5755: 5752: 5749: 5746: 5743: 5740: 5731: 5730: 5727: 5724: 5721: 5718: 5715: 5712: 5706: 5705: 5702: 5699: 5696: 5693: 5690: 5687: 5681: 5680: 5677: 5674: 5671: 5668: 5665: 5662: 5656: 5655: 5652: 5649: 5646: 5643: 5640: 5637: 5631: 5630: 5627: 5624: 5621: 5618: 5615: 5612: 5606: 5605: 5602: 5599: 5596: 5593: 5590: 5587: 5581: 5580: 5577: 5574: 5571: 5568: 5565: 5562: 5556: 5555: 5552: 5549: 5546: 5543: 5540: 5537: 5531: 5530: 5527: 5524: 5521: 5518: 5515: 5512: 5506: 5505: 5502: 5499: 5496: 5493: 5490: 5487: 5481: 5480: 5477: 5474: 5471: 5468: 5465: 5462: 5456: 5455: 5452: 5449: 5446: 5443: 5440: 5437: 5431: 5430: 5427: 5424: 5421: 5418: 5415: 5412: 5406: 5405: 5402: 5399: 5396: 5393: 5390: 5387: 5381: 5380: 5377: 5374: 5371: 5368: 5367:<0.001–0.01 5365: 5362: 5356: 5355: 5352: 5349: 5346: 5343: 5340: 5337: 5331: 5330: 5327: 5324: 5321: 5318: 5315: 5312: 5306: 5305: 5302: 5299: 5296: 5293: 5290: 5287: 5281: 5280: 5277: 5274: 5271: 5268: 5265: 5262: 5256: 5255: 5252: 5249: 5246: 5243: 5240: 5237: 5231: 5230: 5227: 5224: 5221: 5218: 5215: 5212: 5206: 5205: 5202: 5199: 5196: 5193: 5190: 5187: 5181: 5180: 5177: 5174: 5171: 5168: 5165: 5162: 5156: 5155: 5152: 5149: 5146: 5143: 5140: 5137: 5131: 5130: 5127: 5124: 5121: 5118: 5115: 5112: 5106: 5105: 5102: 5099: 5096: 5093: 5090: 5087: 5081: 5080: 5077: 5074: 5071: 5068: 5065: 5062: 5056: 5055: 5052: 5049: 5046: 5043: 5040: 5037: 5031: 5030: 5027: 5024: 5021: 5018: 5015: 5012: 5006: 5005: 5002: 4999: 4996: 4993: 4990: 4987: 4981: 4980: 4977: 4974: 4971: 4968: 4965: 4962: 4956: 4955: 4952: 4949: 4946: 4943: 4940: 4937: 4931: 4930: 4927: 4924: 4921: 4918: 4915: 4912: 4906: 4905: 4902: 4899: 4896: 4893: 4890: 4887: 4881: 4880: 4877: 4874: 4871: 4868: 4865: 4862: 4856: 4855: 4852: 4849: 4846: 4843: 4840: 4837: 4831: 4830: 4827: 4824: 4821: 4818: 4815: 4812: 4806: 4805: 4802: 4799: 4796: 4793: 4790: 4787: 4781: 4780: 4777: 4774: 4771: 4768: 4765: 4762: 4756: 4755: 4752: 4749: 4746: 4743: 4740: 4737: 4731: 4730: 4727: 4724: 4721: 4718: 4715: 4712: 4706: 4705: 4702: 4699: 4696: 4693: 4690: 4687: 4681: 4680: 4677: 4674: 4671: 4668: 4667:41.2 (7.8–69) 4665: 4662: 4656: 4655: 4652: 4649: 4646: 4643: 4640: 4637: 4631: 4630: 4627: 4624: 4621: 4618: 4615: 4612: 4606: 4605: 4602: 4599: 4596: 4593: 4590: 4587: 4581: 4580: 4577: 4574: 4571: 4568: 4565: 4562: 4556: 4555: 4552: 4549: 4546: 4545:10 (0.98–339) 4543: 4540: 4537: 4531: 4530: 4527: 4524: 4521: 4520:3.33 (0.28–6) 4518: 4515: 4512: 4506: 4505: 4502: 4499: 4496: 4493: 4490: 4487: 4481: 4480: 4477: 4474: 4471: 4468: 4465: 4462: 4456: 4455: 4452: 4449: 4446: 4443: 4440: 4437: 4431: 4430: 4427: 4424: 4421: 4418: 4415: 4412: 4406: 4405: 4402: 4399: 4396: 4393: 4392:37 (20.4–223) 4390: 4387: 4381: 4380: 4377: 4374: 4371: 4368: 4365: 4362: 4356: 4355: 4352: 4349: 4346: 4343: 4340: 4337: 4331: 4330: 4327: 4324: 4321: 4318: 4315: 4312: 4306: 4305: 4302: 4299: 4296: 4293: 4290: 4287: 4281: 4280: 4277: 4274: 4271: 4268: 4265: 4262: 4256: 4255: 4252: 4249: 4246: 4243: 4240: 4237: 4233: 4232: 4229: 4226: 4223: 4220: 4217: 4214: 4208: 4207: 4204: 4201: 4198: 4195: 4192: 4189: 4183: 4182: 4179: 4176: 4173: 4170: 4167: 4164: 4158: 4157: 4154: 4151: 4148: 4145: 4142: 4139: 4133: 4132: 4129: 4126: 4123: 4120: 4117: 4114: 4108: 4107: 4104: 4101: 4098: 4095: 4092: 4089: 4083: 4082: 4079: 4076: 4073: 4070: 4067: 4064: 4058: 4057: 4054: 4051: 4048: 4045: 4044:13 (4.0–28.9) 4042: 4039: 4033: 4032: 4029: 4026: 4023: 4020: 4017: 4014: 4005: 4004: 4001: 3998: 3995: 3992: 3989: 3986: 3980: 3979: 3976: 3973: 3970: 3967: 3964: 3961: 3955: 3954: 3951: 3948: 3945: 3942: 3939: 3936: 3930: 3929: 3926: 3923: 3920: 3917: 3914: 3911: 3905: 3904: 3901: 3898: 3895: 3892: 3889: 3886: 3880: 3879: 3876: 3873: 3870: 3867: 3864: 3861: 3855: 3854: 3851: 3848: 3845: 3842: 3839: 3836: 3830: 3829: 3826: 3823: 3820: 3817: 3814: 3811: 3805: 3804: 3801: 3798: 3795: 3792: 3789: 3786: 3780: 3779: 3776: 3773: 3770: 3767: 3764: 3761: 3755: 3754: 3751: 3748: 3745: 3742: 3739: 3736: 3730: 3729: 3726: 3723: 3720: 3717: 3714: 3711: 3705: 3704: 3701: 3698: 3695: 3692: 3689: 3686: 3680: 3679: 3676: 3673: 3670: 3667: 3664: 3661: 3655: 3654: 3651: 3648: 3645: 3642: 3639: 3636: 3630: 3629: 3626: 3623: 3620: 3617: 3614: 3611: 3605: 3604: 3601: 3598: 3595: 3592: 3589: 3586: 3580: 3579: 3576: 3573: 3570: 3567: 3564: 3561: 3555: 3554: 3551: 3548: 3545: 3542: 3539: 3536: 3530: 3529: 3526: 3523: 3520: 3517: 3514: 3511: 3505: 3504: 3501: 3498: 3495: 3492: 3489: 3486: 3480: 3479: 3476: 3473: 3470: 3467: 3464: 3461: 3455: 3454: 3451: 3448: 3445: 3442: 3439: 3436: 3430: 3429: 3426: 3423: 3420: 3417: 3416:20.5 (7–80.1) 3414: 3411: 3405: 3404: 3401: 3398: 3395: 3392: 3389: 3386: 3380: 3379: 3376: 3373: 3370: 3367: 3364: 3361: 3355: 3354: 3351: 3348: 3345: 3344:6.5 (1.36–52) 3342: 3339: 3336: 3330: 3329: 3326: 3323: 3320: 3317: 3314: 3311: 3305: 3304: 3299: 3294: 3289: 3283: 3282: 3279: 3275: 3269: 3263: 3260: 3248: 3247: 3240: 3233: 3225: 3117: 3114: 3112: 3109: 2933:troleandomycin 2862: 2859: 2844: 2841: 2794:fathead minnow 2770: 2767: 2763:dimethisterone 2754: 2753:Uterine cancer 2751: 2733:by 50%, while 2655:hepatotoxicity 2647: 2644: 2601:cardiovascular 2589:cardiovascular 2572: 2569: 2566: 2565: 2523: 2522: 2519: 2513: 2512: 2509: 2503: 2502: 2499: 2493: 2492: 2489: 2483: 2482: 2479: 2473: 2472: 2469: 2463: 2462: 2459: 2454: 2449: 2443: 2442: 2439: 2432: 2431: 2428: 2422: 2416: 2415: 2412: 2402: 2401: 2394: 2384: 2378: 2377: 2374: 2367: 2366: 2363: 2356: 2355: 2348: 2332: 2331: 2328: 2322: 2321: 2318: 2308: 2307: 2300: 2284: 2283: 2276: 2260: 2259: 2256: 2250: 2249: 2242: 2231: 2230: 2223: 2213: 2208: 2202: 2201: 2186: 2183: 2180: 2172: 2171: 2164: 2157: 2149: 2106:levonorgestrel 2038:levonorgestrel 1983: 1980: 1977: 1976: 1962: 1961: 1958: 1953: 1951: 1948: 1947: 1944: 1938: 1936: 1933: 1932: 1929: 1923: 1920: 1914: 1913: 1910: 1904: 1901: 1894: 1893: 1890: 1885: 1882: 1876: 1875: 1872: 1867: 1864: 1857: 1856: 1853: 1847: 1844: 1841:Ovarian cancer 1837: 1836: 1833: 1828: 1825: 1822:Ovarian cancer 1818: 1817: 1814: 1809: 1806: 1800: 1799: 1796: 1791: 1788: 1782: 1781: 1778: 1773: 1770: 1764: 1763: 1760: 1755: 1752: 1746: 1745: 1742: 1737: 1734: 1728: 1727: 1724: 1714: 1711: 1705: 1704: 1701: 1695: 1692: 1681: 1680: 1677: 1671: 1668: 1661: 1660: 1657: 1647: 1644: 1638: 1637: 1634: 1624: 1621: 1615: 1614: 1611: 1601: 1598: 1592: 1591: 1588: 1582: 1579: 1573: 1572: 1569: 1563: 1560: 1554: 1553: 1543: 1538: 1528: 1522: 1521: 1516: 1504: 1501: 1427: 1426: 1412:levonorgestrel 1408:norethisterone 1392: 1391: 1388: 1385: 1382: 1379: 1375: 1374: 1371: 1368: 1365: 1362: 1358: 1357: 1354: 1351: 1348: 1345: 1341: 1340: 1337: 1334: 1331: 1328: 1324: 1323: 1317: 1314: 1311: 1308: 1290: 1287: 1279:hepatic tumors 1248: 1247: 1241: 1234: 1228: 1225: 1218: 1212: 1207: 1201: 1196: 1189: 1186: 1183: 1181:anticoagulants 1153:cardiovascular 1136: 1133: 1108: 1105: 1011: 1008: 972:levonorgestrel 956:norethisterone 842:of EE include 819:, and certain 785: 784: 773: 772: 770: 769: 766: 764: 761: 753: 752: 751: 748: 747: 745: 744: 741: 733: 732: 731: 728: 727: 724: 718: 717: 715: 714: 706: 704: 696: 695: 689: 683: 682: 679: 673: 667: 662: 656: 655: 651: 650: 640: 632: 631: 629: 628: 615: 613: 600: 599: 597: 596: 588: 586: 580: 579: 577: 576: 568: 566: 560: 559: 557: 556: 548: 546: 540: 539: 537: 536: 528: 526: 520: 519: 517: 516: 508: 506: 500: 499: 497: 496: 488: 486: 480: 479: 477: 476: 468: 466: 460: 459: 457: 456: 448: 446: 435: 434: 432: 431: 423: 421: 415: 414: 412: 411: 384: 376: 375: 374: 371: 370: 366: 365: 354: 348: 347: 344: 335: 334: 326: 320: 319: 309: 303: 302: 286: 280: 279: 276: 270: 269: 262: 261: 259: 258: 254: 252: 246: 245: 241: 240: 238: 237: 214: 212: 206: 205: 200: 194: 193: 179: 177:administration 171: 170: 163: 157: 156: 149: 139: 138: 135: 131: 130: 127: 121: 120: 53: 49: 48: 44: 43: 35: 34: 15: 9: 6: 4: 3: 2: 20469: 20458: 20455: 20453: 20450: 20448: 20445: 20443: 20440: 20438: 20435: 20433: 20430: 20428: 20425: 20423: 20422:GPER agonists 20420: 20418: 20415: 20413: 20410: 20408: 20405: 20403: 20400: 20399: 20397: 20387: 20377: 20376: 20373: 20360: 20359: 20355: 20352: 20351: 20348: 20342: 20339: 20337: 20334: 20331: 20330: 20327: 20324: 20322: 20319: 20317: 20314: 20312: 20309: 20307: 20304: 20302: 20299: 20297: 20294: 20292: 20289: 20287: 20284: 20282: 20279: 20277: 20274: 20272: 20269: 20267: 20264: 20262: 20259: 20257: 20254: 20252: 20251:Sulfisoxazole 20249: 20247: 20244: 20242: 20239: 20237: 20234: 20232: 20229: 20227: 20224: 20222: 20219: 20217: 20214: 20212: 20209: 20207: 20204: 20202: 20199: 20197: 20194: 20192: 20189: 20187: 20184: 20182: 20179: 20177: 20174: 20172: 20169: 20167: 20164: 20162: 20159: 20157: 20154: 20152: 20149: 20147: 20144: 20142: 20139: 20137: 20134: 20132: 20129: 20127: 20126:Phenobarbital 20124: 20122: 20119: 20117: 20114: 20112: 20109: 20107: 20104: 20102: 20099: 20097: 20094: 20092: 20089: 20087: 20084: 20082: 20079: 20077: 20074: 20072: 20069: 20067: 20064: 20062: 20059: 20057: 20054: 20052: 20049: 20047: 20044: 20042: 20039: 20037: 20034: 20032: 20029: 20027: 20024: 20022: 20018: 20014: 20012: 20011:Levothyroxine 20009: 20007: 20004: 20002: 19999: 19997: 19995: 19991: 19989: 19986: 19984: 19981: 19979: 19976: 19974: 19973:Guggulsterone 19971: 19969: 19966: 19964: 19961: 19959: 19956: 19954: 19951: 19949: 19946: 19944: 19941: 19939: 19936: 19934: 19931: 19929: 19926: 19924: 19921: 19919: 19916: 19914: 19911: 19909: 19906: 19904: 19901: 19899: 19896: 19894: 19891: 19889: 19886: 19884: 19881: 19879: 19876: 19874: 19871: 19869: 19868:Dicloxacillin 19866: 19864: 19861: 19859: 19856: 19853: 19849: 19846: 19843: 19839: 19836: 19834: 19833:Dexamethasone 19831: 19829: 19826: 19824: 19821: 19819: 19816: 19814: 19811: 19809: 19806: 19804: 19801: 19799: 19796: 19794: 19791: 19789: 19786: 19784: 19781: 19779: 19776: 19774: 19771: 19769: 19768:Cephaloridine 19766: 19764: 19761: 19759: 19756: 19754: 19751: 19749: 19746: 19744: 19741: 19739: 19736: 19734: 19731: 19729: 19726: 19724: 19721: 19719: 19716: 19714: 19711: 19709: 19706: 19704: 19701: 19699: 19696: 19694: 19691: 19689: 19686: 19684: 19681: 19679: 19676: 19674: 19671: 19669: 19666: 19664: 19661: 19658: 19657: 19655: 19650: 19644: 19638: 19635: 19633: 19630: 19628: 19625: 19623: 19620: 19618: 19615: 19613: 19610: 19608: 19605: 19603: 19600: 19598: 19595: 19593: 19590: 19588: 19585: 19583: 19580: 19578: 19575: 19572: 19571: 19568: 19567:Valproic acid 19565: 19563: 19560: 19558: 19555: 19553: 19550: 19548: 19545: 19543: 19540: 19538: 19535: 19533: 19530: 19528: 19527:Phenobarbital 19525: 19523: 19520: 19518: 19515: 19513: 19510: 19508: 19505: 19503: 19500: 19498: 19495: 19493: 19490: 19488: 19485: 19483: 19480: 19478: 19475: 19472: 19468: 19465: 19463: 19460: 19458: 19455: 19453: 19450: 19448: 19445: 19443: 19440: 19438: 19435: 19433: 19430: 19428: 19427:Carbamazepine 19425: 19423: 19420: 19418: 19415: 19413: 19410: 19408: 19405: 19402: 19401: 19399: 19394: 19388: 19384: 19381: 19374: 19369: 19367: 19362: 19360: 19355: 19354: 19351: 19339: 19336: 19334: 19331: 19329: 19326: 19324: 19321: 19319: 19316: 19313: 19312: 19309: 19299: 19296: 19294: 19291: 19290: 19288: 19284: 19278: 19275: 19273: 19270: 19268: 19265: 19263: 19260: 19258: 19255: 19254: 19252: 19248: 19242: 19239: 19237: 19234: 19232: 19229: 19227: 19224: 19222: 19219: 19217: 19214: 19212: 19209: 19206: 19202: 19199: 19197: 19194: 19192: 19189: 19187: 19184: 19182: 19179: 19177: 19174: 19172: 19169: 19167: 19164: 19162: 19159: 19157: 19154: 19152: 19149: 19147: 19144: 19142: 19139: 19137: 19134: 19132: 19129: 19127: 19124: 19121: 19117: 19113: 19110: 19108: 19105: 19103: 19100: 19098: 19095: 19093: 19090: 19088: 19085: 19083: 19080: 19078: 19075: 19074: 19072: 19068: 19065: 19060: 19054: 19044: 19041: 19038: 19037: 19034: 19031: 19028: 19027: 19024: 19021: 19019: 19016: 19014: 19011: 19009: 19006: 19004: 19001: 18999: 18996: 18994: 18991: 18989: 18986: 18984: 18981: 18979: 18976: 18974: 18971: 18969: 18966: 18964: 18961: 18959: 18956: 18954: 18951: 18949: 18946: 18944: 18941: 18938: 18934: 18930: 18926: 18922: 18919: 18917: 18914: 18912: 18909: 18907: 18904: 18902: 18899: 18897: 18894: 18892: 18889: 18887: 18884: 18882: 18879: 18877: 18874: 18873: 18871: 18867: 18861: 18858: 18856: 18853: 18851: 18848: 18846: 18843: 18841: 18838: 18836: 18833: 18831: 18828: 18826: 18823: 18821: 18818: 18816: 18813: 18811: 18808: 18806: 18803: 18801: 18798: 18796: 18793: 18791: 18788: 18786: 18785:Pipendoxifene 18783: 18781: 18778: 18776: 18773: 18771: 18768: 18766: 18763: 18761: 18758: 18756: 18753: 18751: 18748: 18746: 18743: 18741: 18738: 18736: 18733: 18731: 18728: 18726: 18723: 18721: 18718: 18716: 18713: 18711: 18708: 18706: 18703: 18701: 18698: 18696: 18693: 18691: 18688: 18686: 18683: 18681: 18678: 18676: 18673: 18671: 18668: 18666: 18663: 18661: 18658: 18656: 18653: 18651: 18648: 18646: 18643: 18641: 18638: 18636: 18633: 18631: 18628: 18626: 18623: 18621: 18620:Clomifenoxide 18618: 18616: 18613: 18611: 18608: 18606: 18603: 18601: 18598: 18596: 18595:Brilanestrant 18593: 18591: 18588: 18586: 18583: 18581: 18578: 18576: 18573: 18571: 18568: 18566: 18563: 18561: 18558: 18556: 18553: 18551: 18548: 18546: 18543: 18541: 18538: 18537: 18535: 18529: 18520: 18513: 18509: 18505: 18502: 18498: 18494: 18490: 18486: 18482: 18478: 18474: 18470: 18466: 18462: 18458: 18455: 18452: 18448: 18444: 18441: 18438: 18434: 18431:-like (e.g., 18430: 18427: 18424: 18420: 18416: 18412: 18408: 18404: 18400: 18397: 18394: 18390: 18386: 18382: 18379: 18376: 18375:guggulsterone 18372: 18368: 18364: 18360: 18359:Phytosteroids 18357: 18354: 18350: 18346: 18342: 18338: 18334: 18330: 18326: 18322: 18318: 18315: 18312: 18308: 18305: 18302: 18300: 18294: 18293:enterolactone 18290: 18286: 18283: 18281: 18278: 18275: 18271: 18267: 18263: 18259: 18255: 18251: 18247: 18243: 18239: 18235: 18231: 18227: 18223: 18219: 18215: 18211: 18207: 18203: 18199: 18195: 18191: 18187: 18183: 18179: 18175: 18171: 18167: 18163: 18159: 18155: 18151: 18147: 18144: 18141: 18137: 18133: 18130: 18127: 18126:wedelolactone 18123: 18119: 18115: 18111: 18108: 18105: 18104:photoanethole 18101: 18097: 18093: 18089: 18085: 18082: 18079: 18078: 18075: 18072: 18070: 18067: 18065: 18062: 18060: 18057: 18054: 18053: 18050: 18047: 18045: 18042: 18040: 18037: 18035: 18032: 18030: 18027: 18025: 18022: 18020: 18017: 18015: 18012: 18010: 18007: 18005: 18002: 18000: 17997: 17995: 17992: 17990: 17987: 17985: 17982: 17980: 17977: 17975: 17972: 17970: 17967: 17965: 17962: 17960: 17959:Pentafluranol 17957: 17955: 17952: 17950: 17947: 17945: 17942: 17940: 17937: 17935: 17932: 17930: 17928: 17924: 17922: 17920: 17916: 17914: 17911: 17909: 17906: 17902: 17899: 17898: 17897: 17894: 17892: 17889: 17887: 17884: 17882: 17879: 17877: 17874: 17872: 17869: 17867: 17864: 17862: 17859: 17857: 17854: 17852: 17849: 17847: 17844: 17842: 17839: 17837: 17834: 17832: 17829: 17827: 17824: 17820: 17817: 17816: 17815: 17812: 17808: 17805: 17804: 17803: 17800: 17798: 17795: 17793: 17790: 17788: 17785: 17783: 17780: 17778: 17775: 17773: 17770: 17768: 17765: 17763: 17760: 17758: 17755: 17753: 17750: 17748: 17745: 17743: 17740: 17738: 17735: 17733: 17730: 17728: 17725: 17723: 17720: 17719:Nonsteroidal: 17717: 17716: 17713: 17710: 17708: 17705: 17703: 17700: 17698: 17695: 17693: 17690: 17688: 17685: 17683: 17680: 17678: 17675: 17673: 17670: 17668: 17665: 17663: 17660: 17658: 17655: 17653: 17650: 17648: 17645: 17643: 17640: 17638: 17635: 17633: 17630: 17628: 17625: 17623: 17620: 17618: 17615: 17613: 17610: 17608: 17605: 17603: 17600: 17598: 17595: 17593: 17590: 17586: 17583: 17581: 17578: 17577: 17576: 17573: 17569: 17568:Ethandrostate 17566: 17565: 17564: 17561: 17559: 17556: 17552: 17549: 17547: 17544: 17542: 17539: 17538: 17537: 17534: 17532: 17529: 17527: 17524: 17522: 17519: 17515: 17512: 17510: 17507: 17506: 17505: 17502: 17500: 17497: 17495: 17492: 17490: 17487: 17485: 17482: 17478: 17475: 17473: 17470: 17468: 17465: 17464: 17463: 17460: 17458: 17455: 17453: 17450: 17448: 17445: 17443: 17440: 17438: 17435: 17433: 17430: 17428: 17425: 17423: 17421: 17417: 17415: 17412: 17410: 17407: 17405: 17402: 17400: 17397: 17395: 17392: 17390: 17387: 17383: 17380: 17379: 17378: 17377:Cloxestradiol 17375: 17373: 17370: 17368: 17365: 17363: 17360: 17358: 17355: 17353: 17350: 17347: 17343: 17339: 17335: 17331: 17327: 17323: 17320: 17318: 17315: 17313: 17310: 17308: 17305: 17303: 17300: 17298: 17295: 17293: 17290: 17288: 17285: 17283: 17280: 17278: 17275: 17273: 17270: 17268: 17265: 17263: 17260: 17257: 17253: 17252:17α-Estradiol 17250: 17248: 17245: 17243: 17240: 17238: 17235: 17233: 17230: 17228: 17225: 17223: 17220: 17218: 17215: 17213: 17210: 17208: 17205: 17203: 17200: 17198: 17195: 17193: 17190: 17188: 17185: 17183: 17180: 17178: 17175: 17173: 17170: 17168: 17165: 17163: 17160: 17158: 17155: 17153: 17150: 17148: 17145: 17143: 17140: 17138: 17135: 17133: 17130: 17128: 17125: 17123: 17120: 17118: 17115: 17113: 17110: 17108: 17105: 17103: 17100: 17098: 17095: 17093: 17090: 17088: 17085: 17083: 17080: 17078: 17075: 17073: 17070: 17068: 17065: 17062: 17061: 17059: 17055: 17052: 17047: 17041: 17037: 17034: 17027: 17022: 17020: 17015: 17013: 17008: 17007: 17004: 16992: 16989: 16987: 16984: 16982: 16979: 16977: 16974: 16971: 16970: 16963: 16961: 16958: 16957: 16955: 16952: 16949: 16946: 16944: 16941: 16940: 16936: 16926: 16923: 16921: 16918: 16915: 16914: 16911: 16908: 16906: 16903: 16900: 16899: 16897: 16893: 16886: 16882: 16878: 16874: 16870: 16866: 16862: 16859: 16856: 16852: 16848: 16842: 16839: 16835: 16831: 16825: 16822: 16818: 16814: 16810: 16806: 16802: 16798: 16794: 16791: 16784: 16781: 16777: 16773: 16769: 16765: 16761: 16757: 16754: 16753: 16751: 16749: 16745: 16739: 16736: 16734: 16731: 16729: 16726: 16723: 16722: 16719: 16716: 16714: 16711: 16708: 16707: 16704: 16701: 16699: 16696: 16693: 16692: 16690: 16688: 16684: 16678: 16675: 16672: 16671: 16668: 16665: 16663: 16660: 16657: 16656: 16653: 16650: 16648: 16645: 16643: 16640: 16638: 16635: 16633: 16630: 16628: 16625: 16623: 16620: 16618: 16615: 16613: 16610: 16608: 16605: 16603: 16600: 16598: 16595: 16593: 16590: 16588: 16585: 16583: 16580: 16579: 16577: 16571: 16562: 16551: 16545: 16542: 16540: 16539:Antiestrogens 16536: 16522: 16513: 16507: 16506:Gonadotropins 16504: 16501: 16497: 16496:(gonadorelin) 16490: 16484: 16481: 16477: 16476:Antiandrogens 16474: 16473: 16471: 16469: 16465: 16459: 16456: 16454: 16451: 16449: 16446: 16444: 16441: 16439: 16436: 16432: 16429: 16428: 16427: 16424: 16422: 16419: 16415: 16412: 16411: 16410: 16407: 16405: 16402: 16398: 16395: 16393: 16390: 16388: 16385: 16384: 16383: 16380: 16378: 16375: 16371: 16368: 16367: 16366: 16363: 16361: 16358: 16356: 16353: 16351: 16348: 16347:Nonsteroidal: 16345: 16344: 16341: 16338: 16336: 16333: 16331: 16328: 16324: 16321: 16319: 16316: 16315: 16314: 16311: 16309: 16306: 16304: 16301: 16299: 16296: 16294: 16291: 16289: 16286: 16282: 16279: 16278: 16277: 16274: 16270: 16267: 16265: 16262: 16261: 16260: 16257: 16255: 16252: 16250: 16247: 16244: 16240: 16236: 16233: 16231: 16228: 16226: 16223: 16220: 16216: 16212: 16208: 16204: 16200: 16196: 16192: 16188: 16184: 16181: 16179: 16176: 16174: 16171: 16169: 16166: 16164: 16161: 16159: 16156: 16154: 16151: 16149: 16146: 16144: 16141: 16139: 16136: 16133: 16129: 16125: 16121: 16117: 16113: 16110: 16106: 16102: 16098: 16094: 16090: 16086: 16082: 16080: 16077: 16074: 16073: 16071: 16065: 16059: 16056: 16054: 16050: 16046: 16045:antiestrogens 16042: 16035: 16030: 16028: 16023: 16021: 16016: 16015: 16012: 16003: 15999: 15995: 15991: 15987: 15983: 15979: 15975: 15969: 15965: 15961: 15957: 15953: 15949: 15945: 15944:Contraception 15940: 15936: 15932: 15928: 15924: 15920: 15916: 15912: 15908: 15903: 15899: 15893: 15889: 15888: 15882: 15881: 15868: 15864: 15858: 15854: 15853: 15845: 15838: 15834: 15828: 15824: 15823: 15814: 15806: 15800: 15796: 15795: 15787: 15779: 15773: 15771: 15769: 15767: 15765: 15763: 15761: 15752: 15746: 15742: 15738: 15734: 15733:Die Gestagene 15727: 15719: 15713: 15709: 15705: 15701: 15694: 15686: 15682: 15678: 15674: 15670: 15666: 15659: 15651: 15647: 15646: 15638: 15634: 15627: 15619: 15615: 15611: 15607: 15603: 15599: 15592: 15584: 15578: 15574: 15569: 15568: 15559: 15551: 15547: 15543: 15539: 15535: 15531: 15524: 15516: 15512: 15508: 15501: 15493: 15489: 15485: 15481: 15477: 15473: 15469: 15465: 15464: 15455: 15447: 15441: 15437: 15436: 15429: 15427: 15425: 15423: 15421: 15419: 15417: 15415: 15413: 15411: 15409: 15400: 15396: 15392: 15388: 15384: 15380: 15376: 15372: 15364: 15362: 15360: 15358: 15349: 15345: 15341: 15337: 15333: 15329: 15325: 15321: 15314: 15306: 15302: 15298: 15294: 15290: 15286: 15279: 15271: 15265: 15261: 15260: 15252: 15250: 15241: 15237: 15233: 15229: 15225: 15221: 15218:(2): 95–136. 15217: 15213: 15206: 15204: 15202: 15193: 15187: 15183: 15182: 15174: 15172: 15163: 15159: 15155: 15151: 15147: 15143: 15139: 15135: 15127: 15125: 15123: 15114: 15110: 15106: 15102: 15098: 15094: 15090: 15086: 15079: 15071: 15065: 15061: 15060: 15059:Contraception 15052: 15044: 15038: 15034: 15033: 15025: 15023: 15021: 15012: 15008: 15004: 15000: 14996: 14993:(in French). 14992: 14985: 14977: 14973: 14969: 14965: 14961: 14957: 14953: 14949: 14942: 14940: 14938: 14929: 14923: 14919: 14918: 14910: 14908: 14906: 14897: 14893: 14889: 14885: 14881: 14877: 14870: 14862: 14856: 14848: 14842: 14838: 14834: 14830: 14823: 14815: 14809: 14805: 14804: 14796: 14788: 14784: 14780: 14776: 14772: 14768: 14764: 14760: 14753: 14745: 14741: 14737: 14735:3-540-05959-8 14731: 14727: 14723: 14719: 14712: 14704: 14698: 14694: 14693: 14685: 14677: 14673: 14669: 14665: 14661: 14657: 14650: 14642: 14638: 14634: 14630: 14625: 14620: 14616: 14612: 14608: 14601: 14593: 14587: 14583: 14582: 14574: 14566: 14560: 14556: 14555: 14547: 14545: 14543: 14534: 14530: 14526: 14522: 14518: 14514: 14510: 14506: 14498: 14490: 14486: 14482: 14478: 14474: 14470: 14466: 14462: 14455: 14453: 14444: 14440: 14436: 14432: 14428: 14424: 14417: 14415: 14406: 14402: 14398: 14394: 14390: 14386: 14382: 14378: 14371: 14363: 14359: 14355: 14351: 14346: 14341: 14337: 14333: 14329: 14322: 14314: 14310: 14305: 14300: 14296: 14292: 14289:(1): 76–105. 14288: 14284: 14280: 14273: 14265: 14261: 14257: 14253: 14246: 14238: 14234: 14229: 14224: 14220: 14216: 14215:Endocrinology 14212: 14205: 14197: 14191: 14187: 14186: 14178: 14176: 14174: 14165: 14161: 14156: 14151: 14147: 14143: 14136: 14129: 14127: 14125: 14116: 14112: 14108: 14104: 14100: 14096: 14089: 14087: 14085: 14076: 14072: 14068: 14064: 14060: 14053: 14045: 14039: 14035: 14031: 14027: 14020: 14012: 14011: 14003: 13995: 13989: 13985: 13984: 13976: 13969: 13964: 13960: 13956: 13952: 13949:(s6): 1–121. 13948: 13944: 13937: 13929: 13925: 13921: 13917: 13914:(2): 175–91. 13913: 13909: 13902: 13894: 13890: 13886: 13882: 13879:(2): 121–39. 13878: 13874: 13867: 13859: 13855: 13850: 13845: 13841: 13837: 13833: 13829: 13825: 13818: 13810: 13806: 13802: 13798: 13794: 13790: 13783: 13775: 13771: 13767: 13761: 13757: 13753: 13749: 13742: 13734: 13730: 13726: 13722: 13718: 13714: 13707: 13699: 13695: 13691: 13687: 13683: 13679: 13672: 13664: 13658: 13654: 13653: 13645: 13637: 13631: 13627: 13623: 13619: 13615: 13608: 13600: 13594: 13590: 13589: 13581: 13573: 13567: 13563: 13562: 13554: 13546: 13540: 13536: 13535: 13527: 13519: 13515: 13511: 13508:(in German). 13507: 13500: 13492: 13488: 13484: 13480: 13476: 13472: 13465: 13457: 13453: 13449: 13445: 13441: 13437: 13430: 13428: 13420: 13415: 13409: 13405: 13404: 13396: 13389: 13384: 13378: 13374: 13373: 13365: 13358: 13353: 13347: 13343: 13342: 13334: 13332: 13324: 13320: 13314: 13310: 13309: 13301: 13299: 13290: 13284: 13280: 13279: 13271: 13263: 13257: 13253: 13252: 13244: 13236: 13232: 13227: 13222: 13218: 13214: 13210: 13206: 13202: 13195: 13188: 13183: 13179: 13174: 13169: 13165: 13161: 13157: 13153: 13149: 13142: 13135: 13131: 13127: 13122: 13117: 13113: 13109: 13105: 13101: 13097: 13090: 13082: 13078: 13073: 13068: 13063: 13058: 13054: 13050: 13046: 13039: 13031: 13027: 13022: 13017: 13013: 13009: 13005: 13001: 12997: 12990: 12982: 12978: 12973: 12968: 12963: 12958: 12954: 12950: 12946: 12939: 12931: 12927: 12923: 12919: 12915: 12911: 12904: 12896: 12892: 12888: 12884: 12880: 12876: 12872: 12868: 12861: 12859: 12857: 12855: 12853: 12851: 12849: 12847: 12845: 12836: 12832: 12828: 12824: 12820: 12816: 12812: 12808: 12801: 12793: 12789: 12785: 12781: 12777: 12773: 12769: 12765: 12758: 12756: 12754: 12745: 12741: 12736: 12731: 12726: 12721: 12717: 12713: 12709: 12705: 12701: 12694: 12692: 12690: 12681: 12675: 12671: 12670: 12662: 12654: 12648: 12644: 12643: 12635: 12633: 12631: 12622: 12618: 12614: 12610: 12606: 12602: 12598: 12594: 12587: 12579: 12575: 12571: 12567: 12563: 12559: 12555: 12551: 12543: 12535: 12531: 12527: 12523: 12519: 12515: 12511: 12507: 12503: 12499: 12492: 12490: 12481: 12477: 12473: 12472: 12464: 12456: 12452: 12448: 12444: 12440: 12436: 12432: 12429:(in German). 12428: 12421: 12419: 12417: 12415: 12413: 12411: 12402: 12396: 12392: 12391: 12383: 12375: 12371: 12367: 12361: 12357: 12353: 12349: 12345: 12341: 12334: 12332: 12330: 12328: 12319: 12313: 12309: 12308: 12300: 12298: 12289: 12283: 12279: 12278: 12270: 12262: 12258: 12253: 12248: 12244: 12240: 12236: 12229: 12227: 12225: 12216: 12210: 12206: 12205: 12197: 12195: 12193: 12184: 12180: 12175: 12170: 12166: 12162: 12158: 12154: 12150: 12143: 12141: 12139: 12137: 12135: 12133: 12131: 12122: 12118: 12114: 12110: 12106: 12102: 12098: 12094: 12087: 12085: 12076: 12072: 12068: 12064: 12060: 12056: 12048: 12046: 12044: 12035: 12031: 12027: 12023: 12019: 12015: 12011: 12007: 12000: 11998: 11996: 11994: 11992: 11983: 11979: 11975: 11971: 11967: 11963: 11959: 11955: 11948: 11946: 11937: 11933: 11929: 11925: 11921: 11917: 11910: 11902: 11898: 11893: 11888: 11884: 11880: 11876: 11869: 11861: 11855: 11851: 11850: 11842: 11840: 11838: 11829: 11825: 11821: 11817: 11813: 11809: 11808:Contraception 11802: 11794: 11790: 11786: 11782: 11777: 11772: 11768: 11764: 11760: 11753: 11745: 11741: 11737: 11733: 11726: 11724: 11722: 11720: 11711: 11707: 11702: 11697: 11693: 11689: 11685: 11681: 11677: 11670: 11662: 11658: 11653: 11648: 11644: 11640: 11636: 11629: 11622: 11617: 11611: 11607: 11606: 11599: 11592: 11588:. NAP:13774. 11587: 11581: 11577: 11576: 11568: 11561: 11556: 11550: 11546: 11545: 11537: 11529: 11525: 11520: 11515: 11511: 11507: 11503: 11496: 11488: 11482: 11478: 11477: 11469: 11467: 11465: 11463: 11461: 11452: 11448: 11443: 11438: 11434: 11430: 11426: 11422: 11418: 11411: 11403: 11399: 11395: 11391: 11387: 11383: 11376: 11374: 11372: 11363: 11359: 11354: 11349: 11345: 11341: 11337: 11330: 11328: 11326: 11324: 11322: 11320: 11318: 11316: 11314: 11305: 11299: 11295: 11294: 11286: 11284: 11275: 11269: 11265: 11264: 11256: 11254: 11245: 11239: 11235: 11234: 11226: 11218: 11212: 11208: 11207: 11199: 11191: 11187: 11182: 11177: 11173: 11169: 11165: 11161: 11157: 11150: 11142: 11138: 11133: 11128: 11124: 11120: 11116: 11112: 11108: 11101: 11099: 11090: 11084: 11080: 11076: 11069: 11067: 11058: 11054: 11050: 11046: 11042: 11038: 11031: 11029: 11020: 11014: 11010: 11009: 11001: 10999: 10997: 10995: 10993: 10991: 10989: 10987: 10985: 10983: 10981: 10979: 10977: 10975: 10966: 10959: 10953: 10951: 10942: 10935: 10929: 10921: 10914: 10908: 10900: 10894: 10890: 10889: 10881: 10879: 10870: 10864: 10860: 10859: 10851: 10849: 10841: 10837: 10833: 10829: 10823: 10819: 10818: 10810: 10803: 10798: 10792: 10788: 10787: 10779: 10771: 10767: 10763: 10762: 10755: 10748: 10744: 10738: 10734: 10733: 10725: 10717: 10711: 10707: 10706: 10698: 10696: 10694: 10685: 10679: 10675: 10674: 10666: 10664: 10662: 10653: 10647: 10639: 10635: 10631: 10627: 10623: 10619: 10615: 10611: 10604: 10596: 10592: 10588: 10584: 10580: 10576: 10572: 10568: 10561: 10553: 10549: 10544: 10539: 10535: 10531: 10527: 10520: 10518: 10509: 10505: 10500: 10495: 10490: 10485: 10481: 10477: 10473: 10466: 10464: 10454: 10449: 10444: 10439: 10435: 10431: 10427: 10420: 10412: 10408: 10404: 10400: 10396: 10392: 10384: 10382: 10366: 10362: 10356: 10340: 10336: 10332: 10326: 10311: 10307: 10301: 10286: 10282: 10276: 10261: 10257: 10251: 10236: 10232: 10226: 10211: 10207: 10201: 10185: 10181: 10177: 10171: 10169: 10167: 10165: 10163: 10161: 10159: 10150: 10144: 10140: 10139: 10138:Contraception 10131: 10123: 10119: 10115: 10111: 10107: 10103: 10096: 10089: 10085: 10079: 10075: 10074: 10066: 10064: 10054: 10050: 10043: 10041: 10032: 10026: 10022: 10021: 10013: 9997: 9993: 9987: 9985: 9983: 9981: 9973: 9968: 9962: 9958: 9954: 9950: 9943: 9941: 9939: 9937: 9928: 9924: 9920: 9916: 9912: 9908: 9907:Contraception 9901: 9899: 9897: 9895: 9893: 9891: 9889: 9887: 9885: 9883: 9881: 9879: 9877: 9875: 9866: 9860: 9856: 9855: 9847: 9845: 9843: 9835: 9831: 9825: 9821: 9820: 9812: 9810: 9808: 9806: 9804: 9802: 9800: 9798: 9796: 9794: 9792: 9790: 9788: 9786: 9784: 9782: 9780: 9778: 9776: 9774: 9772: 9770: 9768: 9766: 9764: 9762: 9760: 9758: 9756: 9754: 9752: 9750: 9748: 9746: 9744: 9742: 9740: 9738: 9736: 9734: 9732: 9730: 9728: 9726: 9724: 9722: 9720: 9711: 9707: 9703: 9699: 9695: 9691: 9687: 9683: 9676: 9674: 9672: 9670: 9668: 9666: 9664: 9662: 9660: 9658: 9656: 9654: 9652: 9650: 9648: 9646: 9644: 9642: 9640: 9638: 9636: 9634: 9632: 9630: 9628: 9626: 9624: 9622: 9620: 9618: 9616: 9614: 9612: 9610: 9608: 9606: 9604: 9602: 9600: 9598: 9596: 9594: 9592: 9590: 9588: 9579: 9573: 9569: 9568: 9560: 9552: 9546: 9542: 9541: 9533: 9531: 9522: 9518: 9514: 9510: 9506: 9502: 9501:Contraception 9495: 9493: 9491: 9489: 9480: 9476: 9471: 9466: 9462: 9458: 9454: 9450: 9446: 9439: 9437: 9428: 9424: 9420: 9416: 9412: 9408: 9401: 9399: 9397: 9395: 9386: 9380: 9376: 9375: 9367: 9365: 9363: 9361: 9359: 9357: 9355: 9353: 9348: 9340: 9332: 9330: 9329: 9324: 9320: 9316: 9315: 9310: 9306: 9302: 9301: 9296: 9295: 9290: 9281: 9277: 9273: 9269: 9265: 9261: 9257: 9253: 9249: 9239: 9237: 9233: 9229: 9224: 9222: 9218: 9214: 9207: 9201: 9197: 9193: 9189: 9182: 9176: 9169: 9163: 9156: 9150: 9146: 9142: 9135: 9126: 9117: 9108: 9102: 9099: 9095: 9089:Generic names 9081: 9078: 9076: 9071: 9069: 9064: 9062: 9058: 9054: 9050: 9046: 9036: 9034: 9030: 9026: 9022: 9018: 9014: 9010: 9006: 9002: 8998: 8994: 8993:substitutions 8990: 8986: 8982: 8978: 8974: 8970: 8966: 8960: 8950: 8948: 8944: 8940: 8937: 8936:17α-alkylated 8933: 8929: 8925: 8921: 8917: 8913: 8909: 8906: 8903: 8893: 8891: 8887: 8883: 8873: 8870: 8867: 8864: 8860: 8856: 8851: 8848: 8844: 8838: 8835: 8831: 8827: 8823: 8819: 8815: 8811: 8810:hydroxylation 8807: 8802: 8799: 8795: 8791: 8787: 8783: 8779: 8775: 8771: 8767: 8763: 8753: 8751: 8747: 8737: 8735: 8731: 8727: 8723: 8719: 8714: 8710: 8708: 8703: 8699: 8694: 8690: 8686: 8683: 8675: 8671: 8667: 8663: 8658: 8640: 8636: 8632: 8629: 8626: 8623: 8619: 8618: 8614: 8611: 8609: 8606: 8603: 8599: 8598: 8594: 8591: 8585: 8579: 8576: 8575: 8571: 8568: 8562: 8556: 8553: 8552: 8548: 8545: 8543: 8540: 8539: 8535: 8532: 8529: 8528: 8524: 8521: 8519: 8513: 8508: 8507: 8503: 8501: 8498: 8495: 8494: 8488: 8485: 8481: 8476: 8473: 8469: 8464: 8461: 8457: 8453: 8449: 8445: 8441: 8437: 8429: 8424: 8414: 8406: 8397: 8395: 8390: 8384: 8382: 8378: 8374: 8370: 8366: 8360: 8357: 8353: 8349: 8345: 8341: 8337: 8333: 8323: 8321: 8317: 8312: 8310: 8306: 8302: 8297: 8291: 8289: 8284: 8280: 8276: 8272: 8267: 8265: 8261: 8257: 8251: 8249: 8245: 8241: 8237: 8233: 8229: 8225: 8221: 8217: 8213: 8209: 8201: 8196: 8173: 8171: 8161: 8159: 8157: 8147: 8145: 8143: 8133: 8129: 8121: 8117: 8108: 8104: 8101: 8098: 8095: 8092: 8089: 8087: 8083: 8079: 8076: 8073: 8070: 8067: 8064: 8062: 8058: 8054: 8051: 8048: 8045: 8042: 8039: 8037: 8033: 8029: 8026: 8023: 8020: 8017: 8014: 8012: 8008: 8004: 8001: 7998: 7995: 7992: 7989: 7987: 7983: 7979: 7976: 7973: 7970: 7967: 7964: 7962: 7958: 7954: 7951: 7948: 7945: 7942: 7939: 7937: 7933: 7929: 7926: 7923: 7920: 7917: 7914: 7912: 7908: 7904: 7901: 7898: 7895: 7892: 7889: 7887: 7883: 7879: 7876: 7873: 7870: 7867: 7864: 7862: 7858: 7854: 7851: 7848: 7845: 7842: 7839: 7835: 7831: 7828: 7825: 7822: 7819: 7816: 7814: 7810: 7806: 7803: 7800: 7797: 7794: 7791: 7789: 7785: 7781: 7778: 7775: 7772: 7769: 7766: 7764: 7760: 7756: 7753: 7750: 7747: 7744: 7741: 7739: 7735: 7731: 7728: 7725: 7722: 7719: 7716: 7714: 7710: 7706: 7703: 7700: 7697: 7694: 7691: 7689: 7685: 7681: 7678: 7675: 7672: 7669: 7666: 7664: 7660: 7656: 7653: 7650: 7647: 7644: 7641: 7639: 7635: 7603: 7595: 7588: 7583: 7581: 7576: 7574: 7569: 7568: 7558:See template. 7557: 7553: 7552:gonadotropins 7549: 7522: 7509: 7496: 7486: 7482: 7481:proliferation 7474: 7467: 7463: 7454: 7450: 7447: 7444: 7441: 7438: 7435: 7432: 7429: 7426: 7423: 7421: 7418: 7417: 7413: 7410: 7407: 7404: 7401: 7398: 7395: 7392: 7389: 7386: 7383: 7382: 7378: 7375: 7372: 7369: 7366: 7363: 7360: 7357: 7354: 7351: 7349: 7346: 7345: 7341: 7338: 7335: 7332: 7329: 7326: 7323: 7320: 7317: 7314: 7312: 7309: 7308: 7304: 7301: 7298: 7295: 7292: 7289: 7286: 7283: 7280: 7277: 7275: 7272: 7271: 7267: 7264: 7261: 7258: 7255: 7252: 7249: 7246: 7243: 7240: 7238: 7235: 7234: 7230: 7227: 7224: 7221: 7218: 7215: 7212: 7209: 7206: 7203: 7201: 7198: 7197: 7193: 7190: 7187: 7184: 7181: 7178: 7175: 7172: 7169: 7166: 7164: 7161: 7160: 7149: 7139: 7129: 7119: 7110: 7100: 7090: 7080: 7070: 7060: 7052: 7051: 7044: 7039: 7037: 7032: 7030: 7025: 7024: 7015: 7008: 7002: 6995: 6989: 6982: 6976: 6969: 6963: 6962:dexamethasone 6956: 6950: 6943: 6937: 6930: 6924: 6920: 6916: 6912: 6908: 6905: 6902: 6899: 6896: 6893: 6890: 6888: 6885: 6884: 6880: 6877: 6874: 6871: 6868: 6865: 6862: 6860: 6857: 6856: 6852: 6849: 6846: 6843: 6840: 6837: 6834: 6832: 6829: 6828: 6824: 6821: 6818: 6815: 6812: 6809: 6806: 6804: 6801: 6800: 6796: 6793: 6790: 6787: 6784: 6781: 6778: 6775: 6774: 6770: 6767: 6764: 6761: 6758: 6755: 6752: 6750: 6747: 6746: 6742: 6739: 6736: 6733: 6730: 6727: 6724: 6722: 6719: 6718: 6714: 6711: 6708: 6705: 6702: 6699: 6696: 6694: 6691: 6690: 6686: 6683: 6680: 6677: 6674: 6671: 6668: 6666: 6663: 6662: 6658: 6655: 6652: 6649: 6646: 6643: 6640: 6638: 6635: 6634: 6630: 6627: 6624: 6621: 6618: 6615: 6612: 6610: 6607: 6606: 6602: 6599: 6596: 6593: 6590: 6587: 6584: 6582: 6579: 6578: 6574: 6571: 6568: 6565: 6562: 6559: 6556: 6554: 6551: 6550: 6546: 6543: 6540: 6537: 6534: 6531: 6528: 6526: 6523: 6522: 6516: 6511: 6506: 6501: 6496: 6491: 6486: 6481: 6476: 6471: 6466: 6461: 6456: 6451: 6450: 6446: 6441: 6437: 6430: 6425: 6423: 6418: 6416: 6411: 6410: 6401: 6397: 6393: 6389: 6386:systems with 6385: 6384: 6378: 6374: 6370: 6366: 6363: 6360: 6357: 6354: 6351: 6349: 6346: 6345: 6341: 6338: 6335: 6332: 6329: 6326: 6324: 6321: 6320: 6316: 6313: 6310: 6308:0.027–<0.1 6307: 6305:0.069–<0.1 6304: 6301: 6299: 6296: 6295: 6291: 6288: 6285: 6282: 6279: 6276: 6274: 6271: 6270: 6266: 6263: 6260: 6257: 6254: 6251: 6249: 6248:Norethynodrel 6246: 6245: 6241: 6238: 6235: 6232: 6229: 6226: 6224: 6221: 6220: 6216: 6213: 6210: 6207: 6205:<0.001–0.6 6204: 6201: 6199: 6196: 6195: 6191: 6188: 6185: 6182: 6179: 6176: 6174: 6171: 6170: 6166: 6163: 6160: 6157: 6154: 6151: 6149: 6146: 6145: 6141: 6138: 6135: 6132: 6129: 6126: 6124: 6121: 6120: 6116: 6113: 6110: 6107: 6104: 6101: 6099: 6096: 6095: 6091: 6088: 6085: 6082: 6079: 6076: 6074: 6071: 6070: 6066: 6063: 6060: 6057: 6054: 6051: 6049: 6046: 6045: 6041: 6038: 6035: 6032: 6029: 6026: 6024: 6021: 6020: 6016: 6013: 6010: 6007: 6004: 6001: 5999: 5996: 5995: 5991: 5988: 5985: 5982: 5979: 5976: 5974: 5971: 5970: 5966: 5963: 5960: 5957: 5954: 5951: 5949: 5946: 5945: 5941: 5938: 5935: 5932: 5929: 5926: 5924: 5921: 5920: 5916: 5913: 5910: 5907: 5904: 5901: 5899: 5896: 5895: 5891: 5888: 5885: 5882: 5879: 5876: 5874: 5871: 5870: 5866: 5863: 5860: 5857: 5854: 5851: 5849: 5846: 5845: 5842:Xenoestrogen 5841: 5838: 5835: 5832: 5829: 5826: 5822: 5820: 5817: 5816: 5813:Xenoestrogen 5812: 5809: 5806: 5803: 5800: 5797: 5794: 5792: 5789: 5788: 5785:Xenoestrogen 5784: 5781: 5778: 5775: 5772: 5769: 5767: 5765: 5761: 5760: 5757:Xenoestrogen 5756: 5753: 5750: 5747: 5744: 5741: 5739: 5737: 5733: 5732: 5729:Xenoestrogen 5728: 5725: 5722: 5719: 5716: 5713: 5711: 5708: 5707: 5704:Xenoestrogen 5703: 5700: 5697: 5694: 5691: 5688: 5686: 5683: 5682: 5679:Xenoestrogen 5678: 5675: 5672: 5669: 5666: 5663: 5661: 5658: 5657: 5654:Xenoestrogen 5653: 5650: 5647: 5644: 5641: 5638: 5636: 5633: 5632: 5629:Xenoestrogen 5628: 5625: 5622: 5619: 5616: 5613: 5611: 5608: 5607: 5604:Xenoestrogen 5603: 5600: 5597: 5594: 5592:16 (13–17.8) 5591: 5588: 5586: 5583: 5582: 5579:Xenoestrogen 5578: 5575: 5572: 5569: 5566: 5563: 5561: 5558: 5557: 5554:Xenoestrogen 5553: 5550: 5547: 5544: 5541: 5538: 5536: 5533: 5532: 5529:Xenoestrogen 5528: 5525: 5522: 5519: 5517:48 (13–52.5) 5516: 5513: 5511: 5508: 5507: 5504:Xenoestrogen 5503: 5500: 5497: 5494: 5491: 5488: 5486: 5483: 5482: 5479:Xenoestrogen 5478: 5475: 5472: 5469: 5466: 5463: 5461: 5458: 5457: 5454:Xenoestrogen 5453: 5450: 5447: 5444: 5441: 5438: 5436: 5433: 5432: 5429:Xenoestrogen 5428: 5425: 5422: 5419: 5416: 5413: 5411: 5408: 5407: 5404:Xenoestrogen 5403: 5400: 5397: 5394: 5391: 5388: 5386: 5383: 5382: 5379:Xenoestrogen 5378: 5375: 5372: 5369: 5366: 5363: 5361: 5358: 5357: 5354:Xenoestrogen 5353: 5350: 5347: 5344: 5341: 5338: 5336: 5333: 5332: 5329:Xenoestrogen 5328: 5325: 5322: 5319: 5316: 5313: 5311: 5308: 5307: 5304:Xenoestrogen 5303: 5300: 5297: 5294: 5291: 5288: 5286: 5283: 5282: 5279:Xenoestrogen 5278: 5275: 5272: 5269: 5266: 5263: 5261: 5258: 5257: 5254:Xenoestrogen 5253: 5250: 5247: 5244: 5241: 5238: 5236: 5233: 5232: 5229:Xenoestrogen 5228: 5225: 5222: 5219: 5216: 5213: 5211: 5208: 5207: 5204:Xenoestrogen 5203: 5200: 5197: 5194: 5191: 5188: 5186: 5183: 5182: 5179:Xenoestrogen 5178: 5175: 5172: 5169: 5166: 5163: 5161: 5158: 5157: 5153: 5150: 5147: 5144: 5141: 5138: 5136: 5133: 5132: 5128: 5125: 5122: 5119: 5116: 5113: 5111: 5108: 5107: 5103: 5100: 5097: 5094: 5091: 5088: 5086: 5083: 5082: 5078: 5075: 5072: 5069: 5066: 5063: 5061: 5058: 5057: 5053: 5050: 5047: 5044: 5041: 5038: 5036: 5033: 5032: 5028: 5025: 5022: 5019: 5016: 5013: 5011: 5008: 5007: 5003: 5000: 4997: 4994: 4991: 4988: 4986: 4983: 4982: 4978: 4975: 4972: 4969: 4966: 4963: 4961: 4958: 4957: 4953: 4950: 4947: 4944: 4941: 4938: 4936: 4933: 4932: 4928: 4925: 4922: 4919: 4916: 4913: 4911: 4908: 4907: 4904:Antiestrogen 4903: 4900: 4897: 4894: 4891: 4888: 4886: 4883: 4882: 4879:Antiestrogen 4878: 4875: 4872: 4869: 4866: 4863: 4861: 4858: 4857: 4853: 4850: 4847: 4844: 4841: 4838: 4836: 4833: 4832: 4828: 4825: 4822: 4819: 4816: 4813: 4811: 4808: 4807: 4803: 4800: 4797: 4794: 4791: 4788: 4786: 4783: 4782: 4778: 4775: 4772: 4769: 4766: 4763: 4761: 4758: 4757: 4753: 4750: 4747: 4744: 4741: 4738: 4736: 4733: 4732: 4728: 4725: 4722: 4719: 4716: 4713: 4711: 4708: 4707: 4703: 4700: 4697: 4694: 4691: 4688: 4686: 4683: 4682: 4678: 4675: 4672: 4669: 4666: 4663: 4661: 4658: 4657: 4653: 4650: 4647: 4644: 4641: 4638: 4636: 4633: 4632: 4628: 4625: 4622: 4619: 4616: 4613: 4611: 4608: 4607: 4603: 4600: 4597: 4594: 4591: 4588: 4586: 4583: 4582: 4578: 4575: 4572: 4569: 4566: 4563: 4561: 4558: 4557: 4553: 4550: 4547: 4544: 4541: 4538: 4536: 4533: 4532: 4528: 4525: 4522: 4519: 4516: 4513: 4511: 4508: 4507: 4503: 4500: 4497: 4494: 4491: 4488: 4486: 4483: 4482: 4478: 4475: 4472: 4469: 4466: 4463: 4461: 4458: 4457: 4453: 4450: 4447: 4444: 4441: 4438: 4436: 4433: 4432: 4428: 4425: 4422: 4419: 4416: 4413: 4411: 4408: 4407: 4403: 4400: 4397: 4394: 4391: 4388: 4386: 4383: 4382: 4378: 4375: 4372: 4369: 4366: 4363: 4361: 4358: 4357: 4353: 4350: 4347: 4344: 4341: 4338: 4336: 4333: 4332: 4328: 4325: 4322: 4319: 4316: 4313: 4311: 4308: 4307: 4303: 4300: 4297: 4294: 4291: 4288: 4286: 4283: 4282: 4278: 4275: 4272: 4269: 4266: 4263: 4261: 4258: 4257: 4253: 4250: 4247: 4244: 4241: 4238: 4235: 4234: 4230: 4227: 4224: 4221: 4218: 4215: 4213: 4210: 4209: 4205: 4202: 4199: 4196: 4193: 4190: 4188: 4185: 4184: 4180: 4177: 4174: 4171: 4168: 4165: 4163: 4160: 4159: 4155: 4152: 4149: 4146: 4143: 4140: 4138: 4135: 4134: 4130: 4127: 4124: 4121: 4119:18.6 (18–41) 4118: 4115: 4113: 4110: 4109: 4105: 4102: 4099: 4096: 4093: 4090: 4088: 4085: 4084: 4080: 4077: 4074: 4071: 4068: 4065: 4063: 4060: 4059: 4055: 4052: 4049: 4046: 4043: 4040: 4038: 4035: 4034: 4030: 4027: 4024: 4021: 4018: 4015: 4013: 4011: 4007: 4006: 4002: 3999: 3996: 3993: 3990: 3987: 3985: 3982: 3981: 3977: 3974: 3971: 3968: 3965: 3962: 3960: 3957: 3956: 3952: 3949: 3946: 3943: 3940: 3937: 3935: 3932: 3931: 3927: 3924: 3921: 3918: 3915: 3912: 3910: 3907: 3906: 3902: 3899: 3896: 3893: 3890: 3887: 3885: 3882: 3881: 3877: 3874: 3871: 3868: 3865: 3862: 3860: 3857: 3856: 3852: 3849: 3846: 3843: 3840: 3837: 3835: 3832: 3831: 3827: 3824: 3821: 3818: 3815: 3812: 3810: 3807: 3806: 3802: 3799: 3796: 3793: 3790: 3787: 3785: 3782: 3781: 3777: 3774: 3771: 3768: 3765: 3762: 3760: 3757: 3756: 3752: 3749: 3746: 3743: 3740: 3737: 3735: 3732: 3731: 3727: 3724: 3721: 3718: 3715: 3712: 3710: 3707: 3706: 3702: 3699: 3696: 3693: 3690: 3687: 3685: 3682: 3681: 3677: 3674: 3671: 3668: 3665: 3662: 3660: 3657: 3656: 3652: 3649: 3646: 3643: 3640: 3637: 3635: 3632: 3631: 3627: 3624: 3621: 3618: 3615: 3612: 3610: 3607: 3606: 3602: 3599: 3596: 3593: 3590: 3587: 3585: 3582: 3581: 3577: 3574: 3571: 3568: 3565: 3562: 3560: 3557: 3556: 3552: 3549: 3546: 3543: 3540: 3537: 3535: 3532: 3531: 3527: 3524: 3521: 3518: 3515: 3512: 3510: 3507: 3506: 3502: 3499: 3496: 3493: 3490: 3487: 3485: 3482: 3481: 3477: 3474: 3471: 3468: 3465: 3462: 3460: 3459:17-Epiestriol 3457: 3456: 3452: 3449: 3446: 3443: 3440: 3437: 3435: 3434:16-Epiestriol 3432: 3431: 3427: 3424: 3421: 3419:8.195 (2–42) 3418: 3415: 3413:17α-Estradiol 3412: 3410: 3407: 3406: 3402: 3399: 3396: 3393: 3390: 3387: 3385: 3382: 3381: 3377: 3374: 3371: 3368: 3365: 3362: 3360: 3357: 3356: 3352: 3349: 3346: 3343: 3340: 3337: 3335: 3332: 3331: 3327: 3324: 3321: 3318: 3315: 3312: 3310: 3307: 3306: 3303: 3300: 3298: 3295: 3293: 3290: 3288: 3285: 3284: 3273: 3268:(RBA, %) 3267: 3259: 3255: 3246: 3241: 3239: 3234: 3232: 3227: 3226: 3222: 3220: 3217: 3213: 3212:intravenously 3209: 3205: 3201: 3196: 3193: 3191: 3187: 3183: 3179: 3175: 3171: 3167: 3163: 3159: 3155: 3151: 3147: 3143: 3139: 3135: 3131: 3127: 3123: 3108: 3106: 3102: 3098: 3092: 3090: 3086: 3082: 3078: 3074: 3070: 3066: 3062: 3058: 3054: 3050: 3046: 3042: 3038: 3034: 3030: 3026: 3022: 3018: 3014: 3010: 3006: 3002: 2998: 2994: 2990: 2986: 2982: 2978: 2973: 2970: 2967: 2963: 2958: 2956: 2955:ascorbic acid 2952: 2948: 2944: 2940: 2936: 2934: 2930: 2926: 2922: 2919: 2915: 2911: 2908: 2904: 2903:carbamazepine 2900: 2899:phenobarbital 2896: 2892: 2888: 2884: 2880: 2876: 2872: 2868: 2858: 2856: 2850: 2840: 2838: 2834: 2831: 2827: 2824:. A study of 2823: 2819: 2815: 2811: 2807: 2804:. EE changed 2803: 2799: 2795: 2791: 2787: 2783: 2779: 2775: 2766: 2764: 2760: 2750: 2748: 2744: 2740: 2736: 2732: 2728: 2724: 2720: 2716: 2712: 2708: 2705: 2701: 2697: 2694: 2690: 2689:ABCB11 (BSEP) 2686: 2683: 2679: 2675: 2671: 2667: 2663: 2660: 2659:17α-alkylated 2657:similarly to 2656: 2653: 2643: 2639: 2637: 2633: 2629: 2625: 2621: 2617: 2613: 2608: 2606: 2602: 2598: 2594: 2590: 2586: 2582: 2578: 2563: 2559: 2555: 2551: 2547: 2544: 2540: 2536: 2532: 2528: 2524: 2520: 2518: 2515: 2514: 2510: 2508: 2505: 2504: 2500: 2498: 2495: 2494: 2490: 2488: 2485: 2484: 2480: 2478: 2475: 2474: 2470: 2468: 2465: 2464: 2460: 2458: 2455: 2453: 2448: 2444: 2440: 2437: 2434: 2433: 2429: 2426: 2423: 2421: 2417: 2413: 2411: 2407: 2404: 2403: 2395: 2388: 2385: 2383: 2379: 2375: 2372: 2369: 2368: 2364: 2361: 2358: 2357: 2349: 2337: 2334: 2333: 2329: 2327: 2324: 2323: 2319: 2317: 2313: 2310: 2309: 2301: 2289: 2286: 2285: 2277: 2265: 2262: 2261: 2257: 2255: 2252: 2251: 2243: 2236: 2233: 2232: 2224: 2217: 2214: 2212: 2207: 2203: 2196: 2190: 2187: 2184: 2181: 2178: 2177: 2170: 2165: 2163: 2158: 2156: 2151: 2150: 2146: 2144: 2140: 2135: 2131: 2127: 2123: 2119: 2115: 2111: 2107: 2103: 2099: 2095: 2091: 2088: 2087:thrombophilia 2083: 2080: 2074: 2071: 2067: 2063: 2059: 2055: 2051: 2047: 2043: 2039: 2035: 2034:absolute risk 2031: 2030:meta-analysis 2026: 2024: 2021: 2017: 2013: 2009: 2005: 2001: 1997: 1993: 1989: 1975: 1971: 1967: 1963: 1959: 1957: 1954: 1952: 1950: 1949: 1945: 1942: 1939: 1937: 1935: 1934: 1930: 1927: 1924: 1921: 1919: 1916: 1915: 1911: 1908: 1905: 1902: 1899: 1896: 1895: 1891: 1889: 1886: 1883: 1881: 1880:Acne vulgaris 1878: 1877: 1873: 1871: 1868: 1865: 1862: 1859: 1858: 1854: 1851: 1848: 1845: 1842: 1839: 1838: 1834: 1832: 1829: 1826: 1823: 1820: 1819: 1815: 1813: 1810: 1807: 1805: 1802: 1801: 1797: 1795: 1792: 1789: 1787: 1784: 1783: 1779: 1777: 1774: 1771: 1769: 1766: 1765: 1761: 1759: 1756: 1753: 1751: 1748: 1747: 1743: 1741: 1738: 1735: 1733: 1730: 1729: 1725: 1722: 1718: 1715: 1712: 1710: 1707: 1706: 1702: 1699: 1696: 1693: 1690: 1686: 1683: 1682: 1678: 1675: 1672: 1669: 1666: 1663: 1662: 1658: 1655: 1651: 1648: 1645: 1643: 1640: 1639: 1635: 1632: 1628: 1625: 1622: 1620: 1617: 1616: 1612: 1609: 1605: 1602: 1599: 1597: 1594: 1593: 1589: 1586: 1583: 1580: 1578: 1575: 1574: 1570: 1567: 1564: 1561: 1559: 1556: 1555: 1549: 1544: 1542: 1539: 1534: 1529: 1527: 1524: 1523: 1520: 1515: 1511: 1500: 1498: 1494: 1490: 1486: 1482: 1478: 1474: 1470: 1466: 1462: 1458: 1454: 1450: 1446: 1442: 1438: 1434: 1424: 1420: 1417: 1413: 1409: 1405: 1401: 1397: 1393: 1389: 1386: 1383: 1380: 1377: 1376: 1372: 1369: 1366: 1363: 1360: 1359: 1355: 1352: 1349: 1346: 1343: 1342: 1338: 1335: 1332: 1329: 1326: 1325: 1318: 1315: 1312: 1309: 1306: 1305: 1301: 1297: 1286: 1284: 1280: 1276: 1272: 1267: 1264: 1260: 1259:breastfeeding 1255: 1253: 1252:breast cancer 1246: 1242: 1239: 1235: 1233: 1229: 1226: 1223: 1219: 1217: 1213: 1211: 1208: 1205: 1202: 1200: 1197: 1194: 1190: 1187: 1184: 1182: 1178: 1174: 1170: 1169: 1168: 1166: 1162: 1158: 1154: 1150: 1146: 1142: 1132: 1128: 1125: 1121: 1117: 1114: 1104: 1102: 1098: 1093: 1091: 1090:sex offenders 1087: 1083: 1082:breast cancer 1079: 1075: 1071: 1066: 1064: 1060: 1056: 1052: 1048: 1044: 1040: 1036: 1031: 1029: 1025: 1024:birth control 1021: 1017: 1016:contraception 1007: 1005: 1001: 997: 989: 981: 973: 965: 957: 952: 950: 945: 943: 939: 935: 931: 927: 923: 919: 916: 912: 908: 904: 900: 896: 891: 889: 885: 881: 877: 873: 869: 865: 861: 857: 853: 849: 845: 841: 836: 834: 830: 826: 822: 818: 814: 811: 807: 803: 799: 795: 791: 781: 774: 765: 760: 759: 756: 749: 740: 739: 736: 729: 725: 723: 722:Melting point 719: 712: 708: 707: 705: 702: 697: 690: 688: 684: 663: 661: 657: 652: 648: 644: 641: 639: 637:ECHA InfoCard 633: 625: 621: 620:DTXSID5020576 617: 616: 614: 605: 601: 594: 590: 589: 587: 585: 581: 574: 570: 569: 567: 565: 561: 554: 550: 549: 547: 545: 541: 534: 530: 529: 527: 525: 521: 514: 510: 509: 507: 505: 501: 494: 490: 489: 487: 485: 481: 474: 470: 469: 467: 465: 461: 454: 450: 449: 447: 440: 436: 429: 425: 424: 422: 420: 416: 408: 404: 400: 396: 392: 388: 383: 382: 379: 372: 367: 363: 358: 355: 353: 349: 345: 343: 336: 331: 327: 325: 321: 317: 313: 310: 308: 304: 297: 291: 287: 285: 281: 277: 275: 271: 267: 263: 256: 255: 253: 251: 247: 242: 234: 229: 224: 219: 216: 215: 213: 211: 207: 204: 201: 199: 195: 192: 188: 184: 180: 178: 172: 168: 164: 162: 158: 154: 150: 148: 144: 140: 136: 132: 128: 126: 122: 116: 54: 52:Pronunciation 50: 47:Clinical data 45: 41: 36: 32: 27: 19: 20427:Hepatotoxins 20356: 20336:Ketoconazole 20333:Antagonists: 20332: 20306:Troglitazone 20281:Tetracycline 20236:Spiroxatrine 20181:Quingestrone 20176:Progesterone 20161:Pregnenolone 20156:Pregnanolone 20146:Pregnanediol 20141:Prednisolone 20066:Mifepristone 19993: 19968:Griseofulvin 19948:Fenbendazole 19933:Famprofazone 19928:Erythromycin 19923:Epothilone B 19908:Eburnamonine 19803:Clotrimazole 19793:Clofenvinfos 19728:Antimycotics 19659: 19622:Okadaic acid 19606: 19574:Antagonists: 19573: 19562:Troglitazone 19497:Mifepristone 19492:Methoxychlor 19487:Griseofulvin 19482:Ellagic acid 19462:Cypermethrin 19452:Clotrimazole 19403: 19140: 19039: 19029: 18953:Mepitiostane 18901:Epitiostanol 18770:Ormeloxifene 18695:Lasofoxifene 18605:Camizestrant 18600:Broparestrol 18590:Bazedoxifene 18512:rotundifuran 18461:alkylphenols 18411:β-zearalenol 18407:α-zearalenol 18393:stigmasterol 18385:β-sitosterol 18381:Phytosterols 18349:triclocarban 18345:methoxychlor 18298: 18280:Lavender oil 18274:tectorigenin 18206:formononetin 18080: 18055: 17926: 17918: 17718: 17702:Quinestradol 17692:Promestriene 17667:Noretynodrel 17574: 17531:Estromustine 17484:Estramustine 17419: 17326:testosterone 17063: 16916: 16901: 16861:Progestogens 16764:testosterone 16724: 16709: 16703:Testolactone 16694: 16673: 16658: 16632:Ormeloxifene 16627:Mepitiostane 16622:Lasofoxifene 16617:Epitiostanol 16597:Broparestrol 16592:Bazedoxifene 16480:bicalutamide 16346: 16335:Quinestradol 16330:Promestriene 16275: 16124:noretynodrel 16105:metandienone 16093:testosterone 16075: 15977: 15973: 15947: 15943: 15910: 15906: 15886: 15866: 15851: 15844: 15836: 15821: 15813: 15793: 15786: 15732: 15726: 15699: 15693: 15668: 15664: 15658: 15649: 15643: 15626: 15601: 15597: 15591: 15566: 15558: 15533: 15529: 15523: 15506: 15500: 15467: 15461: 15454: 15434: 15374: 15370: 15326:(1): 13–17. 15323: 15319: 15313: 15291:(1): 69–75. 15288: 15284: 15278: 15258: 15215: 15211: 15180: 15140:(1): 52–58. 15137: 15133: 15091:(2): 63–75. 15088: 15084: 15078: 15058: 15051: 15031: 14994: 14990: 14984: 14951: 14947: 14916: 14879: 14875: 14869: 14828: 14822: 14802: 14795: 14762: 14758: 14752: 14717: 14711: 14691: 14684: 14659: 14655: 14649: 14614: 14610: 14600: 14580: 14573: 14553: 14508: 14504: 14497: 14464: 14461:The Prostate 14460: 14426: 14422: 14380: 14376: 14370: 14338:(1): 18–40. 14335: 14331: 14321: 14286: 14282: 14272: 14255: 14251: 14245: 14218: 14214: 14204: 14184: 14145: 14141: 14098: 14094: 14066: 14062: 14052: 14025: 14019: 14009: 14002: 13982: 13975: 13966: 13946: 13942: 13936: 13911: 13907: 13901: 13876: 13872: 13866: 13834:(1): 74–81. 13831: 13827: 13817: 13792: 13788: 13782: 13747: 13741: 13716: 13712: 13706: 13681: 13677: 13671: 13651: 13644: 13617: 13607: 13587: 13580: 13560: 13553: 13533: 13526: 13509: 13505: 13499: 13474: 13470: 13464: 13439: 13435: 13417: 13402: 13395: 13386: 13371: 13364: 13355: 13340: 13322: 13307: 13277: 13270: 13250: 13243: 13208: 13204: 13194: 13185: 13155: 13151: 13141: 13133: 13103: 13099: 13089: 13052: 13048: 13038: 13003: 12999: 12989: 12952: 12948: 12938: 12913: 12909: 12903: 12870: 12866: 12810: 12806: 12800: 12767: 12763: 12707: 12703: 12668: 12661: 12641: 12596: 12592: 12586: 12553: 12549: 12542: 12501: 12497: 12470: 12463: 12430: 12426: 12389: 12382: 12339: 12306: 12276: 12269: 12242: 12238: 12203: 12159:(1): 42–47. 12156: 12152: 12096: 12092: 12058: 12054: 12009: 12006:The Prostate 12005: 11957: 11953: 11919: 11915: 11909: 11882: 11878: 11868: 11848: 11811: 11807: 11801: 11766: 11762: 11752: 11735: 11731: 11683: 11679: 11669: 11642: 11638: 11628: 11619: 11604: 11598: 11589: 11574: 11567: 11558: 11543: 11536: 11509: 11505: 11495: 11475: 11424: 11420: 11410: 11388:(1): 25–34. 11385: 11381: 11346:(1): 43–51. 11343: 11339: 11292: 11262: 11232: 11225: 11205: 11198: 11163: 11159: 11149: 11117:(1): 90–96. 11114: 11110: 11078: 11043:(1): 32–37. 11040: 11036: 11007: 10964: 10940: 10928: 10919: 10907: 10887: 10857: 10839: 10816: 10809: 10800: 10785: 10778: 10760: 10754: 10746: 10731: 10724: 10704: 10672: 10646: 10613: 10609: 10603: 10570: 10566: 10560: 10533: 10529: 10479: 10475: 10433: 10429: 10419: 10394: 10390: 10368:. Retrieved 10364: 10355: 10343:. Retrieved 10334: 10325: 10313:. Retrieved 10309: 10300: 10288:. Retrieved 10284: 10275: 10263:. Retrieved 10259: 10250: 10238:. Retrieved 10234: 10225: 10213:. Retrieved 10209: 10200: 10188:. Retrieved 10179: 10137: 10130: 10105: 10101: 10095: 10087: 10072: 10019: 10012: 10000:. Retrieved 9970: 9948: 9910: 9906: 9853: 9833: 9818: 9685: 9681: 9566: 9559: 9539: 9507:(2): 59–69. 9504: 9500: 9452: 9448: 9410: 9406: 9373: 9338: 9335:Availability 9326: 9312: 9309:etonogestrel 9298: 9292: 9279: 9275: 9271: 9267: 9263: 9259: 9255: 9251: 9247: 9245: 9231: 9227: 9225: 9220: 9212: 9195: 9187: 9161: 9148: 9144: 9140: 9101:generic name 9093: 9092: 9079: 9072: 9065: 9042: 9007:derivatives 8963:A number of 8962: 8924:testosterone 8899: 8879: 8852: 8839: 8803: 8782:glucuronides 8759: 8743: 8740:Distribution 8715: 8711: 8679: 8638: 8477: 8465: 8433: 8385: 8361: 8348:triglyceride 8329: 8313: 8292: 8268: 8252: 8208:antiandrogen 8205: 8132: 8120: 7555: 7479:= Increased 7465: 7461: 7013: 6936:testosterone 6923:progesterone 6921:(100%) were 6914: 6572:<0.1–0.16 6399: 6381: 6372: 6367:Progestogen 6342:Progestogen 6317:Progestogen 6292:Progestogen 6267:Progestogen 6258:<0.1–0.22 6242:Progestogen 6217:Progestogen 6198:Progesterone 5886:221–>5000 5848:Testosterone 5824: 5795: 5791:Methoxychlor 5763: 5735: 5589:β-Zearalanol 5564:α-Zearalanol 5535:β-Zearalenol 5510:α-Zearalenol 5460:β-Sitosterol 5154:ERβ agonist 5129:ERβ agonist 5104:ERβ agonist 5079:ERβ agonist 5054:ERβ agonist 5029:ERβ agonist 4979:ERα agonist 4954:ERα agonist 4929:ERα agonist 4810:Bazedoxifene 4735:Ormeloxifene 4710:Lasofoxifene 4009: 3197: 3194: 3119: 3111:Pharmacology 3105:etonogestrel 3093: 3053:theophylline 2974: 2959: 2937: 2895:ethosuximide 2864: 2861:Interactions 2852: 2810:vitellogenin 2772: 2756: 2729:by 19%, and 2693:MRP2 (ABCC2) 2649: 2646:Liver damage 2640: 2609: 2581:bioidentical 2574: 2561: 2560:< 0.01). 2557: 2549: 2546:progesterone 2543:Bioidentical 2526: 2118:drospirenone 2092: 2084: 2075: 2054:drospirenone 2027: 2023:inactivation 1985: 1973: 1965: 1642:Dysmenorrhea 1477:hypogonadism 1475:in general, 1473:feminization 1469:gynecomastia 1430: 1422: 1418: 1415: 1399: 1395: 1298:and risk of 1289:Side effects 1268: 1256: 1249: 1243:Complicated 1204:Hypertension 1185:Acute DVT/PE 1138: 1129: 1110: 1094: 1070:hypogonadism 1067: 1047:night sweats 1032: 1013: 1010:Medical uses 1000:drospirenone 980:etonogestrel 964:norgestimate 953: 946: 892: 884:liver damage 872:hypogonadism 870:in general, 868:feminization 840:side effects 838:The general 837: 833:vaginal ring 793: 789: 788: 777: 406: 402: 398: 394: 390: 386: 339:Elimination 250:Legal status 244:Legal status 18: 20321:Zafirlukast 20291:Thiothixene 20271:Terconazole 20221:Simvastatin 20096:Nisoldipine 20091:Nilvadipine 20076:Nicardipine 20046:Metacycline 19873:Dimercaprol 19828:Demecolcine 19788:Clindamycin 19783:Ciglitazone 19733:Artemisinin 19713:Ambrisentan 19617:Nigramide J 19552:Telmisartan 19512:Nicardipine 19422:Benfuracarb 19417:Artemisinin 19298:Zearalenone 19250:Antagonists 19226:Resveratrol 19191:Nonylphenol 19186:Niacinamide 19102:Bisphenol A 19092:Aldosterone 18921:Glyceollins 18869:Antagonists 18860:Zuclomifene 18855:Zindoxifene 18765:NNC 45-1506 18760:NNC 45-0781 18755:NNC 45-0320 18750:NNC 45-0095 18745:Nitromifene 18725:Miproxifene 18675:Fispemifene 18650:Enclomifene 18645:Droloxifene 18625:CN-55945-27 18570:Afimoxifene 18560:Acefluranol 18451:rhaponticin 18447:resveratrol 18443:Stilbenoids 18415:zearalenone 18403:zearalanone 18389:campesterol 18321:alternariol 18254:pinocembrin 18198:epicatechin 18170:biochanin A 18110:Chalconoids 18004:Terfluranol 17979:Quadrosilan 17851:Elacestrant 17752:Allenestrol 17627:Lynestrenol 17551:Estropipate 17521:Estrofurate 17372:Clomestrone 17352:Atrimustine 17302:Abiraterone 17256:alfatradiol 16950:from market 16847:antagonists 16834:leuprorelin 16813:haloperidol 16809:risperidone 16801:domperidone 16793:antagonists 16776:oxandrolone 16728:Anastrozole 16667:Fulvestrant 16662:Elacestrant 16612:Enclomifene 16555:antagonists 16500:leuprorelin 16443:Quadrosilan 16219:Climacteron 16138:Clomestrone 16079:Alfatradiol 15907:Climacteric 12556:: 110–121. 12099:(1): 4–14. 11560:tenderness. 10002:22 December 9682:Climacteric 9242:Brand names 9045:Schering AG 9033:methandriol 8965:derivatives 8928:ethisterone 8884:62% in the 8876:Elimination 8806:metabolized 8615:~500–1,500 8525:2–5 × 10 M 8468:endometrium 8373:desogestrel 8342:(CBG), and 8164:Dosed daily 7473:hot flashes 6975:aldosterone 6721:Alfatradiol 5883:0.0059–0.17 5714:Chlordecone 5660:Bisphenol A 5635:Zearalanone 5610:Zearalenone 5485:Resveratrol 5385:Ipriflavone 5370:0.002–0.040 5260:Biochanin A 5089:WAY-202,196 4960:16α-Iodo-E2 4889:ICI-182,780 4885:Fulvestrant 4860:ICI-164,384 4739:Centchroman 4535:Afimoxifene 4517:3 (0.1–47) 4187:Δ-Estradiol 4016:1-Estradiol 3928:Metabolite 3903:Metabolite 3878:Metabolite 3853:Metabolite 3828:Metabolite 3803:Metabolite 3778:Metabolite 3753:Metabolite 3728:Metabolite 3703:Metabolite 3678:Metabolite 3653:Metabolite 3628:Metabolite 3603:Metabolite 3578:Metabolite 3553:Metabolite 3528:Metabolite 3503:Metabolite 3478:Metabolite 3453:Metabolite 3428:Metabolite 3409:Alfatradiol 3262:Other names 3208:estropipate 3101:desogestrel 3089:propranolol 3077:lamotrigine 3041:propranolol 3021:mephenytoin 2939:Paracetamol 2921:antibiotics 2914:fluconazole 2910:antifungals 2837:green frogs 2828:found more 2685:metabolites 2682:Glucuronide 2652:cholestatic 2616:transdermal 2410:progestogen 2382:Transdermal 2185:Medications 2110:desogestrel 2102:coagulation 2085:Women with 2050:desogestrel 1982:Blood clots 1824:(incidence) 1667:(incidence) 1577:Menorrhagia 1481:infertility 1457:weight gain 1313:Woman-years 1230:History of 1171:History of 1149:blood clots 1113:transdermal 1101:progestogen 1099:; giving a 1080:in men and 1043:hot flashes 880:blood clots 848:enlargement 694: g·mol 643:100.000.311 369:Identifiers 324:Metabolites 314:(primarily 288:97–98% (to 187:Transdermal 161:MedlinePlus 134:Other names 125:Trade names 20396:Categories 20301:Tianeptine 20266:Tenylidone 20261:Tacrolimus 20206:Rimexolone 20196:Rifampicin 20136:Plicamycin 20121:Paclitaxel 20106:Omeprazole 20086:Nifedipine 20061:Mevastatin 20056:Metyrapone 20036:Lovastatin 20031:Loratadine 19988:Hyperforin 19978:Haloprogin 19943:Felodipine 19918:Enzacamene 19898:Dronabinol 19863:Diclazuril 19842:prasterone 19798:Chloroxine 19773:Cephradine 19743:Bile acids 19557:Tolnaftate 19522:Permethrin 19507:Nevirapine 19502:Nefazodone 19471:prasterone 19432:Carvedilol 19412:Amiodarone 19383:modulators 19241:Tectoridin 19221:Raloxifene 19196:Oleuropein 19043:Trilostane 18988:Prochloraz 18948:MDL-101906 18943:ICI-164384 18830:Trioxifene 18825:Toremifene 18795:Raloxifene 18780:Panomifene 18775:Ospemifene 18740:Nafoxidine 18630:Cyclofenil 18585:Arzoxifene 18565:Acolbifene 18497:phthalates 18465:bisphenols 18437:miroestrol 18341:methiocarb 18329:endosulfan 18317:Pesticides 18289:enterodiol 18270:tectoridin 18250:penduletin 18246:naringenin 18230:kaempferol 18146:Flavonoids 18140:psoralidin 18136:coumestrol 18132:Coumestans 18096:dianethole 18049:WAY-214156 18039:WAY-200070 18034:WAY-169916 18029:WAY-166818 17999:SKF-82,958 17964:Phenestrol 17944:Methestrol 17929:-Hexestrol 17921:-Butestrol 17802:Dienestrol 17782:Carbestrol 17767:Bifluranol 17762:Benzestrol 17707:Quinestrol 17657:Nilestriol 17499:Estrazinol 17432:Epimestrol 17422:-Estradiol 17404:Cyclotriol 17342:nandrolone 17317:Almestrone 17152:7-Oxo-DHEA 17064:Steroidal: 17036:modulators 16910:Gestrinone 16851:cetrorelix 16733:Exemestane 16718:Formestane 16677:Trilostane 16652:Toremifene 16642:Raloxifene 16637:Ospemifene 16607:Cyclofenil 16582:Acolbifene 16365:Dienestrol 16355:Bifluranol 16350:Benzestrol 16340:Quinestrol 16308:Nilestriol 16163:Epimestrol 16158:Epiestriol 16116:progestins 16076:Steroidal: 15700:Gynecology 13388:necessary. 13357:mestranol. 11621:estradiol. 10836:1058058829 10370:14 January 10345:14 January 10315:14 January 10290:14 January 10265:14 January 10240:14 January 10215:14 January 10190:14 January 9343:References 9294:Ortho Evra 9276:Spanestrin 9017:Androstane 9013:nilestriol 8973:quinestrol 8957:See also: 8912:derivative 8882:eliminated 8859:metabolite 8770:conjugated 8762:intestines 8756:Metabolism 8736:exposure. 8652:Absorption 8546:90 minutes 8496:Parameters 8484:parenteral 8296:norgestrel 8212:production 7986:Dienestrol 7886:Quinestrol 7871:300–600 μg 7826:0.625–1.25 6917:Reference 6749:Epiestriol 6373:Footnotes: 6298:Δ-Tibolone 6130:<0.0001 5933:0.019–0.07 5898:Nandrolone 5745:0.0073–0.4 5717:0.0069–0.2 5685:Endosulfan 5410:Miroestrol 5310:Naringenin 5285:Kaempferol 5160:Coumestrol 5060:Prinaberel 4785:Ospemifene 4714:CP-336,156 4689:LY-353,381 4685:Arzoxifene 4673:0.188–0.52 4660:Raloxifene 4635:Nafoxidine 4610:Cyclofenil 4560:Toremifene 4514:ICI-46,474 4385:Dienestrol 4022:9.44–80.07 4019:1.31–12.34 4012:-Estradiol 3566:13 (8–70) 3541:0.0027–2.0 3516:22 (7–81) 3073:clofibrate 3061:selegiline 3057:tizanidine 3049:selegiline 3037:omeprazole 3033:nifedipine 2929:rifampicin 2847:See also: 2826:mink frogs 2782:freshwater 2774:Wastewater 2739:morphology 2731:leukocytes 2727:hematocrit 2636:parenteral 2550:Footnotes: 2371:Raloxifene 2189:Odds ratio 2058:postpartum 2016:structural 1998:(DVT) and 1988:blood clot 1970:Odds ratio 1966:Footnotes: 1941:Cervicitis 1907:Dermatitis 1423:Additional 1406:, such as 1396:Footnotes: 1263:postpartum 988:norgestrel 930:metabolism 918:derivative 913:. It is a 810:menopausal 806:progestins 699:3D model ( 687:Molar mass 573:CHEBI:4903 533:423D2T571U 504:ChemSpider 464:IUPHAR/BPS 419:CAS Number 378:IUPAC name 346:7–36 hours 307:Metabolism 198:Drug class 20226:Sirolimus 20216:Ritonavir 20211:Riodipine 20201:Rifaximin 20186:Reserpine 20171:Proadifen 20116:Oxatomide 20071:Nafcillin 20041:Meclizine 19903:Droxidopa 19883:Docetaxel 19808:Colforsin 19758:Bumecaine 19748:Bithionol 19660:Agonists: 19637:T-0901317 19612:Meclizine 19542:Reserpine 19532:Phenytoin 19517:Octicizer 19477:Efavirenz 19404:Agonists: 19236:Tamoxifen 19216:Quercetin 19156:Genistein 19136:Estradiol 19120:o',p'-DDE 19023:ZK-191703 19018:ZK-164015 18978:Phenytoin 18876:(R,R)-THC 18815:Tamoxifen 18790:Promensil 18715:LY-117018 18690:Idoxifene 18685:ICI-55548 18670:Femarelle 18655:Endoxifen 18615:Clomifene 18371:diosgenin 18367:digitalis 18363:digitoxin 18353:triclosan 18333:fenarimol 18266:quercetin 18242:myricetin 18238:mirificin 18226:glycitein 18218:genistein 18214:glabridin 18174:calycosin 18162:baicalein 18118:phloretin 18074:ZK-283197 17934:Mestilbol 17896:Hexestrol 17871:Fenestrel 17846:Efavirenz 17777:Butestrol 17732:2,8-DHHHC 17727:(S,S)-THC 17722:(R,R)-THC 17677:Pentolame 17672:Orestrate 17647:Moxestrol 17637:Mestranol 17602:Etynodiol 17462:Estradiol 17437:Equilenin 17399:Cyclodiol 17357:Bolandiol 16960:Phase III 16948:Withdrawn 16838:goserelin 16821:sulpiride 16797:prolactin 16756:Androgens 16738:Letrozole 16713:Fadrozole 16647:Tamoxifen 16602:Clomifene 16409:Hexestrol 16303:Moxestrol 16293:Mestranol 16178:Estradiol 16085:androgens 16053:Estrogens 16041:Estrogens 15470:(6): 96. 14855:cite book 14362:259361637 14164:2380-548X 13963:0001-6349 13774:0172-777X 13733:0001-6349 13684:: 47–61. 13471:Maturitas 12621:260318275 12578:128359413 12374:0171-2004 12356:1865-0325 11885:(1): 85. 11879:MedGenMed 10536:: 11–23. 10530:Maturitas 9268:Novestrol 9215:, and in 9075:mestranol 8989:analogues 8981:moxestrol 8969:mestranol 8953:Analogues 8939:androgens 8916:estradiol 8902:synthetic 8896:Chemistry 8855:oxidative 8778:sulfation 8676:in women. 8625:pituitary 8620:Relative 8600:Relative 8555:Substrate 8536:24 hours 8533:6–8 hours 8500:Estradiol 8460:oxidation 8369:triphasic 8301:ovulation 8256:pregnancy 8248:hirsutism 8230:from the 8228:secretion 8036:Hexestrol 7877:>80 μg 7861:Mestranol 7597:Compound 7305:0.56–1.7 7163:Estradiol 6949:estradiol 6859:Moxestrol 6803:Mestranol 6525:Estradiol 6358:0.070–0.1 6283:0.2–0.076 6192:Estrogen 6167:Estrogen 6142:Androgen 6117:Androgen 6114:>10000 6111:>10000 6092:Androgen 6089:>10000 6086:>10000 6067:Androgen 6042:Androgen 6017:Androgen 6014:>10000 6011:>10000 5992:Androgen 5967:Androgen 5942:Androgen 5917:Androgen 5892:Androgen 5867:Androgen 5804:0.01–0.13 5585:Taleranol 5360:Quercetin 5217:0.2–0.287 5185:Genistein 5176:0.07–27.0 5173:0.14–80.0 5110:Erteberel 5017:0.12–0.25 4795:0.59–1.22 4792:0.82–2.63 4639:U-11,000A 4585:Clomifene 4573:7.14–20.3 4510:Tamoxifen 4504:Estrogen 4479:Estrogen 4454:Estrogen 4429:Estrogen 4404:Estrogen 4379:Estrogen 4360:Hexestrol 4354:Estrogen 4329:Estrogen 4304:Estrogen 4285:Moxestrol 4279:Estrogen 4260:Mestranol 4254:Estrogen 4251:0.29–0.81 4248:0.02–0.05 4231:Estrogen 4212:Δ-Estrone 4206:Estrogen 4181:Estrogen 4156:Estrogen 4131:Estrogen 4106:Estrogen 4081:Estrogen 4062:Equilenin 4056:Estrogen 4031:Estrogen 4003:Estrogen 3978:Estrogen 3953:Estrogen 3888:E2-3G-17S 3403:Estrogen 3378:Estrogen 3353:Estrogen 3328:Estrogen 3309:Estradiol 3219:mestranol 3190:pregnancy 3186:ovulation 3176:(LH) and 3154:estradiol 3120:EE is an 3097:gestodene 3081:lorazepam 3069:sulfation 3045:proguanil 3025:midazolam 3013:bupropion 2918:rifamycin 2891:primidone 2887:phenytoin 2820:in their 2806:oogenesis 2790:amphibian 2707:excretion 2704:bile salt 2702:flow and 2662:androgens 2628:morbidity 2620:mortality 2577:synthetic 2535:QResearch 2425:Estradiol 2406:Estradiol 2387:Estradiol 2216:Estradiol 2139:estradiol 2122:dienogest 2114:gestodene 2012:estradiol 1986:VTE is a 1928:(melasma) 1852:(itching) 1827:0.37–0.64 1808:0.40–0.50 1700:(strokes) 1453:dizziness 1319:Adjusted 1283:hepatitis 1281:, active 1236:Systemic 1191:Advanced 1175:(DVT) or 1118:and as a 1086:sex drive 1063:estradiol 996:etynodiol 922:estradiol 915:synthetic 911:estradiol 893:EE is an 593:ChEMBL691 352:Excretion 341:half-life 175:Routes of 147:Drugs.com 20417:Estranes 20386:Medicine 20353:See also 20241:SR-12813 20131:Piperine 20111:Orlistat 20081:Nicotine 19953:Fentanyl 19938:Febantel 19913:Ecopipam 19878:Dinaline 19763:Cafestol 19753:Bosentan 19627:PK-11195 19314:See also 19116:p,p'-DDT 19107:Daidzein 19097:Atrazine 19070:Agonists 18998:RU-58668 18993:RU-39411 18840:U-11555A 18835:TZE-5323 18580:Anordrin 18575:Anordiol 18508:agnuside 18485:parabens 18325:dieldrin 18297:nyasol ( 18262:puerarin 18258:prunetin 18222:genistin 18210:glabrene 18182:daidzein 18178:catechin 18166:baicalin 18158:apigenin 18088:anethole 17876:FERb 033 17712:Tibolone 17697:RU-16117 17682:Prodiame 17617:Hippulin 17612:Hexolame 17457:Estetrol 17367:Butolame 17057:Agonists 16972:See also 16855:elagolix 16830:agonists 16790:receptor 16587:Anordrin 16489:agonists 16173:Estetrol 16132:tibolone 16114:Certain 16083:Certain 16069:agonists 16002:11212469 15994:25099693 15964:23375353 15935:24616324 15927:16112947 15685:13359169 15618:16389046 15492:46648877 15399:11212469 15391:25099693 15348:73487051 15340:30809949 15240:43298472 15181:Migraine 15162:27729272 15154:12520628 15113:23760705 15105:21538049 15011:22244780 14787:53246678 14779:30325245 14633:29603164 14533:40497389 14489:33063805 14405:44335732 14397:22950535 14354:37419659 14313:24082040 14264:18338653 14237:22294742 14075:13370006 13928:14902290 13893:15432047 13858:29756046 13809:29603164 13235:23841731 13182:24530924 13130:21844907 13081:20403194 13030:26023144 12981:21321128 12930:16554039 12895:71784426 12887:17253885 12835:86245855 12827:15304426 12792:32669410 12784:16152976 12744:17517636 12613:18814084 12570:31009688 12526:17261770 12480:30020636 12455:73398961 12261:28667081 12183:24932461 12121:34563641 12113:24256023 12034:21510744 11982:32650111 11936:22011208 11901:16915215 11828:18692609 11793:20803995 11785:22469296 11744:12047300 11710:23904209 11661:27678035 11528:28376481 11451:32431379 11402:23384743 11362:27793376 11190:23904209 10638:10971754 10595:14949511 10587:20459370 10552:27889048 10508:28078219 10411:16860174 10365:ClinCalc 10339:Archived 10335:ClinCalc 10310:ClinCalc 10285:ClinCalc 10260:ClinCalc 10235:ClinCalc 10210:ClinCalc 10184:Archived 10180:ClinCalc 10122:25841596 9927:23375353 9710:24616324 9702:16112947 9479:22468839 9314:NuvaRing 9280:Ylestrol 9256:Feminone 9202:and its 9177:and its 9061:Schering 9057:Schering 8985:prodrugs 8918:with an 8639:Sources: 8549:7 hours 8522:1 × 10 M 8518:affinity 8446:express 7899:25–50 μg 7874:25–30 μg 7849:20–40 μg 7829:>3.75 7645:≥120–300 7556:Sources: 7526:levels. 7513:levels. 7451:5.7–7.5 7414:2.9–5.0 7342:1.3–4.5 7053:Estrogen 7014:Sources: 7001:cortisol 6977:for the 6964:for the 6951:for the 6938:for the 6925:for the 6909:<0.1 6881:<0.1 6825:<0.1 6797:<0.1 6687:<0.1 6631:<0.1 6575:<0.1 6547:<0.1 6440:Estrogen 6400:Sources: 6383:in-vitro 6273:Tibolone 6158:<0.07 6108:<0.01 6105:<0.01 6083:<0.01 6080:<0.01 6052:3β-Adiol 6027:3α-Adiol 6008:<0.01 6005:<0.01 5936:245–1053 5864:>5000 5861:>5000 5695:<0.01 5395:<0.01 5392:<0.01 5235:Daidzein 5201:0.3–12.8 4835:Etacstil 4717:10.2–166 4551:0.04–4.8 4523:3.4–9.69 3763:4-MeO-E3 3688:4-MeO-E1 3638:2-MeO-E1 3588:4-MeO-E2 3538:2-MeO-E2 3425:0.43–1.2 3422:0.2–0.52 3384:Estetrol 3150:affinity 3134:isoforms 3122:estrogen 3085:oxazepam 3029:nicotine 3017:caffeine 2979:several 2925:rifampin 2879:inducers 2877:. Thus, 2855:overdose 2843:Overdose 2833:tadpoles 2830:intersex 2696:proteins 2678:jaundice 2674:pruritus 2579:and non- 2360:Tibolone 2079:Cochrane 2048:such as 1974:Sources: 1926:Chloasma 1909:(eczema) 1850:Pruritus 1465:fullness 1445:bloating 1437:headache 1416:Sources: 1316:VTE rate 1206:≥160/100 1141:arterial 1051:flushing 1041:such as 949:combined 897:, or an 895:estrogen 852:headache 825:by mouth 813:symptoms 798:estrogen 796:) is an 780:(verify) 484:DrugBank 333:• Others 210:ATC code 203:Estrogen 183:By mouth 20452:Phenols 20341:Sesamin 20326:Zeranol 20256:Suramin 20026:LOE-908 19718:AMI-193 19632:S-07662 19547:TCPOBOP 19442:Chrysin 19286:Unknown 19262:Estriol 19166:GPER-L2 19161:GPER-L1 18845:U-11634 18720:Menerba 18710:LN-2299 18705:LN-1643 18680:GW-7604 18635:D-15413 18467:(e.g., 18459:(e.g., 18445:(e.g., 18429:Steroid 18401:(e.g., 18383:(e.g., 18361:(e.g., 18319:(e.g., 18311:cadmium 18309:(e.g., 18287:(e.g., 18285:Lignans 18186:daidzin 18150:7,8-DHF 18148:(incl. 18134:(e.g., 18112:(e.g., 17994:SERBA-2 17989:SC-4289 17984:SC-3296 17891:GTx-758 17787:D-15414 17737:β-LGND1 17687:Prolame 17536:Estrone 17504:Estriol 17442:Equilin 17324:(e.g., 17237:16α-LE2 16905:Danazol 16863:(e.g., 16849:(e.g., 16832:(e.g., 16762:(e.g., 16557:(incl. 16508:(e.g., 16491:(e.g., 16478:(e.g., 16458:Zeranol 16254:Estrone 16237:(e.g., 16230:Estriol 16185:(e.g., 16118:(e.g., 16091:(e.g., 15550:4098492 15472:Bibcode 15305:7195405 15232:6342899 14976:6815423 14968:7586614 14896:1146927 14744:4574573 14676:4568621 14641:4492779 14525:2630306 14481:3217277 14443:7000222 14304:3845679 14115:4359746 13849:5944393 13491:2215269 13456:6291391 13226:3823379 13173:4040308 13121:3474542 13072:2864220 13021:4485017 12972:3075970 12735:1874224 12712:Bibcode 12534:7932937 12506:Bibcode 12447:2086334 12174:4052190 12075:3817605 12026:2664738 11974:3242384 11892:1682006 11701:7173696 11442:6322116 11181:7173696 11141:1983923 11132:1404924 11057:1983896 10770:7074861 10630:4607733 10499:5182227 9994:. U.S. 9972:organs. 9521:8842581 9470:3399636 9427:2256522 9272:Palonyl 9264:Menolyn 9260:Lynoral 9252:Estinyl 9234:in the 9200:Italian 9192:Spanish 9098:English 9096:is the 9039:History 9005:estriol 8908:steroid 8905:estrane 8869:enzymes 8790:estrone 8750:albumin 8670:tablets 8662:fasting 8627:potency 8608:potency 8560:17β-HSD 8456:estrone 8068:>100 7999:0.5–4.0 7949:0.5–2.0 7868:1.5–3.0 7855:100 μg 7770:140–150 7745:120–150 7738:Estriol 7433:2.9–3.4 7408:500–600 7405:500–600 7336:1.3–1.5 7333:3.0–3.2 7324:1.1–1.3 7302:1.4–1.5 7299:0.5–0.7 7287:0.8–0.9 7237:Estriol 7200:Estrone 6919:ligands 6906:<0.1 6878:<0.2 6875:<0.1 6866:<0.1 6822:<0.1 6779:100–112 6693:Equilin 6684:<0.1 6665:Estriol 6609:Estrone 6388:labeled 6333:0.6–0.8 5939:163–515 5889:73–1688 5830:1.2–1.7 5827:-OH-DDT 5560:Zeranol 5198:2.6–126 5135:SERBA-2 5085:ERB-196 5045:22.0–83 4942:14.6–57 4935:16α-LE2 4839:GW-5638 4642:30.9–44 4617:151–152 4097:7.9–108 4094:7.9–113 4047:13.0–49 4037:Equilin 3738:2-OH-E3 3716:2.0–6.5 3666:1.0–2.0 3663:4-OH-E1 3619:0.2–0.4 3616:2.0–4.0 3613:2-OH-E1 3563:4-OH-E2 3513:2-OH-E2 3359:Estriol 3334:Estrone 3281:Action 3216:prodrug 3136:of the 3005:inducer 2997:CYP2C19 2977:inhibit 2969:enzymes 2962:smoking 2818:encoded 2562:Sources 2420:Vaginal 2028:A 2012 1843:(death) 1721:smokers 1719:(heavy 1676:(total) 1654:smokers 1652:(heavy 1631:smokers 1629:(light 1608:smokers 1568:(total) 1541:Disease 1526:Disease 1384:245,000 1333:127,000 1159:(VTE), 926:natural 901:of the 899:agonist 692:296.410 660:Formula 493:DB00977 439:PubChem 428:57-63-6 290:albumin 230: ( 228:L02AA03 226:) 220: ( 218:G03CA01 191:Vaginal 167:a604032 20372:Portal 19848:DHEA-S 19688:AA-861 19181:Niacin 19176:Kepone 19033:ERX-11 19003:SS1020 18911:ERB-88 18906:ERA-90 18810:SS1010 18735:MRL-37 18100:dianol 18069:ERB-79 18064:ERA-45 18059:ERB-26 17792:DCW234 17747:AC-186 17414:DHEA-S 17346:esters 17330:esters 17182:8β-VE2 16943:WHO-EM 16895:Others 16000: 15992: 15962: 15933: 15925: 15894: 15859: 15829: 15801: 15747: 15714: 15683: 15616: 15579: 15575:–225. 15548: 15515:543168 15513: 15490: 15442: 15397: 15389: 15346: 15338: 15303: 15266: 15238: 15230: 15188: 15160: 15152: 15111: 15103: 15066: 15039: 15009: 14974: 14966: 14924: 14894: 14843: 14810: 14785: 14777: 14742: 14732: 14699: 14674: 14639: 14631: 14611:Cancer 14588: 14561: 14531: 14523: 14487: 14479: 14441: 14403: 14395: 14360: 14352: 14311: 14301: 14262: 14235: 14192: 14162: 14113: 14073: 14040: 13990: 13961: 13926: 13891: 13856: 13846: 13807: 13789:Cancer 13772: 13762: 13731: 13698:779393 13696: 13659: 13632: 13595: 13568: 13541: 13518:559617 13516: 13489: 13454: 13410: 13379: 13348: 13315: 13285: 13258: 13233: 13223: 13187:2010). 13180: 13170: 13128: 13118: 13079: 13069: 13055:: 20. 13028: 13018: 12979: 12969: 12928: 12893: 12885: 12833: 12825: 12790: 12782: 12742: 12732: 12676: 12649: 12619: 12611: 12576: 12568: 12532: 12524: 12478: 12453: 12445: 12397: 12372: 12362: 12354: 12314: 12284: 12259: 12211: 12181: 12171: 12119: 12111: 12073: 12032: 12024: 11980: 11972: 11934: 11899: 11889: 11856: 11826: 11791: 11783: 11742: 11708: 11698: 11659: 11612: 11582: 11551: 11526: 11483: 11449: 11439: 11400: 11360: 11300: 11270: 11240: 11213: 11188: 11178: 11139: 11129: 11085: 11055: 11015: 10895: 10865: 10834: 10824: 10793: 10768: 10739: 10712: 10680: 10636: 10628: 10593: 10585: 10550: 10506: 10496: 10409: 10145: 10120: 10080: 10027: 9963: 9925: 9861: 9826: 9708: 9700: 9574: 9547: 9519: 9477: 9467: 9425: 9381: 9328:FemHRT 9300:Xulane 9278:, and 9248:Esteed 9230:or as 9175:French 9147:, and 9130:, and 9049:Berlin 9031:, and 8910:and a 8880:EE is 8818:CYP3A4 8452:enzyme 8444:uterus 8236:gonads 8077:>48 8043:70–110 7896:500 μg 7890:300 μg 7865:300 μg 7852:100 μg 7846:280 μg 7840:200 μg 7823:8.4–25 7773:28–126 7748:28–126 7720:60–140 7707:>8 7682:>8 7542:, and 7462:Notes: 7396:60–150 6999:, and 6915:Notes: 6544:8.7–12 6375:= (1) 5710:Kepone 5567:48–111 5035:8β-VE2 5020:6.6–18 4589:MRL-41 4395:56–404 4370:60–234 4147:90–100 4072:7.0–20 4069:2.0–15 3963:E2-17B 3925:>10 3922:>10 3891:0.0001 3866:0.0015 3863:E2-17G 3841:0.0079 3816:0.0004 3258:Ligand 3158:potent 3103:, and 3087:, and 3055:, and 3009:CYP2A6 3001:CYP3A4 2999:, and 2993:CYP2C9 2989:CYP2B6 2985:CYP1A2 2916:; and 2901:, and 2875:CYP2C9 2871:CYP3A4 2597:stroke 2595:, and 2527:Notes: 2042:third- 1489:libido 1483:, and 1455:, and 1449:nausea 1400:Notes: 1367:20,000 1350:98,000 1302:(VTE) 1163:, and 1124:tablet 1049:, and 992: 984: 976: 968: 960: 942:uterus 905:, the 886:, and 874:, and 860:nausea 858:, and 735:SMILES 584:ChEMBL 553:D00554 316:CYP3A4 278:38–48% 119: 19447:CITCO 19257:CCL18 19131:Equol 19013:ZB716 18983:PHTPP 18850:Y-134 18527:SERMs 18522:Mixed 18202:equol 18084:Anise 17913:M2613 16569:SERDs 16560:SERMs 15998:S2CID 15931:S2CID 15640:(PDF) 15631:U.S. 15488:S2CID 15395:S2CID 15344:S2CID 15236:S2CID 15158:S2CID 15109:S2CID 14972:S2CID 14783:S2CID 14637:S2CID 14529:S2CID 14485:S2CID 14401:S2CID 14377:Drugs 14358:S2CID 14252:Cutis 14148:(3). 14138:(PDF) 12891:S2CID 12831:S2CID 12788:S2CID 12617:S2CID 12574:S2CID 12530:S2CID 12451:S2CID 12352:eISSN 12117:S2CID 12030:S2CID 11978:S2CID 11789:S2CID 10961:(PDF) 10937:(PDF) 10916:(PDF) 10634:S2CID 10591:S2CID 10047:U.S. 9998:(FDA) 9706:S2CID 9317:as a 9303:as a 9217:Latin 9198:, in 9190:, in 8945:like 8890:urine 8886:feces 8812:into 8766:liver 8605:liver 8578:Bound 8440:liver 8242:like 8226:(LH) 8220:liver 8018:30–60 7993:30–40 7968:15–30 7952:>5 7943:20–30 7820:60–80 7754:>5 7698:14–42 7695:60–80 7679:>5 7673:14–42 7670:60–80 7445:25–37 7442:26–28 7268:0.67 7156:Liver 6847:<1 6791:<1 6785:15–25 6765:<1 6762:<1 6759:<1 6756:<1 6737:<1 6734:<1 6731:<1 6728:<1 6681:<1 6678:<1 6675:<1 6672:<1 6669:10–15 6625:<1 6622:<1 6619:<1 6616:<1 6613:11–35 5210:Equol 5070:67–72 4945:0.089 4854:SERM 4829:SERM 4823:0.053 4804:SERM 4779:SERM 4754:SERM 4748:0.313 4729:SERM 4723:0.229 4704:SERM 4698:0.179 4679:SERM 4654:SERM 4629:SERM 4604:SERM 4579:SERM 4554:SERM 4529:SERM 4467:0.074 4448:15.30 4292:35–43 4144:35–68 4122:14–32 3991:0.145 3919:<1 3916:<1 3838:E2-3G 3794:<1 3791:<1 3694:<1 3691:<1 3644:<1 3519:11–35 3469:79–80 3278:, nM) 2923:like 2912:like 2907:azole 2885:like 2822:genes 2438:alone 2427:alone 2389:alone 2373:alone 2362:alone 2237:alone 2218:alone 2191:(95% 2182:Route 2020:liver 1990:in a 1606:(non- 938:liver 829:patch 755:InChI 701:JSmol 564:ChEBI 364:: 38% 362:Urine 359:: 62% 357:Feces 312:Liver 20019:and 19838:DHEA 19602:AITC 19467:DHEA 19277:MIBE 19272:G-36 19267:G-15 19201:PCBs 19058:GPER 18968:MIBE 18501:PCBs 18493:PHBA 18489:PBBs 18337:HPTE 18194:EGCG 18092:anol 17927:meso 17919:meso 17409:DHEA 17344:and 17328:and 16845:GnRH 16828:GnRH 16494:GnRH 16487:GnRH 16043:and 15990:PMID 15960:PMID 15923:PMID 15892:ISBN 15857:ISBN 15827:ISBN 15799:ISBN 15745:ISBN 15712:ISBN 15681:PMID 15614:PMID 15577:ISBN 15546:PMID 15511:OCLC 15440:ISBN 15387:PMID 15336:PMID 15301:PMID 15264:ISBN 15228:PMID 15186:ISBN 15150:PMID 15101:PMID 15064:ISBN 15037:ISBN 15007:PMID 14964:PMID 14922:ISBN 14892:PMID 14861:link 14841:ISBN 14808:ISBN 14775:PMID 14740:PMID 14730:ISBN 14697:ISBN 14672:PMID 14629:PMID 14586:ISBN 14559:ISBN 14521:PMID 14477:PMID 14439:PMID 14393:PMID 14350:PMID 14309:PMID 14260:PMID 14233:PMID 14190:ISBN 14160:ISSN 14111:PMID 14071:PMID 14038:ISBN 13988:ISBN 13959:ISSN 13924:PMID 13889:PMID 13854:PMID 13805:PMID 13770:ISSN 13760:ISBN 13729:ISSN 13694:PMID 13657:ISBN 13630:ISBN 13593:ISBN 13566:ISBN 13539:ISBN 13514:PMID 13487:PMID 13452:PMID 13408:ISBN 13377:ISBN 13346:ISBN 13313:ISBN 13283:ISBN 13256:ISBN 13231:PMID 13178:PMID 13126:PMID 13077:PMID 13026:PMID 12977:PMID 12926:PMID 12883:PMID 12823:PMID 12780:PMID 12740:PMID 12674:ISBN 12647:ISBN 12609:PMID 12566:PMID 12522:PMID 12502:1089 12476:PMID 12443:PMID 12395:ISBN 12370:ISSN 12360:ISBN 12312:ISBN 12282:ISBN 12257:PMID 12209:ISBN 12179:PMID 12109:PMID 12071:PMID 12022:PMID 11970:PMID 11932:PMID 11897:PMID 11854:ISBN 11824:PMID 11781:PMID 11740:PMID 11706:PMID 11684:2013 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