621:. In the rat model, it has been shown that the antiandrogenic effects of vinclozolin are most prominent during the developmental stages. In utero, this sensitive period of fetal development occurs between gestation days 16-17. Embryonic exposure to vinclozolin can influence sexual differentiation, gonadal formation, and reproductive functions. In bird models, vinclozolin and its metabolites were shown in vitro and in vivo to inhibit androgen receptor binding and gene expression. Vinclozolin caused reduced egg laying, reduced fertility rate, and a reduction in successful hatches. Androgens also play a role in puberty, and it has been shown an antiandrogen like vinclozolin can delay pubertal maturation. Antiandrogenic toxins are also known to alter sexual differentiation and reproduction in the rabbit model. Male rabbits exposed to vinclozolin in utero or during infancy did not show a sexual interest in females or did not ejaculate. Since the androgen receptor is widely conserved across species lines, antiandrogenic effects would be expected in humans. In vertebrates, vinclozolin also acts as a neuroendocrine disruptor, affecting behaviors tied to locomotion, cognition, and anxiety.
658:. Other studies conducted experiments where rat embryos were exposed to vinclozolin during sex determination. F1 (first generation) vinclozolin treated males were bred with F1 vinclozolin treated females. This pattern continued for three generations. The initial F0 mother was the only subject that was directly exposed to doses of vinclozolin. F1-F4 generation males all showed an increase in the prevalence of tumors, prostate disease, kidney disease, test abnormalities and immune failures when compared to the control group. F1-F4 females also showed an increased incidence of tumors and kidney disease. Furthermore, transgenerationally transmitted changes in mate preference and anxiety behavior have also been observed in rats following exposure to vinclozolin. It has been reported that these transgenerational reports correlate with epigenetic changes, specifically, an alteration in DNA methylation in the male germ line. However, these transgenerational changes have not been successfully reproduced by BASF scientists, the manufacturer of vinclozolin
617:. Vinclozolin can mimic male hormones, like testosterone, and bind to androgen receptors, while not necessarily activating those receptors properly. There is evidence that vinclozolin itself binds weakly to the androgen receptor but that at least two of its metabolites are responsible for much of the antiandrogenic activity. When male rats were given low dose levels (>3 mg/kg/day) of vinclozolin, effects such as decreased prostate weight, weight reduction in sex organs, nipple development, and decreased ano-genital distance were noted. At higher dose levels, male sex organ weight decreased further, and sex organ malformations were seen, such as reduced penis size, the appearance of vaginal pouches and
588:
easily reduce their exposure because fungicides are not removed from produce that is washed with tap water. A key example of exposure to vinclozolin is through wine grapes which is considered to account for about 2% of total vinclozolin exposure. It has been determined that people may be exposed to residues of vinclozolin and its metabolites containing the 3,5-dichloroaniline moiety (3,5-DCA) through diet, and thus tolerance limits have been established for each crop. Although vinclozolin is not registered for use by homeowners, it is still possible for people to come into contact with the fungicide and its residues. For example, golfers playing on treated golf courses, and families playing on
641:. Just as with androgens, the timing of the exposure to vinclozolin determines the magnitude of the effects related to these hormones. In a study with rats, in vitro research showed the ability of two vinclozolin metabolites to bind to the progesterone receptor. However, the same study in vivo using adult male rats showed no effects. When mice experienced vinclozolin exposure in utero, male offspring exhibited up-regulated estrogen receptor and up-regulated progesterone receptor. In females, vinclozolin down-regulated expression of estrogen receptors and up-regulated progesterone receptor expression. This result causes
279:
184:
505:
plums, 163; raspberries, 3,247; and strawberries, 41,006. In 1997, two applications totaling 285 pounds each, were applied to kiwifruit in
California to prevent the gray mold and soft rot caused by Botrytis cinerea. In general, the United States has seen an overall decline in the national use of vinclozolin. In 1992, a total of approximately 135,000 pounds were used. However, in 1997 this number dropped to 122,000 and in 2002 it was down to 55,000 pounds.
27:
484:(U.S. EPA). In addition to these restrictions within the United States, as of 2006 the use of this pesticide was banned in several countries, including Denmark, Finland, Norway, and Sweden. It has gone through a series of tests and regulations in order to evaluate the risks and hazards to the environment and animals. Among the research, a main finding is that vinclozolin has been shown to be an
412:
654:
utero, but in males born for three generations and beyond. Furthermore, when affected males were mated with normal females, some of the offspring were sterile and some had reduced fertility. After three generations, male offspring continued to show low sperm count, prostate disease and high rates of testicular cell
653:
In rats, vinclozolin has been demonstrated to have trangenerational effects, meaning that not only is the initial animal affected, but effects are also seen in subsequent generations. One study demonstrated that vinclozolin impaired male fertility not only in the first generation that was exposed in
587:
The U.S. EPA has examined dietary (food and water), non-dietary, and occupational exposure to vinclozolin or its metabolites. In general, fungicides have been shown to circulate through the water and air, and it possible for them to end up on untreated foods after application. Consumers alone cannot
678:
Laboratory test indicate that vinclozolin easily breaks down and dissipates in the environment with the help of microbes. Of its several metabolites 3,5-dichloroaniline resists further degradation. In terrestrial field dissipation studies conducted in various states, vinclozolin dissipated with a
570:
On July 18, 2000 the EPA established that certain meat, bean and dairy products have a 3-year time-limited tolerances for vinclozolin and its metabolites. This led to a phase-out of most domestic food uses for vinclozolin. In
September 2000, the EPA received objections to the issued tolerance for
553:
All pesticides sold or distributed in the United States must be registered by U.S. EPA. Pesticides that were first registered before
November 1, 1984, were reregistered so that they can be retested using the now more advanced methods. Because vinclozolin was released in 1981, it has gone through
544:
Vinclozolin is then formulated into a dry flowable or extruded granular. It can be applied by through the air (aerial), through irrigation systems (chemigation), or by ground equipment. Vinclozolin is also applied to some plants, such as decorative flowers, as a dip treatment where the plant is
504:
and has been registered for use in the United States since 1981. The following is a compilation of data indicating the national use of vinclozolin per crop (lbs AI/yr) in 1987: apricots, 124; cherries, 3,301; green beans, 13,437; lettuce, 24,779; nectarines, 1,449; onions, 829; peaches, 15,203;
467:
used to control diseases, such as blights, rots and molds in vineyards, and on fruits and vegetables such as raspberries, lettuce, kiwi, snap beans, and onions. It is also used on turf on golf courses. Two common fungi that vinclozolin is used to protect crops against are
687:
Since the phase-out of vinclozolin, farmers are faced with fewer options to control gray and white mold. The New York State
Agricultural Experiment Station has carried out efficacy trials for gray and white mold. Research has showed potential alternatives to vinclozolin.
1433:
Schneider, Steffen; Marxfeld, Heike; Gröters, Sibylle; Buesen, Roland; van
Ravenzwaay, Bennard (2013). "Vinclozolin—No transgenerational inheritance of anti-androgenic effects after maternal exposure during organogenesis via the intraperitoneal route".
708:(Topsin M) was as effective as vinclozolin in controlling white molds. Switch was the most promising alternative to vinclozolin for controlling both gray and white mold on pods and for increasing marketable yield.
1477:
574:
Other measures that BASF has taken to reduce risks: cancel use on decorative plants and set up new restrictions on turf which state that the application to turf restricted to golf courses and industrial
1055:
906:
1608:
3321:
1862:
1233:"Embryonic exposure to the fungicide vinclozolin causes virilization of females and alteration of progesterone receptor expression in vivo: an experimental study in mice"
3484:
1179:
León-Olea, Martha; Martyniuk, Christopher J.; Orlando, Edward F.; Ottinger, Mary Ann; Rosenfeld, Cheryl S.; Wolstenholme, Jennifer T.; Trudeau, Vance L. (1 July 2014).
592:
which has been previously treated may be at risk for exposure. Occupationally, workers can be exposed to vinclozolin while doing activities such as loading and mixing.
558:
A Data Call-In (DCI), requiring data on product and residue chemistry, toxicity, environmental fate, and ecological effects, have been requested in 1991, 1995 and 1996.
1852:
2176:
1488:
1086:
Gray, L. E.; Ostby, J; Furr, J; Wolf, C. J.; Lambright, C; Parks, L; Veeramachaneni, D. N.; Wilson, V; Price, M; Hotchkiss, A; Orlando, E; Guillette, L (2001).
1550:
679:
half-life between 34 and 94 days. Half-lives including residues can reach up to 1,000 days. Residues may accumulate and be available for future crop uptake.
605:
As part of the reregistration process, the U.S. EPA reviewed all toxicity studies on vinclozolin. The main effect induced by vinclozolin is related to its
806:
425:
1007:"Perinatal Exposure to Low Levels of the Environmental Antiandrogen Vinclozolin Alters Sex-Differentiated Social Play and Sexual Behaviors in the Rat"
3298:
689:
1982:
1005:
Colbert, Nathan K.W.; Pelletier, Nicole C.; Cote, Joyce M.; Concannon, John B.; Jurdak, Nicole A.; Minott, Sara B.; Markowski, Vincent P. (2005).
101:
480:. First registered in 1981, vinclozolin is widely used but its overall application has declined. As a pesticide, vinclozolin is regulated by the
2870:
2860:
3303:
481:
3344:
3339:
3124:
2900:
2890:
917:
697:
545:
dipped into the fungicide solution and then dried. It is also common to spray a vinclozolin solution using thermal foggers in greenhouses.
328:
3643:
3578:
3573:
3523:
3354:
3268:
2880:
564:
In April 1997, BASF proposed a new use for vinclozolin and thus all risks were reevaluated under the Food
Quality Protection Act (FQPA).
3638:
3513:
3464:
3288:
3273:
3204:
2915:
2825:
1543:
3797:
3104:
3099:
3089:
2930:
2760:
3633:
3454:
2805:
670:
tumors in rats. The 3,5-DCA metabolite is thought to possess a mode of tumor induction based on its similarity to p-choroaniline.
3848:
3802:
2282:
870:
567:
In June 1998 the EPA put a new safety factor on vinclozolin. BASF voluntarily cancelled vinclozolin use on some fruits and turf.
2795:
3792:
2744:
1536:
1306:
1877:
1056:"Vinclozolin; Notice of Filing a Pesticide Petition To Establish a Tolerance for a Certain Pesticide Chemical in or on Food"
3787:
1783:
578:
BASF has proposed to immediately eliminate or phase-out uses such that only use on canola and turf will remain after 2004.
561:
Agricultural Data Call-In (AGDCI), to estimate what happens to workers after they apply the fungicide, was issued in 1995.
3838:
2132:
2539:
2534:
420:
1972:
2201:
1778:
819:
293:
2984:
3383:
2288:
2251:
2081:
2046:
1977:
432:
2206:
554:
both preliminary and a subsequent reregistration. Below is a list of the history of regulations for vinclozolin:
1736:
2974:
3828:
1643:
1623:
825:
533:, followed by hydrolysis of the nitrile. Vinclozolin is also prepared by the reaction of 3,5-dichlorophenyl
3782:
3752:
3317:
2611:
1999:
666:
The U.S. EPA has classified vinclozolin as a possible human carcinogen. Vinclozolin induces an increase in
236:
179:
2472:
1825:
1638:
749:
2689:
2051:
1653:
1478:"Alternatives to Vinclozolin (Ronilan) for Controlling Gray and White Mold on Snap Bean Pods in New York"
257:
141:
2674:
2669:
2477:
3843:
2211:
1830:
2979:
941:
Franz Müller, Peter
Ackermann and Paul Margot "Fungicides, Agricultural, 2. Individual Fungicides" in
2041:
1768:
1714:
1374:
Gaetano, Carlo; Guerrero-Bosagna, Carlos; Settles, Matthew; Lucker, Ben; Skinner, Michael K. (2010).
1820:
3853:
2631:
2600:
2320:
2261:
1994:
1772:
1648:
1598:
630:
476:
464:
274:
2969:
2704:
2684:
3500:
2427:
1989:
1889:
2171:
1376:"Epigenetic Transgenerational Actions of Vinclozolin on Promoter Regions of the Sperm Epigenome"
3492:
2627:
2266:
2137:
2009:
1857:
1726:
1675:
610:
2964:
1324:"Epigenetic Transgenerational Actions of Vinclozolin on the Development of Disease and Cancer"
3823:
3024:
2512:
2362:
2256:
1921:
1603:
39:
1088:"Effects of environmental antiandrogens on reproductive development in experimental animals"
3184:
2652:
2623:
2596:
2462:
2350:
2159:
2127:
2093:
1731:
1702:
1443:
1387:
1244:
245:
161:
77:
1815:
1132:"Endocrine Disruptor Vinclozolin Induced Epigenetic Transgenerational Adult-Onset Disease"
8:
3833:
3707:
3702:
3434:
3394:
3239:
3159:
3059:
3049:
2994:
2574:
2110:
1867:
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522:
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485:
67:
1521:
1447:
1391:
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278:
183:
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1031:
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705:
121:
881:
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2999:
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1302:
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1161:
1109:
1036:
815:
614:
302:
InChI=1S/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3
513:
The following chemical reactions are used to make vinclozolin: One method combines
312:
InChI=1/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3
3444:
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489:
1257:
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3333:
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2246:
2231:
2196:
2191:
1945:
1916:
1231:
Buckley, Jill; Willingham, Emily; Agras, Koray; Baskin, Laurence (2006).
1147:
701:
667:
618:
530:
3717:
3684:
3533:
3528:
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3479:
3399:
3364:
3359:
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2729:
2637:
2586:
2437:
2387:
2340:
2330:
2149:
2117:
2076:
2026:
2016:
1962:
1950:
1911:
1763:
1758:
1753:
1748:
1743:
1665:
907:"Pesticide Use in U.S. Crop Production: 2002 Fungicides and Herbicides"
534:
388:
152:
3738:
3712:
3692:
3688:
3676:
3553:
3518:
3459:
3419:
3414:
3313:
3293:
3229:
3194:
3169:
3164:
3149:
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2820:
2810:
2800:
2734:
2581:
2569:
2325:
2216:
2144:
2105:
2031:
2004:
1933:
1687:
1670:
1022:
808:
The Food We Eat: An
International Comparison of Pesticide Regulations
693:
655:
1373:
402:
Except where otherwise noted, data are given for materials in their
3724:
3603:
3598:
3593:
3588:
3583:
3389:
3144:
3079:
2895:
2850:
2845:
2840:
2835:
2830:
2785:
2724:
2719:
2659:
1840:
1682:
638:
526:
200:
1130:
Anway, Matthew D.; Leathers, Charles; Skinner, Michael K. (2006).
100:
3680:
3469:
3409:
3209:
3094:
2935:
2910:
2765:
2507:
2457:
2397:
2058:
1178:
858:
212:
3731:
3672:
3657:
3563:
1053:
132:
1432:
814:. Vancouver, BC, Canada: David Suzuki Foundation. p. 12.
645:
and the feminization of males and masculinization of females.
47:)-3-(3,5-Dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione
26:
3263:
2945:
2855:
2786:
Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
2745:
1629:
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
1004:
112:
90:
1230:
624:
262:
3696:
3009:
501:
191:
3379:
589:
2470:
17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:
1973:
7α-Methyl-19-norandrostenedione (MENT dione, trestione)
2667:
5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:
541:. Ring closure is achieved at elevated temperature.
3753:
1237:
Environmental Health: A Global Access
Science Source
1129:
629:
In rats, vinclozolin has been shown to affect other
500:
Vinclozolin is manufactured by the chemical company
2101:
Normethandrone (methylestrenolone, normethisterone)
595:
548:
978:"Reregistration Eligibility Decision: Vinclozolin"
850:
848:
846:
744:
742:
740:
2313:17α-Alkylated 5α-dihydrotestosterone derivatives:
1085:
1054:Environmental Protection Agency (26 March 2003).
738:
736:
734:
732:
730:
728:
726:
724:
722:
720:
3815:
1558:
1299:Integrating Epigenetics, Medicine, and Evolution
224:
2532:5α-Dihydro-17α-ethynyltestosterone derivatives:
1322:Skinner, Michael K.; Anway, Matthew D. (2007).
1181:"Current concepts in neuroendocrine disruption"
843:
76:
1983:11β-Methyl-19-nortestosterone dodecylcarbonate
943:Ullmann's Encyclopedia of Industrial Chemistry
717:
508:
2750:Tooltip Selective androgen receptor modulator
2395:17α-Alkylated 19-nortestosterone derivatives:
1544:
482:United States Environmental Protection Agency
2801:Enobosarm (ostarine, MK-2866, GTx-024, S-22)
1321:
1301:]. MA: Sinauer Associates. p. 231.
648:
2552:17α-Ethynyl-19-nortestosterone derivatives:
1525:in the Pesticide Properties DataBase (PPDB)
1292:
495:
2274:Methylclostebol (chloromethyltestosterone)
2169:5α-Dihydro-19-nortestosterone derivatives:
1551:
1537:
529:. This process involves formation of the
277:
182:
160:
2495:17α-Vinyl-19-nortestosterone derivatives:
2111:Oxabolone cipionate (oxabolone cypionate)
1727:DHEA (androstenolone, prasterone; 5-DHEA)
1571:
1409:
1399:
1347:
1266:
1256:
1204:
1155:
1103:
1030:
682:
625:Progesterone and estrogen effects in rats
244:
2202:Chlorodehydromethylandrostenediol (CDMA)
537:with an alkyl ester of 2-hydroxy-2-vinyl
3803:List of androgens and anabolic steroids
2189:17α-Alkylated testosterone derivatives:
1288:
1286:
863:
273:
16:Fungicide used on fruits and vegetables
3816:
2207:Chlorodehydromethyltestosterone (CDMT)
1963:Testifenon (testiphenon, testiphenone)
1369:
1367:
1226:
1224:
1125:
1123:
1081:
1079:
1077:
173:
2488:Norvinisterone (vinylnortestosterone)
2022:Bolmantalate (nandrolone adamantoate)
2017:Bolandione (19-nor-4-androstenedione)
1732:DHEA enanthate (prasterone enanthate)
1532:
1470:
1185:General and Comparative Endocrinology
972:
970:
968:
966:
964:
962:
960:
958:
871:"Crop Profile for Kiwi in California"
609:activity and its ability to act as a
336:O=C2OC(C(=O)N2c1cc(Cl)cc(Cl)c1)(C=C)C
305:Key: FSCWZHGZWWDELK-UHFFFAOYSA-N
140:
120:
3758:Tooltip Sex hormone-binding globulin
2505:17α-Ethynyltestosterone derivatives:
1784:Polytestosterone phloretin phosphate
1293:Gilbert, Scott; Epel, David (2009).
1283:
804:
582:
2428:Methylhydroxynandrolone (MOHN, MHN)
2133:Trenbolone hexahydrobenzylcarbonate
1793:5α-Dihydrotestosterone derivatives:
1661:Androstenedione (4-androstenedione)
1364:
1315:
1221:
1120:
1074:
315:Key: FSCWZHGZWWDELK-UHFFFAOYAN
215:
199:
13:
2485:17α-Vinyltestosterone derivatives:
2247:Methandriol (methylandrostenediol)
1516:BBC article on Vinclozolin in rats
998:
955:
899:
661:
14:
3865:
2525:Ethisterone (ethynyltestosterone)
2242:Metandienone (methandrostenolone)
2072:Methoxydienone (methoxygonadiene)
1683:Boldione (1,4-androstadienedione)
1634:Androstenediol (5-androstenediol)
1599:4-Dehydroepiandrosterone (4-DHEA)
1509:
1011:Environmental Health Perspectives
770:
3798:Progesterone receptor modulators
2289:Methyltestosterone 3-hexyl ether
2252:Methandriol bisenanthoyl acetate
2212:Chloromethylandrostenediol (CMA)
2047:Dimethandrolone dodecylcarbonate
1806:1-Androsterone (1-andro, 1-DHEA)
1295:Ecological Developmental Biology
596:Environmental and health impacts
549:History of regulations in the US
410:
375:
369:
363:
25:
1970:19-Nortestosterone derivatives:
1426:
1328:Critical Reviews in Oncogenesis
1172:
1047:
805:Boyd, David R. (October 2006).
600:
406:(at 25 °C , 100 kPa).
3849:Suspected testicular toxicants
2985:15β-Hydroxycyproterone acetate
2876:OPK-88004 (LY-2452473, TT-701)
1456:10.1016/j.reprotox.2012.12.003
1340:10.1615/CritRevOncog.v13.i1.30
935:
798:
673:
378:
357:
1:
3783:Receptor/signaling modulators
2540:17α-Ethynyl-3β-androstanediol
2535:17α-Ethynyl-3α-androstanediol
1978:11β-Methyl-19-nortestosterone
785:Santa Cruz Biotechnology, Inc
711:
3793:Estrogen receptor modulators
3240:Trimethyltrienolone (R-2956)
2612:Lynestrenol phenylpropionate
2000:19-Nordehydroepiandrosterone
1401:10.1371/journal.pone.0013100
704:(Switch) control gray mold.
7:
3788:Androgens and antiandrogens
3559:Ralaniten acetate (EPI-506)
2975:7α-Thiomethylspironolactone
2690:Medroxyprogesterone acetate
2052:Dimethandrolone undecanoate
1863:Dihydromethylandrostenediol
1654:Androstenediol dipropionate
1197:10.1016/j.ygcen.2014.02.005
509:Preparation and application
10:
3870:
3839:Nonsteroidal antiandrogens
1878:Dihydrotestosterone esters
1831:11-Ketodihydrotestosterone
1644:Androstenediol 17β-acetate
1624:11β-Hydroxyandrostenedione
1609:4,17α-Dimethyltestosterone
3775:
3665:
3656:
2954:
2743:
2682:Progesterone derivatives:
2473:5α-Dihydronorethandrolone
2042:Dimethandrolone buciclate
1872:androstanolone, stanolone
1868:Dihydrotestosterone (DHT)
1826:7β-Hydroxyepiandrosterone
1715:Cloxotestosterone acetate
1639:Androstenediol 3β-acetate
1591:Testosterone derivatives:
1583:
1576:Tooltip Androgen receptor
1569:
1092:Human Reproduction Update
750:"R.E.D Facts Vinclozolin"
649:Transgenerational effects
631:steroid hormone receptors
400:
344:
324:
289:
60:
52:
38:
33:
24:
3488:-Butylbenzenesulfonamide
2675:5α-Dihydronorethisterone
2670:5α-Dihydrolevonorgestrel
2632:norethisterone enanthate
2601:levonorgestrel butanoate
2478:5α-Dihydronormethandrone
2331:Mebolazine (dimethazine)
2321:Desoxymethyltestosterone
2262:Methandriol dipropionate
2059:LS-1727 (nandrolone 17β-
1995:19-Nor-5-androstenedione
1853:Dihydroethyltestosterone
1649:Androstenediol diacetate
1485:Plant Management Network
951:10.1002/14356007.o12_o06
496:Use in the United States
477:Sclerotinia sclerotiorum
3619:Topilutamide (fluridil)
2980:11α-Hydroxyprogesterone
1990:19-Nor-5-androstenediol
1890:Drostanolone propionate
1436:Reproductive Toxicology
945:, Wiley-VCH, Weinheim.
465:dicarboximide fungicide
3504:-Desmethylenzalutamide
3210:SC-5233 (spirolactone)
2628:norethisterone acetate
2267:Methandriol propionate
2138:Trenbolone undecanoate
2010:Bolandiol dipropionate
1858:Dihydrofluoxymesterone
1821:5α-Androst-2-en-17-one
1676:Boldenone undecylenate
1105:10.1093/humupd/7.3.248
683:Alternative fungicides
611:competitive antagonist
3496:-Desmethylapalutamide
3025:Chlormadinone acetate
2970:7α-Thiospironolactone
2841:LGD-2941 (LGD-122941)
2831:LG121071 (LGD-121071)
2705:3-Keto-5α-abiraterone
2685:6α-Methylprogesterone
2624:Norethisterone esters
2597:Levonorgestrel esters
2513:Ethinylandrostenediol
2363:Methyl-1-testosterone
2283:+esterified estrogens
2257:Methandriol diacetate
1922:Mesterolone cipionate
1604:4-Hydroxytestosterone
1258:10.1186/1476-069X-5-4
3829:Endocrine disruptors
3185:Potassium canrenoate
2653:Quingestanol acetate
2463:Tetrahydrogestrinone
2351:Metenolone enanthate
2177:5α-Dihydrotrestolone
2172:5α-Dihydronandrolone
2160:Trestolone enanthate
2128:Trenbolone enanthate
2094:Norclostebol acetate
1703:Clostebol propionate
1148:10.1210/en.2006-0640
923:on 27 September 2011
914:Crop Life Foundation
3708:Dihydrotestosterone
3703:Dehydroandrosterone
3554:Ralaniten (EPI-002)
3435:Inocoterone acetate
3160:Nomegestrol acetate
3060:Delmadinone acetate
3050:Cyproterone acetate
2995:Abiraterone acetate
2965:7α-Thioprogesterone
2575:Etynodiol diacetate
1779:Testosterone esters
1722:Dehydroandrosterone
1619:11-Ketotestosterone
1448:2013RepTx..37....6S
1392:2010PLoSO...513100G
1249:2006EnvHe...5....4B
633:, such as those of
523:3,5-dichloroaniline
515:methyl vinyl ketone
486:endocrine disruptor
396: g·mol
21:
2545:Dihydroethisterone
2408:Dimethyltrienolone
2368:Methylepitiostanol
2346:Metenolone acetate
2279:Methyltestosterone
2182:19-Norandrosterone
2155:Trestolone acetate
2123:Trenbolone acetate
2067:-nitrosocarbamate)
1956:Stenbolone acetate
1846:Bolazine capronate
1698:Clostebol caproate
706:Thiophanate-methyl
433:Infobox references
19:
3844:Oxazolidinediones
3811:
3810:
3771:
3770:
3741:
3734:
3727:
3720:
3652:
3651:
3175:Osaterone acetate
3135:Megestrol acetate
3000:Allyltestosterone
2776:Acetothiolutamide
2695:Megestrol acetate
2498:Vinyltestosterone
2403:Dimethyldienolone
2222:Ethyltestosterone
2150:Trestolone (MENT)
2082:Nandrolone esters
2063:-(2-chloroethyl)-
1939:Nisterime acetate
1816:3α-Androstanediol
1801:1-Androstenedione
1710:Cloxotestosterone
1693:Clostebol acetate
1614:5-Androstenedione
1560:Androgen receptor
1308:978-0-87893-299-3
615:androgen receptor
583:Means of exposure
441:Chemical compound
439:
438:
258:CompTox Dashboard
102:Interactive image
3861:
3759:
3755:
3739:
3732:
3725:
3718:
3663:
3662:
3445:Ketodarolutamide
3425:Hydroxyflutamide
3382:(via metabolite
2751:
2747:
2702:Others/unsorted:
2373:Methylstenbolone
2237:Hydroxystenozole
1796:1-Androstenediol
1594:4-Androstenediol
1581:
1580:
1577:
1573:
1553:
1546:
1539:
1530:
1529:
1504:
1503:
1501:
1499:
1494:on 25 April 2012
1493:
1487:. Archived from
1482:
1474:
1468:
1467:
1430:
1424:
1423:
1413:
1403:
1371:
1362:
1361:
1351:
1319:
1313:
1312:
1290:
1281:
1280:
1270:
1260:
1228:
1219:
1218:
1208:
1176:
1170:
1169:
1159:
1127:
1118:
1117:
1107:
1083:
1072:
1071:
1069:
1067:
1060:Federal Register
1051:
1045:
1044:
1034:
1023:10.1289/ehp.7509
1002:
996:
995:
993:
991:
982:
974:
953:
939:
933:
932:
930:
928:
922:
916:. Archived from
911:
903:
897:
896:
894:
892:
887:on 30 April 2012
886:
880:. Archived from
875:
867:
861:
852:
841:
840:
838:
836:
830:
824:. Archived from
813:
802:
796:
795:
793:
791:
782:
774:
768:
767:
765:
763:
754:
746:
471:Botrytis cinerea
423:
417:
414:
413:
395:
380:
377:
371:
365:
359:
352:Chemical formula
282:
281:
266:
264:
248:
228:
217:
203:
186:
175:
164:
144:
124:
104:
80:
29:
22:
18:
3869:
3868:
3864:
3863:
3862:
3860:
3859:
3858:
3854:Vinyl compounds
3814:
3813:
3812:
3807:
3767:
3757:
3648:
3370:Cyanonilutamide
3299:Bavdegalutamide
3110:Epitestosterone
2950:
2781:Acetoxolutamide
2749:
2739:
2448:Norethandrolone
2423:Methyldienolone
2227:Fluoxymesterone
2037:Dimethandrolone
1897:Epiandrosterone
1575:
1565:
1557:
1512:
1507:
1497:
1495:
1491:
1480:
1476:
1475:
1471:
1431:
1427:
1372:
1365:
1320:
1316:
1309:
1291:
1284:
1229:
1222:
1177:
1173:
1142:(12): 5515–23.
1128:
1121:
1084:
1075:
1065:
1063:
1052:
1048:
1003:
999:
989:
987:
980:
976:
975:
956:
940:
936:
926:
924:
920:
909:
905:
904:
900:
890:
888:
884:
873:
869:
868:
864:
853:
844:
834:
832:
828:
822:
811:
803:
799:
789:
787:
780:
776:
775:
771:
761:
759:
752:
748:
747:
718:
714:
690:Trifloxystrobin
685:
676:
664:
662:Links to cancer
651:
627:
603:
598:
585:
551:
511:
498:
442:
435:
430:
429:
428: ?)
419:
415:
411:
407:
393:
383:
374:
368:
362:
354:
340:
337:
332:
331:
320:
317:
316:
313:
307:
306:
303:
297:
296:
285:
267:
260:
251:
231:
218:
206:
167:
147:
127:
107:
94:
83:
70:
56:
48:
17:
12:
11:
5:
3867:
3857:
3856:
3851:
3846:
3841:
3836:
3831:
3826:
3809:
3808:
3806:
3805:
3800:
3795:
3790:
3785:
3780:
3776:
3773:
3772:
3769:
3768:
3766:
3765:
3760:
3750:
3745:
3721:-α-Amino acids
3715:
3710:
3705:
3700:
3669:
3667:
3660:
3654:
3653:
3650:
3649:
3647:
3646:
3641:
3636:
3631:
3626:
3621:
3616:
3611:
3606:
3601:
3596:
3591:
3586:
3581:
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3536:
3531:
3526:
3521:
3516:
3511:
3506:
3498:
3490:
3482:
3477:
3472:
3467:
3462:
3457:
3452:
3447:
3442:
3437:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3392:
3387:
3377:
3372:
3367:
3362:
3357:
3352:
3347:
3342:
3337:
3311:
3306:
3301:
3296:
3291:
3286:
3281:
3276:
3271:
3266:
3261:
3248:
3247:
3242:
3237:
3232:
3227:
3222:
3217:
3215:Spironolactone
3212:
3207:
3202:
3197:
3192:
3187:
3182:
3177:
3172:
3167:
3162:
3157:
3152:
3147:
3142:
3137:
3132:
3127:
3122:
3117:
3112:
3107:
3102:
3097:
3092:
3087:
3082:
3077:
3072:
3067:
3062:
3057:
3052:
3047:
3042:
3040:Cyproheptadine
3037:
3032:
3027:
3022:
3017:
3015:Canrenoic acid
3012:
3007:
3002:
2997:
2992:
2987:
2982:
2977:
2972:
2967:
2958:
2956:
2952:
2951:
2949:
2948:
2943:
2938:
2933:
2924:
2923:
2918:
2913:
2908:
2903:
2898:
2893:
2888:
2883:
2878:
2873:
2868:
2863:
2858:
2853:
2848:
2843:
2838:
2833:
2828:
2823:
2818:
2813:
2808:
2803:
2798:
2793:
2788:
2783:
2778:
2773:
2768:
2763:
2754:
2752:
2741:
2740:
2738:
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2698:
2697:
2692:
2687:
2678:
2677:
2672:
2663:
2662:
2657:
2656:
2655:
2645:
2643:Norgestrienone
2640:
2635:
2621:
2619:Norethisterone
2616:
2615:
2614:
2604:
2594:
2592:Levonorgestrel
2589:
2584:
2579:
2578:
2577:
2567:
2562:
2557:
2548:
2547:
2542:
2537:
2528:
2527:
2522:
2521:
2520:
2510:
2501:
2500:
2491:
2490:
2481:
2480:
2475:
2466:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2413:Ethyldienolone
2410:
2405:
2400:
2391:
2390:
2385:
2380:
2375:
2370:
2365:
2360:
2355:
2354:
2353:
2348:
2338:
2333:
2328:
2323:
2318:
2316:Androisoxazole
2309:
2308:
2303:
2298:
2293:
2292:
2291:
2276:
2271:
2270:
2269:
2264:
2259:
2254:
2244:
2239:
2234:
2229:
2224:
2219:
2214:
2209:
2204:
2199:
2194:
2185:
2184:
2179:
2174:
2165:
2164:
2163:
2162:
2157:
2147:
2142:
2141:
2140:
2135:
2130:
2125:
2115:
2114:
2113:
2103:
2098:
2097:
2096:
2086:
2085:
2084:
2074:
2069:
2056:
2055:
2054:
2049:
2044:
2034:
2029:
2024:
2019:
2014:
2013:
2012:
2002:
1997:
1992:
1987:
1986:
1985:
1975:
1966:
1965:
1960:
1959:
1958:
1948:
1943:
1942:
1941:
1931:
1929:Methyldiazinol
1926:
1925:
1924:
1914:
1909:
1904:
1899:
1894:
1893:
1892:
1882:
1881:
1880:
1865:
1860:
1855:
1850:
1849:
1848:
1838:
1833:
1828:
1823:
1818:
1813:
1811:1-Testosterone
1808:
1803:
1798:
1789:
1788:
1787:
1786:
1781:
1766:
1761:
1756:
1751:
1746:
1741:
1740:
1739:
1734:
1724:
1719:
1718:
1717:
1707:
1706:
1705:
1700:
1695:
1685:
1680:
1679:
1678:
1668:
1663:
1658:
1657:
1656:
1651:
1646:
1641:
1631:
1626:
1621:
1616:
1611:
1606:
1601:
1596:
1587:
1585:
1578:
1567:
1566:
1556:
1555:
1548:
1541:
1533:
1527:
1526:
1518:
1511:
1510:External links
1508:
1506:
1505:
1469:
1425:
1363:
1314:
1307:
1282:
1220:
1171:
1119:
1073:
1046:
997:
954:
934:
898:
862:
842:
820:
797:
769:
715:
713:
710:
696:(Rovral), and
684:
681:
675:
672:
663:
660:
650:
647:
626:
623:
607:antiandrogenic
602:
599:
597:
594:
584:
581:
580:
579:
576:
572:
568:
565:
562:
559:
550:
547:
539:propionic acid
519:sodium cyanide
510:
507:
497:
494:
490:antiandrogenic
463:) is a common
440:
437:
436:
431:
409:
408:
404:standard state
401:
398:
397:
391:
385:
384:
381:
372:
366:
360:
355:
350:
347:
346:
342:
341:
339:
338:
335:
327:
326:
325:
322:
321:
319:
318:
314:
311:
310:
308:
304:
301:
300:
292:
291:
290:
287:
286:
284:
283:
270:
268:
256:
253:
252:
250:
249:
241:
239:
233:
232:
230:
229:
221:
219:
211:
208:
207:
205:
204:
196:
194:
188:
187:
177:
169:
168:
166:
165:
157:
155:
149:
148:
146:
145:
137:
135:
129:
128:
126:
125:
117:
115:
109:
108:
106:
105:
97:
95:
88:
85:
84:
82:
81:
73:
71:
66:
63:
62:
58:
57:
54:
50:
49:
42:
36:
35:
31:
30:
15:
9:
6:
4:
3:
2:
3866:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3835:
3832:
3830:
3827:
3825:
3822:
3821:
3819:
3804:
3801:
3799:
3796:
3794:
3791:
3789:
3786:
3784:
3781:
3778:
3777:
3774:
3764:
3761:
3756:
3751:
3749:
3746:
3743:
3736:
3729:
3722:
3716:
3714:
3711:
3709:
3706:
3704:
3701:
3698:
3694:
3690:
3686:
3682:
3678:
3674:
3671:
3670:
3668:
3664:
3661:
3659:
3655:
3645:
3642:
3640:
3637:
3635:
3632:
3630:
3627:
3625:
3624:Valproic acid
3622:
3620:
3617:
3615:
3612:
3610:
3607:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3582:
3580:
3577:
3575:
3572:
3570:
3569:Rezvilutamide
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3544:Proxalutamide
3542:
3540:
3537:
3535:
3532:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3503:
3499:
3497:
3495:
3491:
3489:
3487:
3483:
3481:
3478:
3476:
3473:
3471:
3468:
3466:
3463:
3461:
3458:
3456:
3453:
3451:
3448:
3446:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3385:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3348:
3346:
3343:
3341:
3338:
3335:
3331:
3327:
3323:
3319:
3315:
3312:
3310:
3307:
3305:
3302:
3300:
3297:
3295:
3292:
3290:
3287:
3285:
3282:
3280:
3277:
3275:
3272:
3270:
3267:
3265:
3262:
3260:
3259:-Bicalutamide
3258:
3253:
3252:Nonsteroidal:
3250:
3249:
3246:
3243:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3181:
3178:
3176:
3173:
3171:
3168:
3166:
3163:
3161:
3158:
3156:
3153:
3151:
3148:
3146:
3143:
3141:
3138:
3136:
3133:
3131:
3128:
3126:
3123:
3121:
3120:Guggulsterone
3118:
3116:
3113:
3111:
3108:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
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3076:
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3018:
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3008:
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2988:
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2799:
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2792:
2789:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2764:
2762:
2759:
2758:Nonsteroidal:
2756:
2755:
2753:
2748:
2742:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2710:5α-Androstane
2708:
2706:
2703:
2700:
2699:
2696:
2693:
2691:
2688:
2686:
2683:
2680:
2679:
2676:
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2668:
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2649:
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2519:
2518:Ethandrostate
2516:
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2502:
2499:
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2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2418:Ethylestrenol
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2393:
2392:
2389:
2386:
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2322:
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2302:
2299:
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2272:
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2260:
2258:
2255:
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2250:
2249:
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2240:
2238:
2235:
2233:
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2225:
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2200:
2198:
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2178:
2175:
2173:
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2167:
2166:
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2148:
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2020:
2018:
2015:
2011:
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1437:
1429:
1421:
1417:
1412:
1407:
1402:
1397:
1393:
1389:
1386:(9): e13100.
1385:
1381:
1377:
1370:
1368:
1359:
1355:
1350:
1345:
1341:
1337:
1333:
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1141:
1137:
1136:Endocrinology
1133:
1126:
1124:
1115:
1111:
1106:
1101:
1098:(3): 248–64.
1097:
1093:
1089:
1082:
1080:
1078:
1062:: 14628–14635
1061:
1057:
1050:
1042:
1038:
1033:
1028:
1024:
1020:
1016:
1012:
1008:
1001:
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856:
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849:
847:
831:on 2015-07-14
827:
823:
821:0-9737599-9-2
817:
810:
809:
801:
786:
779:
778:"Vinclozolin"
773:
758:
751:
745:
743:
741:
739:
737:
735:
733:
731:
729:
727:
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723:
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447:(trade names
446:
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405:
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275:DTXSID4022361
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174:ECHA InfoCard
171:
170:
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51:
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41:
37:
32:
28:
23:
3824:Chloroarenes
3763:Testosterone
3628:
3549:Pyrilutamide
3501:
3493:
3485:
3450:Lavender oil
3440:Ketoconazole
3405:Enzalutamide
3375:Darolutamide
3309:Bicalutamide
3284:Atraric acid
3256:
3251:
3235:Trimegestone
3190:Promegestone
3155:Mifepristone
3130:Medrogestone
3075:Drospirenone
3030:Clascoterone
2961:
2927:
2871:JNJ-37654032
2866:JNJ-28330835
2861:JNJ-26146900
2757:
2701:
2681:
2666:
2648:Quingestanol
2565:Etonogestrel
2551:
2531:
2504:
2494:
2484:
2469:
2453:Propetandrol
2394:
2383:Oxymetholone
2358:Methasterone
2312:
2306:Tiomesterone
2296:Oxymesterone
2188:
2168:
2089:Norclostebol
2064:
2060:
1969:
1907:Mepitiostane
1902:Epitiostanol
1885:Drostanolone
1836:Androsterone
1792:
1773:+dutasteride
1769:Testosterone
1737:DHEA sulfate
1590:
1520:
1496:. Retrieved
1489:the original
1484:
1472:
1439:
1435:
1428:
1383:
1379:
1334:(1): 75–82.
1331:
1327:
1317:
1298:
1294:
1240:
1236:
1188:
1184:
1174:
1139:
1135:
1095:
1091:
1064:. Retrieved
1059:
1049:
1017:(6): 700–7.
1014:
1010:
1000:
988:. Retrieved
984:
942:
937:
925:. Retrieved
918:the original
913:
901:
889:. Retrieved
882:the original
877:
865:
833:. Retrieved
826:the original
807:
800:
788:. Retrieved
784:
772:
760:. Retrieved
756:
686:
677:
665:
652:
643:virilization
635:progesterone
628:
604:
601:Antiandrogen
586:
552:
543:
512:
499:
475:
469:
460:
456:
452:
448:
444:
443:
142:ChEMBL513221
61:Identifiers
55:Vinclozoline
53:Other names
44:
20:Vinclozolin
3748:Osteocalcin
3629:Vinclozolin
3614:Thalidomide
3609:Seviteronel
3539:Procymidone
3475:Masofaniten
3430:Inocoterone
3334:bisphenol S
3330:bisphenol F
3326:bisphenol A
3304:BAY-1024767
3279:Apalutamide
3225:Spiroxasone
3220:Spirorenone
3200:Rosterolone
3140:Mespirenone
3085:Edogestrone
3055:Delanterone
3045:Cyproterone
3035:Clometerone
3005:Benorterone
2990:Abiraterone
2955:Antagonists
2886:PF-06260414
2791:BMS-564,929
2715:Alternariol
2607:Lynestrenol
2560:Desogestrel
2443:Norboletone
2433:Metribolone
2378:Oxandrolone
2336:Mestanolone
2301:Penmesterol
2232:Formebolone
2197:Calusterone
2192:Bolasterone
1946:Prostanozol
1917:Mesterolone
1522:Vinclozolin
1498:12 December
1191:: 158–173.
855:Vinclozolin
702:fludioxonil
674:Environment
668:leydig cell
619:hypospadias
531:cyanohydrin
445:Vinclozolin
345:Properties
180:100.051.437
3834:Fungicides
3818:Categories
3742:-ornithine
3685:gadolinium
3534:Prochloraz
3529:Phenothrin
3509:Nilutamide
3480:Methiocarb
3400:Endosulfan
3365:Cioteronel
3360:Cimetidine
3350:BMS-641988
3345:BMS-570511
3340:BMS-501949
3314:Bisphenols
3269:Antarlides
3245:Zanoterone
3180:Oxendolone
3125:Ludaterone
3115:Galeterone
3065:Dicirenone
2962:Steroidal:
2928:Steroidal:
2921:Vosilasarm
2816:GSK2881078
2771:AC-262,536
2730:Trilostane
2638:Norgestrel
2587:Gestrinone
2555:Δ-Tibolone
2438:Mibolerone
2388:Stanozolol
2341:Metenolone
2118:Trenbolone
2077:Nandrolone
2027:Dienedione
1951:Stenbolone
1912:Mesabolone
1764:Silandrone
1759:Quinbolone
1754:Plomestane
1749:Formestane
1744:Exemestane
1666:Atamestane
1563:modulators
1066:8 February
990:22 October
927:2 November
891:2 November
835:9 February
790:31 October
762:22 October
712:References
698:cyprodinil
535:isocyanate
389:Molar mass
246:JJ258EZN1I
153:ChemSpider
122:CHEBI:9986
89:3D model (
78:50471-44-8
68:CAS Number
40:IUPAC name
3728:-arginine
3713:Estradiol
3693:strontium
3689:magnesium
3677:aluminium
3644:YM-175735
3579:Ro 5-2537
3574:Ro 2-7239
3524:PF-998425
3519:Pentomone
3460:LG-120907
3420:Flutamide
3415:Fenarimol
3355:CH5137291
3294:Bakuchiol
3230:Topterone
3195:Prorenone
3170:Osaterone
3165:Nordinone
3150:Mexrenone
3070:Dienogest
3020:Canrenone
2941:TFM-4AS-1
2881:ORM-11984
2821:GSK-4336A
2811:GLPG-0492
2735:ZM-182345
2582:Gestodene
2570:Etynodiol
2326:Furazabol
2217:Enestebol
2145:Trendione
2106:Oxabolone
2032:Dienolone
2005:Bolandiol
1934:Nisterime
1688:Clostebol
1671:Boldenone
694:iprodione
692:(Flint),
656:apoptosis
492:effects.
3779:See also
3666:Agonists
3639:YM-92088
3604:RU-58841
3599:RU-58642
3594:RU-57073
3589:RU-56187
3584:RU-22930
3514:ONC1-13B
3465:LGD-1331
3390:Dieldrin
3384:p,p’-DDE
3289:AZD-3514
3274:Arabilin
3205:RU-15328
3145:Metogest
3080:DU-41165
2916:S-101479
2896:RU-59063
2851:LGD-4033
2846:LGD-3303
2836:LGD-2226
2826:GSK-8698
2725:Drupanol
2720:Cl-4AS-1
2660:Tibolone
1841:Bolazine
1584:Agonists
1464:23313085
1442:: 6–14.
1420:20927350
1380:PLOS ONE
1358:17956218
1277:16504050
1243:(1): 4.
1215:24530523
1166:16973726
1114:11392371
1041:15929892
878:UC Davis
639:estrogen
527:phosgene
3735:-lysine
3723:(incl.
3681:calcium
3675:(incl.
3673:Cations
3470:Linuron
3410:EPI-001
3316:(e.g.,
3105:EM-6537
3100:EM-5855
3095:EM-5854
3090:EM-4350
2936:MK-0773
2931:EM-9017
2911:S-40503
2766:ACP-105
2761:198RL26
2626:(e.g.,
2599:(e.g.,
2508:Danazol
2458:RU-2309
2398:Bolenol
1444:Bibcode
1411:2948035
1388:Bibcode
1349:5940343
1268:1403752
1245:Bibcode
1206:4133337
1157:5940332
1032:1257594
859:PubChem
613:of the
453:Curalan
449:Ronilan
426:what is
424: (
213:PubChem
3658:GPRC6A
3634:YM-580
3564:RD-162
3455:LG-105
2806:FTBU-1
1462:
1418:
1408:
1356:
1346:
1305:
1275:
1265:
1213:
1203:
1164:
1154:
1112:
1039:
1029:
818:
575:sites.
571:beans.
525:, and
461:Touche
457:Vorlan
421:verify
418:
394:286.11
329:SMILES
201:C10981
133:ChEMBL
34:Names
3322:BFDGE
3318:BADGE
3264:AA560
2946:YK-11
2856:LY305
2746:SARMs
1492:(PDF)
1481:(PDF)
1297:[
981:(PDF)
921:(PDF)
910:(PDF)
885:(PDF)
874:(PDF)
857:from
829:(PDF)
812:(PDF)
781:(PDF)
753:(PDF)
700:plus
488:with
294:InChI
226:39676
162:36278
113:ChEBI
91:JSmol
3754:SHBG
3697:zinc
3395:DIMP
3010:BOMT
2906:S-23
2796:DTIB
1500:2011
1460:PMID
1416:PMID
1354:PMID
1303:ISBN
1273:PMID
1211:PMID
1162:PMID
1110:PMID
1068:2015
1037:PMID
992:2011
929:2011
893:2011
837:2015
816:ISBN
792:2011
764:2011
637:and
502:BASF
474:and
237:UNII
192:KEGG
3380:DDT
2901:S-1
2891:R-1
1452:doi
1406:PMC
1396:doi
1344:PMC
1336:doi
1263:PMC
1253:doi
1201:PMC
1193:doi
1189:203
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