373:
226:
47:
932:
686:
38:
778:
989:, twice daily application over 3 months of 20% AzA significantly reduced the number of comedones, papules, and pustules; at this strength, it’s considered to be as effective as benzoyl peroxide 5%, tretinoin 0.05%, erythromycin 2%, and oral tetracycline at 500 mg-1000 mg. In a comparative review of effects of topical AzA,
976:
In topical pharmaceutical preparations and scientific research AzA is typically used in concentrations between 15% and 20% but some research demonstrates that in certain vehicle formulations the pharmaceutical effects of 10% Azelaic acid has the potential to be fully comparable to that of some 20%
1071:
Brand names for azelaic acid include Dermaz 99, Crema Pella
Perfetta (micronized azelaic acid, kojic dipalmitate, and liquorice extract), Azepur99, Azetec99, Azaclear (azelaic acid and niacinamide), AzClear Action, Azelex, White Action cream, Finacea, Finevin, Melazepam, Skinoren, Ezanic, Azelac,
1001:, AzA had more high-quality evidence of effectiveness than the rest. Results can be expected after 4 weeks of twice-daily treatment. The effectiveness of long term use is unclear, but it’s been recommended that AzA be used for at least 6 months continuously for maintenance.
1112:
Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and
Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq),
5016:
944:
Esters of this dicarboxylic acid find applications in lubrication and plasticizers. In lubricant industries it is used as a thickening agent in lithium complex grease. With hexamethylenediamine, azelaic acid forms
694:
666:
5023:
2232:
2796:
4509:
1531:
Liu, R. H.; Smith, M. K.; Basta, S. A.; Farmer, E. R. (2006). "Azelaic acid in the treatment of papulopustular rosacea – A systematic review of randomized controlled trials".
3050:
848:. It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners. AzA inhibits
1954:"Evidence-based topical treatments (azelaic acid, salicylic acid, nicotinamide, sulfur, zinc, and fruit acid) for acne: an abridged version of a Cochrane systematic review"
638:
4672:
744:
3040:
3364:
2738:
557:
907:
In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It serves as a signal that induces the accumulation of
5009:
2090:
Stamatiadis, D; Bulteau-Portois, Marie-Claire; Mowszowicz, Irene (1988). "Inhibition of 5α-reductase activity in human skin by zinc and azelaic acid".
791:
4486:
3170:
1093:
4058:
4048:
2306:
1337:
4491:
4532:
4527:
4312:
4088:
4078:
1048:. In vitro research during mid-1980s evaluating azelaic acid's depigmenting (whitening) capability concluded it is effective (cytotoxic to
957:
Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne. It belongs to a class of medication called
422:
4831:
4766:
4761:
4711:
4542:
4456:
4068:
4826:
4701:
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4476:
4461:
4392:
4103:
4013:
2731:
4985:
4292:
4287:
4277:
4118:
3948:
1705:[Azelaic acid 15% gel in the treatment of acne vulgaris. Combined results of two double-blind clinical comparative studies].
4821:
4642:
3993:
4990:
3470:
1059:
after a period of application of three months without the latter's adverse effects and even more effective if applied along with
985:
Azelaic acid is effective for mild to moderate acne when applied topically at a 15%-20% concentration. In patients with moderate
3983:
2638:
1822:"Azelaic acid. A review of its pharmacological properties and therapeutic efficacy in acne and hyperpigmentary skin disorders"
4980:
3932:
2724:
2682:
2067:
1313:
274:
3065:
4975:
2971:
1390:
Jung, H. W.; Tschaplinski, T. J.; Wang, L.; Glazebrook, J.; Greenberg, J. T. (2009). "Priming in
Systemic Plant Immunity".
5032:
3320:
919:
The mechanism of action in humans is thought to be through the inhibition of hyperactive protease activity that converts
5293:
1490:
786:
3727:
3722:
2299:
2258:
3160:
3389:
2966:
387:
4172:
4571:
3476:
3439:
3269:
3234:
2699:
3165:
798:
111:
5303:
3394:
623:
1878:
Morelli V, Calmet E, Jhingade V (June 2010). "Alternative therapies for common dermatologic disorders, part 2".
2924:
1363:
1227:
4162:
2133:
Pathak, M. A.; Ciganek, E. R.; Wick, M.; Sober, A. J.; Farinelli, W. A.; Fitzpatrick, T. B. (September 1985).
2653:
2292:
2831:
2811:
4970:
4940:
4505:
3799:
3187:
2643:
726:
330:
221:
3660:
3013:
2826:
1567:
1090:
5298:
5274:
3877:
3239:
2841:
965:, which is a natural substance that promotes the growth of acne bacteria. Azelaic acid is also used as a
351:
3862:
3857:
3665:
736:
3399:
3018:
2668:
2633:
1952:
Liu, Haibo; Yu, Haiyan; Xia, Jun; Liu, Ling; Liu, Guanjian; Sang, Hong; Peinemann, Frank (2020-11-01).
1341:
685:
533:
163:
4167:
2184:"Melanin hyperpigmentation of skin: melasma, topical treatment with azelaic acid, and other therapies"
3229:
2956:
2902:
2658:
1793:
1566:
Burchacka, E.; Potaczek, P.; Paduszyński, P.; Karłowicz-Bodalska, K.; Han, T.; Han, S. (2016-10-01).
233:
5001:
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2220:
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3819:
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3508:
3449:
3182:
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2786:
2460:
368:
4157:
3892:
3872:
4688:
3615:
3177:
3077:
2687:
2271:
2135:"An evaluation of the effectiveness of azelaic acid as a depigmenting and chemotherapeutic agent"
1568:"New effective azelaic acid liposomal gel formulation of enhanced pharmaceutical bioavailability"
973:, due to its ability to reduce inflammation. It clears the bumps and swelling caused by rosacea.
578:
3359:
961:. It works by killing acne bacteria that infect skin pores. It also decreases the production of
4680:
3815:
3454:
3325:
3197:
3045:
2914:
2863:
1703:"15% Azelainsauregel in der Behandlung der Akne. Zwei doppelblinde klinische Vergleichsstudien"
4152:
4212:
3700:
3550:
3444:
3109:
2791:
2648:
2057:
1017:, particularly in those with darker skin types. It has been recommended as an alternative to
708:
678:
1357:
756:
4372:
3840:
3811:
3784:
3650:
3538:
3347:
3315:
3281:
2919:
2890:
2663:
1399:
1166:"The use of topical azelaic acid for common skin disorders other than inflammatory rosacea"
752:
612:
339:
59:
3003:
183:
8:
4895:
4890:
4622:
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4182:
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87:
77:
1403:
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225:
143:
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3533:
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3342:
3310:
3143:
3033:
2885:
2750:
2346:
2115:
2103:
2038:
1989:
1857:
1730:
1683:
1634:
1467:
1443:"Cathelicidin LL-37: An Antimicrobial Peptide with a Role in Inflammatory Skin Disease"
1442:
1423:
1331:
1280:
1247:
998:
123:
1513:
4746:
4362:
4322:
4187:
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2008:
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958:
874:
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651:
2119:
2042:
1861:
1734:
1613:
Sieber MA, Hegel JK (November 2013). "Azelaic acid: Properties and mode of action".
4632:
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2821:
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2020:
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1407:
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1259:
1246:
Pillaiyar, Thanigaimalai; Manickam, Manoj; Namasivayam, Vigneshwaran (2017-01-18).
1215:
1146:
818:
591:
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1263:
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3635:
3610:
3461:
3414:
3224:
3084:
2151:
2134:
1915:"Retinoids and azelaic acid to treat acne and hyperpigmentation in skin of color"
1583:
1248:"Skin whitening agents: medicinal chemistry perspective of tyrosinase inhibitors"
1097:
891:
829:
600:
319:
252:
1756:"Versatility of azelaic acid 15% gel in treatment of inflammatory acne vulgaris"
1544:
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931:
5287:
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4731:
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2816:
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2422:
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2199:
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1977:
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1845:
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1323:
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1219:
1181:
869:
511:
501:
214:
1953:
1914:
1755:
1702:
1411:
1165:
19:"Finevin" redirects here. The term may also refer to a former settlement in
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5131:
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4950:
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1985:
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1419:
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563:
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1303:
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2469:
2464:
2440:
2432:
2407:
2366:
2276:
1045:
1041:
748:
396:
InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
740:
406:
InChI=1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
203:
4905:
4872:
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4667:
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4547:
4537:
4432:
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4003:
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2951:
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2941:
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2931:
2853:
2571:
2328:
1969:
1049:
1022:
865:
861:
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473:
264:
234:
174:
46:
20:
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1622:
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5031:
4926:
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4501:
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4352:
4337:
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3998:
3988:
3922:
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3757:
3513:
3404:
3332:
3293:
3219:
3192:
3121:
2875:
2858:
2617:
2576:
2556:
2531:
2513:
2412:
1913:
Woolery-Lloyd, Heather C.; Keri, Jonette; Doig, Stefan (2013-04-01).
1060:
2089:
1206:
Cornils, Boy; Lappe, Peter (2006). "Dicarboxylic Acids, Aliphatic".
1029:. According to one report in 1988, azelaic acid in combination with
768:
Except where otherwise noted, data are given for materials in their
4912:
4791:
4786:
4781:
4776:
4771:
4577:
4332:
4267:
4083:
4038:
4033:
4028:
4023:
4018:
3973:
3912:
3907:
3847:
3028:
2870:
2607:
2602:
2548:
2526:
1211:
1033:
1009:
Azelaic acid is used for treatment of skin pigmentation, including
294:
194:
24:
110:
4868:
4657:
4597:
4397:
4282:
4123:
4098:
3953:
3695:
3645:
3585:
3246:
2612:
2485:
2445:
2417:
2221:
https://pharmaceutical.basf.com/en/APIs-Raw-Materials/Dermaz.html
1026:
1010:
970:
962:
732:
491:
306:
4919:
4860:
4845:
4751:
2009:"Skin lightening preparations and the hydroquinone controversy"
845:
154:
37:
1389:
4451:
4133:
4043:
3974:
Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
3933:
2817:
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
1495:
946:
883:
837:
760:
134:
100:
1245:
356:
4884:
4197:
1072:
Azaderm, (Acnegen, Eziderm, Acnicam, Azelexin in
Pakistan)
986:
887:
718:
506:
109 to 111 °C (228 to 232 °F; 382 to 384 K)
285:
911:, an important component of a plant's defensive response.
4567:
1308:. David Rakel (Fourth ed.). Philadelphia, PA. 2018.
841:
3658:
17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:
1111:
3161:
7α-Methyl-19-norandrostenedione (MENT dione, trestione)
1440:
3855:
5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:
2132:
1700:
2062:. Lippincott Williams & Wilkins. pp. 74 ff.
2059:
Aesthetics and
Cosmetic Surgery for Darker Skin Types
1912:
1877:
1701:
Gollnick, H. P.; Graupe, K.; Zaumseil, R. P. (2004).
1241:
1239:
4941:
1252:
Journal of Enzyme
Inhibition and Medicinal Chemistry
714:
3289:
Normethandrone (methylestrenolone, normethisterone)
1707:
Journal der
Deutschen Dermatologischen Gesellschaft
1530:
273:
1356:
1236:
516:286 °C (547 °F; 559 K) at 100 mmHg
3501:17α-Alkylated 5α-dihydrotestosterone derivatives:
1654:"Treatment of acne vulgaris in pregnant patients"
1651:
1055:A 1996 review claimed 20% AzA is as potent as 4%
949:-6,9, which finds specialized uses as a plastic.
939:
5285:
2746:
1441:Reinholz, M.; Ruzicka, T.; Schauber, J. (2012).
318:
3720:5α-Dihydro-17α-ethynyltestosterone derivatives:
86:
3171:11β-Methyl-19-nortestosterone dodecylcarbonate
2314:
1645:
1208:Ullmann's Encyclopedia of Industrial Chemistry
5017:
3938:Tooltip Selective androgen receptor modulator
3583:17α-Alkylated 19-nortestosterone derivatives:
2732:
2300:
1025:inhibitor, azelaic acid reduces synthesis of
860:Azelaic acid is industrially produced by the
3989:Enobosarm (ostarine, MK-2866, GTx-024, S-22)
1508:
1506:
1354:
1205:
3740:17α-Ethynyl-19-nortestosterone derivatives:
2083:
1951:
1873:
1871:
1617:(Review). 27 Suppl 1 (Supplement 1): 9–17.
1612:
1133:NI(aq) at Different Ionic Strengths and at
923:into the antimicrobial skin peptide LL-37.
5024:
5010:
3462:Methylclostebol (chloromethyltestosterone)
3357:5α-Dihydro-19-nortestosterone derivatives:
2739:
2725:
2307:
2293:
2181:
2049:
1606:
1336:: CS1 maint: location missing publisher (
1036:was found to be a potent (90% inhibition)
371:
224:
182:
3683:17α-Vinyl-19-nortestosterone derivatives:
3299:Oxabolone cipionate (oxabolone cypionate)
2915:DHEA (androstenolone, prasterone; 5-DHEA)
2759:
2150:
2024:
1819:
1753:
1669:
1503:
1466:
1279:
1163:
1086:
1084:
836:exists as a white powder. It is found in
338:
3390:Chlorodehydromethylandrostenediol (CDMA)
2139:The Journal of Investigative Dermatology
1868:
930:
4991:List of androgens and anabolic steroids
3377:17α-Alkylated testosterone derivatives:
2006:
367:
202:
5286:
3395:Chlorodehydromethyltestosterone (CDMT)
3151:Testifenon (testiphenon, testiphenone)
2639:Clindamycin/adapalene/benzoyl peroxide
2055:
1081:
897:
215:
5005:
3676:Norvinisterone (vinylnortestosterone)
3210:Bolmantalate (nandrolone adamantoate)
3205:Bolandione (19-nor-4-androstenedione)
2920:DHEA enanthate (prasterone enanthate)
2720:
2288:
1815:
1813:
1652:Pugashetti R, Shinkai K (July 2013).
1201:
1199:
1107:
1105:
935:Azelaic acid cream labeled in Russian
645:
399:Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N
162:
142:
4946:Tooltip Sex hormone-binding globulin
3693:17α-Ethynyltestosterone derivatives:
2972:Polytestosterone phloretin phosphate
567:
5033:Linear saturated dicarboxylic acids
3616:Methylhydroxynandrolone (MOHN, MHN)
3321:Trenbolone hexahydrobenzylcarbonate
2981:5α-Dihydrotestosterone derivatives:
2849:Androstenedione (4-androstenedione)
1820:Fitton, A.; Goa, K. L. (May 1991).
409:Key: BDJRBEYXGGNYIS-UHFFFAOYAK
309:
293:
13:
3673:17α-Vinyltestosterone derivatives:
3435:Methandriol (methylandrostenediol)
2104:10.1111/j.1365-2133.1988.tb03474.x
1958:Journal of Evidence-Based Medicine
1906:
1810:
1196:
1164:Del Rosso, James Q. (2006-02-01).
1102:
1004:
14:
5315:
3713:Ethisterone (ethynyltestosterone)
3430:Metandienone (methandrostenolone)
3260:Methoxydienone (methoxygonadiene)
2871:Boldione (1,4-androstadienedione)
2822:Androstenediol (5-androstenediol)
2787:4-Dehydroepiandrosterone (4-DHEA)
2252:
2233:"Azelaic Acid brands in Pakistan"
1754:Thiboutot, Diane (January 2008).
1572:Biomedicine & Pharmacotherapy
1355:Sarah Everts (January 31, 2011).
1040:, similar to the hair loss drugs
980:
902:
632:
4986:Progesterone receptor modulators
3477:Methyltestosterone 3-hexyl ether
3440:Methandriol bisenanthoyl acetate
3400:Chloromethylandrostenediol (CMA)
3235:Dimethandrolone dodecylcarbonate
2994:1-Androsterone (1-andro, 1-DHEA)
2182:Breathnach, A. S. (1996-01-01).
2026:10.1111/j.1529-8019.2007.00144.x
1838:10.2165/00003495-199141050-00007
1719:10.1046/j.1439-0353.2004.04731.x
1615:Skin Pharmacology and Physiology
914:
776:
684:
457:
45:
36:
3158:19-Nortestosterone derivatives:
2225:
2214:
2175:
2126:
2056:Grimes, Pearl E. (2007-07-01).
2000:
1945:
1919:Journal of Drugs in Dermatology
1794:"Azelaic Acid And Its Benefits"
1786:
1760:Journal of Drugs in Dermatology
1747:
1694:
1559:
1524:
1483:
1364:Chemical & Engineering News
1052:) at only high concentrations.
926:
890:. The bacterial degradation of
772:(at 25 °C , 100 kPa).
4173:15β-Hydroxycyproterone acetate
4064:OPK-88004 (LY-2452473, TT-701)
2092:British Journal of Dermatology
1434:
1383:
1348:
1296:
1157:
1066:
940:Polymers and related materials
872:. It is produced naturally by
463:
451:
1:
4971:Receptor/signaling modulators
3728:17α-Ethynyl-3β-androstanediol
3723:17α-Ethynyl-3α-androstanediol
3166:11β-Methyl-19-nortestosterone
2654:Erythromycin/benzoyl peroxide
1264:10.1080/14756366.2016.1256882
1075:
1063:for the same period of time.
855:
4981:Estrogen receptor modulators
4428:Trimethyltrienolone (R-2956)
3800:Lynestrenol phenylpropionate
3188:19-Nordehydroepiandrosterone
2644:Clindamycin/benzoyl peroxide
2152:10.1111/1523-1747.ep12276684
2007:Draelos, Z. (Sep–Oct 2007).
1584:10.1016/j.biopha.2016.07.014
7:
5275:Category:Dicarboxylic acids
4976:Androgens and antiandrogens
4747:Ralaniten acetate (EPI-506)
4163:7α-Thiomethylspironolactone
3878:Medroxyprogesterone acetate
3240:Dimethandrolone undecanoate
3051:Dihydromethylandrostenediol
2842:Androstenediol dipropionate
1545:10.1001/archderm.142.8.1047
10:
5320:
3066:Dihydrotestosterone esters
3019:11-Ketodihydrotestosterone
2832:Androstenediol 17β-acetate
2812:11β-Hydroxyandrostenedione
2797:4,17α-Dimethyltestosterone
2669:Tretinoin/benzoyl peroxide
2634:Adapalene/benzoyl peroxide
952:
478:188.22 g/mol
18:
5272:
5234:Hexadecanedioic acid
5048:
4963:
4853:
4844:
4142:
3931:
3870:Progesterone derivatives:
3661:5α-Dihydronorethandrolone
3230:Dimethandrolone buciclate
3060:androstanolone, stanolone
3056:Dihydrotestosterone (DHT)
3014:7β-Hydroxyepiandrosterone
2903:Cloxotestosterone acetate
2827:Androstenediol 3β-acetate
2779:Testosterone derivatives:
2771:
2764:Tooltip Androgen receptor
2757:
2677:
2659:Erythromycin/isotretinoin
2626:
2590:
2547:
2484:
2431:
2398:
2365:
2327:
1892:10.1016/j.pop.2010.02.005
1377:10.1021/cen-v089n005.p053
766:
665:
660:
590:
550:
438:
418:
383:
70:
58:
53:
44:
35:
16:Organic chemical compound
5253:(Phelogenic acid) C
5217:Tredecanedioic acid
4676:-Butylbenzenesulfonamide
3863:5α-Dihydronorethisterone
3858:5α-Dihydrolevonorgestrel
3820:norethisterone enanthate
3789:levonorgestrel butanoate
3666:5α-Dihydronormethandrone
3519:Mebolazine (dimethazine)
3509:Desoxymethyltestosterone
3450:Methandriol dipropionate
3247:LS-1727 (nandrolone 17β-
3183:19-Nor-5-androstenedione
3041:Dihydroethyltestosterone
2837:Androstenediol diacetate
1459:10.5021/ad.2012.24.2.126
1220:10.1002/14356007.a08_523
821:with the formula HOOC(CH
727:Precautionary statements
5294:5α-Reductase inhibitors
5200:Dodecanedioic acid
4807:Topilutamide (fluridil)
4168:11α-Hydroxyprogesterone
3178:19-Nor-5-androstenediol
3078:Drostanolone propionate
2263:treatments/azelaic-acid
1533:Archives of Dermatology
1491:"Azelaic Acid for Acne"
1412:10.1126/science.1170025
5304:Anti-acne preparations
5132:Heptanedioic acid
5098:(Glutaric acid) C
5096:Pentanedioic acid
5080:(Succinic acid) C
5066:(Malonic acid) CH
5064:Propanedioic acid
5056:(Oxalic acid) (CO
4692:-Desmethylenzalutamide
4398:SC-5233 (spirolactone)
3816:norethisterone acetate
3455:Methandriol propionate
3326:Trenbolone undecanoate
3198:Bolandiol dipropionate
3046:Dihydrofluoxymesterone
3009:5α-Androst-2-en-17-one
2864:Boldenone undecylenate
2272:"Azelaic Acid Topical"
1514:"Azelaic acid topical"
1096:April 9, 2008, at the
1038:5α-reductase inhibitor
936:
868:. The side product is
5236:(Thapsic acid) C
5185:(Sebacic acid) C
5183:Decanedioic acid
5168:(Azelaic acid) C
5166:Nonanedioic acid
5151:(Suberic acid) C
5149:Octanedioic acid
5134:(Pimelic acid) C
5114:Hexanedioic acid
5078:Butanedioic acid
5054:Ethanedioic acid
4684:-Desmethylapalutamide
4213:Chlormadinone acetate
4158:7α-Thiospironolactone
4029:LGD-2941 (LGD-122941)
4019:LG121071 (LGD-121071)
3893:3-Keto-5α-abiraterone
3873:6α-Methylprogesterone
3812:Norethisterone esters
3785:Levonorgestrel esters
3701:Ethinylandrostenediol
3551:Methyl-1-testosterone
3471:+esterified estrogens
3445:Methandriol diacetate
3110:Mesterolone cipionate
2792:4-Hydroxytestosterone
2649:Clindamycin/tretinoin
1447:Annals of Dermatology
1340:) CS1 maint: others (
1091:Sigma-Aldrich catalog
1013:and postinflammatory
934:
886:that lives on normal
5116:(Adipic acid) C
4373:Potassium canrenoate
3841:Quingestanol acetate
3651:Tetrahydrogestrinone
3539:Metenolone enanthate
3365:5α-Dihydrotrestolone
3360:5α-Dihydronandrolone
3348:Trestolone enanthate
3316:Trenbolone enanthate
3282:Norclostebol acetate
2891:Clostebol propionate
2664:Sulfacetamide/sulfur
2013:Dermatologic Therapy
1658:Dermatologic Therapy
1358:"Vegetative Warfare"
1305:Integrative medicine
997:, Sulfur, Zinc, and
894:gives azelaic acid.
613:Biological half-life
60:Preferred IUPAC name
4896:Dihydrotestosterone
4891:Dehydroandrosterone
4742:Ralaniten (EPI-002)
4623:Inocoterone acetate
4348:Nomegestrol acetate
4248:Delmadinone acetate
4238:Cyproterone acetate
4183:Abiraterone acetate
4153:7α-Thioprogesterone
3763:Etynodiol diacetate
2967:Testosterone esters
2910:Dehydroandrosterone
2807:11-Ketotestosterone
2504:Cyproterone acetate
2237:www.druginfosys.com
1404:2009Sci...324...89W
898:Biological function
523:Solubility in water
430:O=C(O)CCCCCCCC(=O)O
124:Beilstein Reference
32:
5299:Dicarboxylic acids
5251:Docosanedioic acid
5219:(Brassylic acid) C
3733:Dihydroethisterone
3596:Dimethyltrienolone
3556:Methylepitiostanol
3534:Metenolone acetate
3467:Methyltestosterone
3370:19-Norandrosterone
3343:Trestolone acetate
3311:Trenbolone acetate
3255:-nitrosocarbamate)
3144:Stenbolone acetate
3034:Bolazine capronate
2886:Clostebol caproate
2704:Never to phase III
2352:Blue light therapy
2347:8-Hydroxyquinoline
2318:-treating agents (
2194:(1 Suppl): 36–45.
1970:10.1111/jebm.12411
1176:(2 Suppl): 22–24.
1139:J. Chem. Eng. Data
999:alpha-hydroxy acid
959:dicarboxylic acids
937:
880:Pityrosporum ovale
799:Infobox references
30:
5281:
5280:
4999:
4998:
4959:
4958:
4929:
4922:
4915:
4908:
4840:
4839:
4363:Osaterone acetate
4323:Megestrol acetate
4188:Allyltestosterone
3964:Acetothiolutamide
3883:Megestrol acetate
3686:Vinyltestosterone
3591:Dimethyldienolone
3410:Ethyltestosterone
3338:Trestolone (MENT)
3270:Nandrolone esters
3251:-(2-chloroethyl)-
3127:Nisterime acetate
3004:3α-Androstanediol
2989:1-Androstenedione
2898:Cloxotestosterone
2881:Clostebol acetate
2802:5-Androstenedione
2748:Androgen receptor
2714:
2713:
2423:Red light therapy
2400:Anti-inflammatory
2069:978-0-7817-8403-0
1671:10.1111/dth.12077
1623:10.1159/000354888
1315:978-0-323-35868-2
1151:10.1021/je060132t
1015:hyperpigmentation
875:Malassezia furfur
834:dicarboxylic acid
832:. This saturated
807:Chemical compound
805:
804:
709:Hazard statements
649:
636:
352:CompTox Dashboard
112:Interactive image
5311:
5026:
5019:
5012:
5003:
5002:
4947:
4943:
4927:
4920:
4913:
4906:
4851:
4850:
4633:Ketodarolutamide
4613:Hydroxyflutamide
4570:(via metabolite
3939:
3935:
3890:Others/unsorted:
3561:Methylstenbolone
3425:Hydroxystenozole
2984:1-Androstenediol
2782:4-Androstenediol
2769:
2768:
2765:
2761:
2741:
2734:
2727:
2718:
2717:
2537:Ethinylestradiol
2390:Benzoyl peroxide
2342:Benzoyl peroxide
2309:
2302:
2295:
2286:
2285:
2281:
2247:
2246:
2244:
2243:
2229:
2223:
2218:
2212:
2211:
2179:
2173:
2172:
2154:
2130:
2124:
2123:
2087:
2081:
2080:
2078:
2076:
2053:
2047:
2046:
2028:
2004:
1998:
1997:
1949:
1943:
1942:
1910:
1904:
1903:
1875:
1866:
1865:
1817:
1808:
1807:
1805:
1804:
1790:
1784:
1783:
1751:
1745:
1744:
1742:
1741:
1698:
1692:
1691:
1673:
1649:
1643:
1642:
1610:
1604:
1603:
1563:
1557:
1556:
1539:(8): 1047–1052.
1528:
1522:
1521:
1510:
1501:
1500:
1487:
1481:
1480:
1470:
1438:
1432:
1431:
1387:
1381:
1380:
1360:
1352:
1346:
1345:
1335:
1327:
1300:
1294:
1293:
1283:
1243:
1234:
1233:
1203:
1194:
1193:
1161:
1155:
1154:
1145:(5): 1660–1667.
1109:
1100:
1088:
819:organic compound
789:
783:
780:
779:
762:
758:
754:
750:
746:
742:
738:
734:
720:
716:
688:
647:
644:
634:
631:
592:Pharmacokinetics
571:
465:
459:
453:
446:Chemical formula
376:
375:
360:
358:
342:
322:
311:
297:
277:
253:Gmelin Reference
236:
228:
217:
206:
186:
166:
146:
114:
90:
64:Nonanedioic acid
49:
40:
33:
29:
5319:
5318:
5314:
5313:
5312:
5310:
5309:
5308:
5284:
5283:
5282:
5277:
5268:
5267:
5264:
5260:
5256:
5247:
5243:
5239:
5230:
5226:
5222:
5213:
5209:
5205:
5196:
5192:
5188:
5179:
5175:
5171:
5162:
5158:
5154:
5145:
5141:
5137:
5127:
5123:
5119:
5109:
5105:
5101:
5091:
5087:
5083:
5073:
5069:
5059:
5044:
5042:
5038:
5030:
5000:
4995:
4955:
4945:
4836:
4558:Cyanonilutamide
4487:Bavdegalutamide
4298:Epitestosterone
4138:
3969:Acetoxolutamide
3937:
3927:
3636:Norethandrolone
3611:Methyldienolone
3415:Fluoxymesterone
3225:Dimethandrolone
3085:Epiandrosterone
2763:
2753:
2745:
2715:
2710:
2709:
2694:Clinical trials
2673:
2622:
2586:
2543:
2480:
2427:
2394:
2361:
2323:
2313:
2270:
2255:
2250:
2241:
2239:
2231:
2230:
2226:
2219:
2215:
2180:
2176:
2131:
2127:
2088:
2084:
2074:
2072:
2070:
2054:
2050:
2005:
2001:
1950:
1946:
1911:
1907:
1876:
1869:
1818:
1811:
1802:
1800:
1798:Chemist at Play
1792:
1791:
1787:
1752:
1748:
1739:
1737:
1713:(10): 841–847.
1699:
1695:
1650:
1646:
1611:
1607:
1564:
1560:
1529:
1525:
1512:
1511:
1504:
1489:
1488:
1484:
1439:
1435:
1398:(5923): 89–91.
1388:
1384:
1353:
1349:
1329:
1328:
1316:
1302:
1301:
1297:
1244:
1237:
1230:
1204:
1197:
1162:
1158:
1132:
1128:
1124:
1121:NCl(aq), and (C
1120:
1116:
1110:
1103:
1098:Wayback Machine
1089:
1082:
1078:
1069:
1007:
1005:Whitening agent
983:
955:
942:
929:
917:
905:
900:
878:(also known as
858:
828:
824:
808:
801:
796:
795:
794: ?)
785:
781:
777:
773:
729:
711:
697:
681:
656:
641:(Pharmacy Only)
615:
603:
601:Bioavailability
583:
580:
560:
542:
525:
468:
462:
456:
448:
434:
431:
426:
425:
414:
411:
410:
407:
401:
400:
397:
391:
390:
379:
361:
354:
345:
325:
312:
300:
280:
267:
255:
246:
209:
189:
169:
149:
126:
117:
104:
93:
80:
66:
65:
28:
17:
12:
11:
5:
5317:
5307:
5306:
5301:
5296:
5279:
5278:
5273:
5270:
5269:
5266:
5265:
5262:
5258:
5254:
5248:
5245:
5241:
5237:
5231:
5228:
5224:
5220:
5214:
5211:
5207:
5203:
5197:
5194:
5190:
5186:
5180:
5177:
5173:
5169:
5163:
5160:
5156:
5152:
5146:
5143:
5139:
5135:
5129:
5125:
5121:
5117:
5111:
5107:
5103:
5099:
5093:
5089:
5085:
5081:
5075:
5071:
5067:
5061:
5057:
5050:
5049:
5046:
5045:
5040:
5036:
5029:
5028:
5021:
5014:
5006:
4997:
4996:
4994:
4993:
4988:
4983:
4978:
4973:
4968:
4964:
4961:
4960:
4957:
4956:
4954:
4953:
4948:
4938:
4933:
4909:-α-Amino acids
4903:
4898:
4893:
4888:
4857:
4855:
4848:
4842:
4841:
4838:
4837:
4835:
4834:
4829:
4824:
4819:
4814:
4809:
4804:
4799:
4794:
4789:
4784:
4779:
4774:
4769:
4764:
4759:
4754:
4749:
4744:
4739:
4734:
4729:
4724:
4719:
4714:
4709:
4704:
4699:
4694:
4686:
4678:
4670:
4665:
4660:
4655:
4650:
4645:
4640:
4635:
4630:
4625:
4620:
4615:
4610:
4605:
4600:
4595:
4590:
4585:
4580:
4575:
4565:
4560:
4555:
4550:
4545:
4540:
4535:
4530:
4525:
4499:
4494:
4489:
4484:
4479:
4474:
4469:
4464:
4459:
4454:
4449:
4436:
4435:
4430:
4425:
4420:
4415:
4410:
4405:
4403:Spironolactone
4400:
4395:
4390:
4385:
4380:
4375:
4370:
4365:
4360:
4355:
4350:
4345:
4340:
4335:
4330:
4325:
4320:
4315:
4310:
4305:
4300:
4295:
4290:
4285:
4280:
4275:
4270:
4265:
4260:
4255:
4250:
4245:
4240:
4235:
4230:
4228:Cyproheptadine
4225:
4220:
4215:
4210:
4205:
4203:Canrenoic acid
4200:
4195:
4190:
4185:
4180:
4175:
4170:
4165:
4160:
4155:
4146:
4144:
4140:
4139:
4137:
4136:
4131:
4126:
4121:
4112:
4111:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4066:
4061:
4056:
4051:
4046:
4041:
4036:
4031:
4026:
4021:
4016:
4011:
4006:
4001:
3996:
3991:
3986:
3981:
3976:
3971:
3966:
3961:
3956:
3951:
3942:
3940:
3929:
3928:
3926:
3925:
3920:
3915:
3910:
3905:
3900:
3895:
3886:
3885:
3880:
3875:
3866:
3865:
3860:
3851:
3850:
3845:
3844:
3843:
3833:
3831:Norgestrienone
3828:
3823:
3809:
3807:Norethisterone
3804:
3803:
3802:
3792:
3782:
3780:Levonorgestrel
3777:
3772:
3767:
3766:
3765:
3755:
3750:
3745:
3736:
3735:
3730:
3725:
3716:
3715:
3710:
3709:
3708:
3698:
3689:
3688:
3679:
3678:
3669:
3668:
3663:
3654:
3653:
3648:
3643:
3638:
3633:
3628:
3623:
3618:
3613:
3608:
3603:
3601:Ethyldienolone
3598:
3593:
3588:
3579:
3578:
3573:
3568:
3563:
3558:
3553:
3548:
3543:
3542:
3541:
3536:
3526:
3521:
3516:
3511:
3506:
3504:Androisoxazole
3497:
3496:
3491:
3486:
3481:
3480:
3479:
3464:
3459:
3458:
3457:
3452:
3447:
3442:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3392:
3387:
3382:
3373:
3372:
3367:
3362:
3353:
3352:
3351:
3350:
3345:
3335:
3330:
3329:
3328:
3323:
3318:
3313:
3303:
3302:
3301:
3291:
3286:
3285:
3284:
3274:
3273:
3272:
3262:
3257:
3244:
3243:
3242:
3237:
3232:
3222:
3217:
3212:
3207:
3202:
3201:
3200:
3190:
3185:
3180:
3175:
3174:
3173:
3163:
3154:
3153:
3148:
3147:
3146:
3136:
3131:
3130:
3129:
3119:
3117:Methyldiazinol
3114:
3113:
3112:
3102:
3097:
3092:
3087:
3082:
3081:
3080:
3070:
3069:
3068:
3053:
3048:
3043:
3038:
3037:
3036:
3026:
3021:
3016:
3011:
3006:
3001:
2999:1-Testosterone
2996:
2991:
2986:
2977:
2976:
2975:
2974:
2969:
2954:
2949:
2944:
2939:
2934:
2929:
2928:
2927:
2922:
2912:
2907:
2906:
2905:
2895:
2894:
2893:
2888:
2883:
2873:
2868:
2867:
2866:
2856:
2851:
2846:
2845:
2844:
2839:
2834:
2829:
2819:
2814:
2809:
2804:
2799:
2794:
2789:
2784:
2775:
2773:
2766:
2755:
2754:
2744:
2743:
2736:
2729:
2721:
2712:
2711:
2708:
2707:
2706:
2705:
2702:
2691:
2685:
2679:
2678:
2675:
2674:
2672:
2671:
2666:
2661:
2656:
2651:
2646:
2641:
2636:
2630:
2628:
2624:
2623:
2621:
2620:
2615:
2610:
2605:
2600:
2594:
2592:
2588:
2587:
2585:
2584:
2579:
2574:
2569:
2564:
2559:
2553:
2551:
2545:
2544:
2542:
2541:
2540:
2539:
2534:
2524:
2523:
2522:
2519:Spironolactone
2516:
2511:
2506:
2501:
2490:
2488:
2482:
2481:
2479:
2478:
2472:
2467:
2458:
2453:
2448:
2443:
2437:
2435:
2429:
2428:
2426:
2425:
2420:
2415:
2410:
2404:
2402:
2396:
2395:
2393:
2392:
2387:
2382:
2380:Salicylic acid
2377:
2371:
2369:
2363:
2362:
2360:
2359:
2354:
2349:
2344:
2339:
2333:
2331:
2325:
2324:
2312:
2311:
2304:
2297:
2289:
2283:
2282:
2267:
2266:
2254:
2253:External links
2251:
2249:
2248:
2224:
2213:
2174:
2145:(3): 222–228.
2125:
2082:
2068:
2048:
2019:(5): 308–313.
1999:
1964:(4): 275–283.
1944:
1925:(4): 434–437.
1905:
1867:
1832:(5): 780–798.
1809:
1785:
1746:
1693:
1644:
1605:
1558:
1523:
1502:
1482:
1453:(2): 126–135.
1433:
1382:
1347:
1314:
1295:
1258:(1): 403–425.
1235:
1228:
1195:
1156:
1130:
1126:
1122:
1118:
1114:
1101:
1079:
1077:
1074:
1068:
1065:
1006:
1003:
991:Salicylic acid
982:
981:Acne treatment
979:
969:treatment for
954:
951:
941:
938:
928:
925:
916:
913:
909:salicylic acid
904:
903:Plants biology
901:
899:
896:
857:
854:
826:
822:
806:
803:
802:
797:
775:
774:
770:standard state
767:
764:
763:
745:P305+P351+P338
730:
725:
722:
721:
712:
707:
704:
703:
698:
693:
690:
689:
682:
677:
674:
673:
663:
662:
658:
657:
655:
654:
642:
628:
626:
620:
619:
616:
611:
608:
607:
604:
599:
596:
595:
588:
587:
584:
581:administration
577:
574:
573:
561:
556:
553:
552:
548:
547:
544:
540:
530:
529:
526:
521:
518:
517:
514:
508:
507:
504:
498:
497:
494:
488:
487:
484:
480:
479:
476:
470:
469:
466:
460:
454:
449:
444:
441:
440:
436:
435:
433:
432:
429:
421:
420:
419:
416:
415:
413:
412:
408:
405:
404:
402:
398:
395:
394:
386:
385:
384:
381:
380:
378:
377:
364:
362:
350:
347:
346:
344:
343:
335:
333:
327:
326:
324:
323:
315:
313:
305:
302:
301:
299:
298:
290:
288:
282:
281:
279:
278:
270:
268:
263:
260:
259:
256:
251:
248:
247:
245:
244:
240:
238:
230:
229:
219:
211:
210:
208:
207:
199:
197:
191:
190:
188:
187:
179:
177:
171:
170:
168:
167:
159:
157:
151:
150:
148:
147:
139:
137:
131:
130:
127:
122:
119:
118:
116:
115:
107:
105:
98:
95:
94:
92:
91:
83:
81:
76:
73:
72:
68:
67:
63:
62:
56:
55:
51:
50:
42:
41:
15:
9:
6:
4:
3:
2:
5316:
5305:
5302:
5300:
5297:
5295:
5292:
5291:
5289:
5276:
5271:
5252:
5249:
5235:
5232:
5218:
5215:
5201:
5198:
5184:
5181:
5167:
5164:
5150:
5147:
5133:
5130:
5115:
5112:
5097:
5094:
5079:
5076:
5065:
5062:
5055:
5052:
5051:
5047:
5034:
5027:
5022:
5020:
5015:
5013:
5008:
5007:
5004:
4992:
4989:
4987:
4984:
4982:
4979:
4977:
4974:
4972:
4969:
4966:
4965:
4962:
4952:
4949:
4944:
4939:
4937:
4934:
4931:
4924:
4917:
4910:
4904:
4902:
4899:
4897:
4894:
4892:
4889:
4886:
4882:
4878:
4874:
4870:
4866:
4862:
4859:
4858:
4856:
4852:
4849:
4847:
4843:
4833:
4830:
4828:
4825:
4823:
4820:
4818:
4815:
4813:
4812:Valproic acid
4810:
4808:
4805:
4803:
4800:
4798:
4795:
4793:
4790:
4788:
4785:
4783:
4780:
4778:
4775:
4773:
4770:
4768:
4765:
4763:
4760:
4758:
4757:Rezvilutamide
4755:
4753:
4750:
4748:
4745:
4743:
4740:
4738:
4735:
4733:
4732:Proxalutamide
4730:
4728:
4725:
4723:
4720:
4718:
4715:
4713:
4710:
4708:
4705:
4703:
4700:
4698:
4695:
4693:
4691:
4687:
4685:
4683:
4679:
4677:
4675:
4671:
4669:
4666:
4664:
4661:
4659:
4656:
4654:
4651:
4649:
4646:
4644:
4641:
4639:
4636:
4634:
4631:
4629:
4626:
4624:
4621:
4619:
4616:
4614:
4611:
4609:
4606:
4604:
4601:
4599:
4596:
4594:
4591:
4589:
4586:
4584:
4581:
4579:
4576:
4573:
4569:
4566:
4564:
4561:
4559:
4556:
4554:
4551:
4549:
4546:
4544:
4541:
4539:
4536:
4534:
4531:
4529:
4526:
4523:
4519:
4515:
4511:
4507:
4503:
4500:
4498:
4495:
4493:
4490:
4488:
4485:
4483:
4480:
4478:
4475:
4473:
4470:
4468:
4465:
4463:
4460:
4458:
4455:
4453:
4450:
4448:
4447:-Bicalutamide
4446:
4441:
4440:Nonsteroidal:
4438:
4437:
4434:
4431:
4429:
4426:
4424:
4421:
4419:
4416:
4414:
4411:
4409:
4406:
4404:
4401:
4399:
4396:
4394:
4391:
4389:
4386:
4384:
4381:
4379:
4376:
4374:
4371:
4369:
4366:
4364:
4361:
4359:
4356:
4354:
4351:
4349:
4346:
4344:
4341:
4339:
4336:
4334:
4331:
4329:
4326:
4324:
4321:
4319:
4316:
4314:
4311:
4309:
4308:Guggulsterone
4306:
4304:
4301:
4299:
4296:
4294:
4291:
4289:
4286:
4284:
4281:
4279:
4276:
4274:
4271:
4269:
4266:
4264:
4261:
4259:
4256:
4254:
4251:
4249:
4246:
4244:
4241:
4239:
4236:
4234:
4231:
4229:
4226:
4224:
4221:
4219:
4216:
4214:
4211:
4209:
4206:
4204:
4201:
4199:
4196:
4194:
4191:
4189:
4186:
4184:
4181:
4179:
4176:
4174:
4171:
4169:
4166:
4164:
4161:
4159:
4156:
4154:
4151:
4148:
4147:
4145:
4141:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4114:
4113:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4065:
4062:
4060:
4057:
4055:
4052:
4050:
4047:
4045:
4042:
4040:
4037:
4035:
4032:
4030:
4027:
4025:
4022:
4020:
4017:
4015:
4012:
4010:
4007:
4005:
4002:
4000:
3997:
3995:
3992:
3990:
3987:
3985:
3982:
3980:
3977:
3975:
3972:
3970:
3967:
3965:
3962:
3960:
3957:
3955:
3952:
3950:
3947:
3946:Nonsteroidal:
3944:
3943:
3941:
3936:
3930:
3924:
3921:
3919:
3916:
3914:
3911:
3909:
3906:
3904:
3901:
3899:
3898:5α-Androstane
3896:
3894:
3891:
3888:
3887:
3884:
3881:
3879:
3876:
3874:
3871:
3868:
3867:
3864:
3861:
3859:
3856:
3853:
3852:
3849:
3846:
3842:
3839:
3838:
3837:
3834:
3832:
3829:
3827:
3824:
3821:
3817:
3813:
3810:
3808:
3805:
3801:
3798:
3797:
3796:
3793:
3790:
3786:
3783:
3781:
3778:
3776:
3773:
3771:
3768:
3764:
3761:
3760:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3738:
3737:
3734:
3731:
3729:
3726:
3724:
3721:
3718:
3717:
3714:
3711:
3707:
3706:Ethandrostate
3704:
3703:
3702:
3699:
3697:
3694:
3691:
3690:
3687:
3684:
3681:
3680:
3677:
3674:
3671:
3670:
3667:
3664:
3662:
3659:
3656:
3655:
3652:
3649:
3647:
3644:
3642:
3639:
3637:
3634:
3632:
3629:
3627:
3624:
3622:
3619:
3617:
3614:
3612:
3609:
3607:
3606:Ethylestrenol
3604:
3602:
3599:
3597:
3594:
3592:
3589:
3587:
3584:
3581:
3580:
3577:
3574:
3572:
3569:
3567:
3564:
3562:
3559:
3557:
3554:
3552:
3549:
3547:
3544:
3540:
3537:
3535:
3532:
3531:
3530:
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3502:
3499:
3498:
3495:
3492:
3490:
3487:
3485:
3482:
3478:
3475:
3474:
3472:
3468:
3465:
3463:
3460:
3456:
3453:
3451:
3448:
3446:
3443:
3441:
3438:
3437:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3386:
3383:
3381:
3378:
3375:
3374:
3371:
3368:
3366:
3363:
3361:
3358:
3355:
3354:
3349:
3346:
3344:
3341:
3340:
3339:
3336:
3334:
3331:
3327:
3324:
3322:
3319:
3317:
3314:
3312:
3309:
3308:
3307:
3304:
3300:
3297:
3296:
3295:
3292:
3290:
3287:
3283:
3280:
3279:
3278:
3275:
3271:
3268:
3267:
3266:
3263:
3261:
3258:
3256:
3254:
3250:
3245:
3241:
3238:
3236:
3233:
3231:
3228:
3227:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3199:
3196:
3195:
3194:
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3172:
3169:
3168:
3167:
3164:
3162:
3159:
3156:
3155:
3152:
3149:
3145:
3142:
3141:
3140:
3137:
3135:
3132:
3128:
3125:
3124:
3123:
3120:
3118:
3115:
3111:
3108:
3107:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
3086:
3083:
3079:
3076:
3075:
3074:
3071:
3067:
3064:
3063:
3061:
3057:
3054:
3052:
3049:
3047:
3044:
3042:
3039:
3035:
3032:
3031:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2990:
2987:
2985:
2982:
2979:
2978:
2973:
2970:
2968:
2965:
2964:
2962:
2958:
2955:
2953:
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2926:
2923:
2921:
2918:
2917:
2916:
2913:
2911:
2908:
2904:
2901:
2900:
2899:
2896:
2892:
2889:
2887:
2884:
2882:
2879:
2878:
2877:
2874:
2872:
2869:
2865:
2862:
2861:
2860:
2857:
2855:
2852:
2850:
2847:
2843:
2840:
2838:
2835:
2833:
2830:
2828:
2825:
2824:
2823:
2820:
2818:
2815:
2813:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2790:
2788:
2785:
2783:
2780:
2777:
2776:
2774:
2770:
2767:
2762:
2756:
2752:
2749:
2742:
2737:
2735:
2730:
2728:
2723:
2722:
2719:
2703:
2701:
2698:
2697:
2695:
2692:
2689:
2686:
2684:
2681:
2680:
2676:
2670:
2667:
2665:
2662:
2660:
2657:
2655:
2652:
2650:
2647:
2645:
2642:
2640:
2637:
2635:
2632:
2631:
2629:
2625:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2599:
2596:
2595:
2593:
2589:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2554:
2552:
2550:
2546:
2538:
2535:
2533:
2530:
2529:
2528:
2525:
2520:
2517:
2515:
2512:
2510:
2507:
2505:
2502:
2500:
2497:
2496:
2495:
2494:Antiandrogens
2492:
2491:
2489:
2487:
2483:
2476:
2473:
2471:
2468:
2466:
2462:
2461:Tetracyclines
2459:
2457:
2456:Sulfacetamide
2454:
2452:
2449:
2447:
2444:
2442:
2439:
2438:
2436:
2434:
2430:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2405:
2403:
2401:
2397:
2391:
2388:
2386:
2383:
2381:
2378:
2376:
2375:Glycolic acid
2373:
2372:
2370:
2368:
2364:
2358:
2355:
2353:
2350:
2348:
2345:
2343:
2340:
2338:
2335:
2334:
2332:
2330:
2329:Antibacterial
2326:
2321:
2317:
2310:
2305:
2303:
2298:
2296:
2291:
2290:
2287:
2279:
2278:
2273:
2269:
2268:
2265:
2264:
2260:
2257:
2256:
2238:
2234:
2228:
2222:
2217:
2209:
2205:
2201:
2197:
2193:
2189:
2185:
2178:
2170:
2166:
2162:
2158:
2153:
2148:
2144:
2140:
2136:
2129:
2121:
2117:
2113:
2109:
2105:
2101:
2098:(5): 627–32.
2097:
2093:
2086:
2071:
2065:
2061:
2060:
2052:
2044:
2040:
2036:
2032:
2027:
2022:
2018:
2014:
2010:
2003:
1995:
1991:
1987:
1983:
1979:
1975:
1971:
1967:
1963:
1959:
1955:
1948:
1940:
1936:
1932:
1928:
1924:
1920:
1916:
1909:
1901:
1897:
1893:
1889:
1886:(2): 285–96.
1885:
1881:
1874:
1872:
1863:
1859:
1855:
1851:
1847:
1843:
1839:
1835:
1831:
1827:
1823:
1816:
1814:
1799:
1795:
1789:
1781:
1777:
1773:
1769:
1765:
1761:
1757:
1750:
1736:
1732:
1728:
1724:
1720:
1716:
1712:
1708:
1704:
1697:
1689:
1685:
1681:
1677:
1672:
1667:
1664:(4): 302–11.
1663:
1659:
1655:
1648:
1640:
1636:
1632:
1628:
1624:
1620:
1616:
1609:
1601:
1597:
1593:
1589:
1585:
1581:
1577:
1573:
1569:
1562:
1554:
1550:
1546:
1542:
1538:
1534:
1527:
1519:
1515:
1509:
1507:
1498:
1497:
1492:
1486:
1478:
1474:
1469:
1464:
1460:
1456:
1452:
1448:
1444:
1437:
1429:
1425:
1421:
1417:
1413:
1409:
1405:
1401:
1397:
1393:
1386:
1378:
1374:
1370:
1366:
1365:
1359:
1351:
1343:
1339:
1333:
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1214:: Wiley-VCH.
1213:
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968:
964:
960:
950:
948:
933:
924:
922:
915:Human biology
912:
910:
895:
893:
892:nonanoic acid
889:
885:
881:
877:
876:
871:
870:nonanoic acid
867:
863:
853:
851:
847:
843:
839:
835:
831:
820:
816:
812:
800:
793:
788:
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731:
728:
724:
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555:
554:
551:Pharmacology
549:
546:4.550, 5.498
545:
539:
535:
532:
531:
527:
524:
520:
519:
515:
513:
512:Boiling point
510:
509:
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502:Melting point
500:
499:
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493:
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481:
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369:DTXSID8021640
366:
365:
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341:
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328:
321:
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257:
254:
250:
249:
242:
241:
239:
237:
232:
231:
227:
223:
220:
218:
216:ECHA InfoCard
213:
212:
205:
201:
200:
198:
196:
193:
192:
185:
181:
180:
178:
176:
173:
172:
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85:
84:
82:
79:
75:
74:
69:
61:
57:
52:
48:
43:
39:
34:
31:Azelaic acid
26:
22:
5165:
4951:Testosterone
4737:Pyrilutamide
4689:
4681:
4673:
4638:Lavender oil
4628:Ketoconazole
4593:Enzalutamide
4563:Darolutamide
4497:Bicalutamide
4472:Atraric acid
4444:
4439:
4423:Trimegestone
4378:Promegestone
4343:Mifepristone
4318:Medrogestone
4263:Drospirenone
4218:Clascoterone
4149:
4115:
4059:JNJ-37654032
4054:JNJ-28330835
4049:JNJ-26146900
3945:
3889:
3869:
3854:
3836:Quingestanol
3753:Etonogestrel
3739:
3719:
3692:
3682:
3672:
3657:
3641:Propetandrol
3582:
3571:Oxymetholone
3546:Methasterone
3500:
3494:Tiomesterone
3484:Oxymesterone
3376:
3356:
3277:Norclostebol
3252:
3248:
3157:
3095:Mepitiostane
3090:Epitiostanol
3073:Drostanolone
3024:Androsterone
2980:
2961:+dutasteride
2957:Testosterone
2925:DHEA sulfate
2778:
2627:Combinations
2562:Isotretinoin
2509:Drospirenone
2499:Bicalutamide
2451:Erythromycin
2357:Tea tree oil
2337:Azelaic acid
2336:
2275:
2261:
2240:. Retrieved
2236:
2227:
2216:
2191:
2187:
2177:
2142:
2138:
2128:
2095:
2091:
2085:
2073:. Retrieved
2058:
2051:
2016:
2012:
2002:
1961:
1957:
1947:
1922:
1918:
1908:
1883:
1880:Primary Care
1879:
1829:
1825:
1801:. Retrieved
1797:
1788:
1766:(1): 13–16.
1763:
1759:
1749:
1738:. Retrieved
1710:
1706:
1696:
1661:
1657:
1647:
1614:
1608:
1575:
1571:
1561:
1536:
1532:
1526:
1517:
1494:
1485:
1450:
1446:
1436:
1395:
1391:
1385:
1371:(5): 53–55.
1368:
1362:
1350:
1304:
1298:
1255:
1251:
1207:
1173:
1169:
1159:
1142:
1138:
1134:
1070:
1057:hydroquinone
1054:
1031:zinc sulfate
1019:hydroquinone
1008:
995:Nicotinamide
984:
975:
956:
943:
927:Applications
921:cathelicidin
918:
906:
879:
873:
859:
814:
811:Azelaic acid
810:
809:
700:
667:
624:Legal status
537:
486:white solid
71:Identifiers
4936:Osteocalcin
4817:Vinclozolin
4802:Thalidomide
4797:Seviteronel
4727:Procymidone
4663:Masofaniten
4618:Inocoterone
4522:bisphenol S
4518:bisphenol F
4514:bisphenol A
4492:BAY-1024767
4467:Apalutamide
4413:Spiroxasone
4408:Spirorenone
4388:Rosterolone
4328:Mespirenone
4273:Edogestrone
4243:Delanterone
4233:Cyproterone
4223:Clometerone
4193:Benorterone
4178:Abiraterone
4143:Antagonists
4074:PF-06260414
3979:BMS-564,929
3903:Alternariol
3795:Lynestrenol
3748:Desogestrel
3631:Norboletone
3621:Metribolone
3566:Oxandrolone
3524:Mestanolone
3489:Penmesterol
3420:Formebolone
3385:Calusterone
3380:Bolasterone
3134:Prostanozol
3105:Mesterolone
2690:from market
2598:Epristeride
2582:Trifarotene
2567:Motretinide
2475:Doxycycline
2470:Minocycline
2465:Lymecycline
2441:Clindamycin
2433:Antibiotics
2408:Niacinamide
2367:Keratolytic
2277:MedlinePlus
1578:: 771–775.
1067:Brand names
1050:melanocytes
1046:dutasteride
1042:finasteride
967:topical gel
695:Signal word
496:1.443 g/mL
483:Appearance
439:Properties
222:100.004.246
144:CHEBI:48131
5288:Categories
4930:-ornithine
4873:gadolinium
4722:Prochloraz
4717:Phenothrin
4697:Nilutamide
4668:Methiocarb
4588:Endosulfan
4553:Cioteronel
4548:Cimetidine
4538:BMS-641988
4533:BMS-570511
4528:BMS-501949
4502:Bisphenols
4457:Antarlides
4433:Zanoterone
4368:Oxendolone
4313:Ludaterone
4303:Galeterone
4253:Dicirenone
4150:Steroidal:
4116:Steroidal:
4109:Vosilasarm
4004:GSK2881078
3959:AC-262,536
3918:Trilostane
3826:Norgestrel
3775:Gestrinone
3743:Δ-Tibolone
3626:Mibolerone
3576:Stanozolol
3529:Metenolone
3306:Trenbolone
3265:Nandrolone
3215:Dienedione
3139:Stenbolone
3100:Mesabolone
2952:Silandrone
2947:Quinbolone
2942:Plomestane
2937:Formestane
2932:Exemestane
2854:Atamestane
2751:modulators
2572:Tazarotene
2242:2021-04-17
1882:(Review).
1803:2022-03-10
1740:2021-05-14
1660:(Review).
1229:3527306730
1137:= 25 °C".
1076:References
1023:tyrosinase
866:oleic acid
862:ozonolysis
856:Production
850:tyrosinase
679:Pictograms
474:Molar mass
340:F2VW3D43YT
265:IUPHAR/BPS
175:ChemSpider
164:ChEMBL1238
99:3D model (
78:CAS Number
21:Sutherland
4916:-arginine
4901:Estradiol
4881:strontium
4877:magnesium
4865:aluminium
4832:YM-175735
4767:Ro 5-2537
4762:Ro 2-7239
4712:PF-998425
4707:Pentomone
4648:LG-120907
4608:Flutamide
4603:Fenarimol
4543:CH5137291
4482:Bakuchiol
4418:Topterone
4383:Prorenone
4358:Osaterone
4353:Nordinone
4338:Mexrenone
4258:Dienogest
4208:Canrenone
4129:TFM-4AS-1
4069:ORM-11984
4009:GSK-4336A
3999:GLPG-0492
3923:ZM-182345
3770:Gestodene
3758:Etynodiol
3514:Furazabol
3405:Enestebol
3333:Trendione
3294:Oxabolone
3220:Dienolone
3193:Bolandiol
3122:Nisterime
2876:Clostebol
2859:Boldenone
2700:Phase III
2688:Withdrawn
2618:Tioxolone
2577:Tretinoin
2557:Adapalene
2549:Retinoids
2532:Estradiol
2527:Estrogens
2514:Flutamide
2413:Ibuprofen
2200:0011-4162
2161:0022-202X
1994:222236883
1978:1756-5391
1931:1545-9616
1846:0012-6667
1772:1545-9616
1592:0753-3322
1518:Drugs.com
1428:206518245
1332:cite book
1324:982188831
1272:1475-6366
1182:0011-4162
1061:tretinoin
757:P337+P313
753:P332+P313
741:P302+P352
670:labelling
606:Very low
579:Routes of
528:2.14 g/L
243:204-669-1
235:EC Number
4967:See also
4854:Agonists
4827:YM-92088
4792:RU-58841
4787:RU-58642
4782:RU-57073
4777:RU-56187
4772:RU-22930
4702:ONC1-13B
4653:LGD-1331
4578:Dieldrin
4572:p,p’-DDE
4477:AZD-3514
4462:Arabilin
4393:RU-15328
4333:Metogest
4268:DU-41165
4104:S-101479
4084:RU-59063
4039:LGD-4033
4034:LGD-3303
4024:LGD-2226
4014:GSK-8698
3913:Drupanol
3908:Cl-4AS-1
3848:Tibolone
3029:Bolazine
2772:Agonists
2608:Pelretin
2603:Mesulfen
2486:Hormonal
2120:28506969
2075:9 August
2043:24913995
2035:18045355
1986:33034949
1939:23652891
1900:20493337
1862:46960738
1780:18246693
1735:58809558
1727:16281587
1680:23914887
1631:24280644
1600:27484346
1553:16924055
1477:22577261
1420:19342588
1290:28097901
1212:Weinheim
1190:16566285
1094:Archived
1034:in vitro
977:creams.
817:) is an
661:Hazards
586:Topical
572:)
558:ATC code
195:DrugBank
129:1101094
88:123-99-9
25:Scotland
4923:-lysine
4911:(incl.
4869:calcium
4863:(incl.
4861:Cations
4658:Linuron
4598:EPI-001
4504:(e.g.,
4293:EM-6537
4288:EM-5855
4283:EM-5854
4278:EM-4350
4124:MK-0773
4119:EM-9017
4099:S-40503
3954:ACP-105
3949:198RL26
3814:(e.g.,
3787:(e.g.,
3696:Danazol
3646:RU-2309
3586:Bolenol
2613:Stridex
2446:Dapsone
2418:Aspirin
2259:DermNet
2208:8654129
2169:4031538
2112:3207614
1854:1712709
1688:5750718
1639:8848543
1468:3346901
1400:Bibcode
1392:Science
1281:6010116
1027:melanin
1021:. As a
1011:melasma
971:rosacea
963:keratin
953:Medical
792:what is
790: (
701:Warning
566: (
564:D10AX03
534:Acidity
492:Density
307:PubChem
258:261342
204:DB00548
5039:C-R-CO
4846:GPRC6A
4822:YM-580
4752:RD-162
4643:LG-105
3994:FTBU-1
2683:WHO-EM
2385:Sulfur
2206:
2198:
2167:
2159:
2118:
2110:
2066:
2041:
2033:
1992:
1984:
1976:
1937:
1929:
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1852:
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1778:
1770:
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1475:
1465:
1426:
1418:
1322:
1312:
1288:
1278:
1270:
1226:
1188:
1180:
846:barley
844:, and
787:verify
784:
652:℞-only
650:
637:
423:SMILES
295:D03034
155:ChEMBL
54:Names
4510:BFDGE
4506:BADGE
4452:AA560
4134:YK-11
4044:LY305
3934:SARMs
2591:Other
2188:Cutis
2116:S2CID
2039:S2CID
1990:S2CID
1858:S2CID
1826:Drugs
1731:S2CID
1684:S2CID
1635:S2CID
1496:WebMD
1424:S2CID
1170:Cutis
947:Nylon
884:yeast
882:), a
838:wheat
618:12 h
388:InChI
135:ChEBI
101:JSmol
4942:SHBG
4885:zinc
4583:DIMP
4198:BOMT
4094:S-23
3984:DTIB
2316:Acne
2204:PMID
2196:ISSN
2165:PMID
2157:ISSN
2108:PMID
2077:2011
2064:ISBN
2031:PMID
1982:PMID
1974:ISSN
1935:PMID
1927:ISSN
1896:PMID
1850:PMID
1842:ISSN
1776:PMID
1768:ISSN
1723:PMID
1676:PMID
1627:PMID
1596:PMID
1588:ISSN
1549:PMID
1473:PMID
1416:PMID
1342:link
1338:link
1320:OCLC
1310:ISBN
1286:PMID
1268:ISSN
1224:ISBN
1186:PMID
1178:ISSN
1044:and
987:acne
888:skin
830:COOH
761:P362
749:P321
737:P280
733:P264
719:H319
715:H315
331:UNII
320:2266
286:KEGG
275:7484
184:2179
5124:(CO
5106:(CO
5088:(CO
5070:(CO
5035:(HO
4568:DDT
4089:S-1
4079:R-1
2320:D10
2147:doi
2100:doi
2096:119
2021:doi
1966:doi
1888:doi
1834:doi
1715:doi
1666:doi
1619:doi
1580:doi
1541:doi
1537:142
1463:PMC
1455:doi
1408:doi
1396:324
1373:doi
1276:PMC
1260:doi
1216:doi
1147:doi
1113:(CH
864:of
842:rye
815:AzA
668:GHS
569:WHO
357:EPA
310:CID
5290::
5259:42
5255:22
5242:30
5238:16
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