246:
47:
1294:
of androgens to the AR. This is the case for norethisterone (Fig. 1, 34), a synthetic 19-nor-17α-ethynyl testosterone derivative, which also undergoes enzyme-mediated 5α-reduction and exerts potent androgenic effects in target organs. 5α-Reduced norethisterone displays a higher AR binding but shows a significantly lower androgenic potency than unchanged norethisterone .
1293:
Many synthetic steroids with high myotrophic activity exhibit myotrophic–androgenic dissociation, since, due to changes introduced in the structure of ring A, they will probably not be substrates for the 5α-reductases . 5α-Reduction does not always amplify the androgenic potency in spite of high RBA
1258:
Fragkaki AG, Angelis YS, Koupparis M, Tsantili-Kakoulidou A, Kokotos G, Georgakopoulos C (February 2009). "Structural characteristics of anabolic androgenic steroids contributing to binding to the androgen receptor and to their anabolic and androgenic activities. Applied modifications in the
576:
1457:
Yamamoto T, Tamura T, Kitawaki J, Osawa Y, Okada H (June 1994). "Suicide inactivation of aromatase in human placenta and uterine leiomyoma by 5 alpha-dihydronorethindrone, a metabolite of norethindrone, and its effect on steroid-producing enzymes".
490:(19-nortestosterone) in rodent bioassays. As such, it appears that the C17α ethynyl group of norethisterone is responsible for its loss of androgenicity upon 5α-reduction. Instead of androgenic activity, 5α-DHNET has been reported to possess some
470:(versus 15% for norethisterone). However, although 5α-DHNET has higher affinity for the AR than does norethisterone, it has significantly diminished and in fact almost abolished androgenic activity in comparison to norethisterone in rodent
569:
562:
508:= 1.7 μM and 9.0 μM, respectively). However, the concentrations required are probably too high to be clinically relevant at typical dosages of norethisterone. 5α-DHNET specifically has been assessed and found to be
313:
62:
5α-DHNET; 5α-Dihydro-NET; Dihydronorethisterone; Dihydronorethindrone; DHNET; 17α-Ethynyl-5α-dihydro-19-nortestosterone; 17α-Ethynyl-5α-estran-17β-ol-3-one; STS-737; NSC-85401; 19-Nor-5α,17α-pregn-20-yn-17-ol-3-one
1373:
Lemus AE, Enríquez J, García GA, Grillasca I, Pérez-Palacios G (January 1997). "5alpha-reduction of norethisterone enhances its binding affinity for androgen receptors but diminishes its androgenic potency".
547:. Since it is not aromatized (and hence cannot be transformed into an estrogenic metabolite), unlike norethisterone, 5α-DHNET has been proposed as a potential therapeutic agent in the treatment of
3795:
4198:
1510:
5423:
4659:
1942:
3978:
3788:
327:
5352:
4970:
1503:
5398:
5388:
3781:
3757:
438:
355:
InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,13,15-18,22H,4-12H2,2H3/t13-,15-,16+,17+,18-,19-,20-/m0/s1
3762:
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5362:
5357:
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1932:
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2211:
2006:
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1125:
659:
75:
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5240:
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3712:
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1959:
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1112:
649:
185:
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4218:
4183:
4063:
2649:
2011:
1613:
225:
4992:
2629:
2437:
1210:
Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration".
1180:
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2001:
1822:
1780:
1728:
1674:
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4589:
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3444:
2591:
2560:
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1954:
1732:
1608:
1558:
880:
3983:
3848:
2929:
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2644:
1812:
1165:
111:)-17-ethynyl-17-hydroxy-13-methyl-1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydrocyclopentaphenanthren-3-one
4664:
4464:
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3460:
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2131:
2041:
1949:
1849:
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31:
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3119:
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2954:
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2070:
1827:
1681:
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509:
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120:
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1227:
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1073:
1060:
619:
609:
548:
513:
457:
390:
5107:
3064:
3059:
3049:
2890:
2720:
429:
Unlike norethisterone which is purely progestogenic, 5α-DHNET has been found to possess both
5418:
5296:
5286:
4813:
4774:
4168:
3593:
3414:
3404:
3384:
2765:
2669:
2332:
2196:
1755:
1593:
1553:
1467:
1426:
1383:
1268:
1219:
818:
418:
262:
5017:
194:
174:
4788:
4749:
4709:
4133:
3998:
3329:
3214:
3069:
2755:
2740:
2407:
2382:
2233:
2186:
1996:
1856:
521:
434:
245:
1417:
Kamischke A, Nieschlag E (January 2004). "Progress towards hormonal male contraception".
482:
metabolite, whereas 5α-reduction enhanced both the AR affinity and androgenic potency of
479:
410:
38:
129:
17:
4887:
4847:
4793:
4759:
4739:
4694:
4620:
4615:
4576:
4571:
4536:
4253:
3943:
3174:
2999:
2974:
2602:
2578:
2551:
2514:
2447:
2372:
2275:
2060:
2031:
1888:
1831:
1770:
1765:
1121:
1108:
671:
585:
540:
394:
1387:
5382:
5216:
5112:
5012:
4917:
4744:
4494:
4454:
4288:
4173:
4043:
3583:
3528:
3503:
3079:
2477:
2377:
1588:
1082:
552:
1403:
1288:
1239:
5327:
5311:
5306:
5301:
5186:
5171:
5136:
5131:
5062:
5032:
5027:
4857:
4630:
4605:
4600:
4595:
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4428:
4413:
4303:
4243:
4208:
4143:
4098:
4088:
3913:
3903:
3773:
3722:
3578:
3508:
3409:
3399:
3364:
3334:
3268:
3243:
3194:
3149:
3114:
3089:
3034:
2989:
2825:
2607:
2524:
2412:
2342:
2317:
2265:
2255:
2201:
2048:
1981:
1866:
1861:
1844:
1795:
1272:
1043:
911:
491:
483:
450:
449:(PR) is greatly reduced relative to that of norethisterone at only 25% of that of
154:
5146:
4892:
4862:
4754:
4551:
4501:
4479:
4459:
4418:
4393:
4383:
4358:
4343:
4298:
4203:
4118:
4108:
4068:
3958:
3888:
3707:
3588:
3573:
3568:
3498:
3434:
3389:
3293:
3289:
3285:
3238:
3184:
3179:
3159:
3099:
3044:
3014:
3004:
2994:
2964:
2949:
2865:
2845:
2750:
2674:
2566:
2519:
2484:
2402:
2392:
2337:
2295:
2260:
2206:
2191:
2156:
2151:
1905:
1876:
1095:
1056:
1004:
536:
475:
467:
430:
1488:
1430:
5176:
5141:
5102:
5092:
5072:
5002:
4957:
4937:
4832:
4808:
4769:
4764:
4699:
4689:
4650:
4625:
4610:
4561:
4531:
4506:
4403:
4268:
4158:
4123:
4078:
4018:
3677:
3644:
3493:
3488:
3468:
3439:
3359:
3324:
3319:
3309:
3204:
3139:
3074:
3024:
2880:
2775:
2730:
2689:
2597:
2546:
2397:
2347:
2300:
2290:
2109:
2077:
2036:
1986:
1976:
1922:
1910:
1871:
1723:
1718:
1713:
1708:
1703:
1625:
1223:
1142:
487:
460:(AR) compared to norethisterone with approximately 27% of the affinity of the
289:
165:
4952:
4942:
4872:
4852:
4827:
4704:
4679:
4526:
4516:
4484:
4469:
4423:
4378:
4333:
4278:
4228:
4003:
3953:
3893:
3698:
3672:
3652:
3648:
3636:
3513:
3478:
3419:
3379:
3374:
3273:
3253:
3189:
3154:
3129:
3124:
3109:
3029:
2979:
2900:
2835:
2780:
2770:
2760:
2694:
2541:
2529:
2285:
2176:
2104:
2065:
1991:
1964:
1893:
1647:
1630:
942:
517:
398:
1438:
1280:
1231:
1479:
1471:
1395:
1354:
1322:
5087:
5042:
4645:
4640:
4398:
4038:
3938:
3933:
3684:
3563:
3558:
3553:
3548:
3543:
3349:
3104:
3039:
2855:
2810:
2805:
2800:
2795:
2790:
2745:
2684:
2679:
2619:
1800:
1642:
471:
464:
406:
402:
4907:
4882:
4877:
4798:
4474:
3640:
3429:
3369:
3169:
3054:
2895:
2870:
2725:
2467:
2417:
2357:
2018:
1146:
140:
4794:
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
3898:
3691:
3632:
3617:
3523:
524:
437:
activity, showing a profile of progestogenic activity like that of a
205:
4971:
3223:
2905:
2815:
414:
312:
303:
3656:
2969:
3777:
1492:
4194:
Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)
3339:
2746:
Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
2705:
1589:
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
4189:
Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)
230:
497:
Norethisterone and 5α-DHNET have been found to act as weak
1376:
The
Journal of Steroid Biochemistry and Molecular Biology
1341:
Chu YH, Li QA, Zhao ZF, Zhou YP, Cao DC (June 1985). "".
30:
For the
Belgian newspaper with the website DHNet.be, see
2430:
17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:
1933:
7α-Methyl-19-norandrostenedione (MENT dione, trestione)
1126:
660:
5241:
4199:
Hydroxyprogesterone heptanoate benzilic acid hydrazone
2627:
5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:
5251:
3713:
1343:
1309:
Fedotov VP, Gudoshnikov VI, Kurishko AI (1988). "".
1113:
650:
409:
activity. 5α-DHNET is formed from norethisterone by
5320:
5264:
5239:
5121:
4966:
3828:
3814:
3625:
3616:
2914:
2703:
2061:
Normethandrone (methylestrenolone, normethisterone)
1543:
1529:
301:
288:
261:
256:
224:
204:
184:
164:
139:
119:
66:
58:
53:
4976:Tooltip Selective progesterone receptor modulators
1100:
640:
2273:17α-Alkylated 5α-dihydrotestosterone derivatives:
153:
5287:11-Deoxycortisol (17α,21-dihydroxyprogesterone)
2492:5α-Dihydro-17α-ethynyltestosterone derivatives:
1087:
630:
128:
4660:11β-Methyl-19-nortestosterone dodecylcarbonate
1943:11β-Methyl-19-nortestosterone dodecylcarbonate
1253:
1251:
1249:
1205:
1203:
1201:
1199:
1197:
1195:
3989:17α-Hydroxyprogesterone (hydroxyprogesterone)
3816:
3789:
2710:Tooltip Selective androgen receptor modulator
2355:17α-Alkylated 19-nortestosterone derivatives:
1504:
1452:
1450:
1448:
1368:
1366:
1364:
1336:
1334:
1332:
1304:
1302:
1048:
600:
570:
8:
3979:16-Methylene-17α-hydroxyprogesterone acetate
2761:Enobosarm (ostarine, MK-2866, GTx-024, S-22)
37:
2512:17α-Ethynyl-19-nortestosterone derivatives:
5424:Selective progesterone receptor modulators
5282:11-Deoxycortisone (21-hydroxyprogesterone)
5261:
4374:Gestonorone caproate (gestronol hexanoate)
3825:
3796:
3782:
3774:
3622:
2234:Methylclostebol (chloromethyltestosterone)
2129:5α-Dihydro-19-nortestosterone derivatives:
1540:
1511:
1497:
1489:
577:
563:
557:
244:
173:
3966:17α-Substituted progesterone derivatives:
3874:17α-Methyl-11-deoxycorticosterone acetate
2455:17α-Vinyl-19-nortestosterone derivatives:
2071:Oxabolone cipionate (oxabolone cypionate)
1687:DHEA (androstenolone, prasterone; 5-DHEA)
1531:
1074:
1061:
620:
610:
439:selective progesterone receptor modulator
383:17α-ethynyl-5α-dihydro-19-nortestosterone
193:
2162:Chlorodehydromethylandrostenediol (CDMA)
4409:Oxogestone phenpropionate (xinogestone)
4369:Gestonorone acetate (gestronol acetate)
3763:List of androgens and anabolic steroids
2149:17α-Alkylated testosterone derivatives:
1191:
1131:Tooltip Corticosteroid-binding globulin
665:Tooltip Corticosteroid binding globulin
456:5α-DHNET shows higher affinity for the
352:
332:
240:
80:
5246:Tooltip Membrane progesterone receptor
3999:Acetomepregenol (mepregenol diacetate)
2167:Chlorodehydromethyltestosterone (CDMT)
1923:Testifenon (testiphenon, testiphenone)
1038:Values are percentages (%). Reference
558:
529:cholesterol side-chain cleavage enzyme
36:
5256:Tooltip Progestin and adipoQ receptor
2448:Norvinisterone (vinylnortestosterone)
1982:Bolmantalate (nandrolone adamantoate)
1977:Bolandione (19-nor-4-androstenedione)
1692:DHEA enanthate (prasterone enanthate)
474:. Similar findings were observed for
397:(norethindrone). Norethisterone is a
213:
7:
3718:Tooltip Sex hormone-binding globulin
2465:17α-Ethynyltestosterone derivatives:
1744:Polytestosterone phloretin phosphate
1118:Tooltip sex hormone-binding globulin
655:Tooltip Sex hormone-binding globulin
2388:Methylhydroxynandrolone (MOHN, MHN)
2093:Trenbolone hexahydrobenzylcarbonate
1753:5α-Dihydrotestosterone derivatives:
1621:Androstenedione (4-androstenedione)
144:
4445:6,6-Difluoronorethisterone acetate
2445:17α-Vinyltestosterone derivatives:
2207:Methandriol (methylandrostenediol)
1419:Trends in Pharmacological Sciences
1105:Tooltip mineralocorticoid receptor
645:Tooltip Mineralocorticoid receptor
478:(17α-ethynyltestosterone) and its
453:(versus 150% for norethisterone).
387:17α-ethynyl-5α-estran-17β-ol-3-one
25:
5353:Progestogens and antiprogestogens
4760:Methoxydienone (methoxygonadiene)
4154:Fluoromedroxyprogesterone acetate
2485:Ethisterone (ethynyltestosterone)
2202:Metandienone (methandrostenolone)
2032:Methoxydienone (methoxygonadiene)
1643:Boldione (1,4-androstadienedione)
1594:Androstenediol (5-androstenediol)
1559:4-Dehydroepiandrosterone (4-DHEA)
1460:European Journal of Endocrinology
4720:Dimethandrolone dodecylcarbonate
4653:; Anabolic–androgenic steroids:
3909:Progesterone 3-acetyl enol ether
3758:Progesterone receptor modulators
2249:Methyltestosterone 3-hexyl ether
2212:Methandriol bisenanthoyl acetate
2172:Chloromethylandrostenediol (CMA)
2007:Dimethandrolone dodecylcarbonate
1766:1-Androsterone (1-andro, 1-DHEA)
1149:, or neither of norethisterone.
273:
45:
4424:Segesterone acetate (nestorone)
4316:19-Norprogesterone derivatives:
3969:6α-Methyl-17α-bromoprogesterone
1930:19-Nortestosterone derivatives:
1092:Tooltip glucocorticoid receptor
635:Tooltip Glucocorticoid receptor
360:Key:OMGILQMNIZWNOK-XDQPPUBWSA-N
335:C12CC3(1CC2(C#C)O)CC43CCC(=O)C4
5389:5α-Reduced steroid metabolites
4577:Norethisterone (norethindrone)
4354:Fluoro furanyl norprogesterone
3974:15β-Hydroxycyproterone acetate
3921:Retroprogesterone derivatives:
2945:15β-Hydroxycyproterone acetate
2836:OPK-88004 (LY-2452473, TT-701)
1273:10.1016/j.steroids.2008.10.016
789:3β,5α-Tetrahydronorethisterone
760:3α,5β-Tetrahydronorethisterone
731:3α,5α-Tetrahydronorethisterone
279:
267:
1:
5348:Receptor/signaling modulators
4655:11β-Methyl-19-nortestosterone
4319:17α-Methyl-19-norprogesterone
3821:Tooltip Progesterone receptor
3743:Receptor/signaling modulators
2500:17α-Ethynyl-3β-androstanediol
2495:17α-Ethynyl-3α-androstanediol
1938:11β-Methyl-19-nortestosterone
1388:10.1016/s0960-0760(96)00172-0
1311:Farmakologiia I Toksikologiia
1053:Tooltip progesterone receptor
605:Tooltip Progesterone receptor
5399:Anabolic–androgenic steroids
5363:Estrogen receptor modulators
5358:Androgen receptor modulators
4745:Ethylestrenol (ethylnandrol)
4675:19-Nordehydroepiandrosterone
4557:Lynestrenol phenylpropionate
4450:17α-Allyl-19-nortestosterone
4349:Fluoro ethyl norprogesterone
4324:18-Methylsegesterone acetate
4224:Medroxyprogesterone caproate
3854:9α-Bromo-11-ketoprogesterone
3753:Estrogen receptor modulators
3200:Trimethyltrienolone (R-2956)
2572:Lynestrenol phenylpropionate
1960:19-Nordehydroepiandrosterone
588:, metabolites, and prodrugs
520:, and does not affect other
4783:nandrolone phenylpropionate
4725:Dimethandrolone undecanoate
4219:Medroxyprogesterone acetate
4184:Hydroxyprogesterone acetate
4064:Chlormethenmadinone acetate
3748:Androgens and antiandrogens
3519:Ralaniten acetate (EPI-506)
2935:7α-Thiomethylspironolactone
2650:Medroxyprogesterone acetate
2012:Dimethandrolone undecanoate
1823:Dihydromethylandrostenediol
1614:Androstenediol dipropionate
584:Relative affinities (%) of
5440:
4440:6,6-Difluoronorethisterone
1838:Dihydrotestosterone esters
1791:11-Ketodihydrotestosterone
1604:Androstenediol 17β-acetate
1584:11β-Hydroxyandrostenedione
1569:4,17α-Dimethyltestosterone
1431:10.1016/j.tips.2003.11.009
257:Chemical and physical data
29:
5340:
4845:Spirolactone derivatives:
4715:Dimethandrolone buciclate
4436:Testosterone derivatives:
4204:Mecigestone (pentarane B)
4034:Bromethenmadinone acetate
3924:20α-Dihydrodydrogesterone
3836:Progesterone derivatives:
3735:
2642:Progesterone derivatives:
2433:5α-Dihydronorethandrolone
2002:Dimethandrolone buciclate
1832:androstanolone, stanolone
1828:Dihydrotestosterone (DHT)
1786:7β-Hydroxyepiandrosterone
1675:Cloxotestosterone acetate
1599:Androstenediol 3β-acetate
1551:Testosterone derivatives:
1536:Tooltip Androgen receptor
1224:10.1080/13697130500148875
1079:Tooltip estrogen receptor
1066:Tooltip androgen receptor
1034:
625:Tooltip Estrogen receptor
615:Tooltip Androgen receptor
343:
323:
71:
44:
4998:5α-Dihydronorethisterone
4993:5α-Dihydrolevonorgestrel
4903:3,8-Dihydrodiligustilide
4670:19-Nor-5-androstenedione
4590:norethisterone enanthate
4546:levonorgestrel butanoate
3448:-Butylbenzenesulfonamide
2635:5α-Dihydronorethisterone
2630:5α-Dihydrolevonorgestrel
2592:norethisterone enanthate
2561:levonorgestrel butanoate
2438:5α-Dihydronormethandrone
2291:Mebolazine (dimethazine)
2281:Desoxymethyltestosterone
2222:Methandriol dipropionate
2019:LS-1727 (nandrolone 17β-
1955:19-Nor-5-androstenedione
1813:Dihydroethyltestosterone
1609:Androstenediol diacetate
1181:5α-Dihydrolevonorgestrel
1176:5α-Dihydronormethandrone
881:Norethisterone enanthate
702:5α-Dihydronorethisterone
371:5α-Dihydronorethisterone
39:5α-Dihydronorethisterone
18:5α-dihydronorethisterone
5292:17α-Hydroxyprogesterone
5028:Metapristone (RU-42633)
4809:Trenbolone (trienolone)
4665:19-Nor-5-androstenediol
4465:Chloroethynylnorgestrel
4379:Gestronol (gestonorone)
4309:Triamcinolone acetonide
4264:Methenmadinone caproate
4139:Fluorometholone acetate
3884:20β-Dihydroprogesterone
3879:20α-Dihydroprogesterone
3869:16α-Hydroxyprogesterone
3579:Topilutamide (fluridil)
2940:11α-Hydroxyprogesterone
1950:19-Nor-5-androstenediol
1850:Drostanolone propionate
5414:Human drug metabolites
5277:5β-Dihydroprogesterone
5272:5α-Dihydroprogesterone
4878:SC-5233 (spirolactone)
4685:Bolandiol dipropionate
4586:norethisterone acetate
4259:Methenmadinone acetate
4054:Chlormadinone caproate
4014:Algestone acetophenide
3994:17α-Methylprogesterone
3929:20α-Dihydrotrengestone
3864:11-Deoxycorticosterone
3859:11-Dehydroprogesterone
3844:5α-Dihydroprogesterone
3839:3β-Dihydroprogesterone
3464:-Desmethylenzalutamide
3170:SC-5233 (spirolactone)
2588:norethisterone acetate
2227:Methandriol propionate
2098:Trenbolone undecanoate
1970:Bolandiol dipropionate
1818:Dihydrofluoxymesterone
1781:5α-Androst-2-en-17-one
1636:Boldenone undecylenate
1259:steroidal structure".
850:Norethisterone acetate
441:(SPRM). Moreover, the
5033:Mifepristone (RU-486)
4582:Norethisterone esters
4542:Levonorgestrel esters
4490:Ethinylandrostenediol
4294:Pentagestrone acetate
4179:Hydromadinone acetate
4049:Chlormadinone acetate
3984:17α-Bromoprogesterone
3849:6α-Methylprogesterone
3805:Progesterone receptor
3456:-Desmethylapalutamide
2985:Chlormadinone acetate
2930:7α-Thiospironolactone
2801:LGD-2941 (LGD-122941)
2791:LG121071 (LGD-121071)
2665:3-Keto-5α-abiraterone
2645:6α-Methylprogesterone
2584:Norethisterone esters
2557:Levonorgestrel esters
2473:Ethinylandrostenediol
2323:Methyl-1-testosterone
2243:+esterified estrogens
2217:Methandriol diacetate
1882:Mesterolone cipionate
1564:4-Hydroxytestosterone
1472:10.1530/eje.0.1300634
1166:5α-Dihydroethisterone
447:progesterone receptor
401:with additional weak
379:dihydronorethisterone
5404:Aromatase inhibitors
5368:List of progestogens
4868:Potassium canrenoate
4822:trenbolone enanthate
4804:Tetrahydrogestrinone
4779:nandrolone decanoate
4755:Metribolone (R-1881)
4636:Quingestanol acetate
4567:Metynodiol diacetate
4249:Melengestrol acetate
4149:Flumedroxone acetate
4094:Clomegestone acetate
3145:Potassium canrenoate
2613:Quingestanol acetate
2423:Tetrahydrogestrinone
2311:Metenolone enanthate
2137:5α-Dihydrotrestolone
2132:5α-Dihydronandrolone
2120:Trestolone enanthate
2088:Trenbolone enanthate
2054:Norclostebol acetate
1663:Clostebol propionate
1171:5α-Dihydronandrolone
502:aromatase inhibitors
445:of 5α-DHNET for the
4522:Etynodiol diacetate
4389:Nomegestrol acetate
4364:Gestadienol acetate
4214:Medroxyprogesterone
4114:Delmadinone acetate
4104:Cyproterone acetate
4074:Cismadinone acetate
4059:Chlormethenmadinone
4009:Algestone acetonide
3668:Dihydrotestosterone
3663:Dehydroandrosterone
3514:Ralaniten (EPI-002)
3395:Inocoterone acetate
3120:Nomegestrol acetate
3020:Delmadinone acetate
3010:Cyproterone acetate
2955:Abiraterone acetate
2925:7α-Thioprogesterone
2535:Etynodiol diacetate
1739:Testosterone esters
1682:Dehydroandrosterone
1579:11-Ketotestosterone
1109:dihydrotestosterone
974:Etynodiol diacetate
589:
41:
5068:Ulipristal acetate
5008:Asoprisnil ecamate
4988:Dihydroethisterone
4838:Trestolone acetate
4818:trenbolone acetate
4735:Dimethyltrienolone
4329:19-Norprogesterone
4274:Mometasone furoate
4239:Megestrol caproate
4129:Flugestone acetate
4084:Clogestone acetate
4039:Butagest (buterol)
4024:Anagestone acetate
2505:Dihydroethisterone
2368:Dimethyltrienolone
2328:Methylepitiostanol
2306:Metenolone acetate
2239:Methyltestosterone
2142:19-Norandrosterone
2115:Trestolone acetate
2083:Trenbolone acetate
2027:-nitrosocarbamate)
1916:Stenbolone acetate
1806:Bolazine capronate
1658:Clostebol caproate
5394:Ethynyl compounds
5376:
5375:
5336:
5335:
5235:
5234:
4814:Trenbolone esters
4775:Nandrolone esters
4730:Dimethyldienolone
4339:Amadinone acetate
4284:Osaterone acetate
4234:Megestrol acetate
4029:Bromethenmadinone
3949:Retroprogesterone
3771:
3770:
3731:
3730:
3701:
3694:
3687:
3680:
3612:
3611:
3135:Osaterone acetate
3095:Megestrol acetate
2960:Allyltestosterone
2736:Acetothiolutamide
2655:Megestrol acetate
2458:Vinyltestosterone
2363:Dimethyldienolone
2182:Ethyltestosterone
2110:Trestolone (MENT)
2042:Nandrolone esters
2023:-(2-chloroethyl)-
1899:Nisterime acetate
1776:3α-Androstanediol
1761:1-Androstenedione
1670:Cloxotestosterone
1653:Clostebol acetate
1574:5-Androstenedione
1520:Androgen receptor
1218:(Suppl 1): 3–63.
1157:
1156:
549:estrogen receptor
458:androgen receptor
435:antiprogestogenic
391:active metabolite
368:
367:
314:Interactive image
226:CompTox Dashboard
32:La Dernière Heure
27:Chemical compound
16:(Redirected from
5431:
5297:Allopregnanolone
5262:
5257:
5253:
5247:
5243:
4977:
4973:
4169:Haloprogesterone
3826:
3822:
3818:
3798:
3791:
3784:
3775:
3719:
3715:
3699:
3692:
3685:
3678:
3623:
3405:Ketodarolutamide
3385:Hydroxyflutamide
3342:(via metabolite
2711:
2707:
2662:Others/unsorted:
2333:Methylstenbolone
2197:Hydroxystenozole
1756:1-Androstenediol
1554:4-Androstenediol
1541:
1537:
1533:
1513:
1506:
1499:
1490:
1484:
1483:
1454:
1443:
1442:
1414:
1408:
1407:
1382:(1–2): 121–129.
1370:
1359:
1358:
1338:
1327:
1326:
1306:
1297:
1296:
1255:
1244:
1243:
1207:
1132:
1128:
1119:
1115:
1106:
1102:
1093:
1089:
1080:
1076:
1067:
1063:
1054:
1050:
819:Ethinylestradiol
666:
662:
656:
652:
646:
642:
636:
632:
626:
622:
616:
612:
606:
602:
590:
579:
572:
565:
316:
296:
281:
275:
269:
249:
248:
234:
232:
217:
197:
177:
157:
147:
146:
132:
49:
42:
40:
21:
5439:
5438:
5434:
5433:
5432:
5430:
5429:
5428:
5379:
5378:
5377:
5372:
5332:
5316:
5255:
5248:
5245:
5231:
5117:
4975:
4968:
4962:
4789:Norethandrolone
4750:Methyldienolone
4710:Dimethandrolone
4134:Fluorometholone
3820:
3810:
3802:
3772:
3767:
3727:
3717:
3608:
3330:Cyanonilutamide
3259:Bavdegalutamide
3070:Epitestosterone
2910:
2741:Acetoxolutamide
2709:
2699:
2408:Norethandrolone
2383:Methyldienolone
2187:Fluoxymesterone
1997:Dimethandrolone
1857:Epiandrosterone
1535:
1525:
1517:
1487:
1456:
1455:
1446:
1416:
1415:
1411:
1372:
1371:
1362:
1340:
1339:
1330:
1308:
1307:
1300:
1257:
1256:
1247:
1209:
1208:
1193:
1189:
1162:
1130:
1117:
1104:
1091:
1078:
1065:
1052:
664:
654:
644:
634:
624:
614:
604:
583:
545:11β-hydroxylase
533:17α-hydroxylase
522:steroidogenesis
507:
427:
364:
361:
356:
351:
350:
339:
336:
331:
330:
319:
294:
284:
278:
272:
252:
228:
220:
200:
180:
160:
143:
135:
115:
112:
79:
78:
35:
28:
23:
22:
15:
12:
11:
5:
5437:
5435:
5427:
5426:
5421:
5416:
5411:
5406:
5401:
5396:
5391:
5381:
5380:
5374:
5373:
5371:
5370:
5365:
5360:
5355:
5350:
5345:
5341:
5338:
5337:
5334:
5333:
5331:
5330:
5324:
5322:
5318:
5317:
5315:
5314:
5309:
5304:
5299:
5294:
5289:
5284:
5279:
5274:
5268:
5266:
5259:
5237:
5236:
5233:
5232:
5230:
5229:
5224:
5219:
5214:
5209:
5204:
5199:
5194:
5189:
5180:
5179:
5174:
5169:
5164:
5159:
5154:
5149:
5144:
5139:
5134:
5125:
5123:
5119:
5118:
5116:
5115:
5110:
5105:
5100:
5095:
5090:
5081:
5080:
5075:
5070:
5065:
5060:
5055:
5050:
5045:
5040:
5035:
5030:
5025:
5020:
5015:
5010:
5005:
5000:
4995:
4990:
4981:
4979:
4964:
4963:
4961:
4960:
4955:
4946:
4945:
4940:
4935:
4930:
4925:
4920:
4915:
4910:
4905:
4896:
4895:
4890:
4888:Spironolactone
4885:
4880:
4875:
4870:
4865:
4860:
4855:
4850:
4848:Canrenoic acid
4841:
4840:
4835:
4830:
4825:
4811:
4806:
4801:
4796:
4791:
4786:
4772:
4767:
4762:
4757:
4752:
4747:
4742:
4740:Ethyldienolone
4737:
4732:
4727:
4722:
4717:
4712:
4707:
4702:
4697:
4695:Dimethisterone
4692:
4687:
4682:
4677:
4672:
4667:
4662:
4657:
4648:
4643:
4638:
4633:
4628:
4623:
4621:Norvinisterone
4618:
4616:Norgestrienone
4613:
4608:
4603:
4598:
4593:
4579:
4574:
4572:Norelgestromin
4569:
4564:
4559:
4554:
4549:
4539:
4537:Levonorgestrel
4534:
4529:
4524:
4519:
4514:
4509:
4504:
4499:
4498:
4497:
4487:
4482:
4477:
4472:
4467:
4462:
4457:
4452:
4447:
4442:
4432:
4431:
4426:
4421:
4416:
4411:
4406:
4401:
4396:
4391:
4386:
4381:
4376:
4371:
4366:
4361:
4356:
4351:
4346:
4341:
4336:
4331:
4326:
4321:
4312:
4311:
4306:
4301:
4296:
4291:
4286:
4281:
4276:
4271:
4266:
4261:
4256:
4254:Methenmadinone
4251:
4246:
4241:
4236:
4231:
4226:
4221:
4216:
4211:
4206:
4201:
4196:
4191:
4186:
4181:
4176:
4171:
4166:
4161:
4156:
4151:
4146:
4141:
4136:
4131:
4126:
4121:
4116:
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:
3962:
3961:
3956:
3951:
3946:
3944:Dydrogesterone
3941:
3936:
3931:
3926:
3917:
3916:
3911:
3906:
3901:
3896:
3891:
3886:
3881:
3876:
3871:
3866:
3861:
3856:
3851:
3846:
3841:
3832:
3830:
3823:
3812:
3811:
3803:
3801:
3800:
3793:
3786:
3778:
3769:
3768:
3766:
3765:
3760:
3755:
3750:
3745:
3740:
3736:
3733:
3732:
3729:
3728:
3726:
3725:
3720:
3710:
3705:
3681:-α-Amino acids
3675:
3670:
3665:
3660:
3629:
3627:
3620:
3614:
3613:
3610:
3609:
3607:
3606:
3601:
3596:
3591:
3586:
3581:
3576:
3571:
3566:
3561:
3556:
3551:
3546:
3541:
3536:
3531:
3526:
3521:
3516:
3511:
3506:
3501:
3496:
3491:
3486:
3481:
3476:
3471:
3466:
3458:
3450:
3442:
3437:
3432:
3427:
3422:
3417:
3412:
3407:
3402:
3397:
3392:
3387:
3382:
3377:
3372:
3367:
3362:
3357:
3352:
3347:
3337:
3332:
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3271:
3266:
3261:
3256:
3251:
3246:
3241:
3236:
3231:
3226:
3221:
3208:
3207:
3202:
3197:
3192:
3187:
3182:
3177:
3175:Spironolactone
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:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3002:
3000:Cyproheptadine
2997:
2992:
2987:
2982:
2977:
2975:Canrenoic acid
2972:
2967:
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2918:
2916:
2912:
2911:
2909:
2908:
2903:
2898:
2893:
2884:
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:
2758:
2753:
2748:
2743:
2738:
2733:
2728:
2723:
2714:
2712:
2701:
2700:
2698:
2697:
2692:
2687:
2682:
2677:
2672:
2667:
2658:
2657:
2652:
2647:
2638:
2637:
2632:
2623:
2622:
2617:
2616:
2615:
2605:
2603:Norgestrienone
2600:
2595:
2581:
2579:Norethisterone
2576:
2575:
2574:
2564:
2554:
2552:Levonorgestrel
2549:
2544:
2539:
2538:
2537:
2527:
2522:
2517:
2508:
2507:
2502:
2497:
2488:
2487:
2482:
2481:
2480:
2470:
2461:
2460:
2451:
2450:
2441:
2440:
2435:
2426:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2373:Ethyldienolone
2370:
2365:
2360:
2351:
2350:
2345:
2340:
2335:
2330:
2325:
2320:
2315:
2314:
2313:
2308:
2298:
2293:
2288:
2283:
2278:
2276:Androisoxazole
2269:
2268:
2263:
2258:
2253:
2252:
2251:
2236:
2231:
2230:
2229:
2224:
2219:
2214:
2204:
2199:
2194:
2189:
2184:
2179:
2174:
2169:
2164:
2159:
2154:
2145:
2144:
2139:
2134:
2125:
2124:
2123:
2122:
2117:
2107:
2102:
2101:
2100:
2095:
2090:
2085:
2075:
2074:
2073:
2063:
2058:
2057:
2056:
2046:
2045:
2044:
2034:
2029:
2016:
2015:
2014:
2009:
2004:
1994:
1989:
1984:
1979:
1974:
1973:
1972:
1962:
1957:
1952:
1947:
1946:
1945:
1935:
1926:
1925:
1920:
1919:
1918:
1908:
1903:
1902:
1901:
1891:
1889:Methyldiazinol
1886:
1885:
1884:
1874:
1869:
1864:
1859:
1854:
1853:
1852:
1842:
1841:
1840:
1825:
1820:
1815:
1810:
1809:
1808:
1798:
1793:
1788:
1783:
1778:
1773:
1771:1-Testosterone
1768:
1763:
1758:
1749:
1748:
1747:
1746:
1741:
1726:
1721:
1716:
1711:
1706:
1701:
1700:
1699:
1694:
1684:
1679:
1678:
1677:
1667:
1666:
1665:
1660:
1655:
1645:
1640:
1639:
1638:
1628:
1623:
1618:
1617:
1616:
1611:
1606:
1601:
1591:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1547:
1545:
1538:
1527:
1526:
1518:
1516:
1515:
1508:
1501:
1493:
1486:
1485:
1466:(6): 634–640.
1444:
1409:
1360:
1349:(2): 125–129.
1345:(in Chinese).
1328:
1313:(in Russian).
1298:
1267:(2): 172–197.
1245:
1190:
1188:
1185:
1184:
1183:
1178:
1173:
1168:
1161:
1158:
1155:
1154:
1153:See template.
1032:
1031:
1028:
1025:
1022:
1019:
1016:
1013:
1010:
1007:
1001:
1000:
997:
994:
991:
988:
985:
982:
979:
976:
970:
969:
966:
963:
960:
957:
954:
951:
948:
945:
939:
938:
935:
932:
929:
926:
923:
920:
917:
914:
908:
907:
904:
901:
898:
895:
892:
889:
886:
883:
877:
876:
873:
870:
867:
864:
861:
858:
855:
852:
846:
845:
842:
839:
836:
833:
830:
827:
824:
821:
815:
814:
811:
808:
805:
802:
799:
796:
793:
790:
786:
785:
782:
779:
776:
773:
770:
767:
764:
761:
757:
756:
753:
750:
747:
744:
741:
738:
735:
732:
728:
727:
724:
721:
718:
715:
712:
709:
706:
703:
699:
698:
695:
692:
689:
686:
683:
680:
677:
674:
672:Norethisterone
668:
667:
657:
647:
637:
627:
617:
607:
597:
594:
586:norethisterone
582:
581:
574:
567:
559:
551:(ER)-positive
541:21-hydroxylase
505:
492:antiandrogenic
426:
423:
395:norethisterone
366:
365:
363:
362:
359:
357:
354:
346:
345:
344:
341:
340:
338:
337:
334:
326:
325:
324:
321:
320:
318:
317:
309:
307:
299:
298:
292:
286:
285:
282:
276:
270:
265:
259:
258:
254:
253:
251:
250:
242:DTXSID30966327
237:
235:
222:
221:
219:
218:
210:
208:
202:
201:
199:
198:
190:
188:
182:
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179:
178:
170:
168:
162:
161:
159:
158:
150:
148:
137:
136:
134:
133:
125:
123:
117:
116:
114:
113:
82:
74:
73:
72:
69:
68:
64:
63:
60:
56:
55:
51:
50:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
5436:
5425:
5422:
5420:
5417:
5415:
5412:
5410:
5407:
5405:
5402:
5400:
5397:
5395:
5392:
5390:
5387:
5386:
5384:
5369:
5366:
5364:
5361:
5359:
5356:
5354:
5351:
5349:
5346:
5343:
5342:
5339:
5329:
5326:
5325:
5323:
5319:
5313:
5310:
5308:
5305:
5303:
5300:
5298:
5295:
5293:
5290:
5288:
5285:
5283:
5280:
5278:
5275:
5273:
5270:
5269:
5267:
5263:
5260:
5254:
5244:
5238:
5228:
5225:
5223:
5220:
5218:
5217:Valproic acid
5215:
5213:
5210:
5208:
5205:
5203:
5200:
5198:
5195:
5193:
5190:
5188:
5185:
5184:Nonsteroidal:
5182:
5181:
5178:
5175:
5173:
5170:
5168:
5165:
5163:
5160:
5158:
5155:
5153:
5150:
5148:
5145:
5143:
5140:
5138:
5135:
5133:
5130:
5127:
5126:
5124:
5120:
5114:
5113:Syringic acid
5111:
5109:
5106:
5104:
5101:
5099:
5096:
5094:
5091:
5089:
5086:
5085:Nonsteroidal:
5083:
5082:
5079:
5076:
5074:
5071:
5069:
5066:
5064:
5061:
5059:
5056:
5054:
5051:
5049:
5046:
5044:
5041:
5039:
5036:
5034:
5031:
5029:
5026:
5024:
5021:
5019:
5016:
5014:
5013:Guggulsterone
5011:
5009:
5006:
5004:
5001:
4999:
4996:
4994:
4991:
4989:
4986:
4983:
4982:
4980:
4974:
4965:
4959:
4956:
4954:
4951:
4948:
4947:
4944:
4941:
4939:
4936:
4934:
4931:
4929:
4926:
4924:
4921:
4919:
4918:Riligustilide
4916:
4914:
4911:
4909:
4906:
4904:
4901:
4900:Nonsteroidal:
4898:
4897:
4894:
4891:
4889:
4886:
4884:
4881:
4879:
4876:
4874:
4871:
4869:
4866:
4864:
4861:
4859:
4856:
4854:
4851:
4849:
4846:
4843:
4842:
4839:
4836:
4834:
4831:
4829:
4826:
4823:
4819:
4815:
4812:
4810:
4807:
4805:
4802:
4800:
4797:
4795:
4792:
4790:
4787:
4784:
4780:
4776:
4773:
4771:
4768:
4766:
4763:
4761:
4758:
4756:
4753:
4751:
4748:
4746:
4743:
4741:
4738:
4736:
4733:
4731:
4728:
4726:
4723:
4721:
4718:
4716:
4713:
4711:
4708:
4706:
4703:
4701:
4698:
4696:
4693:
4691:
4688:
4686:
4683:
4681:
4678:
4676:
4673:
4671:
4668:
4666:
4663:
4661:
4658:
4656:
4652:
4649:
4647:
4644:
4642:
4639:
4637:
4634:
4632:
4629:
4627:
4624:
4622:
4619:
4617:
4614:
4612:
4609:
4607:
4604:
4602:
4599:
4597:
4594:
4591:
4587:
4583:
4580:
4578:
4575:
4573:
4570:
4568:
4565:
4563:
4560:
4558:
4555:
4553:
4550:
4547:
4543:
4540:
4538:
4535:
4533:
4530:
4528:
4525:
4523:
4520:
4518:
4515:
4513:
4510:
4508:
4505:
4503:
4500:
4496:
4495:Ethandrostate
4493:
4492:
4491:
4488:
4486:
4483:
4481:
4478:
4476:
4473:
4471:
4468:
4466:
4463:
4461:
4458:
4456:
4455:Allylestrenol
4453:
4451:
4448:
4446:
4443:
4441:
4437:
4434:
4433:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4400:
4397:
4395:
4392:
4390:
4387:
4385:
4382:
4380:
4377:
4375:
4372:
4370:
4367:
4365:
4362:
4360:
4357:
4355:
4352:
4350:
4347:
4345:
4342:
4340:
4337:
4335:
4332:
4330:
4327:
4325:
4322:
4320:
4317:
4314:
4313:
4310:
4307:
4305:
4302:
4300:
4297:
4295:
4292:
4290:
4289:Pentagestrone
4287:
4285:
4282:
4280:
4277:
4275:
4272:
4270:
4267:
4265:
4262:
4260:
4257:
4255:
4252:
4250:
4247:
4245:
4242:
4240:
4237:
4235:
4232:
4230:
4227:
4225:
4222:
4220:
4217:
4215:
4212:
4210:
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4175:
4174:Hydromadinone
4172:
4170:
4167:
4165:
4164:Gestobutanoyl
4162:
4160:
4157:
4155:
4152:
4150:
4147:
4145:
4142:
4140:
4137:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4115:
4112:
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:
4044:Chlormadinone
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:
3964:
3963:
3960:
3957:
3955:
3952:
3950:
3947:
3945:
3942:
3940:
3937:
3935:
3932:
3930:
3927:
3925:
3922:
3919:
3918:
3915:
3912:
3910:
3907:
3905:
3902:
3900:
3897:
3895:
3892:
3890:
3887:
3885:
3882:
3880:
3877:
3875:
3872:
3870:
3867:
3865:
3862:
3860:
3857:
3855:
3852:
3850:
3847:
3845:
3842:
3840:
3837:
3834:
3833:
3831:
3827:
3824:
3819:
3813:
3809:
3806:
3799:
3794:
3792:
3787:
3785:
3780:
3779:
3776:
3764:
3761:
3759:
3756:
3754:
3751:
3749:
3746:
3744:
3741:
3738:
3737:
3734:
3724:
3721:
3716:
3711:
3709:
3706:
3703:
3696:
3689:
3682:
3676:
3674:
3671:
3669:
3666:
3664:
3661:
3658:
3654:
3650:
3646:
3642:
3638:
3634:
3631:
3630:
3628:
3624:
3621:
3619:
3615:
3605:
3602:
3600:
3597:
3595:
3592:
3590:
3587:
3585:
3584:Valproic acid
3582:
3580:
3577:
3575:
3572:
3570:
3567:
3565:
3562:
3560:
3557:
3555:
3552:
3550:
3547:
3545:
3542:
3540:
3537:
3535:
3532:
3530:
3529:Rezvilutamide
3527:
3525:
3522:
3520:
3517:
3515:
3512:
3510:
3507:
3505:
3504:Proxalutamide
3502:
3500:
3497:
3495:
3492:
3490:
3487:
3485:
3482:
3480:
3477:
3475:
3472:
3470:
3467:
3465:
3463:
3459:
3457:
3455:
3451:
3449:
3447:
3443:
3441:
3438:
3436:
3433:
3431:
3428:
3426:
3423:
3421:
3418:
3416:
3413:
3411:
3408:
3406:
3403:
3401:
3398:
3396:
3393:
3391:
3388:
3386:
3383:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3348:
3345:
3341:
3338:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3295:
3291:
3287:
3283:
3279:
3275:
3272:
3270:
3267:
3265:
3262:
3260:
3257:
3255:
3252:
3250:
3247:
3245:
3242:
3240:
3237:
3235:
3232:
3230:
3227:
3225:
3222:
3220:
3219:-Bicalutamide
3218:
3213:
3212:Nonsteroidal:
3210:
3209:
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:
3118:
3116:
3113:
3111:
3108:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
3086:
3083:
3081:
3080:Guggulsterone
3078:
3076:
3073:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2920:
2919:
2917:
2913:
2907:
2904:
2902:
2899:
2897:
2894:
2892:
2889:
2886:
2885:
2882:
2879:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2852:
2849:
2847:
2844:
2842:
2839:
2837:
2834:
2832:
2829:
2827:
2824:
2822:
2819:
2817:
2814:
2812:
2809:
2807:
2804:
2802:
2799:
2797:
2794:
2792:
2789:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2764:
2762:
2759:
2757:
2754:
2752:
2749:
2747:
2744:
2742:
2739:
2737:
2734:
2732:
2729:
2727:
2724:
2722:
2719:
2718:Nonsteroidal:
2716:
2715:
2713:
2708:
2702:
2696:
2693:
2691:
2688:
2686:
2683:
2681:
2678:
2676:
2673:
2671:
2670:5α-Androstane
2668:
2666:
2663:
2660:
2659:
2656:
2653:
2651:
2648:
2646:
2643:
2640:
2639:
2636:
2633:
2631:
2628:
2625:
2624:
2621:
2618:
2614:
2611:
2610:
2609:
2606:
2604:
2601:
2599:
2596:
2593:
2589:
2585:
2582:
2580:
2577:
2573:
2570:
2569:
2568:
2565:
2562:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2536:
2533:
2532:
2531:
2528:
2526:
2523:
2521:
2518:
2516:
2513:
2510:
2509:
2506:
2503:
2501:
2498:
2496:
2493:
2490:
2489:
2486:
2483:
2479:
2478:Ethandrostate
2476:
2475:
2474:
2471:
2469:
2466:
2463:
2462:
2459:
2456:
2453:
2452:
2449:
2446:
2443:
2442:
2439:
2436:
2434:
2431:
2428:
2427:
2424:
2421:
2419:
2416:
2414:
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2386:
2384:
2381:
2379:
2378:Ethylestrenol
2376:
2374:
2371:
2369:
2366:
2364:
2361:
2359:
2356:
2353:
2352:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2312:
2309:
2307:
2304:
2303:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2271:
2270:
2267:
2264:
2262:
2259:
2257:
2254:
2250:
2247:
2246:
2244:
2240:
2237:
2235:
2232:
2228:
2225:
2223:
2220:
2218:
2215:
2213:
2210:
2209:
2208:
2205:
2203:
2200:
2198:
2195:
2193:
2190:
2188:
2185:
2183:
2180:
2178:
2175:
2173:
2170:
2168:
2165:
2163:
2160:
2158:
2155:
2153:
2150:
2147:
2146:
2143:
2140:
2138:
2135:
2133:
2130:
2127:
2126:
2121:
2118:
2116:
2113:
2112:
2111:
2108:
2106:
2103:
2099:
2096:
2094:
2091:
2089:
2086:
2084:
2081:
2080:
2079:
2076:
2072:
2069:
2068:
2067:
2064:
2062:
2059:
2055:
2052:
2051:
2050:
2047:
2043:
2040:
2039:
2038:
2035:
2033:
2030:
2028:
2026:
2022:
2017:
2013:
2010:
2008:
2005:
2003:
2000:
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1136:
1129:
1123:
1116:
1110:
1103:
1097:
1090:
1084:
1083:dexamethasone
1077:
1071:
1064:
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1045:
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1037:
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1026:
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797:
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628:
623:
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608:
603:
598:
595:
592:
591:
587:
580:
575:
573:
568:
566:
561:
560:
556:
554:
553:breast cancer
550:
546:
542:
538:
534:
530:
526:
523:
519:
515:
511:
503:
500:
495:
493:
489:
485:
481:
477:
473:
469:
466:
463:
459:
454:
452:
448:
444:
440:
436:
432:
431:progestogenic
424:
422:
420:
416:
412:
408:
404:
400:
396:
392:
389:) is a major
388:
384:
380:
376:
372:
358:
353:
349:
342:
333:
329:
322:
315:
311:
310:
308:
305:
300:
293:
291:
287:
266:
264:
260:
255:
247:
243:
239:
238:
236:
227:
223:
216:
215:ChEMBL3273987
212:
211:
209:
207:
203:
196:
192:
191:
189:
187:
183:
176:
172:
171:
169:
167:
163:
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152:
151:
149:
142:
138:
131:
127:
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122:
118:
110:
106:
102:
98:
94:
90:
86:
81:
77:
70:
65:
61:
57:
54:Clinical data
52:
48:
43:
33:
19:
5328:Mifepristone
5312:Progesterone
5307:Pregnenolone
5302:Mifepristone
5187:Darolutamide
5183:
5172:Toripristone
5167:RTI 3021–022
5137:Lilopristone
5132:Aglepristone
5128:
5084:
5063:Telapristone
4997:
4984:
4949:
4899:
4858:Drospirenone
4844:
4631:Quingestanol
4606:Norgestimate
4601:Norgesterone
4596:Noretynodrel
4512:Etonogestrel
4438:Progestins:
4435:
4429:Trimegestone
4414:Promegestone
4315:
4304:Proligestone
4244:Melengestrol
4209:Medrogestone
4144:Flumedroxone
4099:Cymegesolate
4089:Clomegestone
3965:
3920:
3914:Quingestrone
3904:Progesterone
3835:
3723:Testosterone
3509:Pyrilutamide
3461:
3453:
3445:
3410:Lavender oil
3400:Ketoconazole
3365:Enzalutamide
3335:Darolutamide
3269:Bicalutamide
3244:Atraric acid
3216:
3211:
3195:Trimegestone
3150:Promegestone
3115:Mifepristone
3090:Medrogestone
3035:Drospirenone
2990:Clascoterone
2921:
2887:
2831:JNJ-37654032
2826:JNJ-28330835
2821:JNJ-26146900
2717:
2661:
2641:
2634:
2626:
2608:Quingestanol
2525:Etonogestrel
2511:
2491:
2464:
2454:
2444:
2429:
2413:Propetandrol
2354:
2343:Oxymetholone
2318:Methasterone
2272:
2266:Tiomesterone
2256:Oxymesterone
2148:
2128:
2049:Norclostebol
2024:
2020:
1929:
1867:Mepitiostane
1862:Epitiostanol
1845:Drostanolone
1796:Androsterone
1752:
1733:+dutasteride
1729:Testosterone
1697:DHEA sulfate
1550:
1463:
1459:
1425:(1): 49–57.
1422:
1418:
1412:
1379:
1375:
1346:
1342:
1317:(5): 57–61.
1314:
1310:
1292:
1264:
1260:
1215:
1211:
1150:
1141:or inactive
1134:
1044:promegestone
1042:(100%) were
1035:
912:Noretynodrel
499:irreversible
496:
484:testosterone
455:
451:progesterone
428:
425:Pharmacology
411:5α-reductase
386:
382:
378:
374:
370:
369:
108:
104:
100:
96:
92:
88:
84:
5321:Antagonists
5147:Onapristone
5122:Antagonists
4893:Spirorenone
4863:Mespirenone
4552:Lynestrenol
4502:Ethisterone
4480:Desogestrel
4460:Altrenogest
4419:Segesterone
4394:Norgestomet
4384:Nomegestrol
4359:Gestadienol
4344:Demegestone
4299:Pentarane A
4119:Edogestrone
4109:Delmadinone
4069:Cismadinone
3959:Trengestone
3889:Dimepregnen
3708:Osteocalcin
3589:Vinclozolin
3574:Thalidomide
3569:Seviteronel
3499:Procymidone
3435:Masofaniten
3390:Inocoterone
3294:bisphenol S
3290:bisphenol F
3286:bisphenol A
3264:BAY-1024767
3239:Apalutamide
3185:Spiroxasone
3180:Spirorenone
3160:Rosterolone
3100:Mespirenone
3045:Edogestrone
3015:Delanterone
3005:Cyproterone
2995:Clometerone
2965:Benorterone
2950:Abiraterone
2915:Antagonists
2846:PF-06260414
2751:BMS-564,929
2675:Alternariol
2567:Lynestrenol
2520:Desogestrel
2403:Norboletone
2393:Metribolone
2338:Oxandrolone
2296:Mestanolone
2261:Penmesterol
2192:Formebolone
2157:Calusterone
2152:Bolasterone
1906:Prostanozol
1877:Mesterolone
1212:Climacteric
1096:aldosterone
1057:metribolone
1005:Lynestrenol
537:17,20-lyase
531:(P450scc),
476:ethisterone
468:metribolone
433:and marked
297: g·mol
67:Identifiers
59:Other names
5383:Categories
5177:Zanoterone
5142:Lonaprisan
5129:Steroidal:
5103:Naringenin
5093:Kaempferol
5073:Vilaprisan
5003:Asoprisnil
4985:Steroidal:
4958:ORG-201745
4938:Tanaproget
4833:Trestolone
4770:Nandrolone
4765:Mibolerone
4700:Dienedione
4690:Bolandione
4651:Tosagestin
4626:Oxendolone
4611:Norgestrel
4562:Metynodiol
4532:Gestrinone
4507:Ethynerone
4404:Oxogestone
4269:Mometasone
4159:Gestaclone
4124:Flugestone
4079:Clogestone
4019:Anagestone
3808:modulators
3702:-ornithine
3645:gadolinium
3494:Prochloraz
3489:Phenothrin
3469:Nilutamide
3440:Methiocarb
3360:Endosulfan
3325:Cioteronel
3320:Cimetidine
3310:BMS-641988
3305:BMS-570511
3300:BMS-501949
3274:Bisphenols
3229:Antarlides
3205:Zanoterone
3140:Oxendolone
3085:Ludaterone
3075:Galeterone
3025:Dicirenone
2922:Steroidal:
2888:Steroidal:
2881:Vosilasarm
2776:GSK2881078
2731:AC-262,536
2690:Trilostane
2598:Norgestrel
2547:Gestrinone
2515:Δ-Tibolone
2398:Mibolerone
2348:Stanozolol
2301:Metenolone
2078:Trenbolone
2037:Nandrolone
1987:Dienedione
1911:Stenbolone
1872:Mesabolone
1724:Silandrone
1719:Quinbolone
1714:Plomestane
1709:Formestane
1704:Exemestane
1626:Atamestane
1523:modulators
1187:References
1143:metabolite
1135:Footnotes:
823:Metabolite
792:Metabolite
763:Metabolite
734:Metabolite
705:Metabolite
514:inhibition
494:activity.
488:nandrolone
480:5α-reduced
417:and other
407:estrogenic
403:androgenic
302:3D model (
290:Molar mass
195:2DD235DD5X
166:ChemSpider
121:CAS Number
76:IUPAC name
5227:ZM-172406
5222:ZM-150271
5212:LG-121046
5207:LG-120830
5202:LG-100128
5197:LG-100127
5192:LG-001447
5162:ORG-33628
5157:ORG-31806
5152:ORG-31710
5098:LG-120920
5078:ZK-137316
5058:RMI-12936
5053:ORG-33628
5048:ORG-31710
5023:LG-120838
4953:ORG-47241
4943:ZM-182345
4933:RWJ-60130
4928:RWJ-49853
4923:RWJ-26819
4913:LG-100128
4873:Prorenone
4853:Canrenone
4828:Trendione
4705:Dienolone
4680:Bolandiol
4527:Gestodene
4517:Etynodiol
4485:Dienogest
4470:Cingestol
4334:Amadinone
4279:Osaterone
4229:Megestrol
4004:Algestone
3954:Ro 6-3129
3894:Diosgenin
3688:-arginine
3673:Estradiol
3653:strontium
3649:magnesium
3637:aluminium
3604:YM-175735
3539:Ro 5-2537
3534:Ro 2-7239
3484:PF-998425
3479:Pentomone
3420:LG-120907
3380:Flutamide
3375:Fenarimol
3315:CH5137291
3254:Bakuchiol
3190:Topterone
3155:Prorenone
3130:Osaterone
3125:Nordinone
3110:Mexrenone
3030:Dienogest
2980:Canrenone
2901:TFM-4AS-1
2841:ORM-11984
2781:GSK-4336A
2771:GLPG-0492
2695:ZM-182345
2542:Gestodene
2530:Etynodiol
2286:Furazabol
2177:Enestebol
2105:Trendione
2066:Oxabolone
1992:Dienolone
1965:Bolandiol
1894:Nisterime
1648:Clostebol
1631:Boldenone
1070:estradiol
943:Etynodiol
518:aromatase
510:selective
472:bioassays
399:progestin
5409:Estranes
5344:See also
5265:Agonists
5088:Apigenin
5043:ORF-9326
5038:ORF-9371
4950:Unknown:
4646:Tigestol
4641:Tibolone
4399:ORG-2058
3939:DU-41165
3934:DU-41164
3829:Agonists
3739:See also
3626:Agonists
3599:YM-92088
3564:RU-58841
3559:RU-58642
3554:RU-57073
3549:RU-56187
3544:RU-22930
3474:ONC1-13B
3425:LGD-1331
3350:Dieldrin
3344:p,p’-DDE
3249:AZD-3514
3234:Arabilin
3165:RU-15328
3105:Metogest
3040:DU-41165
2876:S-101479
2856:RU-59063
2811:LGD-4033
2806:LGD-3303
2796:LGD-2226
2786:GSK-8698
2685:Drupanol
2680:Cl-4AS-1
2620:Tibolone
1801:Bolazine
1544:Agonists
1439:14723979
1404:33771349
1289:41356223
1281:19028512
1261:Steroids
1240:24616324
1232:16112947
1160:See also
1151:Sources:
1122:cortisol
1098:for the
1085:for the
1072:for the
1059:for the
1046:for the
593:Compound
527:such as
465:androgen
443:affinity
375:5α-DHNET
5419:Ketones
5108:PRA-910
4908:LG-2527
4883:SC-8109
4816:(e.g.,
4799:RU-2309
4777:(e.g.,
4584:(e.g.,
4544:(e.g.,
4475:Danazol
3695:-lysine
3683:(incl.
3641:calcium
3635:(incl.
3633:Cations
3430:Linuron
3370:EPI-001
3276:(e.g.,
3065:EM-6537
3060:EM-5855
3055:EM-5854
3050:EM-4350
2896:MK-0773
2891:EM-9017
2871:S-40503
2726:ACP-105
2721:198RL26
2586:(e.g.,
2559:(e.g.,
2468:Danazol
2418:RU-2309
2358:Bolenol
1480:8205267
1396:9182866
1355:2934946
1323:3208885
1147:prodrug
1040:ligands
1009:Prodrug
978:Prodrug
947:Prodrug
916:Prodrug
885:Prodrug
854:Prodrug
525:enzymes
512:in its
419:tissues
413:in the
295:300.442
263:Formula
141:PubChem
130:52-79-9
3899:P1-185
3618:GPRC6A
3594:YM-580
3524:RD-162
3415:LG-105
2766:FTBU-1
1478:
1437:
1402:
1394:
1353:
1321:
1287:
1279:
1238:
1230:
1139:Active
1120:, and
1036:Notes:
462:potent
328:SMILES
206:ChEMBL
5018:J1042
4972:SPRMs
4967:Mixed
3282:BFDGE
3278:BADGE
3224:AA560
2906:YK-11
2816:LY305
2706:SARMs
1400:S2CID
1285:S2CID
1236:S2CID
956:11–18
826:15–25
679:67–75
543:, or
415:liver
385:, or
348:InChI
304:JSmol
175:56721
155:63023
5252:PAQR
3714:SHBG
3657:zinc
3355:DIMP
2970:BOMT
2866:S-23
2756:DTIB
1476:PMID
1435:PMID
1392:PMID
1351:PMID
1319:PMID
1277:PMID
1228:PMID
1124:for
1114:SHBG
1111:for
841:0.18
651:SHBG
596:Type
486:and
405:and
186:UNII
5242:mPR
3340:DDT
2861:S-1
2851:R-1
1468:doi
1464:130
1427:doi
1384:doi
1269:doi
1220:doi
1127:CBG
835:1–3
832:112
829:1–3
801:0–8
743:0–1
691:0–3
688:0–1
661:CBG
516:of
393:of
231:EPA
145:CID
107:,17
103:,14
99:,13
95:,10
5385::
4820:,
4781:,
4588:,
3817:PR
3697:,
3690:,
3655:,
3651:,
3647:,
3643:,
3639:,
3292:,
3288:,
3284:,
3280:,
2590:,
2245:)
1834:)
1735:)
1532:AR
1474:.
1462:.
1447:^
1433:.
1423:25
1421:.
1398:.
1390:.
1380:60
1378:.
1363:^
1331:^
1315:51
1301:^
1291:.
1283:.
1275:.
1265:74
1263:.
1248:^
1234:.
1226:.
1214:.
1194:^
1145:,
1137:=
1133:.
1107:,
1101:MR
1094:,
1088:GR
1081:,
1075:ER
1068:,
1062:AR
1055:,
1049:PR
1030:?
999:?
968:?
937:0
906:?
875:?
857:20
844:0
813:?
784:?
755:?
726:?
711:27
708:25
697:0
694:16
682:15
641:MR
631:GR
621:ER
611:AR
601:PR
555:.
539:,
504:(K
421:.
381:,
377:,
277:28
271:20
91:,9
87:,8
83:(5
5258:)
5249:(
4978:)
4969:(
4824:)
4785:)
4592:)
4548:)
3797:e
3790:t
3783:v
3704:)
3700:L
3693:L
3686:L
3679:L
3659:)
3462:N
3454:N
3446:N
3346:)
3296:)
3217:N
3215:5
2594:)
2563:)
2241:(
2025:N
2021:N
1830:(
1731:(
1512:e
1505:t
1498:v
1482:.
1470::
1441:.
1429::
1406:.
1386::
1357:.
1347:6
1325:.
1271::
1242:.
1222::
1216:8
1027:?
1024:0
1021:0
1018:3
1015:1
1012:1
996:?
993:0
990:0
987:0
984:0
981:1
965:?
962:?
959:0
953:0
950:1
934:0
931:0
928:0
925:2
922:0
919:6
903:?
900:?
897:?
894:?
891:?
888:?
872:?
869:0
866:0
863:1
860:5
838:0
810:?
807:?
804:0
798:0
795:1
781:?
778:?
775:?
772:0
769:0
766:?
752:?
749:?
746:0
740:0
737:1
723:?
720:?
717:0
714:0
685:0
676:–
578:e
571:t
564:v
535:/
506:i
373:(
306:)
283:2
280:O
274:H
268:C
233:)
229:(
109:R
105:S
101:S
97:S
93:R
89:R
85:S
34:.
20:)
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