302:
51:
66:
427:(which he had isolated in 1929) in his first publication on the substance (and later referred to as folliculine, with the name estrone not finally being adopted until 1935). Aside from Progynon and Progynon 2, the Progynon name has also been used in a variety of other estrogenic products marketed by Schering, including Progynon-B (
460:
960:
Batisweiler J (1928). "Placentaextrakt
Progynon (Schering-Kahlbaum) bei Menstruationsstörungen und Kastrationsfolgen" [Placenta extract Progynon (Schering-Kahlbaum) for menstrual disorders and the consequences of castration.].
567:
constitute more than 90% of the estrogens in the urine of pregnant women. Of these conjugates, 35 to 46% are estriol glucuronides and 15 to 22% are estriol 3-sulfate in late pregnancy; the double conjugate
415:
constitute more than 90% of the estrogens in the urine of pregnant women. Of these conjugates, 35 to 46% are estriol glucuronides and 15 to 22% are estriol 3-sulfate in late pregnancy; the double conjugate
2551:
1559:
537:
and
Progynon 2, respectively. Premarin was introduced by Ayerst in 1941 and has become not only a very widely used estrogen, but one of the most widely prescribed drugs in
301:
2604:
2714:
506:, which was equivalent in composition but was less expensive to source, and was essentially the same product as Progynon, a related estrogen developed by
4911:
2544:
2513:
2095:
609:
4860:
1552:
388:) in 1941. Premarin soon superseded Emmenin and has since become not only a very widely used estrogen, but one of the most widely prescribed drugs in
138:
Conjugated human estriol; Conjugated oestriol; Conjugated human oestriol; CE3; CHE3; Conjugated human estrogens; Conjugated human oestrogens; CHEs
4053:
2086:
1390:
Campbell AD, Collip JB (1930). "Treatment of menopausal symptoms and menstrual disorders with extracts of human placenta and pregnancy urine".
4855:
2537:
2503:
2470:
1525:
1495:
1269:
1240:
1169:
1139:
1109:
1079:
1049:
1017:
987:
941:
859:
791:
741:
2824:
293:
in tissues that express this enzyme. Consequently, estrogen conjugates have estrogenic activity via conversion into unconjugated estrogens.
4850:
2508:
1545:
4584:
2809:
2804:
878:
Streck A (1928). ""Progynon"-Schering, ein Neues Zyklus-Hormonpräparat" ["Progynon"-Schering, a new cycle hormone preparation].
521:
To reduce the costs of manufacturing
Emmenin and Progynon, Ayerst and Schering eventually switched to using the urine of pregnant
4008:
3259:
2020:
4845:
4609:
3159:
2719:
2694:
2404:
2037:
1791:
182:
58:, the primary active component in conjugated estriol (estriol glucuronides constitute about 35 to 46% of total content).
4906:
4865:
3107:
2518:
2487:
2408:
1410:
569:
417:
108:
676:
Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration".
238:
women and were used as medications in the 1920s and 1930s. Conjugated estriol is analogous to and was superseded by
3112:
1808:
548:
526:
385:
376:
To further reduce the costs of manufacturing
Progynon, Schering eventually switched to using the urine of pregnant
55:
4500:
4167:
4077:
3299:
2619:
2614:
1620:
4886:
4728:
4490:
4403:
4028:
3721:
3254:
3249:
3149:
1815:
556:
404:
336:
product and hence also the first estrogen product to be introduced for medical use. Progynon was originally an
4732:
2774:
4916:
4896:
4072:
4016:
3926:
3551:
3541:
3476:
3428:
3346:
3068:
3036:
3004:
2994:
2873:
2857:
2814:
2789:
2729:
2724:
2475:
2299:
2295:
1980:
1958:
1941:
1909:
1786:
1762:
1742:
1738:
1710:
1636:
1624:
143:
3984:
3536:
3016:
2941:
2936:
2889:
2744:
1975:
1752:
1705:
573:
436:
432:
73:, the second major active component in conjugated estriol (constitutes about 15 to 22% of total content).
4257:
4082:
4020:
3546:
3090:
3053:
3041:
2909:
2392:
1776:
1770:
1700:
1670:
1580:
1568:
589:
475:
317:
215:
113:
101:
89:
4647:
2819:
2794:
2769:
2754:
2689:
2629:
2624:
289:, among others. Likewise, estrogen sulfates can be desulfated into the corresponding free estrogens by
3677:
3334:
3073:
2979:
2921:
2759:
2699:
2634:
2609:
2400:
1897:
1845:
1781:
1757:
1730:
1695:
1680:
948:
The first sex steroid used as pharmacological agent was
Progynon, first sold by Schering AG in 1928.
599:
594:
448:
239:
31:
4413:
4738:
4653:
4464:
4456:
3717:
3501:
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3134:
2834:
2749:
2452:
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2320:
2214:
2046:
1726:
1722:
1655:
552:
471:
468:
400:
313:
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258:
251:
247:
219:
162:
150:
84:
4039:
4901:
4820:
4799:
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4485:
4292:
4287:
4282:
4152:
4067:
3681:
3341:
2999:
2861:
2704:
2664:
2654:
2594:
2563:
1904:
1850:
1734:
1718:
1628:
903:
701:
604:
518:. These estrogen products were the first orally active estrogens to be marketed for medical use.
444:
428:
35:
4758:
4678:
4475:
4408:
3777:
3561:
2684:
266:
4550:
4545:
4317:
4242:
4891:
4525:
4520:
4418:
4367:
4362:
4192:
3641:
2799:
2649:
2644:
2571:
2560:
2412:
2225:
2075:
1766:
1714:
1589:
1521:
1491:
1463:
1372:
1337:
1302:
1265:
1257:
1236:
1230:
1211:
1165:
1159:
1135:
1129:
1105:
1099:
1075:
1069:
1045:
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1007:
983:
977:
937:
931:
895:
855:
849:
787:
737:
693:
655:
290:
227:
125:
70:
4693:
4688:
4372:
4207:
4162:
3511:
3264:
1515:
1485:
781:
731:
572:(probably estriol 3-sulfate 16α-glucuronide) also occurs. Unlike unconjugated estrogens like
4668:
4530:
4438:
4433:
4423:
4337:
4262:
4137:
3274:
3102:
2849:
2779:
2734:
2674:
2669:
2659:
2639:
2599:
2287:
2275:
1887:
1803:
1616:
1453:
1422:
1364:
1329:
1294:
1201:
1037:
887:
823:
685:
645:
440:
352:. This form of Progynon was essentially the same product as Emmenin, which was developed by
270:
223:
218:
medication which was previously used for estrogen-type indications such as the treatment of
4377:
191:
4227:
3960:
3834:
3466:
3413:
3368:
3169:
2371:
2307:
1995:
1948:
1825:
564:
530:
507:
412:
321:
262:
96:
3938:
3934:
3912:
1071:
Recent
Progress in Hormone Research: The Proceedings of the Laurentian Hormone Conference
851:
National
Cultures and International Competition: The Experience of Schering AG, 1851-1950
265:. Estrogen glucuronides can be deglucuronidated into the corresponding free estrogens by
171:
4698:
4460:
4332:
3761:
3481:
3453:
3445:
3284:
3189:
3179:
3124:
3119:
3021:
2839:
2739:
2481:
2344:
2332:
1965:
1647:
1458:
1441:
1487:
J.B. Collip and the
Development of Medical Research in Canada: Extracts and Enterprise
1333:
828:
380:
and called its new product
Progynon 2. Ayerst followed suit, with the introduction of
4880:
4312:
4147:
4122:
3902:
3820:
3653:
3631:
3486:
3363:
3095:
2946:
2904:
1931:
1320:
Macfarlane C (1936). "Observations on the use of Collip's emmenin in the menopause".
538:
491:
389:
365:
278:
907:
705:
4480:
4452:
4428:
4297:
4222:
4132:
4127:
4117:
3920:
3886:
3876:
3872:
3807:
3801:
3733:
3229:
3219:
3194:
3058:
3011:
2865:
2853:
2354:
2291:
2230:
2159:
2154:
2149:
2144:
2124:
2119:
2066:
2033:
2013:
2007:
2003:
1862:
1857:
1651:
1632:
1572:
479:
353:
50:
42:
634:"Functional role of estrogen metabolism in target cells: review and perspectives"
4825:
4753:
4718:
4713:
4673:
4643:
4629:
4619:
4614:
4443:
4387:
4382:
4277:
4272:
4252:
4202:
4177:
4172:
4097:
4087:
4004:
4000:
3996:
3988:
3978:
3974:
3942:
3930:
3916:
3908:
3848:
3781:
3725:
3697:
3531:
3506:
3378:
3279:
3154:
3078:
3048:
2899:
2879:
2829:
2783:
2679:
2388:
2361:
2340:
2336:
2328:
2313:
2303:
2255:
2194:
2189:
2139:
2027:
1970:
1796:
1746:
1665:
1606:
511:
333:
325:
65:
2529:
4768:
4748:
4723:
4570:
4515:
4470:
4448:
4357:
4352:
4322:
4307:
4302:
4267:
4157:
4112:
4092:
3970:
3964:
3868:
3856:
3816:
3797:
3773:
3757:
3667:
3663:
3637:
3623:
3576:
3571:
3566:
3556:
3526:
3496:
3491:
3471:
3408:
3329:
3309:
3294:
3289:
3269:
3234:
3184:
3085:
3026:
2959:
2954:
2931:
2869:
2844:
2764:
2437:
2378:
2260:
2245:
2204:
2179:
2169:
2164:
2134:
2109:
1953:
1919:
1892:
1882:
1877:
1867:
1840:
1835:
1690:
1685:
1537:
1368:
689:
545:
459:
396:
1376:
1355:
Campbell AD (1933). "Concerning
Placental Hormones and Menstrual Disorders".
1341:
1306:
899:
4763:
4743:
4683:
4663:
4505:
4342:
4217:
4212:
4197:
4182:
4142:
4024:
3992:
3950:
3898:
3894:
3890:
3880:
3860:
3844:
3793:
3769:
3765:
3753:
3745:
3741:
3701:
3689:
3673:
3659:
3649:
3645:
3601:
3461:
3435:
3423:
3398:
3388:
3373:
3353:
3304:
3204:
3199:
3174:
3164:
3129:
2989:
2964:
2926:
2884:
2365:
2348:
2324:
2265:
2240:
2174:
2129:
1936:
1924:
1914:
1830:
1820:
1643:
811:
733:
The Greatest Experiment Ever Performed on Women: Exploding the Estrogen Myth
650:
633:
503:
349:
235:
2709:
1467:
1285:
Collip JB, Browne JS, Thomson DL (1934). "The Chemical Nature of Emmenin".
1215:
697:
1206:
1189:
659:
4634:
4624:
4327:
4187:
4107:
4102:
4035:
3852:
3789:
3785:
3749:
3737:
3709:
3705:
3693:
3685:
3615:
3403:
3393:
3239:
3224:
3209:
3144:
3139:
2984:
2894:
2447:
2382:
2283:
2114:
1659:
1612:
1298:
1190:"Quantitative estimation of estrogen conjugates in late pregnancy plasma"
534:
495:
381:
341:
1426:
812:"The Preparation of the Crystalline Follicular Ovarian Hormone: Theelin"
242:(brand name Premarin), which is manufactured from the urine of pregnant
4789:
4535:
4347:
4247:
4237:
4232:
4012:
3956:
3946:
3838:
3713:
3521:
3516:
3418:
3383:
3314:
3214:
3063:
3031:
2969:
2432:
1985:
891:
577:
560:
515:
424:
408:
329:
17:
1098:
Creasy RK, Resnik R, Lockwood CJ, Iams JD, Greene MF, Moore T (2013).
344:
extract, but Schering soon switched for economic reasons to using the
4708:
4703:
4560:
3824:
3812:
3627:
3596:
3591:
3586:
3319:
2974:
487:
483:
361:
357:
286:
274:
1101:
Creasy and Resnik's Maternal-Fetal Medicine: Principles and Practice
498:. At some point, it seems to have been changed to an extract of the
4784:
4658:
4540:
4510:
3729:
3611:
3440:
2096:
499:
458:
345:
337:
300:
282:
231:
4804:
4495:
3864:
3619:
522:
377:
243:
2533:
1541:
1446:
Canadian Journal of Comparative Medicine and Veterinary Science
4639:
4054:
2087:
1012:. Jaypee Brothers Medical Publishers Pvt. Ltd. pp. 326–.
1009:
Textbook of Cardiology: A Clinical and Historical Perspective
4585:
494:
in 1934. It was originally an extract obtained from human
423:
Progynon was also the name that Butenandt originally gave
420:(probably estriol 3-sulfate 16α-glucuronide) also occurs.
936:. Springer Science & Business Media. pp. 549–.
2955:
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
2372:
2355:
2021:
2014:
925:
923:
921:
919:
917:
979:
Poulsson's Text-Book of Pharmacology and Therapeutics
2038:
1959:
Methestrol dipropionate (promethestrol dipropionate)
1194:
The Journal of Clinical Endocrinology and Metabolism
4813:
4777:
4597:
4583:
4396:
4049:
2584:
2570:
2422:
2274:
2213:
2074:
2065:
1994:
1588:
1579:
1093:
1091:
399:estrogens, which was determined later to be mostly
181:
161:
156:
142:
134:
124:
119:
107:
95:
83:
78:
2101:Tooltip selective estrogen receptor downregulators
1411:"The Management of Functional Menstrual Disorders"
1235:. Chemical Heritage Foundation. pp. 253–254.
1161:Phase II Conjugation Enzymes and Transport Systems
246:. Conjugated estriol was among the first forms of
544:Both Emmenin and Progynon contained a mixture of
395:Both Progynon and Emmenin contained a mixture of
1925:Mestilbol (diethylstilbestrol monomethyl ether)
1264:. Vol. 12. Academic Press. pp. 136–.
1183:
1181:
1164:. Gulf Professional Publishing. pp. 294–.
230:which were manufactured from the estrogen-rich
170:
4059:Tooltip Selective estrogen receptor modulators
3414:Furostilbestrol (diethylstilbestrol difuroate)
2775:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
2092:Tooltip selective estrogen receptor modulators
1123:
1121:
1063:
1061:
1038:"Bioactivation of Estrogens to Toxic Quinones"
1031:
1029:
1001:
999:
671:
669:
257:The main components of conjugated estriol are
250:estrogen to be used in medicine. It was taken
2605:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
2545:
1915:Dimestrol (diethylstilbestrol dimethyl ether)
1553:
1509:
1507:
1490:. McGill-Queen's Press - MQUP. pp. 86–.
1322:American Journal of Obstetrics and Gynecology
873:
871:
854:. Cambridge University Press. pp. 119–.
843:
841:
839:
775:
773:
725:
723:
721:
719:
717:
715:
627:
625:
8:
2715:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
1153:
1151:
805:
803:
771:
769:
767:
765:
763:
761:
759:
757:
755:
753:
41:
4590:Tooltip G protein-coupled estrogen receptor
3409:Fosfestrol (diethylstilbestrol diphosphate)
2047:
1920:Fosfestrol (diethylstilbestrol diphosphate)
1104:. Elsevier Health Sciences. pp. 104–.
447:), and Progynon Depot (estradiol valerate,
4594:
3552:Triphenylmethylethylene (triphenylpropene)
2876:, many others; via estrogenic metabolites)
2800:17α-Epiestriol (16α-hydroxy-17α-estradiol)
2581:
2552:
2538:
2530:
2071:
1585:
1560:
1546:
1538:
933:Sex and Gender Differences in Pharmacology
610:List of combined sex-hormonal preparations
222:in women. The term specifically refers to
2572:
2076:
1841:Prasterone (dehydroepiandrosterone; DHEA)
1590:
1479:
1477:
1457:
1205:
827:
649:
551:estrogens, later determined to be mostly
190:
1797:Estropipate (piperazine estrone sulfate)
1006:Chopra HK, Nanda NC (15 December 2013).
1520:. Penguin Books Limited. pp. 25–.
1232:Nobel Laureates in Chemistry, 1901-1992
621:
1442:"Pregnant Mares' Urine and Oestrogens"
1262:Analytical Profiles of Drug Substances
1044:. Vol. 1. Elsevier. pp. 4–.
580:, these estrogens were orally active.
40:
810:Veler CD, Thayer S, Doisy EA (1930).
736:. Seven Stories Press. pp. 22–.
366:
332:in 1928. It was reportedly the first
7:
2043:Tooltip follicle-stimulating hormone
1392:Canadian Medical Association Journal
930:Regitz-Zagrosek V (2 October 2012).
1188:Smith OW, Hagerman DD (June 1965).
1074:. Elsevier Science. pp. 307–.
435:; "dihydroxyestrin"), Progynon-DP (
2448:Androvax (androstenedione albumin)
632:Zhu BT, Conney AH (January 1998).
25:
4912:Sex hormone esters and conjugates
3951:taleranol (teranol, β-zearalanol)
2866:metandienone (methandrostenolone)
2514:Progestogens and antiprogestogens
4861:Progesterone receptor modulators
4615:Afimoxifene (4-hydroxytamoxifen)
3497:Prinaberel (ERB-041, WAY-202041)
1910:Diethylstilbestrol esters/ethers
1905:Diethylstilbestrol (stilbestrol)
1042:Advances in Molecular Toxicology
533:) and called their new products
64:
49:
4558:Coregulator-binding modulators:
2825:17β-Methyl-17α-dihydroequilenin
816:Journal of Biological Chemistry
3389:Erteberel (SERBA-1, LY-500307)
2453:Ovandrotone albumin (Fecundin)
1639:) (via estrogenic metabolites)
1440:Stevenson WG (November 1945).
1128:Assali NS (3 September 2013).
1:
4846:Receptor/signaling modulators
2810:17α-Ethynyl-3β-androstanediol
2805:17α-Ethynyl-3α-androstanediol
1334:10.1016/S0002-9378(36)90468-4
1229:Laylin JK (30 October 1993).
1036:Bolton JL (13 October 2006).
976:Alstead S (22 October 2013).
829:10.1016/S0021-9258(18)76871-3
563:like estriol glucuronide and
411:like estriol glucuronide and
206:, sold under the brand names
4856:Androgen receptor modulators
3160:Lynestrenol phenylpropionate
2504:Estrogen receptor modulators
2405:hydroxyprogesterone caproate
1068:Pincus G (22 October 2013).
4851:Estrogens and antiestrogens
4501:Oxabicycloheptene sulfonate
4188:Etacstil (GW-5638, DPC-974)
3364:Doisynoestrol (fenocycline)
3108:Ethinylestradiol 3-benzoate
2620:3β,5α-Dihydrolevonorgestrel
2615:3α,5α-Dihydrolevonorgestrel
2509:Androgens and antiandrogens
2445:Androstenedione immunogens:
2409:medroxyprogesterone acetate
2052:Tooltip luteinizing hormone
1932:Doisynoestrol (fenocycline)
1514:Gluck M (1 February 2010).
1357:Annals of Internal Medicine
1256:Booth D (2 November 1983).
1134:. Elsevier. pp. 339–.
982:. Elsevier. pp. 195–.
848:Kobrak C (7 October 2002).
786:. MSU Press. pp. 54–.
730:Seaman B (4 January 2011).
570:estriol sulfate glucuronide
527:conjugated equine estrogens
418:estriol sulfate glucuronide
386:conjugated equine estrogens
109:Estriol sulfate glucuronide
4933:
4568:Noncompetitive inhibitors:
4193:Ethamoxytriphetol (MER-25)
3354:Dimestrol (dianisylhexene)
3113:Ethinylestradiol sulfonate
2430:Mixed mechanism of action:
2202:Noncompetitive inhibitors:
1954:Methestrol (promethestrol)
1809:Ethinylestradiol sulfonate
1415:Cleveland Clinic Quarterly
780:Rooke T (1 January 2012).
502:of women who were in late
348:of women who were in late
29:
4838:
4610:7β-Hydroxyepiandrosterone
4168:Desmethylchlorotrianisene
3347:Diethylstilbestrol esters
3300:Bisdehydrodoisynolic acid
2720:11β-Chloromethylestradiol
2695:7β-Hydroxyepiandrosterone
2577:Tooltip Estrogen receptor
2465:
2187:Exclusively antagonistic:
2081:Tooltip Estrogen receptor
1595:Tooltip Estrogen receptor
1369:10.7326/0003-4819-7-3-330
1158:Sies H, Packer L (2005).
690:10.1080/13697130500148875
63:
48:
4674:Fulvestrant (ICI-182780)
4491:Methylpiperidinopyrazole
4444:Fulvestrant (ICI-182780)
3927:Resorcylic acid lactones
3150:Hydroxyestrone diacetate
3086:Etamestrol (eptamestrol)
1816:Hydroxyestrone diacetate
1743:estradiol ester mixtures
1484:Li A (27 October 2003).
30:Not to be confused with
3985:Synthetic xenoestrogens
3542:Triphenylchloroethylene
3477:Methestrol dipropionate
3005:Polyestradiol phosphate
1981:Triphenylchloroethylene
1739:polyestradiol phosphate
965:(in German): 2227–2232.
880:Klinische Wochenschrift
783:The Quest for Cortisone
261:and to a lesser extent
56:Estriol 16α-glucuronide
4078:4'-Hydroxynorendoxifen
4073:2-Phenylbenzothiophene
3947:zeranol (α-zearalanol)
3650:phlorizin (phloridzin)
3537:Triphenylbromoethylene
3436:ICI-85966 (Stilbostat)
3017:Estramustine phosphate
2890:Bolandiol dipropionate
1976:Triphenylbromoethylene
1753:Estramustine phosphate
1517:It Must Be My Hormones
478:that was developed by
464:
437:estradiol dipropionate
320:that was developed by
306:
4258:Miproxifene phosphate
4083:27-Hydroxycholesterol
3547:Triphenyliodoethylene
3091:Ethinylandrostenediol
3054:Estrogenic substances
3042:Polyestriol phosphate
2910:Cloxestradiol acetate
2393:chlormadinone acetate
1777:Estrogenic substances
1771:polyestriol phosphate
1671:Cloxestradiol acetate
1409:McCullagh EP (1935).
1260:. In Florey K (ed.).
1207:10.1210/jcem-25-6-732
1131:The Maternal Organism
651:10.1093/carcin/19.1.1
590:Estrogenic substances
462:
371:Tooltip United States
304:
3572:WAY-204688 (SIM-688)
3384:ERB-196 (WAY-202196)
3335:Dienestrol diacetate
3074:Estrone methyl ether
2980:Esterified estrogens
2922:Conjugated estrogens
2815:17β-Dihydroequilenin
2790:17α-Dihydroequilenin
2730:15α-Hydroxyestradiol
2725:11β-Methoxyestradiol
2700:8,9-Dehydroestradiol
2401:gestonorone caproate
2215:Aromatase inhibitors
1898:Dienestrol diacetate
1846:Prasterone enanthate
1731:estradiol undecylate
1696:Esterified estrogens
1681:Conjugated estrogens
1299:10.1210/endo-18-1-71
600:Esterified estrogens
595:Conjugated estrogens
449:estradiol undecylate
364:in 1930 (and in the
305:Progynon (Schering).
259:estriol glucuronides
240:conjugated estrogens
32:Conjugated estrogens
4739:Propylpyrazoletriol
4654:Diarylpropionitrile
3502:Propylpyrazoletriol
3359:Dimethylstilbestrol
3325:Diarylpropionitrile
3135:Etynodiol diacetate
2835:Abiraterone acetate
2745:16α-Fluoroestradiol
2397:cyproterone acetate
2296:testosterone esters
1727:estradiol enanthate
1723:estradiol cypionate
1656:etynodiol diacetate
1625:testosterone esters
1427:10.3949/ccjm.2.4.52
553:estriol glucuronide
401:estriol glucuronide
220:menopausal symptoms
85:Estriol glucuronide
45:
27:Pharmaceutical drug
4907:Glucuronide esters
4821:Diethylstilbestrol
4605:2-Methoxyestradiol
4536:TAS-108 (SR-16234)
4486:Methylepitiostanol
4424:EM-800 (SCH-57050)
4348:TAS-108 (SR-16234)
4068:2-Phenylbenzofuran
3682:8-prenylnaringenin
3342:Diethylstilbestrol
3000:Lipoidal estradiol
2975:ERA-63 (ORG-37663)
2917:Conjugated estriol
2862:methyltestosterone
2820:17β-Dihydroequilin
2795:17α-Dihydroequilin
2770:16β-Hydroxyestrone
2755:16α-Hydroxyestrone
2705:8,9-Dehydroestrone
2690:7α-Methylestradiol
2665:4-Methoxyestradiol
2655:4-Hydroxyestradiol
2630:3β-Hydroxytibolone
2625:3α-Hydroxytibolone
2595:2-Hydroxyestradiol
2492:Never to phase III
2327:releasers) (e.g.,
2238:Second-generation:
1851:Prasterone sulfate
1735:estradiol valerate
1719:estradiol benzoate
1676:Conjugated estriol
1629:methyltestosterone
892:10.1007/BF01738283
605:Estrogen conjugate
514:and introduced in
486:and introduced in
465:
445:estradiol valerate
429:estradiol benzoate
360:and introduced in
328:and introduced in
307:
273:that express this
228:estriol conjugates
204:Conjugated estriol
43:Conjugated estriol
36:Estrogen conjugate
4874:
4873:
4866:List of estrogens
4834:
4833:
4579:
4578:
4419:Cytestrol acetate
3642:isoliquiritigenin
3584:Unknown/unsorted:
3270:β-LGND2 (GTx-878)
2850:Anabolic steroids
2760:16α-Iodoestradiol
2650:4-Fluoroestradiol
2645:4-Androstenedione
2635:3β-Androstanediol
2610:3α-Androstanediol
2561:Estrogen receptor
2527:
2526:
2519:List of estrogens
2461:
2460:
2413:megestrol acetate
2300:nandrolone esters
2288:anabolic steroids
2276:Antigonadotropins
2253:Third-generation:
2226:Aminoglutethimide
2223:First-generation:
2061:
2060:
1767:estriol succinate
1715:estradiol acetate
1637:nandrolone esters
1617:anabolic steroids
1527:978-0-85796-510-3
1497:978-0-7735-2609-9
1271:978-0-08-086107-4
1242:978-0-8412-2690-6
1171:978-0-12-182805-9
1141:978-1-4832-6380-9
1111:978-1-4557-1137-6
1081:978-1-4832-1945-5
1051:978-0-08-046538-8
1019:978-93-5090-803-7
989:978-1-4832-2584-5
943:978-3-642-30725-6
886:(25): 1172–1178.
861:978-0-521-81481-2
793:978-1-60917-326-5
743:978-1-60980-062-8
684:(Suppl 1): 3–63.
463:Emmenin (Ayerst).
291:steroid sulfatase
201:
200:
130:Progynon, Emmenin
71:Estriol 3-sulfate
16:(Redirected from
4924:
4733:2,2',5'-PCB-4-OH
4669:Ethinylestradiol
4595:
4591:
4587:
4328:Rimostil (P-081)
4138:Chlorotrianisene
4060:
4056:
3835:Metalloestrogens
3614:-related (e.g.,
3429:Hexestrol esters
3103:Ethinylestradiol
2995:Estradiol esters
2750:16α-Hydroxy-DHEA
2735:16-Ketoestradiol
2675:5-Androstenediol
2670:4-Methoxyestrone
2660:4-Hydroxyestrone
2640:4-Androstenediol
2600:2-Hydroxyestrone
2582:
2578:
2574:
2554:
2547:
2540:
2531:
2374:
2357:
2102:
2098:
2093:
2089:
2082:
2078:
2072:
2053:
2049:
2044:
2040:
2023:
2016:
1996:Progonadotropins
1942:Hexestrol esters
1888:Chlorotrianisene
1804:Ethinylestradiol
1711:Estradiol esters
1596:
1592:
1586:
1562:
1555:
1548:
1539:
1532:
1531:
1511:
1502:
1501:
1481:
1472:
1471:
1461:
1437:
1431:
1430:
1406:
1400:
1399:
1387:
1381:
1380:
1352:
1346:
1345:
1317:
1311:
1310:
1282:
1276:
1275:
1253:
1247:
1246:
1226:
1220:
1219:
1209:
1185:
1176:
1175:
1155:
1146:
1145:
1125:
1116:
1115:
1095:
1086:
1085:
1065:
1056:
1055:
1033:
1024:
1023:
1003:
994:
993:
973:
967:
966:
957:
951:
950:
927:
912:
911:
875:
866:
865:
845:
834:
833:
831:
807:
798:
797:
777:
748:
747:
727:
710:
709:
673:
664:
663:
653:
629:
525:(which contains
490:in 1930 and the
441:ethinylestradiol
431:), Progynon-DH (
372:
368:
309:Progynon was an
263:estriol sulfates
194:
174:
68:
53:
46:
44:
21:
4932:
4931:
4927:
4926:
4925:
4923:
4922:
4921:
4887:Abandoned drugs
4877:
4876:
4875:
4870:
4830:
4809:
4773:
4589:
4575:
4409:7β-Hydroxy-DHEA
4392:
4228:Levormeloxifene
4058:
4051:
4045:
3961:deoxymiroestrol
3829:-hinokiresinol)
3467:Methallenestril
3369:Doisynolic acid
3170:Methylestradiol
2685:7α-Hydroxy-DHEA
2576:
2566:
2558:
2528:
2523:
2497:
2482:Clinical trials
2457:
2418:
2317:
2308:fluoxymesterone
2270:
2209:
2100:
2091:
2084:
2080:
2057:
2051:
2042:
1990:
1949:Methallenestril
1826:Methylestradiol
1792:Estrone sulfate
1594:
1575:
1566:
1536:
1535:
1528:
1513:
1512:
1505:
1498:
1483:
1482:
1475:
1452:(11): 293–301.
1439:
1438:
1434:
1408:
1407:
1403:
1389:
1388:
1384:
1354:
1353:
1349:
1319:
1318:
1314:
1284:
1283:
1279:
1272:
1255:
1254:
1250:
1243:
1228:
1227:
1223:
1187:
1186:
1179:
1172:
1157:
1156:
1149:
1142:
1127:
1126:
1119:
1112:
1097:
1096:
1089:
1082:
1067:
1066:
1059:
1052:
1035:
1034:
1027:
1020:
1005:
1004:
997:
990:
975:
974:
970:
959:
958:
954:
944:
929:
928:
915:
877:
876:
869:
862:
847:
846:
837:
809:
808:
801:
794:
779:
778:
751:
744:
729:
728:
713:
675:
674:
667:
631:
630:
623:
618:
586:
565:estriol sulfate
531:estrone sulfate
508:Adolf Butenandt
467:Emmenin was an
457:
439:), Progynon-C (
413:estriol sulfate
370:
322:Adolf Butenandt
299:
267:β-glucuronidase
197:
177:
145:
97:Estriol sulfate
74:
59:
39:
28:
23:
22:
15:
12:
11:
5:
4930:
4928:
4920:
4919:
4917:Sulfate esters
4914:
4909:
4904:
4899:
4897:Estriol esters
4894:
4889:
4879:
4878:
4872:
4871:
4869:
4868:
4863:
4858:
4853:
4848:
4843:
4839:
4836:
4835:
4832:
4831:
4829:
4828:
4823:
4817:
4815:
4811:
4810:
4808:
4807:
4802:
4797:
4792:
4787:
4781:
4779:
4775:
4774:
4772:
4771:
4766:
4761:
4756:
4751:
4746:
4741:
4736:
4726:
4721:
4716:
4711:
4706:
4701:
4699:Hydroxytyrosol
4696:
4691:
4686:
4681:
4676:
4671:
4666:
4661:
4656:
4651:
4637:
4632:
4627:
4622:
4617:
4612:
4607:
4601:
4599:
4592:
4581:
4580:
4577:
4576:
4574:
4573:
4564:
4563:
4554:
4553:
4548:
4543:
4538:
4533:
4528:
4523:
4518:
4513:
4508:
4503:
4498:
4493:
4488:
4483:
4478:
4473:
4468:
4446:
4441:
4436:
4431:
4426:
4421:
4416:
4414:Chloroindazole
4411:
4406:
4400:
4398:
4394:
4393:
4391:
4390:
4385:
4380:
4375:
4370:
4365:
4360:
4355:
4350:
4345:
4340:
4335:
4333:Spironolactone
4330:
4325:
4320:
4315:
4310:
4305:
4300:
4295:
4290:
4285:
4280:
4275:
4270:
4265:
4260:
4255:
4250:
4245:
4240:
4235:
4230:
4225:
4220:
4215:
4210:
4205:
4200:
4195:
4190:
4185:
4180:
4175:
4170:
4165:
4160:
4155:
4150:
4145:
4140:
4135:
4130:
4125:
4120:
4115:
4110:
4105:
4100:
4095:
4090:
4085:
4080:
4075:
4070:
4064:
4062:
4047:
4046:
4044:
4043:
4034:Others (e.g.,
4032:
3982:
3968:
3954:
3924:
3906:
3884:
3842:
3832:
3810:
3805:
3762:liquiritigenin
3671:
3657:
3635:
3609:Xenoestrogens:
3605:
3604:
3599:
3594:
3589:
3580:
3579:
3574:
3569:
3564:
3559:
3554:
3549:
3544:
3539:
3534:
3529:
3524:
3519:
3514:
3509:
3504:
3499:
3494:
3489:
3484:
3482:Paroxypropione
3479:
3474:
3469:
3464:
3459:
3451:
3443:
3438:
3433:
3432:
3431:
3421:
3416:
3411:
3406:
3401:
3396:
3394:Estrobin (DBE)
3391:
3386:
3381:
3376:
3371:
3366:
3361:
3356:
3351:
3350:
3349:
3339:
3338:
3337:
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3292:
3287:
3285:Allenolic acid
3282:
3277:
3272:
3267:
3262:
3257:
3252:
3243:
3242:
3237:
3232:
3227:
3222:
3217:
3212:
3207:
3202:
3197:
3192:
3190:Norethisterone
3187:
3182:
3180:Mytatrienediol
3177:
3172:
3167:
3162:
3157:
3152:
3147:
3142:
3137:
3132:
3127:
3125:Ethylestradiol
3122:
3120:Ethinylestriol
3117:
3116:
3115:
3110:
3100:
3099:
3098:
3088:
3083:
3082:
3081:
3076:
3071:
3069:Estrone esters
3061:
3056:
3051:
3046:
3045:
3044:
3039:
3037:Estriol esters
3029:
3024:
3022:Estrapronicate
3019:
3014:
3009:
3008:
3007:
3002:
2997:
2987:
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2944:
2939:
2934:
2929:
2924:
2919:
2914:
2913:
2912:
2902:
2897:
2892:
2887:
2882:
2877:
2847:
2842:
2840:Alestramustine
2837:
2832:
2827:
2822:
2817:
2812:
2807:
2802:
2797:
2792:
2787:
2777:
2772:
2767:
2762:
2757:
2752:
2747:
2742:
2740:16-Ketoestrone
2737:
2732:
2727:
2722:
2717:
2712:
2707:
2702:
2697:
2692:
2687:
2682:
2677:
2672:
2667:
2662:
2657:
2652:
2647:
2642:
2637:
2632:
2627:
2622:
2617:
2612:
2607:
2602:
2597:
2588:
2586:
2579:
2568:
2567:
2559:
2557:
2556:
2549:
2542:
2534:
2525:
2524:
2522:
2521:
2516:
2511:
2506:
2501:
2496:
2495:
2494:
2493:
2490:
2479:
2473:
2467:
2466:
2463:
2462:
2459:
2458:
2456:
2455:
2450:
2441:
2440:
2435:
2426:
2424:
2420:
2419:
2417:
2416:
2386:
2369:
2352:
2345:chlorpromazine
2333:metoclopramide
2315:
2311:
2280:
2278:
2272:
2271:
2269:
2268:
2263:
2258:
2249:
2248:
2243:
2234:
2233:
2228:
2219:
2217:
2211:
2210:
2208:
2207:
2198:
2197:
2192:
2183:
2182:
2177:
2172:
2167:
2162:
2157:
2152:
2147:
2142:
2137:
2132:
2127:
2122:
2117:
2112:
2106:
2104:
2069:
2063:
2062:
2059:
2058:
2056:
2055:
2031:
2011:
2000:
1998:
1992:
1991:
1989:
1988:
1983:
1978:
1973:
1968:
1966:Paroxypropione
1963:
1962:
1961:
1951:
1946:
1945:
1944:
1934:
1929:
1928:
1927:
1922:
1917:
1907:
1902:
1901:
1900:
1890:
1885:
1880:
1871:
1870:
1865:
1860:
1855:
1854:
1853:
1848:
1838:
1833:
1828:
1823:
1818:
1813:
1812:
1811:
1801:
1800:
1799:
1794:
1787:Estrone esters
1784:
1779:
1774:
1763:Estriol esters
1760:
1755:
1750:
1708:
1703:
1698:
1693:
1688:
1683:
1678:
1673:
1668:
1663:
1648:norethisterone
1640:
1609:
1600:
1598:
1583:
1577:
1576:
1567:
1565:
1564:
1557:
1550:
1542:
1534:
1533:
1526:
1503:
1496:
1473:
1432:
1401:
1382:
1347:
1328:(4): 663–666.
1312:
1277:
1270:
1248:
1241:
1221:
1200:(6): 732–741.
1177:
1170:
1147:
1140:
1117:
1110:
1087:
1080:
1057:
1050:
1025:
1018:
995:
988:
968:
952:
942:
913:
867:
860:
835:
822:(2): 357–371.
799:
792:
749:
742:
711:
665:
638:Carcinogenesis
620:
619:
617:
614:
613:
612:
607:
602:
597:
592:
585:
582:
456:
453:
443:), Progynova (
298:
295:
277:, such as the
248:pharmaceutical
199:
198:
196:
195:
187:
185:
179:
178:
176:
175:
167:
165:
159:
158:
154:
153:
148:
146:administration
140:
139:
136:
132:
131:
128:
122:
121:
117:
116:
111:
105:
104:
99:
93:
92:
87:
81:
80:
79:Combination of
76:
75:
69:
61:
60:
54:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
4929:
4918:
4915:
4913:
4910:
4908:
4905:
4903:
4900:
4898:
4895:
4893:
4890:
4888:
4885:
4884:
4882:
4867:
4864:
4862:
4859:
4857:
4854:
4852:
4849:
4847:
4844:
4841:
4840:
4837:
4827:
4824:
4822:
4819:
4818:
4816:
4812:
4806:
4803:
4801:
4798:
4796:
4793:
4791:
4788:
4786:
4783:
4782:
4780:
4776:
4770:
4767:
4765:
4762:
4760:
4757:
4755:
4752:
4750:
4747:
4745:
4742:
4740:
4737:
4734:
4730:
4727:
4725:
4722:
4720:
4717:
4715:
4712:
4710:
4707:
4705:
4702:
4700:
4697:
4695:
4692:
4690:
4687:
4685:
4682:
4680:
4677:
4675:
4672:
4670:
4667:
4665:
4662:
4660:
4657:
4655:
4652:
4649:
4645:
4641:
4638:
4636:
4633:
4631:
4628:
4626:
4623:
4621:
4618:
4616:
4613:
4611:
4608:
4606:
4603:
4602:
4600:
4596:
4593:
4588:
4582:
4572:
4569:
4566:
4565:
4562:
4559:
4556:
4555:
4552:
4549:
4547:
4544:
4542:
4539:
4537:
4534:
4532:
4529:
4527:
4524:
4522:
4519:
4517:
4514:
4512:
4509:
4507:
4504:
4502:
4499:
4497:
4494:
4492:
4489:
4487:
4484:
4482:
4479:
4477:
4474:
4472:
4469:
4466:
4462:
4458:
4454:
4450:
4447:
4445:
4442:
4440:
4437:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4401:
4399:
4395:
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:
4313:Pipendoxifene
4311:
4309:
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:
4149:
4148:Clomifenoxide
4146:
4144:
4141:
4139:
4136:
4134:
4131:
4129:
4126:
4124:
4123:Brilanestrant
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4104:
4101:
4099:
4096:
4094:
4091:
4089:
4086:
4084:
4081:
4079:
4076:
4074:
4071:
4069:
4066:
4065:
4063:
4057:
4048:
4041:
4037:
4033:
4030:
4026:
4022:
4018:
4014:
4010:
4006:
4002:
3998:
3994:
3990:
3986:
3983:
3980:
3976:
3972:
3969:
3966:
3962:
3959:-like (e.g.,
3958:
3955:
3952:
3948:
3944:
3940:
3936:
3932:
3928:
3925:
3922:
3918:
3914:
3910:
3907:
3904:
3903:guggulsterone
3900:
3896:
3892:
3888:
3887:Phytosteroids
3885:
3882:
3878:
3874:
3870:
3866:
3862:
3858:
3854:
3850:
3846:
3843:
3840:
3836:
3833:
3830:
3828:
3822:
3821:enterolactone
3818:
3814:
3811:
3809:
3806:
3803:
3799:
3795:
3791:
3787:
3783:
3779:
3775:
3771:
3767:
3763:
3759:
3755:
3751:
3747:
3743:
3739:
3735:
3731:
3727:
3723:
3719:
3715:
3711:
3707:
3703:
3699:
3695:
3691:
3687:
3683:
3679:
3675:
3672:
3669:
3665:
3661:
3658:
3655:
3654:wedelolactone
3651:
3647:
3643:
3639:
3636:
3633:
3632:photoanethole
3629:
3625:
3621:
3617:
3613:
3610:
3607:
3606:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3582:
3581:
3578:
3575:
3573:
3570:
3568:
3565:
3563:
3560:
3558:
3555:
3553:
3550:
3548:
3545:
3543:
3540:
3538:
3535:
3533:
3530:
3528:
3525:
3523:
3520:
3518:
3515:
3513:
3510:
3508:
3505:
3503:
3500:
3498:
3495:
3493:
3490:
3488:
3487:Pentafluranol
3485:
3483:
3480:
3478:
3475:
3473:
3470:
3468:
3465:
3463:
3460:
3458:
3456:
3452:
3450:
3448:
3444:
3442:
3439:
3437:
3434:
3430:
3427:
3426:
3425:
3422:
3420:
3417:
3415:
3412:
3410:
3407:
3405:
3402:
3400:
3397:
3395:
3392:
3390:
3387:
3385:
3382:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3348:
3345:
3344:
3343:
3340:
3336:
3333:
3332:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3291:
3288:
3286:
3283:
3281:
3278:
3276:
3273:
3271:
3268:
3266:
3263:
3261:
3258:
3256:
3253:
3251:
3248:
3247:Nonsteroidal:
3245:
3244:
3241:
3238:
3236:
3233:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3206:
3203:
3201:
3198:
3196:
3193:
3191:
3188:
3186:
3183:
3181:
3178:
3176:
3173:
3171:
3168:
3166:
3163:
3161:
3158:
3156:
3153:
3151:
3148:
3146:
3143:
3141:
3138:
3136:
3133:
3131:
3128:
3126:
3123:
3121:
3118:
3114:
3111:
3109:
3106:
3105:
3104:
3101:
3097:
3096:Ethandrostate
3094:
3093:
3092:
3089:
3087:
3084:
3080:
3077:
3075:
3072:
3070:
3067:
3066:
3065:
3062:
3060:
3057:
3055:
3052:
3050:
3047:
3043:
3040:
3038:
3035:
3034:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3006:
3003:
3001:
2998:
2996:
2993:
2992:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2949:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2928:
2925:
2923:
2920:
2918:
2915:
2911:
2908:
2907:
2906:
2905:Cloxestradiol
2903:
2901:
2898:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2875:
2871:
2867:
2863:
2859:
2855:
2851:
2848:
2846:
2843:
2841:
2838:
2836:
2833:
2831:
2828:
2826:
2823:
2821:
2818:
2816:
2813:
2811:
2808:
2806:
2803:
2801:
2798:
2796:
2793:
2791:
2788:
2785:
2781:
2780:17α-Estradiol
2778:
2776:
2773:
2771:
2768:
2766:
2763:
2761:
2758:
2756:
2753:
2751:
2748:
2746:
2743:
2741:
2738:
2736:
2733:
2731:
2728:
2726:
2723:
2721:
2718:
2716:
2713:
2711:
2708:
2706:
2703:
2701:
2698:
2696:
2693:
2691:
2688:
2686:
2683:
2681:
2678:
2676:
2673:
2671:
2668:
2666:
2663:
2661:
2658:
2656:
2653:
2651:
2648:
2646:
2643:
2641:
2638:
2636:
2633:
2631:
2628:
2626:
2623:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2590:
2589:
2587:
2583:
2580:
2575:
2569:
2565:
2562:
2555:
2550:
2548:
2543:
2541:
2536:
2535:
2532:
2520:
2517:
2515:
2512:
2510:
2507:
2505:
2502:
2499:
2498:
2491:
2489:
2486:
2485:
2483:
2480:
2477:
2474:
2472:
2469:
2468:
2464:
2454:
2451:
2449:
2446:
2443:
2442:
2439:
2436:
2434:
2431:
2428:
2427:
2425:
2421:
2414:
2410:
2406:
2402:
2398:
2394:
2390:
2387:
2384:
2380:
2376:
2370:
2367:
2363:
2359:
2353:
2350:
2346:
2342:
2338:
2334:
2330:
2326:
2322:
2319:
2312:
2309:
2305:
2301:
2297:
2293:
2289:
2285:
2282:
2281:
2279:
2277:
2273:
2267:
2264:
2262:
2259:
2257:
2254:
2251:
2250:
2247:
2244:
2242:
2239:
2236:
2235:
2232:
2229:
2227:
2224:
2221:
2220:
2218:
2216:
2212:
2206:
2203:
2200:
2199:
2196:
2193:
2191:
2188:
2185:
2184:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2161:
2158:
2156:
2153:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2133:
2131:
2128:
2126:
2123:
2121:
2118:
2116:
2113:
2111:
2108:
2107:
2105:
2099:
2090:
2079:
2073:
2070:
2068:
2067:Antiestrogens
2064:
2050:
2041:
2035:
2034:Gonadotropins
2032:
2029:
2025:
2024:(gonadorelin)
2018:
2012:
2009:
2005:
2004:Antiandrogens
2002:
2001:
1999:
1997:
1993:
1987:
1984:
1982:
1979:
1977:
1974:
1972:
1969:
1967:
1964:
1960:
1957:
1956:
1955:
1952:
1950:
1947:
1943:
1940:
1939:
1938:
1935:
1933:
1930:
1926:
1923:
1921:
1918:
1916:
1913:
1912:
1911:
1908:
1906:
1903:
1899:
1896:
1895:
1894:
1891:
1889:
1886:
1884:
1881:
1879:
1876:
1875:Nonsteroidal:
1873:
1872:
1869:
1866:
1864:
1861:
1859:
1856:
1852:
1849:
1847:
1844:
1843:
1842:
1839:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1817:
1814:
1810:
1807:
1806:
1805:
1802:
1798:
1795:
1793:
1790:
1789:
1788:
1785:
1783:
1780:
1778:
1775:
1772:
1768:
1764:
1761:
1759:
1756:
1754:
1751:
1748:
1744:
1740:
1736:
1732:
1728:
1724:
1720:
1716:
1712:
1709:
1707:
1704:
1702:
1699:
1697:
1694:
1692:
1689:
1687:
1684:
1682:
1679:
1677:
1674:
1672:
1669:
1667:
1664:
1661:
1657:
1653:
1649:
1645:
1641:
1638:
1634:
1630:
1626:
1622:
1618:
1614:
1610:
1608:
1605:
1602:
1601:
1599:
1593:
1587:
1584:
1582:
1578:
1574:
1573:antiestrogens
1570:
1563:
1558:
1556:
1551:
1549:
1544:
1543:
1540:
1529:
1523:
1519:
1518:
1510:
1508:
1504:
1499:
1493:
1489:
1488:
1480:
1478:
1474:
1469:
1465:
1460:
1455:
1451:
1447:
1443:
1436:
1433:
1428:
1424:
1420:
1416:
1412:
1405:
1402:
1397:
1393:
1386:
1383:
1378:
1374:
1370:
1366:
1362:
1358:
1351:
1348:
1343:
1339:
1335:
1331:
1327:
1323:
1316:
1313:
1308:
1304:
1300:
1296:
1292:
1288:
1287:Endocrinology
1281:
1278:
1273:
1267:
1263:
1259:
1252:
1249:
1244:
1238:
1234:
1233:
1225:
1222:
1217:
1213:
1208:
1203:
1199:
1195:
1191:
1184:
1182:
1178:
1173:
1167:
1163:
1162:
1154:
1152:
1148:
1143:
1137:
1133:
1132:
1124:
1122:
1118:
1113:
1107:
1103:
1102:
1094:
1092:
1088:
1083:
1077:
1073:
1072:
1064:
1062:
1058:
1053:
1047:
1043:
1039:
1032:
1030:
1026:
1021:
1015:
1011:
1010:
1002:
1000:
996:
991:
985:
981:
980:
972:
969:
964:
956:
953:
949:
945:
939:
935:
934:
926:
924:
922:
920:
918:
914:
909:
905:
901:
897:
893:
889:
885:
882:(in German).
881:
874:
872:
868:
863:
857:
853:
852:
844:
842:
840:
836:
830:
825:
821:
817:
813:
806:
804:
800:
795:
789:
785:
784:
776:
774:
772:
770:
768:
766:
764:
762:
760:
758:
756:
754:
750:
745:
739:
735:
734:
726:
724:
722:
720:
718:
716:
712:
707:
703:
699:
695:
691:
687:
683:
679:
672:
670:
666:
661:
657:
652:
647:
643:
639:
635:
628:
626:
622:
615:
611:
608:
606:
603:
601:
598:
596:
593:
591:
588:
587:
583:
581:
579:
575:
571:
566:
562:
558:
554:
550:
547:
546:water-soluble
542:
540:
539:North America
536:
532:
528:
524:
519:
517:
513:
509:
505:
501:
497:
493:
492:United States
489:
485:
481:
477:
473:
470:
469:orally active
461:
454:
452:
450:
446:
442:
438:
434:
430:
426:
421:
419:
414:
410:
406:
402:
398:
397:water-soluble
393:
391:
390:North America
387:
383:
379:
374:
369:
363:
359:
355:
351:
347:
343:
339:
335:
331:
327:
323:
319:
315:
312:
311:orally active
303:
296:
294:
292:
288:
284:
280:
279:mammary gland
276:
272:
268:
264:
260:
255:
253:
249:
245:
241:
237:
233:
229:
225:
221:
217:
213:
209:
205:
193:
189:
188:
186:
184:
180:
173:
169:
168:
166:
164:
160:
155:
152:
149:
147:
141:
137:
133:
129:
127:
123:
120:Clinical data
118:
115:
112:
110:
106:
103:
100:
98:
94:
91:
88:
86:
82:
77:
72:
67:
62:
57:
52:
47:
37:
33:
19:
4567:
4557:
4481:Mepitiostane
4429:Epitiostanol
4298:Ormeloxifene
4223:Lasofoxifene
4133:Camizestrant
4128:Broparestrol
4118:Bazedoxifene
4040:rotundifuran
3989:alkylphenols
3939:β-zearalenol
3935:α-zearalenol
3921:stigmasterol
3913:β-sitosterol
3909:Phytosterols
3877:triclocarban
3873:methoxychlor
3826:
3808:Lavender oil
3802:tectorigenin
3734:formononetin
3608:
3583:
3454:
3446:
3246:
3230:Quinestradol
3220:Promestriene
3195:Noretynodrel
3059:Estromustine
3012:Estramustine
2947:
2916:
2854:testosterone
2591:
2444:
2429:
2389:Progestogens
2292:testosterone
2252:
2237:
2231:Testolactone
2222:
2201:
2186:
2160:Ormeloxifene
2155:Mepitiostane
2150:Lasofoxifene
2145:Epitiostanol
2125:Broparestrol
2120:Bazedoxifene
2008:bicalutamide
1874:
1863:Quinestradol
1858:Promestriene
1675:
1652:noretynodrel
1633:metandienone
1621:testosterone
1603:
1516:
1486:
1449:
1445:
1435:
1421:(4): 52–64.
1418:
1414:
1404:
1395:
1391:
1385:
1360:
1356:
1350:
1325:
1321:
1315:
1293:(1): 71–74.
1290:
1286:
1280:
1261:
1251:
1231:
1224:
1197:
1193:
1160:
1130:
1100:
1070:
1041:
1008:
978:
971:
962:
955:
947:
932:
883:
879:
850:
819:
815:
782:
732:
681:
677:
641:
637:
543:
529:, primarily
520:
480:James Collip
466:
422:
394:
375:
354:James Collip
308:
256:
224:formulations
211:
207:
203:
202:
4826:Zearalenone
4778:Antagonists
4754:Resveratrol
4719:Nonylphenol
4714:Niacinamide
4630:Bisphenol A
4620:Aldosterone
4449:Glyceollins
4397:Antagonists
4388:Zuclomifene
4383:Zindoxifene
4293:NNC 45-1506
4288:NNC 45-0781
4283:NNC 45-0320
4278:NNC 45-0095
4273:Nitromifene
4253:Miproxifene
4203:Fispemifene
4178:Enclomifene
4173:Droloxifene
4153:CN-55945-27
4098:Afimoxifene
4088:Acefluranol
3979:rhaponticin
3975:resveratrol
3971:Stilbenoids
3943:zearalenone
3931:zearalanone
3917:campesterol
3849:alternariol
3782:pinocembrin
3726:epicatechin
3698:biochanin A
3638:Chalconoids
3532:Terfluranol
3507:Quadrosilan
3379:Elacestrant
3280:Allenestrol
3155:Lynestrenol
3079:Estropipate
3049:Estrofurate
2900:Clomestrone
2880:Atrimustine
2830:Abiraterone
2784:alfatradiol
2478:from market
2375:antagonists
2362:leuprorelin
2341:haloperidol
2337:risperidone
2329:domperidone
2321:antagonists
2304:oxandrolone
2256:Anastrozole
2195:Fulvestrant
2190:Elacestrant
2140:Enclomifene
2083:antagonists
2028:leuprorelin
1971:Quadrosilan
1747:Climacteron
1666:Clomestrone
1607:Alfatradiol
678:Climacteric
644:(1): 1–27.
472:formulation
334:sex hormone
314:formulation
157:Identifiers
135:Other names
126:Trade names
4881:Categories
4769:Tectoridin
4749:Raloxifene
4724:Oleuropein
4571:Trilostane
4516:Prochloraz
4476:MDL-101906
4471:ICI-164384
4358:Trioxifene
4353:Toremifene
4323:Raloxifene
4308:Panomifene
4303:Ospemifene
4268:Nafoxidine
4158:Cyclofenil
4113:Arzoxifene
4093:Acolbifene
4025:phthalates
3993:bisphenols
3965:miroestrol
3869:methiocarb
3857:endosulfan
3845:Pesticides
3817:enterodiol
3798:tectoridin
3778:penduletin
3774:naringenin
3758:kaempferol
3674:Flavonoids
3668:psoralidin
3664:coumestrol
3660:Coumestans
3624:dianethole
3577:WAY-214156
3567:WAY-200070
3562:WAY-169916
3557:WAY-166818
3527:SKF-82,958
3492:Phenestrol
3472:Methestrol
3457:-Hexestrol
3449:-Butestrol
3330:Dienestrol
3310:Carbestrol
3295:Bifluranol
3290:Benzestrol
3235:Quinestrol
3185:Nilestriol
3027:Estrazinol
2960:Epimestrol
2950:-Estradiol
2932:Cyclotriol
2870:nandrolone
2845:Almestrone
2680:7-Oxo-DHEA
2592:Steroidal:
2564:modulators
2438:Gestrinone
2379:cetrorelix
2261:Exemestane
2246:Formestane
2205:Trilostane
2180:Toremifene
2170:Raloxifene
2165:Ospemifene
2135:Cyclofenil
2110:Acolbifene
1893:Dienestrol
1883:Bifluranol
1878:Benzestrol
1868:Quinestrol
1836:Nilestriol
1691:Epimestrol
1686:Epiestriol
1644:progestins
1604:Steroidal:
1398:: 633–641.
1363:(3): 330.
963:ZBL. Gynäk
616:References
557:Conjugates
549:conjugated
405:Conjugates
373:in 1934).
192:NIG5418BXB
163:CAS Number
4902:Estrogens
4764:Tamoxifen
4744:Quercetin
4684:Genistein
4664:Estradiol
4648:o',p'-DDE
4551:ZK-191703
4546:ZK-164015
4506:Phenytoin
4404:(R,R)-THC
4343:Tamoxifen
4318:Promensil
4243:LY-117018
4218:Idoxifene
4213:ICI-55548
4198:Femarelle
4183:Endoxifen
4143:Clomifene
3899:diosgenin
3895:digitalis
3891:digitoxin
3881:triclosan
3861:fenarimol
3794:quercetin
3770:myricetin
3766:mirificin
3754:glycitein
3746:genistein
3742:glabridin
3702:calycosin
3690:baicalein
3646:phloretin
3602:ZK-283197
3462:Mestilbol
3424:Hexestrol
3399:Fenestrel
3374:Efavirenz
3305:Butestrol
3260:2,8-DHHHC
3255:(S,S)-THC
3250:(R,R)-THC
3205:Pentolame
3200:Orestrate
3175:Moxestrol
3165:Mestranol
3130:Etynodiol
2990:Estradiol
2965:Equilenin
2927:Cyclodiol
2885:Bolandiol
2488:Phase III
2476:Withdrawn
2366:goserelin
2349:sulpiride
2325:prolactin
2284:Androgens
2266:Letrozole
2241:Fadrozole
2175:Tamoxifen
2130:Clomifene
1937:Hexestrol
1831:Moxestrol
1821:Mestranol
1706:Estradiol
1613:androgens
1581:Estrogens
1569:Estrogens
1377:0003-4819
1342:0002-9378
1307:0013-7227
1258:"Estrone"
900:0023-2173
574:estradiol
504:pregnancy
433:estradiol
350:pregnancy
342:placental
144:Routes of
4892:Estranes
4842:See also
4644:p,p'-DDT
4635:Daidzein
4625:Atrazine
4598:Agonists
4526:RU-58668
4521:RU-39411
4368:U-11555A
4363:TZE-5323
4108:Anordrin
4103:Anordiol
4036:agnuside
4013:parabens
3853:dieldrin
3825:nyasol (
3790:puerarin
3786:prunetin
3750:genistin
3738:glabrene
3710:daidzein
3706:catechin
3694:baicalin
3686:apigenin
3616:anethole
3404:FERb 033
3240:Tibolone
3225:RU-16117
3210:Prodiame
3145:Hippulin
3140:Hexolame
2985:Estetrol
2895:Butolame
2585:Agonists
2500:See also
2383:elagolix
2358:agonists
2318:receptor
2115:Anordrin
2017:agonists
1701:Estetrol
1660:tibolone
1642:Certain
1611:Certain
1597:agonists
1468:17648157
1216:14296256
908:35945534
706:24616324
698:16112947
584:See also
535:Premarin
512:Schering
496:placenta
476:estrogen
382:Premarin
326:Schering
318:estrogen
297:Progynon
252:by mouth
236:pregnant
216:estrogen
214:, is an
208:Progynon
172:113-38-2
151:By mouth
114:Estrogen
102:Estrogen
90:Estrogen
4814:Unknown
4790:Estriol
4694:GPER-L2
4689:GPER-L1
4373:U-11634
4248:Menerba
4238:LN-2299
4233:LN-1643
4208:GW-7604
4163:D-15413
3995:(e.g.,
3987:(e.g.,
3973:(e.g.,
3957:Steroid
3929:(e.g.,
3911:(e.g.,
3889:(e.g.,
3847:(e.g.,
3839:cadmium
3837:(e.g.,
3815:(e.g.,
3813:Lignans
3714:daidzin
3678:7,8-DHF
3676:(incl.
3662:(e.g.,
3640:(e.g.,
3522:SERBA-2
3517:SC-4289
3512:SC-3296
3419:GTx-758
3315:D-15414
3265:β-LGND1
3215:Prolame
3064:Estrone
3032:Estriol
2970:Equilin
2852:(e.g.,
2765:16α-LE2
2433:Danazol
2391:(e.g.,
2377:(e.g.,
2360:(e.g.,
2290:(e.g.,
2085:(incl.
2036:(e.g.,
2019:(e.g.,
2006:(e.g.,
1986:Zeranol
1782:Estrone
1765:(e.g.,
1758:Estriol
1713:(e.g.,
1646:(e.g.,
1619:(e.g.,
1459:1661006
660:9472688
578:estrone
561:estriol
516:Germany
455:Emmenin
425:estrone
409:estriol
338:ovarian
330:Germany
271:tissues
212:Emmenin
18:Emmenin
4709:Niacin
4704:Kepone
4561:ERX-11
4531:SS1020
4439:ERB-88
4434:ERA-90
4338:SS1010
4263:MRL-37
3628:dianol
3597:ERB-79
3592:ERA-45
3587:ERB-26
3320:DCW234
3275:AC-186
2942:DHEA-S
2874:esters
2858:esters
2710:8β-VE2
2471:WHO-EM
2423:Others
1524:
1494:
1466:
1456:
1375:
1340:
1305:
1268:
1239:
1214:
1168:
1138:
1108:
1078:
1048:
1016:
986:
940:
906:
898:
858:
790:
740:
704:
696:
658:
488:Canada
484:Ayerst
362:Canada
358:Ayerst
287:kidney
285:, and
275:enzyme
4785:CCL18
4659:Equol
4541:ZB716
4511:PHTPP
4378:Y-134
4055:SERMs
4050:Mixed
3730:equol
3612:Anise
3441:M2613
2097:SERDs
2088:SERMs
904:S2CID
702:S2CID
523:mares
500:urine
378:mares
346:urine
283:liver
244:mares
232:urine
4805:MIBE
4800:G-36
4795:G-15
4729:PCBs
4586:GPER
4496:MIBE
4029:PCBs
4021:PHBA
4017:PBBs
3865:HPTE
3722:EGCG
3620:anol
3455:meso
3447:meso
2937:DHEA
2872:and
2856:and
2373:GnRH
2356:GnRH
2022:GnRH
2015:GnRH
1571:and
1522:ISBN
1492:ISBN
1464:PMID
1373:ISSN
1338:ISSN
1303:ISSN
1266:ISBN
1237:ISBN
1212:PMID
1166:ISBN
1136:ISBN
1106:ISBN
1076:ISBN
1046:ISBN
1014:ISBN
984:ISBN
938:ISBN
896:ISSN
856:ISBN
788:ISBN
738:ISBN
694:PMID
656:PMID
576:and
367:U.S.
210:and
183:UNII
4759:STX
4679:G-1
4640:DDT
4461:III
4009:DDT
4007:),
4005:BPS
4001:BPF
3997:BPA
3897:),
3827:cis
3718:ECG
2948:ent
2039:FSH
1454:PMC
1423:doi
1365:doi
1330:doi
1295:doi
1202:doi
888:doi
824:doi
686:doi
646:doi
559:of
510:at
482:at
474:of
451:).
407:of
356:at
340:or
324:at
316:of
269:in
234:of
226:of
34:or
4883::
4646:,
4465:IV
4463:,
4459:,
4457:II
4455:,
4038:,
4027:,
4023:,
4019:,
4015:,
4011:,
4003:,
3999:,
3991:,
3977:,
3963:,
3949:,
3945:,
3941:,
3937:,
3933:,
3919:,
3915:,
3901:,
3879:,
3875:,
3871:,
3867:,
3863:,
3859:,
3855:,
3851:,
3823:,
3819:,
3800:,
3796:,
3792:,
3788:,
3784:,
3780:,
3776:,
3772:,
3768:,
3764:,
3760:,
3756:,
3752:,
3748:,
3744:,
3740:,
3736:,
3732:,
3728:,
3724:,
3720:,
3716:,
3712:,
3708:,
3704:,
3700:,
3696:,
3692:,
3688:,
3684:,
3680:,
3666:,
3652:,
3648:,
3644:,
3630:,
3626:,
3622:,
3618:,
2868:,
2864:,
2860:,
2573:ER
2484::
2411:,
2407:,
2403:,
2399:,
2395:,
2381:,
2364:,
2347:,
2343:,
2339:,
2335:,
2331:,
2306:,
2302:,
2298:,
2294:,
2077:ER
2048:LH
2045:,
2026:,
1769:,
1749:))
1741:,
1737:,
1733:,
1729:,
1725:,
1721:,
1717:,
1658:,
1654:,
1650:,
1635:,
1631:,
1627:,
1623:,
1591:ER
1506:^
1476:^
1462:.
1448:.
1444:.
1417:.
1413:.
1396:23
1394:.
1371:.
1359:.
1336:.
1326:31
1324:.
1301:.
1291:18
1289:.
1210:.
1198:25
1196:.
1192:.
1180:^
1150:^
1120:^
1090:^
1060:^
1040:.
1028:^
998:^
946:.
916:^
902:.
894:.
870:^
838:^
820:87
818:.
814:.
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4731:(
4650:)
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4467:)
4453:I
4451:(
4061:)
4052:(
4042:)
4031:)
3981:)
3967:)
3953:)
3923:)
3905:)
3893:(
3883:)
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3804:)
3670:)
3656:)
3634:)
2786:)
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2323:(
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708:.
688::
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648::
384:(
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20:)
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