287:
264:
29:
622:, and chlormadinone acetate have continued to be used). According to Hughes et al., "It is still doubtful how much relevance these findings have for humans as the dog mammary gland seems to be the only one which can be directly maintained by progestogens." Subsequent research revealed species differences between dogs and humans and established that there is no similar risk in humans.
891:
Progestational activity depends on the presence of a 3-keto group in ring A of the steroid skeleton. Most of the progestogens used today do indeed carry such a group in their original molecules. However, the 3-keto group is initially missing in the case of desogestrel and norgestimate. They are
350:
609:
were not found to produce such nodules. Because of these findings, anagestone acetate was voluntarily withdrawn from the market by the manufacturer in 1969. The findings also led to the virtual disappearance of most
1165:
1771:
904:
McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (May 2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay".
589:
after extensive treatment (2–7 years) with very high doses (10–25 times the recommended human dose), though notably not with 1–2 times the human dosage. In contrast, the non-halogenated
2174:
392:
InChI=1S/C24H36O3/c1-15-14-18-20(22(4)11-7-6-8-19(15)22)9-12-23(5)21(18)10-13-24(23,16(2)25)27-17(3)26/h8,15,18,20-21H,6-7,9-14H2,1-5H3/t15-,18+,20-,21-,22-,23-,24-/m0/s1
2635:
1954:
1158:
1764:
364:
3328:
2946:
1623:
1151:
1757:
1723:
3338:
3333:
1690:
1131:
1102:
1073:
978:
884:
857:
815:
758:
731:
1944:
1733:
1728:
1065:
Consolidated List of
Products Whose Consumption And/or Sale Have Been Banned, Withdrawn, Severely Restricted Or Not Approved by Governments
2420:
961:
Casey HW, Giles RC, Kwapien RP (1979). "Mammary
Neoplasia in Animals: Pathologic Aspects and the Effects of Contraceptive Steroids".
2129:
384:
1949:
2695:
2630:
2294:
1884:
442:
1575:
498:
Anagestone acetate, also known as 3-deketo-6α-methyl-17α-acetoxyprogesterone or as 6α-methyl-17α-acetoxypregn-4-en-20-one, is a
2425:
1849:
1829:
101:
3343:
3216:
2169:
1738:
1308:
3226:
54:
ORF-1658; Anapregnone acetate; 3-Deketo-6α-methyl-17α-acetoxyprogesterone; 6α-Methyl-17α-hydroxypregn-4-en-20-one acetate
3323:
2650:
2532:
2299:
2199:
2164:
1899:
1303:
183:
3384:
2758:
2700:
2194:
2159:
2039:
1707:
1313:
1298:
1273:
567:
532:
531:, which, in contrast to anagestone acetate, was never marketed. Anagestone acetate is closely related structurally to
469:
243:
2973:
2968:
2329:
3267:
2415:
1964:
1859:
1854:
1844:
1025:
Diczfalusy E (July 1979). "Gregory Pincus and steroidal contraception: a new departure in the history of mankind".
643:
611:
517:
493:
2324:
663:
Anagestone acetate was marketed under the brand names
Anatropin and Neo-Novum, the latter in combination with the
3252:
3247:
2690:
2384:
2009:
1969:
1904:
1819:
1814:
1220:
555:
513:
3394:
2878:
2645:
2565:
2521:
1473:
1186:
1174:
575:
78:
1959:
1824:
3364:
2640:
2440:
2284:
2239:
2114:
1695:
59:
282:
3257:
2660:
2561:
2234:
2029:
1989:
1839:
1834:
1468:
1328:
1258:
615:
2034:
3389:
2465:
2269:
2154:
2024:
1791:
1780:
1651:
1338:
1268:
1201:
664:
559:
435:
2004:
2843:
2797:
2779:
2754:
2611:
2557:
2542:
2517:
2349:
2224:
2124:
2069:
1508:
1370:
1323:
1293:
548:
485:
259:
2497:
2364:
2344:
2339:
2189:
2139:
2089:
2079:
2049:
1984:
1659:
1453:
1385:
1375:
1283:
1278:
619:
606:
509:
118:
66:
3142:
3374:
3043:
2983:
2963:
2813:
2793:
2710:
2304:
2249:
2214:
2104:
2059:
1783:
1641:
1288:
996:
929:
590:
544:
499:
457:
445:
844:
Streffer C, Bolt H, Follesdal D, Hall P, Hengstler JG, Jacob P, et al. (11 November 2013).
3202:
3197:
3187:
3182:
3177:
3172:
3167:
3137:
3132:
3127:
3073:
3053:
3033:
3028:
3023:
2998:
2908:
2903:
2898:
2888:
232:
3379:
3013:
2705:
2314:
2259:
2209:
1924:
1333:
1318:
1127:
1119:
1098:
1090:
1069:
1042:
984:
974:
921:
880:
853:
845:
811:
803:
754:
748:
727:
563:
489:
473:
86:
41:
3083:
1063:
721:
3369:
3272:
3262:
2789:
2750:
2144:
1591:
1583:
1357:
1034:
966:
913:
299:
172:
2993:
938:
Prodrugs (lack 3-keto): Ethylestrenol, Lynestrenol, Ethynodiol, Allylestrenol, Norgestimate
192:
2764:
2725:
2685:
2109:
1974:
1614:
1599:
1253:
1178:
1008:
687:
286:
263:
127:
2863:
2823:
2769:
2735:
2715:
2670:
2596:
2591:
2552:
2547:
2512:
2229:
1919:
1701:
1545:
1540:
1498:
1493:
1488:
1463:
1420:
1235:
598:
423:
1093:. In Hughes A, Hasan SH, Oertel GW, Voss HE, Bahner F, Neumann F, et al. (eds.).
3358:
3192:
3088:
2988:
2893:
2720:
2470:
2430:
2264:
2149:
2019:
1595:
1438:
1038:
892:
prodrugs which undergo metabolic conversion to active 3-keto derivatives in the body.
579:
275:
1143:
723:
The
Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies
3303:
3287:
3282:
3277:
3162:
3147:
3112:
3107:
3038:
3008:
3003:
2833:
2606:
2581:
2576:
2571:
2487:
2404:
2389:
2279:
2219:
2184:
2119:
2074:
2064:
1889:
1879:
1749:
1672:
1667:
1636:
1565:
1550:
1525:
1483:
1478:
1402:
1397:
1350:
1343:
1225:
933:
639:
602:
152:
20:
28:
874:
3122:
2868:
2838:
2730:
2527:
2477:
2455:
2435:
2394:
2369:
2359:
2334:
2319:
2274:
2179:
2094:
2084:
2044:
1934:
1864:
1520:
1458:
1443:
1425:
1392:
1380:
1240:
970:
917:
850:
Low Dose
Exposures in the Environment: Dose-Effect Relations and Risk Evaluation
775:
3152:
3117:
3078:
3068:
3048:
2978:
2933:
2913:
2808:
2784:
2745:
2740:
2675:
2665:
2626:
2601:
2586:
2537:
2507:
2482:
2379:
2244:
2134:
2099:
2054:
1994:
1587:
1579:
1555:
1535:
1503:
594:
571:
528:
326:
163:
73:
774:
IARC Working Group on the
Evaluation of Carcinogenic Risks to Humans (1987).
678:
Anagestone acetate was withdrawn from the market and is no longer available.
2928:
2918:
2848:
2828:
2803:
2680:
2655:
2502:
2492:
2460:
2445:
2399:
2354:
2309:
2254:
2204:
1979:
1929:
1869:
1530:
1448:
1191:
667:
438:
419:
82:
925:
3063:
3018:
2621:
2616:
2374:
2014:
1914:
1909:
1513:
1046:
988:
502:
2883:
2858:
2853:
2774:
2450:
1415:
1209:
521:
505:
465:
138:
2770:
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
1874:
586:
543:
Anagestone acetate was introduced in combination with mestranol as a
461:
426:
from medical use due to carcinogenicity observed in animal studies.
212:
2947:
1624:
582:
524:
349:
340:
223:
203:
1753:
1147:
1095:
2170:
Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)
554:
In 1969, along with a variety of other progestogens including
2165:
Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)
578:, anagestone acetate was found to induce the development of
248:
1259:
Algestone acetophenide (dihydroxyprogesterone acetophenide)
1126:. Springer Science & Business Media. pp. 134–135.
1248:
17α-Hydroxyprogesterone (and closely related) derivatives:
906:
The
Journal of Steroid Biochemistry and Molecular Biology
1097:. Springer Science & Business Media. pp. 531–.
852:. Springer Science & Business Media. pp. 135–.
810:. Springer Science & Business Media. pp. 571–.
3217:
2175:
Hydroxyprogesterone heptanoate benzilic acid hydrazone
750:
3227:
1089:
Gräf KJ, Brotherton J, Neumann F (27 November 2013).
1020:
1018:
618:
from the market (though medroxyprogesterone acetate,
1058:
1056:
434:
Anagestone acetate was used in combination with the
3296:
3240:
3215:
3097:
2942:
1804:
1790:
1650:
1622:
1613:
1200:
1185:
1068:. United Nations Publications. 1983. pp. 25–.
338:
325:
298:
293:
274:
242:
222:
202:
182:
162:
137:
117:
92:
72:
58:
50:
40:
35:
2952:Tooltip Selective progesterone receptor modulators
1629:Tooltip Selective progesterone receptor modulators
1118:Runnebaum BC, Rabe T, Kiesel L (6 December 2012).
839:
837:
835:
833:
831:
829:
827:
651:. It is also known by its developmental code name
644:
151:
3263:11-Deoxycortisol (17α,21-dihydroxyprogesterone)
876:Estrogens and Progestogens in Clinical Practice
126:
2636:11β-Methyl-19-nortestosterone dodecylcarbonate
956:
954:
952:
950:
948:
946:
464:, it is probable that anagestone acetate is a
1965:17α-Hydroxyprogesterone (hydroxyprogesterone)
1792:
1765:
1652:
1202:
1159:
797:
795:
780:. International Agency for Research on Cancer
747:William Andrew Publishing (22 October 2013).
8:
1955:16-Methylene-17α-hydroxyprogesterone acetate
1386:Segesterone acetate (nestorone, elcometrine)
19:
808:Clinical Endocrinology: Theory and Practice
372:C1C2(CC3(2CC3(C(=O)C)OC(=O)C)C)4(C1=CCCC4)C
3258:11-Deoxycortisone (21-hydroxyprogesterone)
3237:
2350:Gestonorone caproate (gestronol hexanoate)
1801:
1772:
1758:
1750:
1619:
1371:Gestonorone caproate (gestronol hexanoate)
1197:
1166:
1152:
1144:
715:
713:
711:
709:
707:
705:
703:
285:
262:
171:
1942:17α-Substituted progesterone derivatives:
1850:17α-Methyl-11-deoxycorticosterone acetate
1289:Flugestone acetate (flurogestone acetate)
191:
965:. Vol. 66. pp. 129–160 (149).
2385:Oxogestone phenpropionate (xinogestone)
2345:Gestonorone acetate (gestronol acetate)
1124:Female Contraception: Update and Trends
699:
389:
369:
258:
106:
3222:Tooltip Membrane progesterone receptor
1975:Acetomepregenol (mepregenol diacetate)
1254:Acetomepregenol (mepregenol diacetate)
1004:
994:
879:. Churchill Livingstone. p. 281.
276:
18:
3232:Tooltip Progestin and adipoQ receptor
535:(6α-methyl-17α-acetoxyprogesterone).
231:
7:
1091:"The Clinical Uses of Antiandrogens"
777:IV. OESTROGEN-PROGESTIN COMBINATIONS
211:
142:
2421:6,6-Difluoronorethisterone acetate
1494:Normethandrone (methylestrenolone)
649:Tooltip United States Adopted Name
14:
3329:Progestogens and antiprogestogens
2736:Methoxydienone (methoxygonadiene)
2130:Fluoromedroxyprogesterone acetate
2696:Dimethandrolone dodecylcarbonate
2629:; Anabolic–androgenic steroids:
1885:Progesterone 3-acetyl enol ether
1724:Progesterone receptor modulators
802:Schreiner WE (6 December 2012).
310:
27:
2400:Segesterone acetate (nestorone)
2292:19-Norprogesterone derivatives:
1945:6α-Methyl-17α-bromoprogesterone
1433:19-Nortestosterone derivatives:
1365:19-Norprogesterone derivatives:
1027:Journal of Steroid Biochemistry
397:Key:KDLNOQQQEBKBQM-DICPTYMLSA-N
2553:Norethisterone (norethindrone)
2330:Fluoro furanyl norprogesterone
1950:15β-Hydroxycyproterone acetate
1897:Retroprogesterone derivatives:
1464:Norethisterone (norethindrone)
1309:Hydroxyprogesterone heptanoate
1233:Retroprogesterone derivatives:
316:
304:
1:
3324:Receptor/signaling modulators
2631:11β-Methyl-19-nortestosterone
2295:17α-Methyl-19-norprogesterone
1797:Tooltip Progesterone receptor
1657:Tooltip Progesterone receptor
1207:Tooltip Progesterone receptor
1120:"Development of Progestogens"
410:, sold under the brand names
3339:Estrogen receptor modulators
3334:Androgen receptor modulators
2721:Ethylestrenol (ethylnandrol)
2651:19-Nordehydroepiandrosterone
2533:Lynestrenol phenylpropionate
2426:17α-Allyl-19-nortestosterone
2325:Fluoro ethyl norprogesterone
2300:18-Methylsegesterone acetate
2200:Medroxyprogesterone caproate
1830:9α-Bromo-11-ketoprogesterone
1576:Anabolic–androgenic steroids
1304:Hydroxyprogesterone caproate
1039:10.1016/0022-4731(79)90271-1
846:"Interspecies Extrapolation"
551:. It was withdrawn in 1969.
2759:nandrolone phenylpropionate
2701:Dimethandrolone undecanoate
2195:Medroxyprogesterone acetate
2160:Hydroxyprogesterone acetate
2040:Chlormethenmadinone acetate
1734:Estrogens and antiestrogens
1729:Androgens and antiandrogens
1314:Medroxyprogesterone acetate
1299:Hydroxyprogesterone acetate
1274:Chlormethenmadinone acetate
971:10.1007/978-3-642-81267-5_4
918:10.1016/j.jsbmb.2007.10.008
753:. Elsevier. pp. 322–.
720:Elks J (14 November 2014).
568:medroxyprogesterone acetate
533:medroxyprogesterone acetate
470:medroxyprogesterone acetate
3411:
2416:6,6-Difluoronorethisterone
726:. Springer. pp. 85–.
494:List of progestogen esters
483:
460:, namely the lack of a C3
294:Chemical and physical data
109:phenanthren-17-yl] acetate
3316:
2821:Spirolactone derivatives:
2691:Dimethandrolone buciclate
2412:Testosterone derivatives:
2180:Mecigestone (pentarane B)
2010:Bromethenmadinone acetate
1900:20α-Dihydrodydrogesterone
1812:Progesterone derivatives:
1685:
1563:Spirolactone derivatives:
1410:Testosterone derivatives:
1218:Progesterone derivatives:
380:
360:
97:
26:
2974:5α-Dihydronorethisterone
2969:5α-Dihydrolevonorgestrel
2879:3,8-Dihydrodiligustilide
2646:19-Nor-5-androstenedione
2566:norethisterone enanthate
2522:levonorgestrel butanoate
1474:Norethisterone enanthate
576:chloroethynyl norgestrel
3268:17α-Hydroxyprogesterone
3004:Metapristone (RU-42633)
2785:Trenbolone (trienolone)
2641:19-Nor-5-androstenediol
2441:Chloroethynylnorgestrel
2355:Gestronol (gestonorone)
2285:Triamcinolone acetonide
2240:Methenmadinone caproate
2115:Fluorometholone acetate
1860:20β-Dihydroprogesterone
1855:20α-Dihydroprogesterone
1845:16α-Hydroxyprogesterone
616:hormonal contraceptives
612:17α-hydroxyprogesterone
518:17α-hydroxyprogesterone
3253:5β-Dihydroprogesterone
3248:5α-Dihydroprogesterone
2854:SC-5233 (spirolactone)
2661:Bolandiol dipropionate
2562:norethisterone acetate
2235:Methenmadinone acetate
2030:Chlormadinone caproate
1990:Algestone acetophenide
1970:17α-Methylprogesterone
1905:20α-Dihydrotrengestone
1840:11-Deoxycorticosterone
1835:11-Dehydroprogesterone
1820:5α-Dihydroprogesterone
1815:3β-Dihydroprogesterone
1469:Norethisterone acetate
1329:Methenmadinone acetate
806:. In Labhart A (ed.).
3009:Mifepristone (RU-486)
2558:Norethisterone esters
2518:Levonorgestrel esters
2466:Ethinylandrostenediol
2270:Pentagestrone acetate
2155:Hydromadinone acetate
2025:Chlormadinone acetate
1960:17α-Bromoprogesterone
1825:6α-Methylprogesterone
1781:Progesterone receptor
1339:Pentagestrone acetate
1269:Chlormadinone acetate
963:Carcinogenic Hormones
560:chlormadinone acetate
422:medication which was
3344:List of progestogens
2844:Potassium canrenoate
2798:trenbolone enanthate
2780:Tetrahydrogestrinone
2755:nandrolone decanoate
2731:Metribolone (R-1881)
2612:Quingestanol acetate
2543:Metynodiol diacetate
2225:Melengestrol acetate
2125:Flumedroxone acetate
2070:Clomegestone acetate
1739:List of progestogens
1509:Quingestanol acetate
1324:Melengestrol acetate
1294:Flumedroxone acetate
642:of the drug and its
549:Ortho Pharmaceutical
486:List of progestogens
46:Anatropin, Neo-Novum
2498:Etynodiol diacetate
2365:Nomegestrol acetate
2340:Gestadienol acetate
2190:Medroxyprogesterone
2090:Delmadinone acetate
2080:Cyproterone acetate
2050:Cismadinone acetate
2035:Chlormethenmadinone
1985:Algestone acetonide
1454:Etynodiol diacetate
1376:Nomegestrol acetate
1284:Delmadinone acetate
1279:Cyproterone acetate
626:Society and culture
620:cyproterone acetate
607:etynodiol diacetate
23:
3385:Progestogen esters
3044:Ulipristal acetate
2984:Asoprisnil ecamate
2964:Dihydroethisterone
2814:Trestolone acetate
2794:trenbolone acetate
2711:Dimethyltrienolone
2305:19-Norprogesterone
2250:Mometasone furoate
2215:Megestrol caproate
2105:Flugestone acetate
2060:Clogestone acetate
2015:Butagest (buterol)
2000:Anagestone acetate
1712:Never to phase III
1642:Ulipristal acetate
1264:Anagestone acetate
873:Fraser IS (1998).
636:Anagestone acetate
591:19-nortestosterone
545:birth control pill
458:chemical structure
446:birth control pill
408:Anagestone acetate
21:Anagestone acetate
3352:
3351:
3312:
3311:
3211:
3210:
2790:Trenbolone esters
2751:Nandrolone esters
2706:Dimethyldienolone
2315:Amadinone acetate
2260:Osaterone acetate
2210:Megestrol acetate
2005:Bromethenmadinone
1925:Retroprogesterone
1747:
1746:
1681:
1680:
1609:
1608:
1368:17α-Hydroxylated:
1334:Osaterone acetate
1319:Megestrol acetate
1251:17α-Hydroxylated:
1133:978-3-642-73790-9
1104:978-3-642-80859-3
1075:978-92-1-130230-1
980:978-3-540-08995-7
886:978-0-443-04706-0
859:978-3-662-08422-9
817:978-3-642-96158-8
760:978-0-8155-1856-3
733:978-1-4757-2085-3
564:megestrol acetate
520:. It is the C17α
490:Progestogen ester
405:
404:
351:Interactive image
244:CompTox Dashboard
87:Progestogen ester
16:Chemical compound
3402:
3273:Allopregnanolone
3238:
3233:
3229:
3223:
3219:
2953:
2949:
2145:Haloprogesterone
1802:
1798:
1794:
1774:
1767:
1760:
1751:
1658:
1654:
1630:
1626:
1620:
1615:Antiprogestogens
1358:Haloprogesterone
1208:
1204:
1198:
1179:antiprogestogens
1168:
1161:
1154:
1145:
1138:
1137:
1115:
1109:
1108:
1086:
1080:
1079:
1060:
1051:
1050:
1022:
1013:
1012:
1006:
1002:
1000:
992:
958:
941:
940:
901:
895:
894:
870:
864:
863:
841:
822:
821:
799:
790:
789:
787:
785:
771:
765:
764:
744:
738:
737:
717:
650:
646:
353:
333:
318:
312:
306:
289:
278:
267:
266:
252:
250:
235:
215:
195:
175:
155:
145:
144:
130:
31:
24:
22:
3410:
3409:
3405:
3404:
3403:
3401:
3400:
3399:
3395:Withdrawn drugs
3355:
3354:
3353:
3348:
3308:
3292:
3231:
3224:
3221:
3207:
3093:
2951:
2944:
2938:
2765:Norethandrolone
2726:Methyldienolone
2686:Dimethandrolone
2110:Fluorometholone
1796:
1786:
1778:
1748:
1743:
1717:
1702:Clinical trials
1677:
1656:
1646:
1628:
1605:
1600:norethandrolone
1390:17α-Methylated:
1348:17α-Methylated:
1206:
1189:
1181:
1172:
1142:
1141:
1134:
1117:
1116:
1112:
1105:
1088:
1087:
1083:
1076:
1062:
1061:
1054:
1024:
1023:
1016:
1003:
993:
981:
960:
959:
944:
903:
902:
898:
887:
872:
871:
867:
860:
843:
842:
825:
818:
801:
800:
793:
783:
781:
773:
772:
768:
761:
746:
745:
741:
734:
719:
718:
701:
696:
688:Acetomepregenol
684:
676:
661:
648:
633:
628:
614:derivatives as
541:
496:
482:
454:
432:
401:
398:
393:
388:
387:
376:
373:
368:
367:
356:
331:
321:
315:
309:
270:
246:
238:
218:
198:
178:
158:
141:
133:
113:
110:
105:
104:
61:
17:
12:
11:
5:
3408:
3406:
3398:
3397:
3392:
3387:
3382:
3377:
3372:
3367:
3365:Acetate esters
3357:
3356:
3350:
3349:
3347:
3346:
3341:
3336:
3331:
3326:
3321:
3317:
3314:
3313:
3310:
3309:
3307:
3306:
3300:
3298:
3294:
3293:
3291:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3255:
3250:
3244:
3242:
3235:
3213:
3212:
3209:
3208:
3206:
3205:
3200:
3195:
3190:
3185:
3180:
3175:
3170:
3165:
3156:
3155:
3150:
3145:
3140:
3135:
3130:
3125:
3120:
3115:
3110:
3101:
3099:
3095:
3094:
3092:
3091:
3086:
3081:
3076:
3071:
3066:
3057:
3056:
3051:
3046:
3041:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2996:
2991:
2986:
2981:
2976:
2971:
2966:
2957:
2955:
2940:
2939:
2937:
2936:
2931:
2922:
2921:
2916:
2911:
2906:
2901:
2896:
2891:
2886:
2881:
2872:
2871:
2866:
2864:Spironolactone
2861:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2824:Canrenoic acid
2817:
2816:
2811:
2806:
2801:
2787:
2782:
2777:
2772:
2767:
2762:
2748:
2743:
2738:
2733:
2728:
2723:
2718:
2716:Ethyldienolone
2713:
2708:
2703:
2698:
2693:
2688:
2683:
2678:
2673:
2671:Dimethisterone
2668:
2663:
2658:
2653:
2648:
2643:
2638:
2633:
2624:
2619:
2614:
2609:
2604:
2599:
2597:Norvinisterone
2594:
2592:Norgestrienone
2589:
2584:
2579:
2574:
2569:
2555:
2550:
2548:Norelgestromin
2545:
2540:
2535:
2530:
2525:
2515:
2513:Levonorgestrel
2510:
2505:
2500:
2495:
2490:
2485:
2480:
2475:
2474:
2473:
2463:
2458:
2453:
2448:
2443:
2438:
2433:
2428:
2423:
2418:
2408:
2407:
2402:
2397:
2392:
2387:
2382:
2377:
2372:
2367:
2362:
2357:
2352:
2347:
2342:
2337:
2332:
2327:
2322:
2317:
2312:
2307:
2302:
2297:
2288:
2287:
2282:
2277:
2272:
2267:
2262:
2257:
2252:
2247:
2242:
2237:
2232:
2230:Methenmadinone
2227:
2222:
2217:
2212:
2207:
2202:
2197:
2192:
2187:
2182:
2177:
2172:
2167:
2162:
2157:
2152:
2147:
2142:
2137:
2132:
2127:
2122:
2117:
2112:
2107:
2102:
2097:
2092:
2087:
2082:
2077:
2072:
2067:
2062:
2057:
2052:
2047:
2042:
2037:
2032:
2027:
2022:
2017:
2012:
2007:
2002:
1997:
1992:
1987:
1982:
1977:
1972:
1967:
1962:
1957:
1952:
1947:
1938:
1937:
1932:
1927:
1922:
1920:Dydrogesterone
1917:
1912:
1907:
1902:
1893:
1892:
1887:
1882:
1877:
1872:
1867:
1862:
1857:
1852:
1847:
1842:
1837:
1832:
1827:
1822:
1817:
1808:
1806:
1799:
1788:
1787:
1779:
1777:
1776:
1769:
1762:
1754:
1745:
1744:
1742:
1741:
1736:
1731:
1726:
1721:
1716:
1715:
1714:
1713:
1710:
1699:
1693:
1687:
1686:
1683:
1682:
1679:
1678:
1676:
1675:
1670:
1664:
1662:
1648:
1647:
1645:
1644:
1639:
1633:
1631:
1617:
1611:
1610:
1607:
1606:
1604:
1603:
1569:
1568:
1559:
1558:
1553:
1548:
1546:Norelgestromin
1543:
1541:Levonorgestrel
1538:
1533:
1528:
1523:
1511:
1506:
1501:
1499:Norvinisterone
1496:
1491:
1489:Norgestrienone
1486:
1481:
1476:
1471:
1466:
1461:
1456:
1451:
1446:
1441:
1429:
1428:
1423:
1421:Dimethisterone
1418:
1406:
1405:
1400:
1395:
1383:
1378:
1373:
1361:
1360:
1341:
1336:
1331:
1326:
1321:
1316:
1311:
1306:
1301:
1296:
1291:
1286:
1281:
1276:
1271:
1266:
1261:
1256:
1244:
1243:
1238:
1236:Dydrogesterone
1229:
1228:
1223:
1214:
1212:
1195:
1183:
1182:
1173:
1171:
1170:
1163:
1156:
1148:
1140:
1139:
1132:
1110:
1103:
1081:
1074:
1052:
1014:
1005:|journal=
979:
942:
912:(1–2): 39–47.
896:
885:
865:
858:
823:
816:
791:
766:
759:
739:
732:
698:
697:
695:
692:
691:
690:
683:
680:
675:
672:
660:
657:
632:
629:
627:
624:
599:norethisterone
540:
537:
481:
478:
453:
450:
431:
428:
403:
402:
400:
399:
396:
394:
391:
383:
382:
381:
378:
377:
375:
374:
371:
363:
362:
361:
358:
357:
355:
354:
346:
344:
336:
335:
329:
323:
322:
319:
313:
307:
302:
296:
295:
291:
290:
280:
272:
271:
269:
268:
260:DTXSID50953411
255:
253:
240:
239:
237:
236:
228:
226:
220:
219:
217:
216:
208:
206:
200:
199:
197:
196:
188:
186:
180:
179:
177:
176:
168:
166:
160:
159:
157:
156:
148:
146:
135:
134:
132:
131:
123:
121:
115:
114:
112:
111:
108:
100:
99:
98:
95:
94:
90:
89:
76:
70:
69:
64:
62:administration
56:
55:
52:
48:
47:
44:
38:
37:
33:
32:
15:
13:
10:
9:
6:
4:
3:
2:
3407:
3396:
3393:
3391:
3388:
3386:
3383:
3381:
3378:
3376:
3373:
3371:
3368:
3366:
3363:
3362:
3360:
3345:
3342:
3340:
3337:
3335:
3332:
3330:
3327:
3325:
3322:
3319:
3318:
3315:
3305:
3302:
3301:
3299:
3295:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3254:
3251:
3249:
3246:
3245:
3243:
3239:
3236:
3230:
3220:
3214:
3204:
3201:
3199:
3196:
3194:
3193:Valproic acid
3191:
3189:
3186:
3184:
3181:
3179:
3176:
3174:
3171:
3169:
3166:
3164:
3161:
3160:Nonsteroidal:
3158:
3157:
3154:
3151:
3149:
3146:
3144:
3141:
3139:
3136:
3134:
3131:
3129:
3126:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3103:
3102:
3100:
3096:
3090:
3089:Syringic acid
3087:
3085:
3082:
3080:
3077:
3075:
3072:
3070:
3067:
3065:
3062:
3061:Nonsteroidal:
3059:
3058:
3055:
3052:
3050:
3047:
3045:
3042:
3040:
3037:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
3000:
2997:
2995:
2992:
2990:
2989:Guggulsterone
2987:
2985:
2982:
2980:
2977:
2975:
2972:
2970:
2967:
2965:
2962:
2959:
2958:
2956:
2950:
2941:
2935:
2932:
2930:
2927:
2924:
2923:
2920:
2917:
2915:
2912:
2910:
2907:
2905:
2902:
2900:
2897:
2895:
2894:Riligustilide
2892:
2890:
2887:
2885:
2882:
2880:
2877:
2876:Nonsteroidal:
2874:
2873:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2819:
2818:
2815:
2812:
2810:
2807:
2805:
2802:
2799:
2795:
2791:
2788:
2786:
2783:
2781:
2778:
2776:
2773:
2771:
2768:
2766:
2763:
2760:
2756:
2752:
2749:
2747:
2744:
2742:
2739:
2737:
2734:
2732:
2729:
2727:
2724:
2722:
2719:
2717:
2714:
2712:
2709:
2707:
2704:
2702:
2699:
2697:
2694:
2692:
2689:
2687:
2684:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2642:
2639:
2637:
2634:
2632:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2567:
2563:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2523:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2472:
2471:Ethandrostate
2469:
2468:
2467:
2464:
2462:
2459:
2457:
2454:
2452:
2449:
2447:
2444:
2442:
2439:
2437:
2434:
2432:
2431:Allylestrenol
2429:
2427:
2424:
2422:
2419:
2417:
2413:
2410:
2409:
2406:
2403:
2401:
2398:
2396:
2393:
2391:
2388:
2386:
2383:
2381:
2378:
2376:
2373:
2371:
2368:
2366:
2363:
2361:
2358:
2356:
2353:
2351:
2348:
2346:
2343:
2341:
2338:
2336:
2333:
2331:
2328:
2326:
2323:
2321:
2318:
2316:
2313:
2311:
2308:
2306:
2303:
2301:
2298:
2296:
2293:
2290:
2289:
2286:
2283:
2281:
2278:
2276:
2273:
2271:
2268:
2266:
2265:Pentagestrone
2263:
2261:
2258:
2256:
2253:
2251:
2248:
2246:
2243:
2241:
2238:
2236:
2233:
2231:
2228:
2226:
2223:
2221:
2218:
2216:
2213:
2211:
2208:
2206:
2203:
2201:
2198:
2196:
2193:
2191:
2188:
2186:
2183:
2181:
2178:
2176:
2173:
2171:
2168:
2166:
2163:
2161:
2158:
2156:
2153:
2151:
2150:Hydromadinone
2148:
2146:
2143:
2141:
2140:Gestobutanoyl
2138:
2136:
2133:
2131:
2128:
2126:
2123:
2121:
2118:
2116:
2113:
2111:
2108:
2106:
2103:
2101:
2098:
2096:
2093:
2091:
2088:
2086:
2083:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2051:
2048:
2046:
2043:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2020:Chlormadinone
2018:
2016:
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1966:
1963:
1961:
1958:
1956:
1953:
1951:
1948:
1946:
1943:
1940:
1939:
1936:
1933:
1931:
1928:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1906:
1903:
1901:
1898:
1895:
1894:
1891:
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1858:
1856:
1853:
1851:
1848:
1846:
1843:
1841:
1838:
1836:
1833:
1831:
1828:
1826:
1823:
1821:
1818:
1816:
1813:
1810:
1809:
1807:
1803:
1800:
1795:
1789:
1785:
1782:
1775:
1770:
1768:
1763:
1761:
1756:
1755:
1752:
1740:
1737:
1735:
1732:
1730:
1727:
1725:
1722:
1719:
1718:
1711:
1709:
1706:
1705:
1703:
1700:
1697:
1694:
1692:
1689:
1688:
1684:
1674:
1671:
1669:
1666:
1665:
1663:
1661:
1655:
1649:
1643:
1640:
1638:
1635:
1634:
1632:
1627:
1621:
1618:
1616:
1612:
1601:
1597:
1596:ethylestrenol
1593:
1589:
1585:
1581:
1577:
1574:
1571:
1570:
1567:
1564:
1561:
1560:
1557:
1554:
1552:
1549:
1547:
1544:
1542:
1539:
1537:
1534:
1532:
1529:
1527:
1524:
1522:
1519:
1515:
1512:
1510:
1507:
1505:
1502:
1500:
1497:
1495:
1492:
1490:
1487:
1485:
1482:
1480:
1477:
1475:
1472:
1470:
1467:
1465:
1462:
1460:
1457:
1455:
1452:
1450:
1447:
1445:
1442:
1440:
1439:Allylestrenol
1437:
1434:
1431:
1430:
1427:
1424:
1422:
1419:
1417:
1414:
1411:
1408:
1407:
1404:
1401:
1399:
1396:
1394:
1391:
1387:
1384:
1382:
1379:
1377:
1374:
1372:
1369:
1366:
1363:
1362:
1359:
1356:
1352:
1349:
1345:
1342:
1340:
1337:
1335:
1332:
1330:
1327:
1325:
1322:
1320:
1317:
1315:
1312:
1310:
1307:
1305:
1302:
1300:
1297:
1295:
1292:
1290:
1287:
1285:
1282:
1280:
1277:
1275:
1272:
1270:
1267:
1265:
1262:
1260:
1257:
1255:
1252:
1249:
1246:
1245:
1242:
1239:
1237:
1234:
1231:
1230:
1227:
1224:
1222:
1219:
1216:
1215:
1213:
1211:
1205:
1199:
1196:
1193:
1188:
1184:
1180:
1176:
1169:
1164:
1162:
1157:
1155:
1150:
1149:
1146:
1135:
1129:
1125:
1121:
1114:
1111:
1106:
1100:
1096:
1092:
1085:
1082:
1077:
1071:
1067:
1066:
1059:
1057:
1053:
1048:
1044:
1040:
1036:
1032:
1028:
1021:
1019:
1015:
1010:
998:
990:
986:
982:
976:
972:
968:
964:
957:
955:
953:
951:
949:
947:
943:
939:
935:
931:
927:
923:
919:
915:
911:
907:
900:
897:
893:
888:
882:
878:
877:
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631:Generic names
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581:
580:mammary gland
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36:Clinical data
34:
30:
25:
3390:Progestogens
3304:Mifepristone
3288:Progesterone
3283:Pregnenolone
3278:Mifepristone
3163:Darolutamide
3159:
3148:Toripristone
3143:RTI 3021–022
3113:Lilopristone
3108:Aglepristone
3104:
3060:
3039:Telapristone
2960:
2925:
2875:
2834:Drospirenone
2820:
2607:Quingestanol
2582:Norgestimate
2577:Norgesterone
2572:Noretynodrel
2488:Etonogestrel
2414:Progestins:
2411:
2405:Trimegestone
2390:Promegestone
2291:
2280:Proligestone
2220:Melengestrol
2185:Medrogestone
2120:Flumedroxone
2075:Cymegesolate
2065:Clomegestone
1999:
1941:
1896:
1890:Quingestrone
1880:Progesterone
1811:
1673:Mifepristone
1668:Aglepristone
1637:Telapristone
1572:
1566:Drospirenone
1562:
1551:Norgestimate
1526:Etonogestrel
1517:
1484:Norgesterone
1479:Noretynodrel
1435:
1432:
1412:
1409:
1403:Trimegestone
1398:Promegestone
1389:
1367:
1364:
1354:
1351:Medrogestone
1347:
1344:Proligestone
1263:
1250:
1247:
1232:
1226:Quingestrone
1221:Progesterone
1217:
1187:Progestogens
1175:Progestogens
1123:
1113:
1094:
1084:
1064:
1033:(1A): 3–11.
1030:
1026:
962:
937:
909:
905:
899:
890:
875:
868:
849:
807:
782:. Retrieved
776:
769:
749:
742:
722:
677:
674:Availability
662:
652:
640:generic name
635:
634:
603:noretynodrel
593:derivatives
556:progesterone
553:
542:
514:progesterone
497:
472:(the 3-keto
455:
452:Pharmacology
433:
430:Medical uses
415:
411:
407:
406:
233:CHEBI:135575
3297:Antagonists
3123:Onapristone
3098:Antagonists
2869:Spirorenone
2839:Mespirenone
2528:Lynestrenol
2478:Ethisterone
2456:Desogestrel
2436:Altrenogest
2395:Segesterone
2370:Norgestomet
2360:Nomegestrol
2335:Gestadienol
2320:Demegestone
2275:Pentarane A
2095:Edogestrone
2085:Delmadinone
2045:Cismadinone
1935:Trengestone
1865:Dimepregnen
1698:from market
1660:antagonists
1521:Desogestrel
1459:Lynestrenol
1444:Altrenogest
1426:Ethisterone
1393:Demegestone
1381:Norgestomet
1241:Trengestone
804:"The Ovary"
659:Brand names
587:Beagle dogs
547:in 1968 by
334: g·mol
283:100.019.578
93:Identifiers
79:Progestogen
51:Other names
42:Trade names
3359:Categories
3153:Zanoterone
3118:Lonaprisan
3105:Steroidal:
3079:Naringenin
3069:Kaempferol
3049:Vilaprisan
2979:Asoprisnil
2961:Steroidal:
2934:ORG-201745
2914:Tanaproget
2809:Trestolone
2746:Nandrolone
2741:Mibolerone
2676:Dienedione
2666:Bolandione
2627:Tosagestin
2602:Oxendolone
2587:Norgestrel
2538:Metynodiol
2508:Gestrinone
2483:Ethynerone
2380:Oxogestone
2245:Mometasone
2135:Gestaclone
2100:Flugestone
2055:Clogestone
1995:Anagestone
1784:modulators
1588:trenbolone
1580:nandrolone
1556:Norgestrel
1536:Gestrinone
1504:Oxendolone
1192:progestins
694:References
595:norgestrel
572:ethynerone
529:anagestone
510:derivative
484:See also:
339:3D model (
327:Molar mass
193:GNT396G9QT
164:ChemSpider
119:CAS Number
102:IUPAC name
74:Drug class
3375:Pregnanes
3203:ZM-172406
3198:ZM-150271
3188:LG-121046
3183:LG-120830
3178:LG-100128
3173:LG-100127
3168:LG-001447
3138:ORG-33628
3133:ORG-31806
3128:ORG-31710
3074:LG-120920
3054:ZK-137316
3034:RMI-12936
3029:ORG-33628
3024:ORG-31710
2999:LG-120838
2929:ORG-47241
2919:ZM-182345
2909:RWJ-60130
2904:RWJ-49853
2899:RWJ-26819
2889:LG-100128
2849:Prorenone
2829:Canrenone
2804:Trendione
2681:Dienolone
2656:Bolandiol
2503:Gestodene
2493:Etynodiol
2461:Dienogest
2446:Cingestol
2310:Amadinone
2255:Osaterone
2205:Megestrol
1980:Algestone
1930:Ro 6-3129
1870:Diosgenin
1708:Phase III
1696:Withdrawn
1602:, others)
1531:Gestodene
1449:Dienogest
1436:Estranes:
1413:Estranes:
1007:ignored (
997:cite book
668:mestranol
500:synthetic
480:Chemistry
439:mestranol
424:withdrawn
420:progestin
416:Neo-Novum
412:Anatropin
128:3137-73-3
83:Progestin
60:Routes of
3380:Prodrugs
3320:See also
3241:Agonists
3064:Apigenin
3019:ORF-9326
3014:ORF-9371
2926:Unknown:
2622:Tigestol
2617:Tibolone
2375:ORG-2058
1915:DU-41165
1910:DU-41164
1805:Agonists
1720:See also
1518:Gonanes:
1514:Tibolone
1210:agonists
926:18395441
682:See also
665:estrogen
653:ORF-1658
503:pregnane
474:analogue
443:combined
436:estrogen
67:By mouth
3370:Ketones
3084:PRA-910
2884:LG-2527
2859:SC-8109
2792:(e.g.,
2775:RU-2309
2753:(e.g.,
2560:(e.g.,
2520:(e.g.,
2451:Danazol
1578:(e.g.,
1573:Others:
1416:Danazol
1355:Others:
934:5612000
784:24 June
638:is the
539:History
522:acetate
506:steroid
466:prodrug
418:, is a
332:372.549
300:Formula
139:PubChem
1875:P1-185
1691:WHO-EM
1592:esters
1584:esters
1130:
1101:
1072:
1047:385985
1045:
989:107546
987:
977:
932:
924:
883:
856:
814:
757:
730:
605:, and
583:tumors
574:, and
508:and a
492:, and
462:ketone
365:SMILES
213:D02932
173:221058
153:252301
2994:J1042
2948:SPRMs
2943:Mixed
1625:SPRMs
1190:(and
930:S2CID
525:ester
441:as a
385:InChI
341:JSmol
224:ChEBI
3228:PAQR
1590:and
1582:and
1177:and
1128:ISBN
1099:ISBN
1070:ISBN
1043:PMID
1009:help
985:PMID
975:ISBN
922:PMID
881:ISBN
854:ISBN
812:ISBN
786:2022
755:ISBN
728:ISBN
645:USAN
516:and
414:and
204:KEGG
184:UNII
3218:mPR
1035:doi
967:doi
914:doi
910:110
585:in
527:of
512:of
476:).
468:of
249:EPA
143:CID
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2796:,
2757:,
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1793:PR
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