252:
585:, GTx-758 suppressed total testosterone levels to a lower extent than leuprorelin but decreased free testosterone and PSA levels to a greater extent, suggesting superior effectiveness. GTx-758 increased median SHBG levels by 495% (at 1000 mg/day) and 583% (at 2000 mg/day), which was considered to account for the greater relative decrease in levels of free testosterone. There was a significantly lesser incidence of
29:
622:(VTE) was observed with GTx-78 (4.1%) relative to leuprorelin (0.0%), and this led to early termination of the clinical trial. The drug was said to be well tolerated aside from VTE. Studies are underway with lower doses of GTx-758 as secondary hormonal therapy in prostate cancer to see if such doses minimize the incidence of VTE.
625:
In a subsequent phase II clinical trial of 150 mg/day and 250 mg/day GTx-758 in castration-resistant prostate cancer, GTx-758 increased median SHBG levels by 301% (with 250 mg/day), decreased free testosterone levels by median 44%, and decreased PSA levels. Similarly to the prior phase
759:
Yu EY, Getzenberg RH, Coss CC, Gittelman MM, Keane T, Tutrone R, et al. (February 2015). "Selective estrogen receptor alpha agonist GTx-758 decreases testosterone with reduced side effects of androgen deprivation therapy in men with advanced prostate cancer".
617:
as well as progression of prostate cancer) increased in the leuprorelin group but decreased in the GTx-758 group. Incidence of gynecomastia was not reported with GTx-758. However, a higher incidence of
458:
via activation of ERβ, which is the predominant isoform of the ER expressed in platelets. It has been said that suppression of free testosterone levels by ERα activation-induced increase in
795:
Jones A, Getzenberg RH, Dalton JT, Veverka KA (2011). "1448 Oral
Administration of GTX-758, a Selective ERα Agonist, Induces Chemical Castration but Not Gynecomastia in Male Monkeys".
874:
328:
626:
II clinical trial, GTx-758 was regarded as well tolerated, and improved bone parameters, but there were still two possibly drug-related severe adverse effects (VTE and
927:
342:
1037:
867:
3183:
3219:
2376:
3178:
860:
1147:
569:
in male monkeys, despite similarly suppressing testosterone levels to the castrate range (≤50 ng/dL) and markedly reducing PSA levels.
3173:
2907:
1132:
1127:
450:= 2.1 and 27 nM, respectively). The selectivity of GTx-758 for ERα over ERβ may confer reduced hypercoagulability and thrombophilia, as
605:) increased in the leuprorelin group but decreased in the GTx-758 group (indicating a beneficial bone-sparing effect for GTx-758), and
598:
3224:
362:
2331:
835:
A phase II open-label trial of GTx-758 in men with castration-resistant prostate cancer: Final analysis of the primary endpoint
101:
68:
1582:
685:"Preclinical characterization of a novel diphenyl benzamide selective ERα agonist for hormone therapy in prostate cancer"
3229:
3168:
2932:
1482:
1042:
1017:
606:
462:
191:
3188:
1430:
408:
231:
1435:
2823:
2490:
2400:
1622:
942:
937:
526:
3051:
2813:
2726:
2351:
2044:
1577:
1572:
1472:
83:
3055:
1097:
593:
in the GTx-758 group. For instance, there was a more than 4-fold lower incidence of hot flashes for GTx-758,
370:
InChI=1S/C19H13F2NO3/c20-13-2-4-14(5-3-13)22(15-6-8-16(23)9-7-15)19(25)12-1-10-18(24)17(21)11-12/h1-11,23-24H
2395:
2339:
2249:
1874:
1864:
1799:
1751:
1669:
1391:
1359:
1327:
1317:
1196:
1180:
1137:
1112:
1052:
1047:
49:
2307:
1859:
1339:
1264:
1259:
1212:
1067:
619:
594:
220:
2580:
2405:
2343:
1869:
1413:
1376:
1364:
1232:
627:
396:
2970:
1142:
1117:
1092:
1077:
1012:
952:
947:
2000:
1657:
1396:
1302:
1244:
1082:
1022:
957:
932:
247:
2736:
3214:
3061:
2976:
2787:
2779:
2040:
1824:
1681:
1647:
1457:
1157:
1072:
654:
586:
558:
466:
126:
56:
2362:
3143:
3122:
3117:
2927:
2808:
2615:
2610:
2605:
2475:
2390:
2004:
1664:
1322:
1239:
1184:
1027:
987:
977:
917:
886:
614:
610:
562:
554:
485:
393:
3081:
3001:
2798:
2731:
2100:
1884:
1007:
2873:
2868:
2640:
2565:
2848:
2843:
2741:
2690:
2685:
2515:
1964:
1122:
972:
967:
894:
883:
812:
777:
706:
493:
432:
180:
3016:
3011:
2695:
2530:
2485:
1834:
1587:
3209:
2991:
2853:
2761:
2756:
2746:
2660:
2585:
2460:
1597:
1425:
1172:
1102:
1057:
997:
992:
982:
962:
922:
838:
804:
769:
696:
534:
497:
400:
268:
135:
2700:
683:
Coss CC, Jones A, Parke DN, Narayanan R, Barrett CM, Kearbey JD, et al. (March 2012).
200:
2550:
2283:
2157:
1789:
1736:
1691:
1492:
582:
538:
404:
251:
2261:
2257:
2235:
3021:
2783:
2655:
2084:
1804:
1776:
1768:
1607:
1512:
1502:
1447:
1442:
1344:
1162:
1062:
522:
411:
3203:
2635:
2470:
2445:
2225:
2143:
1976:
1954:
1809:
1686:
1418:
1269:
1227:
602:
577:
In a phase II clinical trial of 1000 mg/day and 2000 mg/day GTx-758 versus
550:
160:
842:
2803:
2775:
2751:
2620:
2545:
2455:
2450:
2440:
2243:
2209:
2199:
2195:
2130:
2124:
2056:
1552:
1542:
1517:
1381:
1334:
1188:
1176:
566:
546:
514:
478:
724:
837:. Genitourinary Cancers Symposium. American Society of Clinical Oncology (ASCO).
773:
3148:
3076:
3041:
3036:
2996:
2966:
2952:
2942:
2937:
2766:
2710:
2705:
2600:
2595:
2575:
2525:
2500:
2495:
2420:
2410:
2327:
2323:
2319:
2311:
2301:
2297:
2265:
2253:
2239:
2231:
2171:
2104:
2048:
2020:
1854:
1829:
1701:
1602:
1477:
1401:
1371:
1222:
1202:
1152:
1106:
1002:
808:
590:
578:
530:
489:
28:
852:
833:
Yu EY, Hancock ML, Babicz T, Tutrone RF, Ng C, Belkoff LH, et al. (2016).
3091:
3071:
3046:
2893:
2838:
2793:
2771:
2680:
2675:
2645:
2630:
2625:
2590:
2480:
2435:
2415:
2293:
2287:
2191:
2179:
2139:
2120:
2096:
2080:
1990:
1986:
1960:
1946:
1899:
1894:
1889:
1879:
1849:
1819:
1814:
1794:
1731:
1652:
1632:
1617:
1612:
1592:
1557:
1507:
1408:
1349:
1282:
1277:
1254:
1192:
1167:
1087:
639:
518:
304:
171:
816:
3086:
3066:
3006:
2986:
2828:
2665:
2540:
2535:
2520:
2505:
2465:
2347:
2315:
2273:
2221:
2217:
2213:
2203:
2183:
2167:
2116:
2092:
2088:
2076:
2068:
2064:
2024:
2012:
1996:
1982:
1972:
1968:
1924:
1784:
1758:
1746:
1721:
1711:
1696:
1676:
1627:
1527:
1522:
1497:
1487:
1452:
1312:
1287:
1249:
1207:
542:
481:
451:
1032:
781:
710:
2957:
2947:
2650:
2510:
2430:
2425:
2358:
2175:
2112:
2108:
2072:
2060:
2032:
2028:
2016:
2008:
1938:
1726:
1716:
1562:
1547:
1532:
1467:
1462:
1307:
1217:
701:
684:
455:
20:
3112:
2858:
2670:
2570:
2560:
2555:
2335:
2279:
2269:
2161:
2036:
1844:
1839:
1706:
1637:
1537:
1386:
1354:
1292:
428:
146:
3031:
3026:
2883:
2147:
2135:
1950:
1919:
1914:
1909:
1642:
1297:
649:
644:
211:
440:
436:
3107:
2981:
2863:
2833:
2052:
1934:
1763:
459:
327:
318:
3127:
2818:
2187:
1942:
444:
856:
77:
2962:
2377:
435:(ER), with a more than 10-fold preference for activation of
236:
2908:
1278:
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
350:
C1=CC(=CC=C1N(C2=CC=C(C=C2)F)C(=O)C3=CC(=C(C=C3)O)F)O
3136:
3100:
2920:
2906:
2719:
2372:
907:
893:
316:
303:
267:
262:
230:
210:
190:
170:
145:
125:
92:
67:
62:
48:
40:
35:
513:In animal studies, GTx-758 reversibly suppresses
469:of GTx-758 in the treatment of prostate cancer.
159:
828:
826:
678:
676:
674:
672:
670:
134:
2382:Tooltip Selective estrogen receptor modulators
1737:Furostilbestrol (diethylstilbestrol difuroate)
1098:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
754:
752:
750:
748:
746:
744:
742:
740:
738:
928:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
868:
609:levels (which are positively associated with
8:
1038:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
19:
2913:Tooltip G protein-coupled estrogen receptor
1732:Fosfestrol (diethylstilbestrol diphosphate)
2917:
1875:Triphenylmethylethylene (triphenylpropene)
1199:, many others; via estrogenic metabolites)
1123:17α-Epiestriol (16α-hydroxy-17α-estradiol)
904:
875:
861:
853:
250:
179:
895:
700:
199:
492:derivatives like diethylstilbestrol and
666:
367:
347:
246:
106:
18:
219:
7:
529:(PSA), but does not induce typical
454:directly produces these effects in
407:. As of 2016, it had completed two
150:
599:bone specific alkaline phosphatase
14:
2274:taleranol (teranol, β-zearalanol)
1189:metandienone (methandrostenolone)
731:. Springer Nature Switzerland AG.
465:(SHBG) production is the primary
3184:Progesterone receptor modulators
2938:Afimoxifene (4-hydroxytamoxifen)
1820:Prinaberel (ERB-041, WAY-202041)
291:
285:
279:
27:
2881:Coregulator-binding modulators:
1148:17β-Methyl-17α-dihydroequilenin
843:10.1200/jco.2016.34.2_suppl.185
565:, GTx-758 also does not induce
399:which was under development by
375:Key:FBCQEUMZZNVQKD-UHFFFAOYSA-N
1712:Erteberel (SERBA-1, LY-500307)
403:for the treatment of advanced
294:
273:
1:
3220:Hormonal antineoplastic drugs
3169:Receptor/signaling modulators
1133:17α-Ethynyl-3β-androstanediol
1128:17α-Ethynyl-3α-androstanediol
3179:Androgen receptor modulators
1483:Lynestrenol phenylpropionate
774:10.1016/j.eururo.2014.06.011
607:insulin-like growth factor-1
463:sex hormone-binding globulin
427:GTx-758 acts as a selective
113:-(4-fluorophenyl)-4-hydroxy-
3174:Estrogens and antiestrogens
2824:Oxabicycloheptene sulfonate
2511:Etacstil (GW-5638, DPC-974)
1687:Doisynoestrol (fenocycline)
1431:Ethinylestradiol 3-benzoate
943:3β,5α-Dihydrolevonorgestrel
938:3α,5α-Dihydrolevonorgestrel
809:10.1016/j.juro.2011.02.1361
117:-(4-hydroxyphenyl)benzamide
3246:
2891:Noncompetitive inhibitors:
2516:Ethamoxytriphetol (MER-25)
1677:Dimestrol (dianisylhexene)
1436:Ethinylestradiol sulfonate
601:(BSAP) levels (markers of
263:Chemical and physical data
3161:
2933:7β-Hydroxyepiandrosterone
2491:Desmethylchlorotrianisene
1670:Diethylstilbestrol esters
1623:Bisdehydrodoisynolic acid
1043:11β-Chloromethylestradiol
1018:7β-Hydroxyepiandrosterone
900:Tooltip Estrogen receptor
527:prostate-specific antigen
358:
338:
97:
26:
3225:4-Fluorophenyl compounds
2997:Fulvestrant (ICI-182780)
2814:Methylpiperidinopyrazole
2767:Fulvestrant (ICI-182780)
2250:Resorcylic acid lactones
1473:Hydroxyestrone diacetate
1409:Etamestrol (eptamestrol)
84:Investigational New Drug
2308:Synthetic xenoestrogens
1865:Triphenylchloroethylene
1800:Methestrol dipropionate
1328:Polyestradiol phosphate
2401:4'-Hydroxynorendoxifen
2396:2-Phenylbenzothiophene
2270:zeranol (α-zearalanol)
1973:phlorizin (phloridzin)
1860:Triphenylbromoethylene
1759:ICI-85966 (Stilbostat)
1340:Estramustine phosphate
1213:Bolandiol dipropionate
797:The Journal of Urology
620:venous thromboembolism
595:C-terminal telopeptide
388:(tentative brand name
2581:Miproxifene phosphate
2406:27-Hydroxycholesterol
1870:Triphenyliodoethylene
1414:Ethinylandrostenediol
1377:Estrogenic substances
1365:Polyestriol phosphate
1233:Cloxestradiol acetate
628:myocardial infarction
581:for the treatment of
397:nonsteroidal estrogen
1895:WAY-204688 (SIM-688)
1707:ERB-196 (WAY-202196)
1658:Dienestrol diacetate
1397:Estrone methyl ether
1303:Esterified estrogens
1245:Conjugated estrogens
1138:17β-Dihydroequilenin
1113:17α-Dihydroequilenin
1053:15α-Hydroxyestradiol
1048:11β-Methoxyestradiol
1023:8,9-Dehydroestradiol
702:10.1210/en.2011-1608
3230:Synthetic estrogens
3062:Propylpyrazoletriol
2977:Diarylpropionitrile
1825:Propylpyrazoletriol
1682:Dimethylstilbestrol
1648:Diarylpropionitrile
1458:Etynodiol diacetate
1158:Abiraterone acetate
1068:16α-Fluoroestradiol
655:Propylpyrazoletriol
587:estrogen deficiency
525:size and levels of
509:Preclinical studies
467:mechanism of action
23:
3144:Diethylstilbestrol
2928:2-Methoxyestradiol
2859:TAS-108 (SR-16234)
2809:Methylepitiostanol
2747:EM-800 (SCH-57050)
2671:TAS-108 (SR-16234)
2391:2-Phenylbenzofuran
2005:8-prenylnaringenin
1665:Diethylstilbestrol
1323:Lipoidal estradiol
1298:ERA-63 (ORG-37663)
1240:Conjugated estriol
1185:methyltestosterone
1143:17β-Dihydroequilin
1118:17α-Dihydroequilin
1093:16β-Hydroxyestrone
1078:16α-Hydroxyestrone
1028:8,9-Dehydroestrone
1013:7α-Methylestradiol
988:4-Methoxyestradiol
978:4-Hydroxyestradiol
953:3β-Hydroxytibolone
948:3α-Hydroxytibolone
918:2-Hydroxyestradiol
615:metabolic syndrome
611:insulin resistance
563:diethylstilbestrol
517:concentrations to
484:and has a similar
3197:
3196:
3189:List of estrogens
3157:
3156:
2902:
2901:
2742:Cytestrol acetate
1965:isoliquiritigenin
1907:Unknown/unsorted:
1593:β-LGND2 (GTx-878)
1173:Anabolic steroids
1083:16α-Iodoestradiol
973:4-Fluoroestradiol
968:4-Androstenedione
958:3β-Androstanediol
933:3α-Androstanediol
884:Estrogen receptor
496:derivatives like
494:triphenylethylene
433:estrogen receptor
383:
382:
329:Interactive image
232:CompTox Dashboard
81:
16:Chemical compound
3237:
3056:2,2',5'-PCB-4-OH
2992:Ethinylestradiol
2918:
2914:
2910:
2651:Rimostil (P-081)
2461:Chlorotrianisene
2383:
2379:
2158:Metalloestrogens
1937:-related (e.g.,
1752:Hexestrol esters
1426:Ethinylestradiol
1318:Estradiol esters
1073:16α-Hydroxy-DHEA
1058:16-Ketoestradiol
998:5-Androstenediol
993:4-Methoxyestrone
983:4-Hydroxyestrone
963:4-Androstenediol
923:2-Hydroxyestrone
905:
901:
897:
877:
870:
863:
854:
847:
846:
830:
821:
820:
792:
786:
785:
762:European Urology
756:
733:
732:
721:
715:
714:
704:
695:(3): 1070–1081.
680:
573:Clinical studies
555:hypercoagulation
535:hyperestrogenism
533:associated with
521:levels, reduces
498:chlorotrianisene
423:Pharmacodynamics
331:
311:
296:
293:
287:
281:
275:
255:
254:
240:
238:
223:
203:
183:
163:
153:
152:
138:
79:
76:
31:
24:
22:
3245:
3244:
3240:
3239:
3238:
3236:
3235:
3234:
3200:
3199:
3198:
3193:
3153:
3132:
3096:
2912:
2898:
2732:7β-Hydroxy-DHEA
2715:
2551:Levormeloxifene
2381:
2374:
2368:
2284:deoxymiroestrol
2152:-hinokiresinol)
1790:Methallenestril
1692:Doisynolic acid
1493:Methylestradiol
1008:7α-Hydroxy-DHEA
899:
889:
881:
851:
850:
832:
831:
824:
794:
793:
789:
758:
757:
736:
723:
722:
718:
682:
681:
668:
663:
636:
583:prostate cancer
575:
557:, or increased
539:hypoestrogenism
511:
506:
477:GTx-758 is a di
475:
448:
425:
420:
412:clinical trials
405:prostate cancer
379:
376:
371:
366:
365:
354:
351:
346:
345:
334:
309:
299:
290:
284:
278:
258:
248:DTXSID401045796
234:
226:
206:
186:
166:
149:
141:
121:
118:
105:
104:
88:
51:
17:
12:
11:
5:
3243:
3241:
3233:
3232:
3227:
3222:
3217:
3212:
3202:
3201:
3195:
3194:
3192:
3191:
3186:
3181:
3176:
3171:
3166:
3162:
3159:
3158:
3155:
3154:
3152:
3151:
3146:
3140:
3138:
3134:
3133:
3131:
3130:
3125:
3120:
3115:
3110:
3104:
3102:
3098:
3097:
3095:
3094:
3089:
3084:
3079:
3074:
3069:
3064:
3059:
3049:
3044:
3039:
3034:
3029:
3024:
3022:Hydroxytyrosol
3019:
3014:
3009:
3004:
2999:
2994:
2989:
2984:
2979:
2974:
2960:
2955:
2950:
2945:
2940:
2935:
2930:
2924:
2922:
2915:
2904:
2903:
2900:
2899:
2897:
2896:
2887:
2886:
2877:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2821:
2816:
2811:
2806:
2801:
2796:
2791:
2769:
2764:
2759:
2754:
2749:
2744:
2739:
2737:Chloroindazole
2734:
2729:
2723:
2721:
2717:
2716:
2714:
2713:
2708:
2703:
2698:
2693:
2688:
2683:
2678:
2673:
2668:
2663:
2658:
2656:Spironolactone
2653:
2648:
2643:
2638:
2633:
2628:
2623:
2618:
2613:
2608:
2603:
2598:
2593:
2588:
2583:
2578:
2573:
2568:
2563:
2558:
2553:
2548:
2543:
2538:
2533:
2528:
2523:
2518:
2513:
2508:
2503:
2498:
2493:
2488:
2483:
2478:
2473:
2468:
2463:
2458:
2453:
2448:
2443:
2438:
2433:
2428:
2423:
2418:
2413:
2408:
2403:
2398:
2393:
2387:
2385:
2370:
2369:
2367:
2366:
2357:Others (e.g.,
2355:
2305:
2291:
2277:
2247:
2229:
2207:
2165:
2155:
2133:
2128:
2085:liquiritigenin
1994:
1980:
1958:
1932:Xenoestrogens:
1928:
1927:
1922:
1917:
1912:
1903:
1902:
1897:
1892:
1887:
1882:
1877:
1872:
1867:
1862:
1857:
1852:
1847:
1842:
1837:
1832:
1827:
1822:
1817:
1812:
1807:
1805:Paroxypropione
1802:
1797:
1792:
1787:
1782:
1774:
1766:
1761:
1756:
1755:
1754:
1744:
1739:
1734:
1729:
1724:
1719:
1717:Estrobin (DBE)
1714:
1709:
1704:
1699:
1694:
1689:
1684:
1679:
1674:
1673:
1672:
1662:
1661:
1660:
1650:
1645:
1640:
1635:
1630:
1625:
1620:
1615:
1610:
1608:Allenolic acid
1605:
1600:
1595:
1590:
1585:
1580:
1575:
1566:
1565:
1560:
1555:
1550:
1545:
1540:
1535:
1530:
1525:
1520:
1515:
1513:Norethisterone
1510:
1505:
1503:Mytatrienediol
1500:
1495:
1490:
1485:
1480:
1475:
1470:
1465:
1460:
1455:
1450:
1448:Ethylestradiol
1445:
1443:Ethinylestriol
1440:
1439:
1438:
1433:
1423:
1422:
1421:
1411:
1406:
1405:
1404:
1399:
1394:
1392:Estrone esters
1384:
1379:
1374:
1369:
1368:
1367:
1362:
1360:Estriol esters
1352:
1347:
1345:Estrapronicate
1342:
1337:
1332:
1331:
1330:
1325:
1320:
1310:
1305:
1300:
1295:
1290:
1285:
1280:
1275:
1267:
1262:
1257:
1252:
1247:
1242:
1237:
1236:
1235:
1225:
1220:
1215:
1210:
1205:
1200:
1170:
1165:
1163:Alestramustine
1160:
1155:
1150:
1145:
1140:
1135:
1130:
1125:
1120:
1115:
1110:
1100:
1095:
1090:
1085:
1080:
1075:
1070:
1065:
1063:16-Ketoestrone
1060:
1055:
1050:
1045:
1040:
1035:
1030:
1025:
1020:
1015:
1010:
1005:
1000:
995:
990:
985:
980:
975:
970:
965:
960:
955:
950:
945:
940:
935:
930:
925:
920:
911:
909:
902:
891:
890:
882:
880:
879:
872:
865:
857:
849:
848:
822:
787:
768:(2): 334–341.
734:
716:
665:
664:
662:
659:
658:
657:
652:
647:
642:
635:
632:
574:
571:
510:
507:
505:
502:
474:
471:
446:
424:
421:
419:
416:
381:
380:
378:
377:
374:
372:
369:
361:
360:
359:
356:
355:
353:
352:
349:
341:
340:
339:
336:
335:
333:
332:
324:
322:
314:
313:
307:
301:
300:
297:
288:
282:
276:
271:
265:
264:
260:
259:
257:
256:
243:
241:
228:
227:
225:
224:
216:
214:
208:
207:
205:
204:
196:
194:
188:
187:
185:
184:
176:
174:
168:
167:
165:
164:
156:
154:
143:
142:
140:
139:
131:
129:
123:
122:
120:
119:
108:
100:
99:
98:
95:
94:
90:
89:
87:
86:
73:
71:
65:
64:
60:
59:
54:
52:administration
46:
45:
42:
38:
37:
33:
32:
15:
13:
10:
9:
6:
4:
3:
2:
3242:
3231:
3228:
3226:
3223:
3221:
3218:
3216:
3213:
3211:
3208:
3207:
3205:
3190:
3187:
3185:
3182:
3180:
3177:
3175:
3172:
3170:
3167:
3164:
3163:
3160:
3150:
3147:
3145:
3142:
3141:
3139:
3135:
3129:
3126:
3124:
3121:
3119:
3116:
3114:
3111:
3109:
3106:
3105:
3103:
3099:
3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3057:
3053:
3050:
3048:
3045:
3043:
3040:
3038:
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2990:
2988:
2985:
2983:
2980:
2978:
2975:
2972:
2968:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2946:
2944:
2941:
2939:
2936:
2934:
2931:
2929:
2926:
2925:
2923:
2919:
2916:
2911:
2905:
2895:
2892:
2889:
2888:
2885:
2882:
2879:
2878:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2822:
2820:
2817:
2815:
2812:
2810:
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2789:
2785:
2781:
2777:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2724:
2722:
2718:
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:
2636:Pipendoxifene
2634:
2632:
2629:
2627:
2624:
2622:
2619:
2617:
2614:
2612:
2609:
2607:
2604:
2602:
2599:
2597:
2594:
2592:
2589:
2587:
2584:
2582:
2579:
2577:
2574:
2572:
2569:
2567:
2564:
2562:
2559:
2557:
2554:
2552:
2549:
2547:
2544:
2542:
2539:
2537:
2534:
2532:
2529:
2527:
2524:
2522:
2519:
2517:
2514:
2512:
2509:
2507:
2504:
2502:
2499:
2497:
2494:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2471:Clomifenoxide
2469:
2467:
2464:
2462:
2459:
2457:
2454:
2452:
2449:
2447:
2446:Brilanestrant
2444:
2442:
2439:
2437:
2434:
2432:
2429:
2427:
2424:
2422:
2419:
2417:
2414:
2412:
2409:
2407:
2404:
2402:
2399:
2397:
2394:
2392:
2389:
2388:
2386:
2380:
2371:
2364:
2360:
2356:
2353:
2349:
2345:
2341:
2337:
2333:
2329:
2325:
2321:
2317:
2313:
2309:
2306:
2303:
2299:
2295:
2292:
2289:
2285:
2282:-like (e.g.,
2281:
2278:
2275:
2271:
2267:
2263:
2259:
2255:
2251:
2248:
2245:
2241:
2237:
2233:
2230:
2227:
2226:guggulsterone
2223:
2219:
2215:
2211:
2210:Phytosteroids
2208:
2205:
2201:
2197:
2193:
2189:
2185:
2181:
2177:
2173:
2169:
2166:
2163:
2159:
2156:
2153:
2151:
2145:
2144:enterolactone
2141:
2137:
2134:
2132:
2129:
2126:
2122:
2118:
2114:
2110:
2106:
2102:
2098:
2094:
2090:
2086:
2082:
2078:
2074:
2070:
2066:
2062:
2058:
2054:
2050:
2046:
2042:
2038:
2034:
2030:
2026:
2022:
2018:
2014:
2010:
2006:
2002:
1998:
1995:
1992:
1988:
1984:
1981:
1978:
1977:wedelolactone
1974:
1970:
1966:
1962:
1959:
1956:
1955:photoanethole
1952:
1948:
1944:
1940:
1936:
1933:
1930:
1929:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1905:
1904:
1901:
1898:
1896:
1893:
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:
1811:
1810:Pentafluranol
1808:
1806:
1803:
1801:
1798:
1796:
1793:
1791:
1788:
1786:
1783:
1781:
1779:
1775:
1773:
1771:
1767:
1765:
1762:
1760:
1757:
1753:
1750:
1749:
1748:
1745:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1725:
1723:
1720:
1718:
1715:
1713:
1710:
1708:
1705:
1703:
1700:
1698:
1695:
1693:
1690:
1688:
1685:
1683:
1680:
1678:
1675:
1671:
1668:
1667:
1666:
1663:
1659:
1656:
1655:
1654:
1651:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1629:
1626:
1624:
1621:
1619:
1616:
1614:
1611:
1609:
1606:
1604:
1601:
1599:
1596:
1594:
1591:
1589:
1586:
1584:
1581:
1579:
1576:
1574:
1571:
1570:Nonsteroidal:
1568:
1567:
1564:
1561:
1559:
1556:
1554:
1551:
1549:
1546:
1544:
1541:
1539:
1536:
1534:
1531:
1529:
1526:
1524:
1521:
1519:
1516:
1514:
1511:
1509:
1506:
1504:
1501:
1499:
1496:
1494:
1491:
1489:
1486:
1484:
1481:
1479:
1476:
1474:
1471:
1469:
1466:
1464:
1461:
1459:
1456:
1454:
1451:
1449:
1446:
1444:
1441:
1437:
1434:
1432:
1429:
1428:
1427:
1424:
1420:
1419:Ethandrostate
1417:
1416:
1415:
1412:
1410:
1407:
1403:
1400:
1398:
1395:
1393:
1390:
1389:
1388:
1385:
1383:
1380:
1378:
1375:
1373:
1370:
1366:
1363:
1361:
1358:
1357:
1356:
1353:
1351:
1348:
1346:
1343:
1341:
1338:
1336:
1333:
1329:
1326:
1324:
1321:
1319:
1316:
1315:
1314:
1311:
1309:
1306:
1304:
1301:
1299:
1296:
1294:
1291:
1289:
1286:
1284:
1281:
1279:
1276:
1274:
1272:
1268:
1266:
1263:
1261:
1258:
1256:
1253:
1251:
1248:
1246:
1243:
1241:
1238:
1234:
1231:
1230:
1229:
1228:Cloxestradiol
1226:
1224:
1221:
1219:
1216:
1214:
1211:
1209:
1206:
1204:
1201:
1198:
1194:
1190:
1186:
1182:
1178:
1174:
1171:
1169:
1166:
1164:
1161:
1159:
1156:
1154:
1151:
1149:
1146:
1144:
1141:
1139:
1136:
1134:
1131:
1129:
1126:
1124:
1121:
1119:
1116:
1114:
1111:
1108:
1104:
1103:17α-Estradiol
1101:
1099:
1096:
1094:
1091:
1089:
1086:
1084:
1081:
1079:
1076:
1074:
1071:
1069:
1066:
1064:
1061:
1059:
1056:
1054:
1051:
1049:
1046:
1044:
1041:
1039:
1036:
1034:
1031:
1029:
1026:
1024:
1021:
1019:
1016:
1014:
1011:
1009:
1006:
1004:
1001:
999:
996:
994:
991:
989:
986:
984:
981:
979:
976:
974:
971:
969:
966:
964:
961:
959:
956:
954:
951:
949:
946:
944:
941:
939:
936:
934:
931:
929:
926:
924:
921:
919:
916:
913:
912:
910:
906:
903:
898:
892:
888:
885:
878:
873:
871:
866:
864:
859:
858:
855:
844:
840:
836:
829:
827:
823:
818:
814:
810:
806:
802:
798:
791:
788:
783:
779:
775:
771:
767:
763:
755:
753:
751:
749:
747:
745:
743:
741:
739:
735:
730:
726:
720:
717:
712:
708:
703:
698:
694:
690:
689:Endocrinology
686:
679:
677:
675:
673:
671:
667:
660:
656:
653:
651:
648:
646:
643:
641:
638:
637:
633:
631:
629:
623:
621:
616:
612:
608:
604:
603:bone turnover
600:
596:
592:
588:
584:
580:
572:
570:
568:
564:
560:
556:
552:
551:thrombophilia
548:
544:
540:
536:
532:
528:
524:
520:
516:
508:
503:
501:
499:
495:
491:
487:
483:
480:
472:
470:
468:
464:
461:
457:
453:
449:
442:
438:
434:
430:
422:
417:
415:
413:
410:
406:
402:
398:
395:
391:
387:
373:
368:
364:
357:
348:
344:
337:
330:
326:
325:
323:
320:
315:
308:
306:
302:
272:
270:
266:
261:
253:
249:
245:
244:
242:
233:
229:
222:
221:ChEMBL3545017
218:
217:
215:
213:
209:
202:
198:
197:
195:
193:
189:
182:
178:
177:
175:
173:
169:
162:
158:
157:
155:
148:
144:
137:
133:
132:
130:
128:
124:
116:
112:
107:
103:
96:
91:
85:
75:
74:
72:
70:
66:
61:
58:
55:
53:
47:
43:
39:
36:Clinical data
34:
30:
25:
2890:
2880:
2804:Mepitiostane
2752:Epitiostanol
2621:Ormeloxifene
2546:Lasofoxifene
2456:Camizestrant
2451:Broparestrol
2441:Bazedoxifene
2363:rotundifuran
2312:alkylphenols
2262:β-zearalenol
2258:α-zearalenol
2244:stigmasterol
2236:β-sitosterol
2232:Phytosterols
2200:triclocarban
2196:methoxychlor
2149:
2131:Lavender oil
2125:tectorigenin
2057:formononetin
1931:
1906:
1777:
1769:
1741:
1569:
1553:Quinestradol
1543:Promestriene
1518:Noretynodrel
1382:Estromustine
1335:Estramustine
1270:
1177:testosterone
914:
834:
800:
796:
790:
765:
761:
728:
719:
692:
688:
624:
591:side effects
589:-associated
576:
567:gynecomastia
541:) including
531:side effects
515:testosterone
512:
476:
439:relative to
426:
418:Pharmacology
389:
385:
384:
114:
110:
69:Legal status
63:Legal status
3149:Zearalenone
3101:Antagonists
3077:Resveratrol
3042:Nonylphenol
3037:Niacinamide
2953:Bisphenol A
2943:Aldosterone
2772:Glyceollins
2720:Antagonists
2711:Zuclomifene
2706:Zindoxifene
2616:NNC 45-1506
2611:NNC 45-0781
2606:NNC 45-0320
2601:NNC 45-0095
2596:Nitromifene
2576:Miproxifene
2526:Fispemifene
2501:Enclomifene
2496:Droloxifene
2476:CN-55945-27
2421:Afimoxifene
2411:Acefluranol
2302:rhaponticin
2298:resveratrol
2294:Stilbenoids
2266:zearalenone
2254:zearalanone
2240:campesterol
2172:alternariol
2105:pinocembrin
2049:epicatechin
2021:biochanin A
1961:Chalconoids
1855:Terfluranol
1830:Quadrosilan
1702:Elacestrant
1603:Allenestrol
1478:Lynestrenol
1402:Estropipate
1372:Estrofurate
1223:Clomestrone
1203:Atrimustine
1153:Abiraterone
1107:alfatradiol
803:(4): e581.
729:AdisInsight
579:leuprorelin
543:hot flashes
490:stilbestrol
312: g·mol
136:938067-78-8
93:Identifiers
41:Other names
3215:Benzamides
3204:Categories
3092:Tectoridin
3072:Raloxifene
3047:Oleuropein
2894:Trilostane
2839:Prochloraz
2799:MDL-101906
2794:ICI-164384
2681:Trioxifene
2676:Toremifene
2646:Raloxifene
2631:Panomifene
2626:Ospemifene
2591:Nafoxidine
2481:Cyclofenil
2436:Arzoxifene
2416:Acolbifene
2348:phthalates
2316:bisphenols
2288:miroestrol
2192:methiocarb
2180:endosulfan
2168:Pesticides
2140:enterodiol
2121:tectoridin
2101:penduletin
2097:naringenin
2081:kaempferol
1997:Flavonoids
1991:psoralidin
1987:coumestrol
1983:Coumestans
1947:dianethole
1900:WAY-214156
1890:WAY-200070
1885:WAY-169916
1880:WAY-166818
1850:SKF-82,958
1815:Phenestrol
1795:Methestrol
1780:-Hexestrol
1772:-Butestrol
1653:Dienestrol
1633:Carbestrol
1618:Bifluranol
1613:Benzestrol
1558:Quinestrol
1508:Nilestriol
1350:Estrazinol
1283:Epimestrol
1273:-Estradiol
1255:Cyclotriol
1193:nandrolone
1168:Almestrone
1003:7-Oxo-DHEA
915:Steroidal:
887:modulators
661:References
597:(CTX) and
317:3D model (
305:Molar mass
201:406GR1485Z
172:ChemSpider
127:CAS Number
102:IUPAC name
3087:Tamoxifen
3067:Quercetin
3007:Genistein
2987:Estradiol
2971:o',p'-DDE
2874:ZK-191703
2869:ZK-164015
2829:Phenytoin
2727:(R,R)-THC
2666:Tamoxifen
2641:Promensil
2566:LY-117018
2541:Idoxifene
2536:ICI-55548
2521:Femarelle
2506:Endoxifen
2466:Clomifene
2222:diosgenin
2218:digitalis
2214:digitoxin
2204:triclosan
2184:fenarimol
2117:quercetin
2093:myricetin
2089:mirificin
2077:glycitein
2069:genistein
2065:glabridin
2025:calycosin
2013:baicalein
1969:phloretin
1925:ZK-283197
1785:Mestilbol
1747:Hexestrol
1722:Fenestrel
1697:Efavirenz
1628:Butestrol
1583:2,8-DHHHC
1578:(S,S)-THC
1573:(R,R)-THC
1528:Pentolame
1523:Orestrate
1498:Moxestrol
1488:Mestranol
1453:Etynodiol
1313:Estradiol
1288:Equilenin
1250:Cyclodiol
1208:Bolandiol
817:0022-5347
725:"GTX 758"
561:. Unlike
547:bone loss
486:structure
482:benzamide
473:Chemistry
456:platelets
452:estradiol
401:GTx, Inc.
394:synthetic
390:Capesaris
109:3-fluoro-
50:Routes of
44:Capesaris
3165:See also
2967:p,p'-DDT
2958:Daidzein
2948:Atrazine
2921:Agonists
2849:RU-58668
2844:RU-39411
2691:U-11555A
2686:TZE-5323
2431:Anordrin
2426:Anordiol
2359:agnuside
2336:parabens
2176:dieldrin
2148:nyasol (
2113:puerarin
2109:prunetin
2073:genistin
2061:glabrene
2033:daidzein
2029:catechin
2017:baicalin
2009:apigenin
1939:anethole
1727:FERb 033
1563:Tibolone
1548:RU-16117
1533:Prodiame
1468:Hippulin
1463:Hexolame
1308:Estetrol
1218:Butolame
908:Agonists
782:24968970
711:22294742
634:See also
559:body fat
523:prostate
519:castrate
504:Research
409:phase II
181:34954411
161:46861578
57:By mouth
3210:Phenols
3137:Unknown
3113:Estriol
3017:GPER-L2
3012:GPER-L1
2696:U-11634
2571:Menerba
2561:LN-2299
2556:LN-1643
2531:GW-7604
2486:D-15413
2318:(e.g.,
2310:(e.g.,
2296:(e.g.,
2280:Steroid
2252:(e.g.,
2234:(e.g.,
2212:(e.g.,
2170:(e.g.,
2162:cadmium
2160:(e.g.,
2138:(e.g.,
2136:Lignans
2037:daidzin
2001:7,8-DHF
1999:(incl.
1985:(e.g.,
1963:(e.g.,
1845:SERBA-2
1840:SC-4289
1835:SC-3296
1742:GTx-758
1638:D-15414
1588:β-LGND1
1538:Prolame
1387:Estrone
1355:Estriol
1293:Equilin
1175:(e.g.,
1088:16α-LE2
640:16α-LE2
460:hepatic
431:of the
429:agonist
392:) is a
386:GTx-758
310:341.314
269:Formula
147:PubChem
21:GTx-758
3032:Niacin
3027:Kepone
2884:ERX-11
2854:SS1020
2762:ERB-88
2757:ERA-90
2661:SS1010
2586:MRL-37
1951:dianol
1920:ERB-79
1915:ERA-45
1910:ERB-26
1643:DCW234
1598:AC-186
1265:DHEA-S
1197:esters
1181:esters
1033:8β-VE2
815:
780:
709:
650:ERA-63
645:ERA-45
479:phenyl
343:SMILES
212:ChEMBL
82:
3108:CCL18
2982:Equol
2864:ZB716
2834:PHTPP
2701:Y-134
2378:SERMs
2373:Mixed
2053:equol
1935:Anise
1764:M2613
363:InChI
319:JSmol
3128:MIBE
3123:G-36
3118:G-15
3052:PCBs
2909:GPER
2819:MIBE
2352:PCBs
2344:PHBA
2340:PBBs
2188:HPTE
2045:EGCG
1943:anol
1778:meso
1770:meso
1260:DHEA
1195:and
1179:and
813:ISSN
778:PMID
707:PMID
613:and
537:(or
192:UNII
3082:STX
3002:G-1
2963:DDT
2784:III
2332:DDT
2330:),
2328:BPS
2324:BPF
2320:BPA
2220:),
2150:cis
2041:ECG
1271:ent
839:doi
805:doi
801:185
770:doi
697:doi
693:153
630:).
488:to
441:ERβ
437:ERα
237:EPA
151:CID
3206::
2969:,
2788:IV
2786:,
2782:,
2780:II
2778:,
2361:,
2350:,
2346:,
2342:,
2338:,
2334:,
2326:,
2322:,
2314:,
2300:,
2286:,
2272:,
2268:,
2264:,
2260:,
2256:,
2242:,
2238:,
2224:,
2202:,
2198:,
2194:,
2190:,
2186:,
2182:,
2178:,
2174:,
2146:,
2142:,
2123:,
2119:,
2115:,
2111:,
2107:,
2103:,
2099:,
2095:,
2091:,
2087:,
2083:,
2079:,
2075:,
2071:,
2067:,
2063:,
2059:,
2055:,
2051:,
2047:,
2043:,
2039:,
2035:,
2031:,
2027:,
2023:,
2019:,
2015:,
2011:,
2007:,
2003:,
1989:,
1975:,
1971:,
1967:,
1953:,
1949:,
1945:,
1941:,
1191:,
1187:,
1183:,
896:ER
825:^
811:.
799:.
776:.
766:67
764:.
737:^
727:.
705:.
691:.
687:.
669:^
553:,
549:,
545:,
500:.
447:50
445:EC
414:.
283:13
277:19
78:US
3058:)
3054:(
2973:)
2965:(
2790:)
2776:I
2774:(
2384:)
2375:(
2365:)
2354:)
2304:)
2290:)
2276:)
2246:)
2228:)
2216:(
2206:)
2164:)
2154:)
2127:)
1993:)
1979:)
1957:)
1109:)
1105:(
876:e
869:t
862:v
845:.
841::
819:.
807::
784:.
772::
713:.
699::
443:(
321:)
298:3
295:O
292:N
289:2
286:F
280:H
274:C
239:)
235:(
115:N
111:N
80::
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
