29:
404:, which in turn accounts for the lack of estrogenicity of EMATE. A short initial peak of estradiol and estrone levels was observed with E2MATE at the start of treatment in humans, followed by very high and long-lasting concentrations of EMATE and estrone sulfate in
504:
and little or no first-pass hepatic impact in humans, but was found to completely lack estrogenic effects. Following this, E2MATE was repurposed as an STS inhibitor, and is now under development for the treatment of endometriosis.
500:. However, estrogenicity was paradoxically observed with EMATE in rodents, and this resulted in clinical development of the compound not being pursued. However, E2MATE was investigated as an estradiol prodrug with improved oral
700:
Elger W, Wyrwa R, Ahmed G, Meece F, Nair HB, Santhamma B, et al. (January 2017). "Estradiol prodrugs (EP) for efficient oral estrogen treatment and abolished effects on estrogen modulated liver functions".
247:
650:
Elger W, Schwarz S, Hedden A, Reddersen G, Schneider B (December 1995). "Sulfamates of various estrogens are prodrugs with increased systemic and reduced hepatic estrogenicity at oral application".
816:
869:
289:
InChI=1S/C18H23NO4S/c1-18-9-8-14-13-5-3-12(23-24(19,21)22)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16H,2,4,6-9H2,1H3,(H2,19,21,22)/t14-,15-,16+,18+/m1/s1
261:
979:
809:
3125:
554:
Elger W, Barth A, Hedden A, Reddersen G, Ritter P, Schneider B, et al. (2001). "Estrogen sulfamates: a new approach to oral estrogen therapy".
604:
Thomas MP, Potter BV (September 2015). "Estrogen O-sulfamates and their analogues: Clinical steroid sulfatase inhibitors with broad potential".
2318:
3166:
3120:
802:
764:
420:
1089:
3115:
2849:
1074:
1069:
281:
396:, it prevents EMATE from entering the liver during the first pass with the oral route. The inhibition of STS by EMATE prevents its
2273:
83:
1524:
450:
3110:
2874:
1424:
984:
959:
485:
3130:
1372:
68:
1377:
3171:
2765:
2432:
2342:
1564:
884:
879:
3151:
2993:
2755:
2668:
2293:
1986:
1519:
1514:
1414:
2997:
1039:
44:
EMATE; J994; Estrone-3-O-sulfamate; 17-Oxoestra-1,3,5(10)-trien-3-yl sulfamate; 3-estra-1,3,5(10)-trien-17-one
3156:
2337:
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480:
of hormonally inactive steroid sulfates into their hormonally active forms (e.g., estrone sulfate into
1942:
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1982:
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757:
Estrogens and
Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen
393:
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cells observed at a concentration of 1 μM. At a dosage of 1 mg/kg orally or
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2577:
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1998:
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780:
134:
20:
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in rats, it effectively abolished estrone and DHEA-S sulfatase activities in all
3090:
3018:
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28:
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1196:
1134:
1109:
1029:
473:
STS activity occurring 7 days after a single 10 mg/kg dose in rats.
439:
358:
223:
145:
63:
484:), STS inhibitors like EMATE have potential applications in the treatment of
3028:
3008:
2948:
2928:
2770:
2607:
2482:
2477:
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2447:
2407:
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2058:
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2018:
2010:
2006:
1966:
1954:
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1700:
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1638:
1618:
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1439:
1429:
1394:
1254:
1229:
1191:
1149:
332:
974:
722:
625:
575:
384:
binding which, in turn, results in EMATE being taken up into and stored in
671:
2899:
2889:
2592:
2452:
2372:
2367:
2300:
2117:
2054:
2050:
2014:
2002:
1974:
1970:
1958:
1950:
1880:
1668:
1658:
1504:
1489:
1474:
1409:
1404:
1249:
1159:
3054:
2800:
2612:
2512:
2502:
2497:
2277:
2221:
2211:
2103:
1978:
1786:
1781:
1683:
1648:
1579:
1479:
1328:
1296:
1234:
481:
350:
120:
2973:
2968:
2825:
2089:
2077:
1892:
1861:
1856:
1851:
1584:
1239:
165:
567:
3049:
2923:
2805:
2775:
1994:
1876:
1705:
470:
454:
432:
389:
335:
246:
237:
3069:
2760:
2129:
1884:
798:
2904:
2319:
753:"Pharmacology of Inhibition of Estrogen-Metabolizing Enzymes"
421:
2850:
759:. Springer Science & Business Media. pp. 233–239.
408:, observations that are in accordance with STS inhibition.
703:
The
Journal of Steroid Biochemistry and Molecular Biology
652:
The
Journal of Steroid Biochemistry and Molecular Biology
606:
The
Journal of Steroid Biochemistry and Molecular Biology
746:
744:
742:
740:
1220:
Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
3078:
3042:
2862:
2848:
2661:
2314:
849:
835:
235:
222:
189:
184:
164:
144:
119:
99:
74:
62:
48:
40:
35:
133:
108:
2324:Tooltip Selective estrogen receptor modulators
1679:Furostilbestrol (diethylstilbestrol difuroate)
1040:16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
695:
693:
691:
689:
599:
597:
595:
593:
591:
589:
587:
585:
549:
547:
545:
543:
541:
539:
537:
535:
331:which has not yet been marketed. It is the C3
870:3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
810:
645:
643:
429:Tooltip half-maximal inhibitory concentration
361:into EMATE and has similar properties to it.
8:
980:10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
438:, with an almost complete inhibition of the
353:of estrogens. A closely related compound is
19:
2855:Tooltip G protein-coupled estrogen receptor
1674:Fosfestrol (diethylstilbestrol diphosphate)
2859:
1817:Triphenylmethylethylene (triphenylpropene)
1141:, many others; via estrogenic metabolites)
1065:17α-Epiestriol (16α-hydroxy-17α-estradiol)
846:
817:
803:
795:
469:, with only a small recovery (<10%) of
419:inhibitor of STS. It was found to have an
269:C12CC3(1CCC2=O)CCC4=C3C=CC(=C4)OS(=O)(=O)N
153:
837:
556:Reproduction, Fertility, and Development
515:List of estrogen esters § Estrone esters
531:
442:of physiological concentrations of the
286:
266:
88:
751:Reed MJ, Purohit A (6 December 2012).
18:
755:. In Oettel M, Schillinger E (eds.).
465:assessed. It also showed a prolonged
173:
7:
431:of 65 pM for STS inhibition in
349:however, EMATE is not an effective
124:
476:Due to its ability to prevent the
14:
2216:taleranol (teranol, β-zearalanol)
1131:metandienone (methandrostenolone)
787:. Springer Nature Switzerland AG.
3126:Progesterone receptor modulators
2880:Afimoxifene (4-hydroxytamoxifen)
1762:Prinaberel (ERB-041, WAY-202041)
207:
201:
27:
2823:Coregulator-binding modulators:
1090:17β-Methyl-17α-dihydroequilenin
357:(E2MATE), which is extensively
294:Key:RVKFQAJIXCZXQY-CBZIJGRNSA-N
1654:Erteberel (SERBA-1, LY-500307)
520:Steroid sulfatase § Inhibitors
451:dehydroepiandrosterone sulfate
216:
210:
195:
1:
3111:Receptor/signaling modulators
1075:17α-Ethynyl-3β-androstanediol
1070:17α-Ethynyl-3α-androstanediol
486:estrogen-dependent conditions
3167:Steroid sulfatase inhibitors
3121:Androgen receptor modulators
1425:Lynestrenol phenylpropionate
664:10.1016/0960-0760(95)00214-6
3116:Estrogens and antiestrogens
2766:Oxabicycloheptene sulfonate
2453:Etacstil (GW-5638, DPC-974)
1629:Doisynoestrol (fenocycline)
1373:Ethinylestradiol 3-benzoate
885:3β,5α-Dihydrolevonorgestrel
880:3α,5α-Dihydrolevonorgestrel
715:10.1016/j.jsbmb.2016.07.008
618:10.1016/j.jsbmb.2015.03.012
392:. Since this occurs in the
368:and undergoes little or no
91:phenanthren-3-yl] sulfamate
69:Steroid sulfatase inhibitor
3188:
2833:Noncompetitive inhibitors:
2458:Ethamoxytriphetol (MER-25)
1619:Dimestrol (dianisylhexene)
1378:Ethinylestradiol sulfonate
311:; developmental code name
185:Chemical and physical data
3103:
2875:7β-Hydroxyepiandrosterone
2433:Desmethylchlorotrianisene
1612:Diethylstilbestrol esters
1565:Bisdehydrodoisynolic acid
985:11β-Chloromethylestradiol
960:7β-Hydroxyepiandrosterone
842:Tooltip Estrogen receptor
277:
257:
79:
26:
2939:Fulvestrant (ICI-182780)
2756:Methylpiperidinopyrazole
2709:Fulvestrant (ICI-182780)
2192:Resorcylic acid lactones
1415:Hydroxyestrone diacetate
1351:Etamestrol (eptamestrol)
2250:Synthetic xenoestrogens
1807:Triphenylchloroethylene
1742:Methestrol dipropionate
1270:Polyestradiol phosphate
2343:4'-Hydroxynorendoxifen
2338:2-Phenylbenzothiophene
2212:zeranol (α-zearalanol)
1915:phlorizin (phloridzin)
1802:Triphenylbromoethylene
1701:ICI-85966 (Stilbostat)
1282:Estramustine phosphate
1155:Bolandiol dipropionate
411:EMATE is an extremely
2523:Miproxifene phosphate
2348:27-Hydroxycholesterol
1812:Triphenyliodoethylene
1356:Ethinylandrostenediol
1319:Estrogenic substances
1307:Polyestriol phosphate
1175:Cloxestradiol acetate
370:first-pass metabolism
1837:WAY-204688 (SIM-688)
1649:ERB-196 (WAY-202196)
1600:Dienestrol diacetate
1339:Estrone methyl ether
1245:Esterified estrogens
1187:Conjugated estrogens
1080:17β-Dihydroequilenin
1055:17α-Dihydroequilenin
995:15α-Hydroxyestradiol
990:11β-Methoxyestradiol
965:8,9-Dehydroestradiol
380:of EMATE results in
3004:Propylpyrazoletriol
2919:Diarylpropionitrile
1767:Propylpyrazoletriol
1624:Dimethylstilbestrol
1590:Diarylpropionitrile
1400:Etynodiol diacetate
1100:Abiraterone acetate
1010:16α-Fluoroestradiol
394:hepatic portal vein
374:oral administration
355:estradiol sulfamate
23:
3086:Diethylstilbestrol
2870:2-Methoxyestradiol
2801:TAS-108 (SR-16234)
2751:Methylepitiostanol
2689:EM-800 (SCH-57050)
2613:TAS-108 (SR-16234)
2333:2-Phenylbenzofuran
1947:8-prenylnaringenin
1607:Diethylstilbestrol
1265:Lipoidal estradiol
1240:ERA-63 (ORG-37663)
1182:Conjugated estriol
1127:methyltestosterone
1085:17β-Dihydroequilin
1060:17α-Dihydroequilin
1035:16β-Hydroxyestrone
1020:16α-Hydroxyestrone
970:8,9-Dehydroestrone
955:7α-Methylestradiol
930:4-Methoxyestradiol
920:4-Hydroxyestradiol
895:3β-Hydroxytibolone
890:3α-Hydroxytibolone
860:2-Hydroxyestradiol
467:duration of action
382:carbonic anhydrase
3139:
3138:
3131:List of estrogens
3099:
3098:
2844:
2843:
2684:Cytestrol acetate
1907:isoliquiritigenin
1849:Unknown/unsorted:
1535:β-LGND2 (GTx-878)
1115:Anabolic steroids
1025:16α-Iodoestradiol
915:4-Fluoroestradiol
910:4-Androstenedione
900:3β-Androstanediol
875:3α-Androstanediol
826:Estrogen receptor
766:978-3-642-60107-1
709:(Pt B): 305–311.
490:estrogen receptor
400:into estrone and
364:EMATE shows high
325:steroid sulfatase
305:Estrone sulfamate
302:
301:
248:Interactive image
21:Estrone sulfamate
16:Chemical compound
3179:
3172:Sulfamate esters
2998:2,2',5'-PCB-4-OH
2934:Ethinylestradiol
2860:
2856:
2852:
2593:Rimostil (P-081)
2403:Chlorotrianisene
2325:
2321:
2100:Metalloestrogens
1879:-related (e.g.,
1694:Hexestrol esters
1368:Ethinylestradiol
1260:Estradiol esters
1015:16α-Hydroxy-DHEA
1000:16-Ketoestradiol
940:5-Androstenediol
935:4-Methoxyestrone
925:4-Hydroxyestrone
905:4-Androstenediol
865:2-Hydroxyestrone
847:
843:
839:
819:
812:
805:
796:
789:
788:
777:
771:
770:
748:
735:
734:
697:
684:
683:
658:(3–4): 395–403.
647:
638:
637:
601:
580:
579:
551:
502:pharmacokinetics
444:steroid sulfates
430:
426:
376:. The sulfamate
250:
230:
218:
212:
209:
203:
197:
177:
157:
137:
127:
126:
112:
31:
24:
22:
3187:
3186:
3182:
3181:
3180:
3178:
3177:
3176:
3152:Abandoned drugs
3142:
3141:
3140:
3135:
3095:
3074:
3038:
2854:
2840:
2674:7β-Hydroxy-DHEA
2657:
2493:Levormeloxifene
2323:
2316:
2310:
2226:deoxymiroestrol
2094:-hinokiresinol)
1732:Methallenestril
1634:Doisynolic acid
1435:Methylestradiol
950:7α-Hydroxy-DHEA
841:
831:
823:
793:
792:
779:
778:
774:
767:
750:
749:
738:
699:
698:
687:
649:
648:
641:
603:
602:
583:
568:10.1071/rd01029
553:
552:
533:
528:
511:
447:estrone sulfate
428:
425:
366:bioavailability
347:estrogen esters
345:. Unlike other
298:
295:
290:
285:
284:
273:
270:
265:
264:
253:
228:
215:
206:
200:
180:
160:
140:
123:
115:
95:
92:
87:
86:
51:
17:
12:
11:
5:
3185:
3183:
3175:
3174:
3169:
3164:
3159:
3157:Estrone esters
3154:
3144:
3143:
3137:
3136:
3134:
3133:
3128:
3123:
3118:
3113:
3108:
3104:
3101:
3100:
3097:
3096:
3094:
3093:
3088:
3082:
3080:
3076:
3075:
3073:
3072:
3067:
3062:
3057:
3052:
3046:
3044:
3040:
3039:
3037:
3036:
3031:
3026:
3021:
3016:
3011:
3006:
3001:
2991:
2986:
2981:
2976:
2971:
2966:
2964:Hydroxytyrosol
2961:
2956:
2951:
2946:
2941:
2936:
2931:
2926:
2921:
2916:
2902:
2897:
2892:
2887:
2882:
2877:
2872:
2866:
2864:
2857:
2846:
2845:
2842:
2841:
2839:
2838:
2829:
2828:
2819:
2818:
2813:
2808:
2803:
2798:
2793:
2788:
2783:
2778:
2773:
2768:
2763:
2758:
2753:
2748:
2743:
2738:
2733:
2711:
2706:
2701:
2696:
2691:
2686:
2681:
2679:Chloroindazole
2676:
2671:
2665:
2663:
2659:
2658:
2656:
2655:
2650:
2645:
2640:
2635:
2630:
2625:
2620:
2615:
2610:
2605:
2600:
2598:Spironolactone
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2490:
2485:
2480:
2475:
2470:
2465:
2460:
2455:
2450:
2445:
2440:
2435:
2430:
2425:
2420:
2415:
2410:
2405:
2400:
2395:
2390:
2385:
2380:
2375:
2370:
2365:
2360:
2355:
2350:
2345:
2340:
2335:
2329:
2327:
2312:
2311:
2309:
2308:
2299:Others (e.g.,
2297:
2247:
2233:
2219:
2189:
2171:
2149:
2107:
2097:
2075:
2070:
2027:liquiritigenin
1936:
1922:
1900:
1874:Xenoestrogens:
1870:
1869:
1864:
1859:
1854:
1845:
1844:
1839:
1834:
1829:
1824:
1819:
1814:
1809:
1804:
1799:
1794:
1789:
1784:
1779:
1774:
1769:
1764:
1759:
1754:
1749:
1747:Paroxypropione
1744:
1739:
1734:
1729:
1724:
1716:
1708:
1703:
1698:
1697:
1696:
1686:
1681:
1676:
1671:
1666:
1661:
1659:Estrobin (DBE)
1656:
1651:
1646:
1641:
1636:
1631:
1626:
1621:
1616:
1615:
1614:
1604:
1603:
1602:
1592:
1587:
1582:
1577:
1572:
1567:
1562:
1557:
1552:
1550:Allenolic acid
1547:
1542:
1537:
1532:
1527:
1522:
1517:
1508:
1507:
1502:
1497:
1492:
1487:
1482:
1477:
1472:
1467:
1462:
1457:
1455:Norethisterone
1452:
1447:
1445:Mytatrienediol
1442:
1437:
1432:
1427:
1422:
1417:
1412:
1407:
1402:
1397:
1392:
1390:Ethylestradiol
1387:
1385:Ethinylestriol
1382:
1381:
1380:
1375:
1365:
1364:
1363:
1353:
1348:
1347:
1346:
1341:
1336:
1334:Estrone esters
1326:
1321:
1316:
1311:
1310:
1309:
1304:
1302:Estriol esters
1294:
1289:
1287:Estrapronicate
1284:
1279:
1274:
1273:
1272:
1267:
1262:
1252:
1247:
1242:
1237:
1232:
1227:
1222:
1217:
1209:
1204:
1199:
1194:
1189:
1184:
1179:
1178:
1177:
1167:
1162:
1157:
1152:
1147:
1142:
1112:
1107:
1105:Alestramustine
1102:
1097:
1092:
1087:
1082:
1077:
1072:
1067:
1062:
1057:
1052:
1042:
1037:
1032:
1027:
1022:
1017:
1012:
1007:
1005:16-Ketoestrone
1002:
997:
992:
987:
982:
977:
972:
967:
962:
957:
952:
947:
942:
937:
932:
927:
922:
917:
912:
907:
902:
897:
892:
887:
882:
877:
872:
867:
862:
853:
851:
844:
833:
832:
824:
822:
821:
814:
807:
799:
791:
790:
772:
765:
736:
685:
639:
581:
562:(4): 297–305.
530:
529:
527:
524:
523:
522:
517:
510:
507:
459:subcutaneously
423:
300:
299:
297:
296:
293:
291:
288:
280:
279:
278:
275:
274:
272:
271:
268:
260:
259:
258:
255:
254:
252:
251:
243:
241:
233:
232:
226:
220:
219:
213:
204:
198:
193:
187:
186:
182:
181:
179:
178:
170:
168:
162:
161:
159:
158:
150:
148:
142:
141:
139:
138:
130:
128:
117:
116:
114:
113:
105:
103:
97:
96:
94:
93:
90:
82:
81:
80:
77:
76:
72:
71:
66:
60:
59:
54:
52:administration
46:
45:
42:
38:
37:
33:
32:
15:
13:
10:
9:
6:
4:
3:
2:
3184:
3173:
3170:
3168:
3165:
3163:
3160:
3158:
3155:
3153:
3150:
3149:
3147:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3106:
3105:
3102:
3092:
3089:
3087:
3084:
3083:
3081:
3077:
3071:
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3047:
3045:
3041:
3035:
3032:
3030:
3027:
3025:
3022:
3020:
3017:
3015:
3012:
3010:
3007:
3005:
3002:
2999:
2995:
2992:
2990:
2987:
2985:
2982:
2980:
2977:
2975:
2972:
2970:
2967:
2965:
2962:
2960:
2957:
2955:
2952:
2950:
2947:
2945:
2942:
2940:
2937:
2935:
2932:
2930:
2927:
2925:
2922:
2920:
2917:
2914:
2910:
2906:
2903:
2901:
2898:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2867:
2865:
2861:
2858:
2853:
2847:
2837:
2834:
2831:
2830:
2827:
2824:
2821:
2820:
2817:
2814:
2812:
2809:
2807:
2804:
2802:
2799:
2797:
2794:
2792:
2789:
2787:
2784:
2782:
2779:
2777:
2774:
2772:
2769:
2767:
2764:
2762:
2759:
2757:
2754:
2752:
2749:
2747:
2744:
2742:
2739:
2737:
2734:
2731:
2727:
2723:
2719:
2715:
2712:
2710:
2707:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2682:
2680:
2677:
2675:
2672:
2670:
2667:
2666:
2664:
2660:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2578:Pipendoxifene
2576:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2416:
2414:
2413:Clomifenoxide
2411:
2409:
2406:
2404:
2401:
2399:
2396:
2394:
2391:
2389:
2388:Brilanestrant
2386:
2384:
2381:
2379:
2376:
2374:
2371:
2369:
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2330:
2328:
2322:
2313:
2306:
2302:
2298:
2295:
2291:
2287:
2283:
2279:
2275:
2271:
2267:
2263:
2259:
2255:
2251:
2248:
2245:
2241:
2237:
2234:
2231:
2227:
2224:-like (e.g.,
2223:
2220:
2217:
2213:
2209:
2205:
2201:
2197:
2193:
2190:
2187:
2183:
2179:
2175:
2172:
2169:
2168:guggulsterone
2165:
2161:
2157:
2153:
2152:Phytosteroids
2150:
2147:
2143:
2139:
2135:
2131:
2127:
2123:
2119:
2115:
2111:
2108:
2105:
2101:
2098:
2095:
2093:
2087:
2086:enterolactone
2083:
2079:
2076:
2074:
2071:
2068:
2064:
2060:
2056:
2052:
2048:
2044:
2040:
2036:
2032:
2028:
2024:
2020:
2016:
2012:
2008:
2004:
2000:
1996:
1992:
1988:
1984:
1980:
1976:
1972:
1968:
1964:
1960:
1956:
1952:
1948:
1944:
1940:
1937:
1934:
1930:
1926:
1923:
1920:
1919:wedelolactone
1916:
1912:
1908:
1904:
1901:
1898:
1897:photoanethole
1894:
1890:
1886:
1882:
1878:
1875:
1872:
1871:
1868:
1865:
1863:
1860:
1858:
1855:
1853:
1850:
1847:
1846:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1823:
1820:
1818:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1778:
1775:
1773:
1770:
1768:
1765:
1763:
1760:
1758:
1755:
1753:
1752:Pentafluranol
1750:
1748:
1745:
1743:
1740:
1738:
1735:
1733:
1730:
1728:
1725:
1723:
1721:
1717:
1715:
1713:
1709:
1707:
1704:
1702:
1699:
1695:
1692:
1691:
1690:
1687:
1685:
1682:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1645:
1642:
1640:
1637:
1635:
1632:
1630:
1627:
1625:
1622:
1620:
1617:
1613:
1610:
1609:
1608:
1605:
1601:
1598:
1597:
1596:
1593:
1591:
1588:
1586:
1583:
1581:
1578:
1576:
1573:
1571:
1568:
1566:
1563:
1561:
1558:
1556:
1553:
1551:
1548:
1546:
1543:
1541:
1538:
1536:
1533:
1531:
1528:
1526:
1523:
1521:
1518:
1516:
1513:
1512:Nonsteroidal:
1510:
1509:
1506:
1503:
1501:
1498:
1496:
1493:
1491:
1488:
1486:
1483:
1481:
1478:
1476:
1473:
1471:
1468:
1466:
1463:
1461:
1458:
1456:
1453:
1451:
1448:
1446:
1443:
1441:
1438:
1436:
1433:
1431:
1428:
1426:
1423:
1421:
1418:
1416:
1413:
1411:
1408:
1406:
1403:
1401:
1398:
1396:
1393:
1391:
1388:
1386:
1383:
1379:
1376:
1374:
1371:
1370:
1369:
1366:
1362:
1361:Ethandrostate
1359:
1358:
1357:
1354:
1352:
1349:
1345:
1342:
1340:
1337:
1335:
1332:
1331:
1330:
1327:
1325:
1322:
1320:
1317:
1315:
1312:
1308:
1305:
1303:
1300:
1299:
1298:
1295:
1293:
1290:
1288:
1285:
1283:
1280:
1278:
1275:
1271:
1268:
1266:
1263:
1261:
1258:
1257:
1256:
1253:
1251:
1248:
1246:
1243:
1241:
1238:
1236:
1233:
1231:
1228:
1226:
1223:
1221:
1218:
1216:
1214:
1210:
1208:
1205:
1203:
1200:
1198:
1195:
1193:
1190:
1188:
1185:
1183:
1180:
1176:
1173:
1172:
1171:
1170:Cloxestradiol
1168:
1166:
1163:
1161:
1158:
1156:
1153:
1151:
1148:
1146:
1143:
1140:
1136:
1132:
1128:
1124:
1120:
1116:
1113:
1111:
1108:
1106:
1103:
1101:
1098:
1096:
1093:
1091:
1088:
1086:
1083:
1081:
1078:
1076:
1073:
1071:
1068:
1066:
1063:
1061:
1058:
1056:
1053:
1050:
1046:
1045:17α-Estradiol
1043:
1041:
1038:
1036:
1033:
1031:
1028:
1026:
1023:
1021:
1018:
1016:
1013:
1011:
1008:
1006:
1003:
1001:
998:
996:
993:
991:
988:
986:
983:
981:
978:
976:
973:
971:
968:
966:
963:
961:
958:
956:
953:
951:
948:
946:
943:
941:
938:
936:
933:
931:
928:
926:
923:
921:
918:
916:
913:
911:
908:
906:
903:
901:
898:
896:
893:
891:
888:
886:
883:
881:
878:
876:
873:
871:
868:
866:
863:
861:
858:
855:
854:
852:
848:
845:
840:
834:
830:
827:
820:
815:
813:
808:
806:
801:
800:
797:
786:
782:
776:
773:
768:
762:
758:
754:
747:
745:
743:
741:
737:
732:
728:
724:
720:
716:
712:
708:
704:
696:
694:
692:
690:
686:
681:
677:
673:
669:
665:
661:
657:
653:
646:
644:
640:
635:
631:
627:
623:
619:
615:
611:
607:
600:
598:
596:
594:
592:
590:
588:
586:
582:
577:
573:
569:
565:
561:
557:
550:
548:
546:
544:
542:
540:
538:
536:
532:
525:
521:
518:
516:
513:
512:
508:
506:
503:
499:
498:endometriosis
495:
494:breast cancer
491:
487:
483:
479:
474:
472:
468:
464:
460:
456:
452:
448:
445:
441:
437:
434:
427:
418:
414:
409:
407:
403:
399:
398:bioactivation
395:
391:
387:
383:
379:
375:
371:
367:
362:
360:
356:
352:
348:
344:
341:
337:
334:
330:
326:
322:
320:
314:
310:
306:
292:
287:
283:
276:
267:
263:
256:
249:
245:
244:
242:
239:
234:
227:
225:
221:
194:
192:
188:
183:
176:
172:
171:
169:
167:
163:
156:
152:
151:
149:
147:
143:
136:
132:
131:
129:
122:
118:
111:
107:
106:
104:
102:
98:
89:
85:
78:
73:
70:
67:
65:
61:
58:
55:
53:
47:
43:
39:
36:Clinical data
34:
30:
25:
2832:
2822:
2746:Mepitiostane
2694:Epitiostanol
2563:Ormeloxifene
2488:Lasofoxifene
2398:Camizestrant
2393:Broparestrol
2383:Bazedoxifene
2305:rotundifuran
2254:alkylphenols
2204:β-zearalenol
2200:α-zearalenol
2186:stigmasterol
2178:β-sitosterol
2174:Phytosterols
2142:triclocarban
2138:methoxychlor
2091:
2073:Lavender oil
2067:tectorigenin
1999:formononetin
1873:
1848:
1719:
1711:
1511:
1495:Quinestradol
1485:Promestriene
1460:Noretynodrel
1324:Estromustine
1277:Estramustine
1212:
1119:testosterone
856:
784:
775:
756:
706:
702:
655:
651:
609:
605:
559:
555:
475:
417:irreversible
410:
406:erythrocytes
386:erythrocytes
363:
318:
316:
312:
308:
304:
303:
175:ChEMBL122708
3091:Zearalenone
3043:Antagonists
3019:Resveratrol
2984:Nonylphenol
2979:Niacinamide
2895:Bisphenol A
2885:Aldosterone
2714:Glyceollins
2662:Antagonists
2653:Zuclomifene
2648:Zindoxifene
2558:NNC 45-1506
2553:NNC 45-0781
2548:NNC 45-0320
2543:NNC 45-0095
2538:Nitromifene
2518:Miproxifene
2468:Fispemifene
2443:Enclomifene
2438:Droloxifene
2418:CN-55945-27
2363:Afimoxifene
2353:Acefluranol
2244:rhaponticin
2240:resveratrol
2236:Stilbenoids
2208:zearalenone
2196:zearalanone
2182:campesterol
2114:alternariol
2047:pinocembrin
1991:epicatechin
1963:biochanin A
1903:Chalconoids
1797:Terfluranol
1772:Quadrosilan
1644:Elacestrant
1545:Allenestrol
1420:Lynestrenol
1344:Estropipate
1314:Estrofurate
1165:Clomestrone
1145:Atrimustine
1095:Abiraterone
1049:alfatradiol
785:AdisInsight
612:: 160–169.
359:metabolized
231: g·mol
110:148672-09-7
75:Identifiers
41:Other names
3146:Categories
3034:Tectoridin
3014:Raloxifene
2989:Oleuropein
2836:Trilostane
2781:Prochloraz
2741:MDL-101906
2736:ICI-164384
2623:Trioxifene
2618:Toremifene
2588:Raloxifene
2573:Panomifene
2568:Ospemifene
2533:Nafoxidine
2423:Cyclofenil
2378:Arzoxifene
2358:Acolbifene
2290:phthalates
2258:bisphenols
2230:miroestrol
2134:methiocarb
2122:endosulfan
2110:Pesticides
2082:enterodiol
2063:tectoridin
2043:penduletin
2039:naringenin
2023:kaempferol
1939:Flavonoids
1933:psoralidin
1929:coumestrol
1925:Coumestans
1889:dianethole
1842:WAY-214156
1832:WAY-200070
1827:WAY-169916
1822:WAY-166818
1792:SKF-82,958
1757:Phenestrol
1737:Methestrol
1722:-Hexestrol
1714:-Butestrol
1595:Dienestrol
1575:Carbestrol
1560:Bifluranol
1555:Benzestrol
1500:Quinestrol
1450:Nilestriol
1292:Estrazinol
1225:Epimestrol
1215:-Estradiol
1197:Cyclotriol
1135:nandrolone
1110:Almestrone
945:7-Oxo-DHEA
857:Steroidal:
829:modulators
526:References
492:-positive
478:conversion
440:hydrolysis
321:-sulfamate
317:estrone-3-
236:3D model (
224:Molar mass
146:ChemSpider
101:CAS Number
84:IUPAC name
64:Drug class
3029:Tamoxifen
3009:Quercetin
2949:Genistein
2929:Estradiol
2913:o',p'-DDE
2816:ZK-191703
2811:ZK-164015
2771:Phenytoin
2669:(R,R)-THC
2608:Tamoxifen
2583:Promensil
2508:LY-117018
2483:Idoxifene
2478:ICI-55548
2463:Femarelle
2448:Endoxifen
2408:Clomifene
2164:diosgenin
2160:digitalis
2156:digitoxin
2146:triclosan
2126:fenarimol
2059:quercetin
2035:myricetin
2031:mirificin
2019:glycitein
2011:genistein
2007:glabridin
1967:calycosin
1955:baicalein
1911:phloretin
1867:ZK-283197
1727:Mestilbol
1689:Hexestrol
1664:Fenestrel
1639:Efavirenz
1570:Butestrol
1525:2,8-DHHHC
1520:(S,S)-THC
1515:(R,R)-THC
1470:Pentolame
1465:Orestrate
1440:Moxestrol
1430:Mestranol
1395:Etynodiol
1255:Estradiol
1230:Equilenin
1192:Cyclodiol
1150:Bolandiol
402:estradiol
333:sulfamate
329:inhibitor
50:Routes of
3107:See also
2909:p,p'-DDT
2900:Daidzein
2890:Atrazine
2863:Agonists
2791:RU-58668
2786:RU-39411
2633:U-11555A
2628:TZE-5323
2373:Anordrin
2368:Anordiol
2301:agnuside
2278:parabens
2118:dieldrin
2090:nyasol (
2055:puerarin
2051:prunetin
2015:genistin
2003:glabrene
1975:daidzein
1971:catechin
1959:baicalin
1951:apigenin
1881:anethole
1669:FERb 033
1505:Tibolone
1490:RU-16117
1475:Prodiame
1410:Hippulin
1405:Hexolame
1250:Estetrol
1160:Butolame
850:Agonists
731:26650319
723:27449818
634:24116740
626:25843211
576:11800168
509:See also
340:estrogen
57:By mouth
3162:Ketones
3079:Unknown
3055:Estriol
2959:GPER-L2
2954:GPER-L1
2638:U-11634
2513:Menerba
2503:LN-2299
2498:LN-1643
2473:GW-7604
2428:D-15413
2260:(e.g.,
2252:(e.g.,
2238:(e.g.,
2222:Steroid
2194:(e.g.,
2176:(e.g.,
2154:(e.g.,
2112:(e.g.,
2104:cadmium
2102:(e.g.,
2080:(e.g.,
2078:Lignans
1979:daidzin
1943:7,8-DHF
1941:(incl.
1927:(e.g.,
1905:(e.g.,
1787:SERBA-2
1782:SC-4289
1777:SC-3296
1684:GTx-758
1580:D-15414
1530:β-LGND1
1480:Prolame
1329:Estrone
1297:Estriol
1235:Equilin
1117:(e.g.,
1030:16α-LE2
781:"PGL 2"
672:8541236
482:estrone
471:hepatic
463:tissues
388:in the
351:prodrug
343:estrone
338:of the
323:, is a
191:Formula
121:PubChem
2974:Niacin
2969:Kepone
2826:ERX-11
2796:SS1020
2704:ERB-88
2699:ERA-90
2603:SS1010
2528:MRL-37
1893:dianol
1862:ERB-79
1857:ERA-45
1852:ERB-26
1585:DCW234
1540:AC-186
1207:DHEA-S
1139:esters
1123:esters
975:8β-VE2
763:
729:
721:
678:
670:
632:
624:
574:
413:potent
378:moiety
327:(STS)
315:), or
262:SMILES
229:349.45
166:ChEMBL
155:113266
135:127676
3050:CCL18
2924:Equol
2806:ZB716
2776:PHTPP
2643:Y-134
2320:SERMs
2315:Mixed
1995:equol
1877:Anise
1706:M2613
727:S2CID
680:31312
676:S2CID
630:S2CID
488:like
455:MCF-7
436:cells
433:MCF-7
390:blood
372:with
336:ester
309:EMATE
282:InChI
238:JSmol
3070:MIBE
3065:G-36
3060:G-15
2994:PCBs
2851:GPER
2761:MIBE
2294:PCBs
2286:PHBA
2282:PBBs
2130:HPTE
1987:EGCG
1885:anol
1720:meso
1712:meso
1202:DHEA
1137:and
1121:and
761:ISBN
719:PMID
668:PMID
622:PMID
572:PMID
496:and
449:and
415:and
313:J994
3024:STX
2944:G-1
2905:DDT
2726:III
2274:DDT
2272:),
2270:BPS
2266:BPF
2262:BPA
2162:),
2092:cis
1983:ECG
1213:ent
711:doi
707:165
660:doi
614:doi
610:153
564:doi
453:in
125:CID
3148::
2911:,
2730:IV
2728:,
2724:,
2722:II
2720:,
2303:,
2292:,
2288:,
2284:,
2280:,
2276:,
2268:,
2264:,
2256:,
2242:,
2228:,
2214:,
2210:,
2206:,
2202:,
2198:,
2184:,
2180:,
2166:,
2144:,
2140:,
2136:,
2132:,
2128:,
2124:,
2120:,
2116:,
2088:,
2084:,
2065:,
2061:,
2057:,
2053:,
2049:,
2045:,
2041:,
2037:,
2033:,
2029:,
2025:,
2021:,
2017:,
2013:,
2009:,
2005:,
2001:,
1997:,
1993:,
1989:,
1985:,
1981:,
1977:,
1973:,
1969:,
1965:,
1961:,
1957:,
1953:,
1949:,
1945:,
1931:,
1917:,
1913:,
1909:,
1895:,
1891:,
1887:,
1883:,
1133:,
1129:,
1125:,
838:ER
783:.
739:^
725:.
717:.
705:.
688:^
674:.
666:.
656:55
654:.
642:^
628:.
620:.
608:.
584:^
570:.
560:13
558:.
534:^
424:50
422:IC
205:23
199:18
3000:)
2996:(
2915:)
2907:(
2732:)
2718:I
2716:(
2326:)
2317:(
2307:)
2296:)
2246:)
2232:)
2218:)
2188:)
2170:)
2158:(
2148:)
2106:)
2096:)
2069:)
1935:)
1921:)
1899:)
1051:)
1047:(
818:e
811:t
804:v
769:.
733:.
713::
682:.
662::
636:.
616::
578:.
566::
319:O
307:(
240:)
217:S
214:4
211:O
208:N
202:H
196:C
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