38:
252:
413:= 330 ng/mL and 2.5 ng/mL, respectively, for doses of 3.0 mg/rat each). As such, EC586 would appear to possess strongly increased oral bioavailability, potency, and systemic exposure relative to testosterone propionate. Additional research and details on the pharmacokinetics and properties of EC586 are to be published "soon".
29:
294:
InChI=1S/C30H39N3O6S/c1-29-13-11-19(34)16-18(29)5-7-21-22-8-10-26(30(22,2)14-12-23(21)29)39-28(36)25-4-3-15-33(25)27(35)24-9-6-20(17-32-24)40(31,37)38/h6,9,16-17,21-23,25-26H,3-5,7-8,10-15H2,1-2H3,(H2,31,37,38)/t21-,22-,23-,25-,26-,29-,30-/m0/s1
542:
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".
416:
The mechanism for the absence of first-pass metabolism and lack of disproportionate liver exposure with oral administration has been elucidated for a closely related sulfonamide–proline
672:
1104:
502:
Ahmed G, Elger W, Meece F, Nair HB, Schneider B, Wyrwa R, Nickisch K (October 2017). "A prodrug design for improved oral absorption and reduced hepatic interaction".
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366:
of testosterone in the body. However, unlike oral testosterone and conventional oral testosterone esters such as
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382:. As such, it may have a variety of desirable advantages over oral testosterone, similarly to
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of oral EC586 have been briefly assessed in rats in a small pilot study. Oral EC586 showed
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testosterone, but with the convenience of oral administration. Evestra intends to seek
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O=C1CC2(C)3()CC4(C)(OC(5CCCN5C(C6=CC=C(S(N())(=O)=O)C=N6)=O)=O)CC4()3()CCC2=C1
228:
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130:)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1
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401:(AUC) levels that were more than 100-fold greater than those of oral
586:
Sokolov MN, Rozhkov VV, Trukhan VM, Shimanovskii NL (1 June 2023).
2385:
2067:
1977:
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347:
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28:
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427:
Clinical trials for EC586 and EC508 are undergoing as of 2023.
2501:
378:, and may not have disproportionate androgenic effects in the
314:
testosterone 17β-(1-((5-(aminosulfonyl)-2-pyridinyl)carbonyl)-
1908:
Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
1867:
751:
Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
545:
The
Journal of Steroid Biochemistry and Molecular Biology
442:
List of investigational sex-hormonal agents § Androgenics
1592:
17α-Alkylated 5α-dihydro-19-nortestosterone derivatives:
1095:
7α-Methyl-19-norandrostenedione (MENT dione, trestione)
1789:
5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives:
57:-proline); Androst-4-en-17β-ol-3-one 17β-(1-carbonyl]-
134:-cyclopentaphenanthren-17-yl (5-sulfamoylpicolinoyl)-
2875:
639:
R&D Research / Research
Pipeline - Evestra, Inc.
2787:
2778:
2076:
1865:
1223:
Normethandrone (methylestrenolone, normethisterone)
705:
691:
240:
227:
191:
186:
166:
146:
89:
69:
49:
44:
587:
1435:17α-Alkylated 5α-dihydrotestosterone derivatives:
328:which is under development by Evestra for use in
390:status for EC586 in the fourth quarter of 2018.
61:-proline); 3-Oxoandrost-4-en-17β-yl 1-carbonyl]-
1654:5α-Dihydro-17α-ethynyltestosterone derivatives:
155:
1105:11β-Methyl-19-nortestosterone dodecylcarbonate
537:
535:
533:
497:
495:
493:
491:
489:
487:
485:
483:
481:
1872:Tooltip Selective androgen receptor modulator
1517:17α-Alkylated 19-nortestosterone derivatives:
666:
437:List of androgen esters § Testosterone esters
424:, which shows the same properties as EC586.
8:
1923:Enobosarm (ostarine, MK-2866, GTx-024, S-22)
19:
1674:17α-Ethynyl-19-nortestosterone derivatives:
2784:
1396:Methylclostebol (chloromethyltestosterone)
1291:5α-Dihydro-19-nortestosterone derivatives:
702:
673:
659:
651:
1617:17α-Vinyl-19-nortestosterone derivatives:
1233:Oxabolone cipionate (oxabolone cypionate)
849:DHEA (androstenolone, prasterone; 5-DHEA)
693:
459:
457:
175:
1324:Chlorodehydromethylandrostenediol (CDMA)
2925:List of androgens and anabolic steroids
1311:17α-Alkylated testosterone derivatives:
453:
291:
271:
103:
1329:Chlorodehydromethyltestosterone (CDMT)
1085:Testifenon (testiphenon, testiphenone)
53:EC-586; Testosterone 17β-(1-carbonyl]-
18:
1610:Norvinisterone (vinylnortestosterone)
1144:Bolmantalate (nandrolone adamantoate)
1139:Bolandione (19-nor-4-androstenedione)
854:DHEA enanthate (prasterone enanthate)
589:"Current Trends in Steroid Chemistry"
7:
2880:Tooltip Sex hormone-binding globulin
1627:17α-Ethynyltestosterone derivatives:
906:Polytestosterone phloretin phosphate
504:Bioorganic & Medicinal Chemistry
1550:Methylhydroxynandrolone (MOHN, MHN)
1255:Trenbolone hexahydrobenzylcarbonate
915:5α-Dihydrotestosterone derivatives:
783:Androstenedione (4-androstenedione)
1607:17α-Vinyltestosterone derivatives:
1369:Methandriol (methylandrostenediol)
14:
1647:Ethisterone (ethynyltestosterone)
1364:Metandienone (methandrostenolone)
1194:Methoxydienone (methoxygonadiene)
805:Boldione (1,4-androstadienedione)
756:Androstenediol (5-androstenediol)
721:4-Dehydroepiandrosterone (4-DHEA)
2920:Progesterone receptor modulators
1411:Methyltestosterone 3-hexyl ether
1374:Methandriol bisenanthoyl acetate
1334:Chloromethylandrostenediol (CMA)
1169:Dimethandrolone dodecylcarbonate
928:1-Androsterone (1-andro, 1-DHEA)
594:Pharmaceutical Chemistry Journal
209:
203:
36:
27:
2961:Experimental sex-hormone agents
1092:19-Nortestosterone derivatives:
299:Key:CYIIXLHIAANHDT-SFEKBMPBSA-N
2107:15β-Hydroxycyproterone acetate
1998:OPK-88004 (LY-2452473, TT-701)
467:. Evestra, Inc. Archived from
221:
215:
197:
1:
2905:Receptor/signaling modulators
1662:17α-Ethynyl-3β-androstanediol
1657:17α-Ethynyl-3α-androstanediol
1100:11β-Methyl-19-nortestosterone
2951:Anabolic–androgenic steroids
2915:Estrogen receptor modulators
2362:Trimethyltrienolone (R-2956)
1734:Lynestrenol phenylpropionate
1122:19-Nordehydroepiandrosterone
330:androgen replacement therapy
2910:Androgens and antiandrogens
2681:Ralaniten acetate (EPI-506)
2097:7α-Thiomethylspironolactone
1812:Medroxyprogesterone acetate
1174:Dimethandrolone undecanoate
985:Dihydromethylandrostenediol
776:Androstenediol dipropionate
557:10.1016/j.jsbmb.2016.07.008
473:EC586: Testosterone prodrug
374:, may undergo little or no
3007:
1000:Dihydrotestosterone esters
953:11-Ketodihydrotestosterone
766:Androstenediol 17β-acetate
746:11β-Hydroxyandrostenedione
731:4,17α-Dimethyltestosterone
606:10.1007/s11094-023-02887-0
409:ester of testosterone (AUC
187:Chemical and physical data
2897:
1804:Progesterone derivatives:
1595:5α-Dihydronorethandrolone
1164:Dimethandrolone buciclate
994:androstanolone, stanolone
990:Dihydrotestosterone (DHT)
948:7β-Hydroxyepiandrosterone
837:Cloxotestosterone acetate
761:Androstenediol 3β-acetate
713:Testosterone derivatives:
698:Tooltip Androgen receptor
516:10.1016/j.bmc.2017.08.027
282:
262:
94:
35:
26:
2610:-Butylbenzenesulfonamide
1797:5α-Dihydronorethisterone
1792:5α-Dihydrolevonorgestrel
1754:norethisterone enanthate
1723:levonorgestrel butanoate
1600:5α-Dihydronormethandrone
1453:Mebolazine (dimethazine)
1443:Desoxymethyltestosterone
1384:Methandriol dipropionate
1181:LS-1727 (nandrolone 17β-
1117:19-Nor-5-androstenedione
975:Dihydroethyltestosterone
771:Androstenediol diacetate
388:Investigational New Drug
368:testosterone undecanoate
2741:Topilutamide (fluridil)
2102:11α-Hydroxyprogesterone
1112:19-Nor-5-androstenediol
1012:Drostanolone propionate
403:testosterone propionate
339:– specifically, a C17β
2626:-Desmethylenzalutamide
2332:SC-5233 (spirolactone)
1750:norethisterone acetate
1389:Methandriol propionate
1260:Trenbolone undecanoate
1132:Bolandiol dipropionate
980:Dihydrofluoxymesterone
943:5α-Androst-2-en-17-one
798:Boldenone undecylenate
370:, EC586 has high oral
2618:-Desmethylapalutamide
2147:Chlormadinone acetate
2092:7α-Thiospironolactone
1963:LGD-2941 (LGD-122941)
1953:LG121071 (LGD-121071)
1827:3-Keto-5α-abiraterone
1807:6α-Methylprogesterone
1746:Norethisterone esters
1719:Levonorgestrel esters
1635:Ethinylandrostenediol
1485:Methyl-1-testosterone
1405:+esterified estrogens
1379:Methandriol diacetate
1044:Mesterolone cipionate
726:4-Hydroxytestosterone
376:first-pass metabolism
2307:Potassium canrenoate
1775:Quingestanol acetate
1585:Tetrahydrogestrinone
1473:Metenolone enanthate
1299:5α-Dihydrotrestolone
1294:5α-Dihydronandrolone
1282:Trestolone enanthate
1250:Trenbolone enanthate
1216:Norclostebol acetate
825:Clostebol propionate
399:area-under-the-curve
2991:Testosterone esters
2830:Dihydrotestosterone
2825:Dehydroandrosterone
2676:Ralaniten (EPI-002)
2557:Inocoterone acetate
2282:Nomegestrol acetate
2182:Delmadinone acetate
2172:Cyproterone acetate
2117:Abiraterone acetate
2087:7α-Thioprogesterone
1697:Etynodiol diacetate
901:Testosterone esters
844:Dehydroandrosterone
741:11-Ketotestosterone
465:"Research Pipeline"
23:
1667:Dihydroethisterone
1530:Dimethyltrienolone
1490:Methylepitiostanol
1468:Metenolone acetate
1401:Methyltestosterone
1304:19-Norandrosterone
1277:Trestolone acetate
1245:Trenbolone acetate
1189:-nitrosocarbamate)
1078:Stenbolone acetate
968:Bolazine capronate
820:Clostebol caproate
644:2017-09-29 at the
2933:
2932:
2893:
2892:
2863:
2856:
2849:
2842:
2774:
2773:
2297:Osaterone acetate
2257:Megestrol acetate
2122:Allyltestosterone
1898:Acetothiolutamide
1817:Megestrol acetate
1620:Vinyltestosterone
1525:Dimethyldienolone
1344:Ethyltestosterone
1272:Trestolone (MENT)
1204:Nandrolone esters
1185:-(2-chloroethyl)-
1061:Nisterime acetate
938:3α-Androstanediol
923:1-Androstenedione
832:Cloxotestosterone
815:Clostebol acetate
736:5-Androstenedione
682:Androgen receptor
551:(Pt B): 305–311.
510:(20): 5569–5575.
471:on 4 March 2018.
332:in men. It is an
307:
306:
253:Interactive image
16:Chemical compound
2998:
2881:
2877:
2861:
2854:
2847:
2840:
2785:
2567:Ketodarolutamide
2547:Hydroxyflutamide
2504:(via metabolite
1873:
1869:
1824:Others/unsorted:
1495:Methylstenbolone
1359:Hydroxystenozole
918:1-Androstenediol
716:4-Androstenediol
703:
699:
695:
675:
668:
661:
652:
626:
625:
591:
583:
577:
576:
539:
528:
527:
499:
476:
475:
461:
395:pharmacokinetics
362:– and acts as a
326:anabolic steroid
317:
312:, also known as
255:
235:
223:
217:
211:
205:
199:
179:
159:
137:
80:Anabolic steroid
64:
60:
56:
40:
31:
24:
22:
3006:
3005:
3001:
3000:
2999:
2997:
2996:
2995:
2976:Androgen esters
2936:
2935:
2934:
2929:
2889:
2879:
2770:
2492:Cyanonilutamide
2421:Bavdegalutamide
2232:Epitestosterone
2072:
1903:Acetoxolutamide
1871:
1861:
1570:Norethandrolone
1545:Methyldienolone
1349:Fluoxymesterone
1159:Dimethandrolone
1019:Epiandrosterone
697:
687:
679:
646:Wayback Machine
635:
630:
629:
585:
584:
580:
541:
540:
531:
501:
500:
479:
463:
462:
455:
450:
433:
418:estradiol ester
412:
315:
303:
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289:
278:
275:
270:
269:
258:
233:
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214:
208:
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182:
162:
142:
139:
135:
102:
101:
62:
58:
54:
17:
12:
11:
5:
3004:
3002:
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2988:
2983:
2978:
2973:
2968:
2963:
2958:
2953:
2948:
2938:
2937:
2931:
2930:
2928:
2927:
2922:
2917:
2912:
2907:
2902:
2898:
2895:
2894:
2891:
2890:
2888:
2887:
2882:
2872:
2867:
2843:-α-Amino acids
2837:
2832:
2827:
2822:
2791:
2789:
2782:
2776:
2775:
2772:
2771:
2769:
2768:
2763:
2758:
2753:
2748:
2743:
2738:
2733:
2728:
2723:
2718:
2713:
2708:
2703:
2698:
2693:
2688:
2683:
2678:
2673:
2668:
2663:
2658:
2653:
2648:
2643:
2638:
2633:
2628:
2620:
2612:
2604:
2599:
2594:
2589:
2584:
2579:
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2499:
2494:
2489:
2484:
2479:
2474:
2469:
2464:
2459:
2433:
2428:
2423:
2418:
2413:
2408:
2403:
2398:
2393:
2388:
2383:
2370:
2369:
2364:
2359:
2354:
2349:
2344:
2339:
2337:Spironolactone
2334:
2329:
2324:
2319:
2314:
2309:
2304:
2299:
2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2229:
2224:
2219:
2214:
2209:
2204:
2199:
2194:
2189:
2184:
2179:
2174:
2169:
2164:
2162:Cyproheptadine
2159:
2154:
2149:
2144:
2139:
2137:Canrenoic acid
2134:
2129:
2124:
2119:
2114:
2109:
2104:
2099:
2094:
2089:
2080:
2078:
2074:
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2071:
2070:
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2055:
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2040:
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2030:
2025:
2020:
2015:
2010:
2005:
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1995:
1990:
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1980:
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1920:
1915:
1910:
1905:
1900:
1895:
1890:
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1765:Norgestrienone
1762:
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1743:
1741:Norethisterone
1738:
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1726:
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1714:Levonorgestrel
1711:
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1497:
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1487:
1482:
1477:
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1431:
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1420:
1415:
1414:
1413:
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1393:
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1051:Methyldiazinol
1048:
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1046:
1036:
1031:
1026:
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1015:
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1003:
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987:
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945:
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933:1-Testosterone
930:
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2666:Proxalutamide
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2380:
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530:
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478:
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460:
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454:
447:
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428:
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385:
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334:orally active
331:
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297:
292:
288:
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272:
268:
261:
254:
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196:
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133:
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117:
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100:
93:
88:
85:
81:
77:
74:
72:
68:
52:
48:
45:Clinical data
43:
39:
34:
30:
25:
2986:Testosterone
2885:Testosterone
2671:Pyrilutamide
2623:
2615:
2607:
2572:Lavender oil
2562:Ketoconazole
2527:Enzalutamide
2497:Darolutamide
2431:Bicalutamide
2406:Atraric acid
2378:
2373:
2357:Trimegestone
2312:Promegestone
2277:Mifepristone
2252:Medrogestone
2197:Drospirenone
2152:Clascoterone
2083:
2049:
1993:JNJ-37654032
1988:JNJ-28330835
1983:JNJ-26146900
1879:
1823:
1803:
1788:
1770:Quingestanol
1687:Etonogestrel
1673:
1653:
1626:
1616:
1606:
1591:
1575:Propetandrol
1516:
1505:Oxymetholone
1480:Methasterone
1434:
1428:Tiomesterone
1418:Oxymesterone
1310:
1290:
1211:Norclostebol
1186:
1182:
1091:
1029:Mepitiostane
1024:Epitiostanol
1007:Drostanolone
958:Androsterone
914:
895:+dutasteride
891:Testosterone
859:DHEA sulfate
712:
597:
593:
581:
548:
544:
507:
503:
472:
469:the original
426:
415:
392:
360:testosterone
356:bioidentical
313:
309:
308:
157:2140269-95-8
131:
127:
123:
119:
115:
111:
107:
2956:Androstanes
2946:Amino acids
2870:Osteocalcin
2751:Vinclozolin
2736:Thalidomide
2731:Seviteronel
2661:Procymidone
2597:Masofaniten
2552:Inocoterone
2456:bisphenol S
2452:bisphenol F
2448:bisphenol A
2426:BAY-1024767
2401:Apalutamide
2347:Spiroxasone
2342:Spirorenone
2322:Rosterolone
2262:Mespirenone
2207:Edogestrone
2177:Delanterone
2167:Cyproterone
2157:Clometerone
2127:Benorterone
2112:Abiraterone
2077:Antagonists
2008:PF-06260414
1913:BMS-564,929
1837:Alternariol
1729:Lynestrenol
1682:Desogestrel
1565:Norboletone
1555:Metribolone
1500:Oxandrolone
1458:Mestanolone
1423:Penmesterol
1354:Formebolone
1319:Calusterone
1314:Bolasterone
1068:Prostanozol
1039:Mesterolone
405:, the C17β
341:sulfonamide
236: g·mol
90:Identifiers
50:Other names
2981:Sulfamates
2940:Categories
2864:-ornithine
2807:gadolinium
2656:Prochloraz
2651:Phenothrin
2631:Nilutamide
2602:Methiocarb
2522:Endosulfan
2487:Cioteronel
2482:Cimetidine
2472:BMS-641988
2467:BMS-570511
2462:BMS-501949
2436:Bisphenols
2391:Antarlides
2367:Zanoterone
2302:Oxendolone
2247:Ludaterone
2237:Galeterone
2187:Dicirenone
2084:Steroidal:
2050:Steroidal:
2043:Vosilasarm
1938:GSK2881078
1893:AC-262,536
1852:Trilostane
1760:Norgestrel
1709:Gestrinone
1677:Δ-Tibolone
1560:Mibolerone
1510:Stanozolol
1463:Metenolone
1240:Trenbolone
1199:Nandrolone
1149:Dienedione
1073:Stenbolone
1034:Mesabolone
886:Silandrone
881:Quinbolone
876:Plomestane
871:Formestane
866:Exemestane
788:Atamestane
685:modulators
448:References
407:propionate
384:parenteral
241:3D model (
229:Molar mass
177:C86SA44JFY
148:CAS Number
138:-prolinate
99:IUPAC name
71:Drug class
2971:Pyridines
2850:-arginine
2835:Estradiol
2815:strontium
2811:magnesium
2799:aluminium
2766:YM-175735
2701:Ro 5-2537
2696:Ro 2-7239
2646:PF-998425
2641:Pentomone
2582:LG-120907
2542:Flutamide
2537:Fenarimol
2477:CH5137291
2416:Bakuchiol
2352:Topterone
2317:Prorenone
2292:Osaterone
2287:Nordinone
2272:Mexrenone
2192:Dienogest
2142:Canrenone
2063:TFM-4AS-1
2003:ORM-11984
1943:GSK-4336A
1933:GLPG-0492
1857:ZM-182345
1704:Gestodene
1692:Etynodiol
1448:Furazabol
1339:Enestebol
1267:Trendione
1228:Oxabolone
1154:Dienolone
1127:Bolandiol
1056:Nisterime
810:Clostebol
793:Boldenone
622:259299284
614:1573-9031
420:known as
358:androgen
318:-proline)
2901:See also
2788:Agonists
2761:YM-92088
2726:RU-58841
2721:RU-58642
2716:RU-57073
2711:RU-56187
2706:RU-22930
2636:ONC1-13B
2587:LGD-1331
2512:Dieldrin
2506:p,p’-DDE
2411:AZD-3514
2396:Arabilin
2327:RU-15328
2267:Metogest
2202:DU-41165
2038:S-101479
2018:RU-59063
1973:LGD-4033
1968:LGD-3303
1958:LGD-2226
1948:GSK-8698
1847:Drupanol
1842:Cl-4AS-1
1782:Tibolone
963:Bolazine
706:Agonists
642:Archived
573:26650319
565:27449818
524:28886996
431:See also
322:androgen
320:, is an
76:Androgen
65:-proline
2857:-lysine
2845:(incl.
2803:calcium
2797:(incl.
2795:Cations
2592:Linuron
2532:EPI-001
2438:(e.g.,
2227:EM-6537
2222:EM-5855
2217:EM-5854
2212:EM-4350
2058:MK-0773
2053:EM-9017
2033:S-40503
1888:ACP-105
1883:198RL26
1748:(e.g.,
1721:(e.g.,
1630:Danazol
1580:RU-2309
1520:Bolenol
372:potency
364:prodrug
352:natural
350:of the
345:proline
193:Formula
2966:Enones
2780:GPRC6A
2756:YM-580
2686:RD-162
2577:LG-105
1928:FTBU-1
620:
612:
571:
563:
522:
267:SMILES
234:569.72
2444:BFDGE
2440:BADGE
2386:AA560
2068:YK-11
1978:LY305
1868:SARMs
618:S2CID
569:S2CID
422:EC508
380:liver
348:ester
310:EC586
287:InChI
243:JSmol
21:EC586
2876:SHBG
2819:zinc
2517:DIMP
2132:BOMT
2028:S-23
1918:DTIB
610:ISSN
561:PMID
520:PMID
411:0-3h
393:The
354:and
324:and
168:UNII
2502:DDT
2023:S-1
2013:R-1
602:doi
553:doi
549:165
512:doi
126:,17
122:,14
118:,13
114:,10
2942::
2859:,
2852:,
2817:,
2813:,
2809:,
2805:,
2801:,
2454:,
2450:,
2446:,
2442:,
1752:,
1407:)
996:)
897:)
694:AR
616:.
608:.
598:57
596:.
592:.
567:.
559:.
547:.
532:^
518:.
508:25
506:.
480:^
456:^
207:39
201:30
110:,9
106:(8
82:;
78:;
2866:)
2862:L
2855:L
2848:L
2841:L
2821:)
2624:N
2616:N
2608:N
2508:)
2458:)
2379:N
2377:5
1756:)
1725:)
1403:(
1187:N
1183:N
992:(
893:(
674:e
667:t
660:v
624:.
604::
575:.
555::
526:.
514::
343:–
316:L
245:)
222:S
219:6
216:O
213:3
210:N
204:H
198:C
136:L
132:H
128:S
124:S
120:S
116:R
112:S
108:R
63:L
59:L
55:L
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