222:
412:
29:
533:
431:
then reduces the ring unsaturation and cleaves the benzylic nitrogen bond on the auxiliary to yield as the optically pure trans isomer. Displacement of bromine with the mercapto benzthiazole completes the synthesis of izonsteride.
566:
392:
The scheme used to produce a somewhat more complex 5-a-reductase inhibitor relies on a chiral auxiliary to yield the final product as a single enantiomer. The first step starts with the reaction of
764:
559:
63:
552:
298:
1507:
757:
496:
312:
750:
423:. The initial step in this case probably involves the acylation of nitrogen on the enamine; conjugate addition then completes the formation of the
1482:
531:, Audia JR, McQuaid LA, Neubauer BL, Rocco VP, "5-alpha-reductase inhibitors", issued 22 April 1997, assigned to Eli Lilly
1487:
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Androgens and androgen receptor : mechanisms, functions, and clinical application
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375:
but was never marketed. Izonsteride may also be useful in the treatment of
1361:
1326:
1316:
1296:
1017:
936:
28:
408:
adds the methyl group at what will be a steroid-like AB ring junction.
401:
356:
136:
951:
497:"Present and future pharmacotherapy for benign prostatic hyperplasia"
424:
360:
353:
349:
410:
297:
288:
956:
746:
548:
103:)-8--4,10b-dimethyl-1,4,4a,5,6,10b-hexahydrobenzoquinolin-3(2
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1213:
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35:
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124:
320:O=C4N(C)5CCc3cc(Sc1nc2c(cccc2s1)CC)ccc35(C)CC4
758:
560:
8:
19:
765:
751:
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1508:Drugs developed by Eli Lilly and Company
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317:
216:
92:
475:. Boston: Kluwer Academic Publishers.
18:
877:Selenium disulfide (selenium sulfide)
427:ring. Treatment of that product with
7:
140:
419:This product is then treated with
14:
887:Zinc pyrithione (pyrithione zinc)
400:-α-phenethylamine to afford the
348:, with dual effects on both the
255:
249:
27:
847:Ciclopirox olamine (ciclopirox)
447:List of 5α-reductase inhibitors
1483:Drugs not assigned an ATC code
363:. It was under development by
264:
261:
243:
1:
577:benign prostatic hyperplasia
373:benign prostatic hyperplasia
1529:
415:Preparation of Izonsteride
233:Chemical and physical data
1180:Potassium channel openers
333:(developmental code name
308:
83:
26:
1488:5α-Reductase inhibitors
1377:Glycopyrronium tosylate
1292:Aminobenzoate potassium
1224:5α-Reductase inhibitors
1172:Topilutamide (fluridil)
1117:5α-Reductase inhibitors
1092:Topical corticosteroids
989:Topical corticosteroids
661:Steroidal antiandrogens
590:5α-Reductase inhibitors
1372:Glycopyrronium bromide
1215:Hair growth inhibitors
902:Calcineurin inhibitors
442:5α-Reductase inhibitor
416:
961:urea-containing cream
414:
371:for the treatment of
365:Eli Lilly and Company
1437:Pregnenolone acetate
1138:Saw palmetto extract
715:Saw palmetto extract
679:Gestonorone caproate
1254:Cyproterone acetate
1157:Cyproterone acetate
1108:Alopecia treatments
1056:Anti-inflammatories
837:Cetrimonium bromide
808:Cyproterone acetate
674:Delmadinone acetate
377:androgenic alopecia
23:
417:
1470:
1469:
1407:Magnesium sulfate
1387:Hydrogen peroxide
1322:Calcium gluconate
981:Lithium succinate
976:Lithium gluconate
872:Piroctone olamine
740:
739:
684:Osaterone acetate
421:acryloyl chloride
328:
327:
299:Interactive image
202:CompTox Dashboard
16:Chemical compound
1520:
1347:Deoxycholic acid
1337:Cromoglicic acid
788:Anti-seborrheics
767:
760:
753:
744:
708:Pygeum africanum
623:Alpha-1 blockers
569:
562:
555:
546:
539:
537:
536:
532:
525:
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500:
493:
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469:Chang C (2002).
466:
404:. Reaction with
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210:
208:
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143:
142:
128:
31:
24:
22:
1528:
1527:
1523:
1522:
1521:
1519:
1518:
1517:
1498:Benzoquinolines
1493:Abandoned drugs
1473:
1472:
1471:
1466:
1432:Povidone-iodine
1382:Hyaluronic acid
1307:Benzoylperoxide
1275:
1209:
1102:
1050:
1027:
1005:Skin lightening
999:
782:
771:
741:
736:
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699:Herbal products
693:
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584:
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526:
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509:
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438:
429:triethyl silane
390:
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74:
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17:
12:
11:
5:
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1503:Benzothiazoles
1500:
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1465:
1464:
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1294:
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1268:
1267:
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1264:Spironolactone
1261:
1256:
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1239:
1238:
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1219:
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1208:
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1167:Spironolactone
1164:
1159:
1154:
1142:
1141:
1140:
1135:
1130:
1125:
1112:
1110:
1104:
1103:
1101:
1100:
1097:hydrocortisone
1087:
1086:
1081:
1076:
1071:
1069:Gamolenic acid
1066:
1060:
1058:
1052:
1051:
1049:
1048:
1043:
1037:
1035:
1033:Skin darkening
1029:
1028:
1026:
1025:
1020:
1015:
1009:
1007:
1001:
1000:
998:
997:
994:hydrocortisone
985:
984:
983:
978:
966:
965:
964:
954:
949:
947:Salicylic acid
944:
939:
927:
922:
921:
920:
915:
910:
898:
895:Antihistamines
891:
890:
889:
884:
879:
874:
869:
864:
859:
854:
849:
844:
834:
822:
821:
820:
818:Spironolactone
815:
810:
805:
792:
790:
784:
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777:preparations (
775:dermatological
772:
770:
769:
762:
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719:
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703:
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619:
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594:
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575:Drugs used in
574:
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541:
540:
520:
502:
488:
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437:
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394:bromotetralone
389:
386:
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381:
326:
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218:DTXSID80170230
213:
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52:administration
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37:
33:
32:
15:
13:
10:
9:
6:
4:
3:
2:
1525:
1514:
1513:Delta-lactams
1511:
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1501:
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1486:
1484:
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1463:
1460:
1458:
1455:
1453:
1450:
1447:
1443:
1440:
1438:
1435:
1433:
1430:
1428:
1427:Oxymetazoline
1425:
1423:
1420:
1418:
1415:
1413:
1410:
1408:
1405:
1403:
1400:
1398:
1395:
1393:
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1265:
1262:
1260:
1257:
1255:
1252:
1250:
1247:
1246:
1245:
1244:
1243:Antiandrogens
1240:
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1233:
1231:
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1225:
1221:
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1216:
1212:
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1199:
1196:
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1191:
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1170:
1168:
1165:
1163:
1160:
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1153:
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1149:
1148:
1147:
1146:Antiandrogens
1143:
1139:
1136:
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1129:
1126:
1124:
1121:
1120:
1119:
1118:
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1088:
1085:
1082:
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1077:
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1072:
1070:
1067:
1065:
1062:
1061:
1059:
1057:
1053:
1047:
1044:
1042:
1041:Afamelanotide
1039:
1038:
1036:
1034:
1030:
1024:
1021:
1019:
1016:
1014:
1011:
1010:
1008:
1006:
1002:
995:
991:
990:
986:
982:
979:
977:
974:
973:
972:
971:
970:Lithium salts
967:
962:
958:
955:
953:
950:
948:
945:
943:
940:
938:
935:
934:
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860:
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855:
853:
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848:
845:
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835:
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829:
828:
827:
823:
819:
816:
814:
811:
809:
806:
804:
801:
800:
799:
798:
797:Antiandrogens
794:
793:
791:
789:
785:
780:
776:
768:
763:
761:
756:
754:
749:
748:
745:
733:
730:
729:
727:
723:
717:
716:
712:
710:
709:
705:
704:
702:
700:
696:
690:
687:
685:
682:
680:
677:
675:
672:
670:
669:Allylestrenol
667:
666:
664:
662:
658:
652:
649:
647:
644:
642:
639:
637:
634:
632:
629:
628:
626:
624:
620:
613:
609:
606:
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595:
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591:
587:
582:
578:
570:
565:
563:
558:
556:
551:
550:
547:
530:
524:
521:
516:
512:
511:"Izonsteride"
506:
503:
498:
492:
489:
484:
482:1-4020-7188-4
478:
474:
473:
465:
463:
459:
452:
448:
445:
443:
440:
439:
435:
433:
430:
426:
422:
413:
409:
407:
406:methyl iodide
403:
399:
395:
387:
382:
380:
378:
374:
370:
366:
362:
358:
355:
351:
347:
343:
340:
336:
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318:
314:
307:
300:
296:
295:
293:
290:
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152:
148:
147:
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138:
134:
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122:
120:
118:
114:
106:
102:
98:
93:
89:
82:
77:
70:
69:
67:
65:
61:
58:
55:
53:
47:
43:
39:
36:Clinical data
34:
30:
25:
1462:Tralokinumab
1446:progesterone
1442:Progestogens
1412:Metandienone
1397:Lebrikizumab
1342:Delgocitinib
1301:testosterone
1271:Eflornithine
1249:Bicalutamide
1241:
1222:
1203:Ritlecitinib
1192:
1178:
1152:Bicalutamide
1144:
1115:
1090:
1079:Pimecrolimus
1064:Alitretinoin
1046:Melanotan II
1013:Hydroquinone
987:
968:
931:Keratolytics
929:
925:Isotretinoin
913:Pimecrolimus
900:
893:
862:Ketoconazole
857:Clotrimazole
824:
803:Bicalutamide
795:
713:
706:
523:
514:
505:
491:
471:
418:
397:
391:
346:5α-reductase
334:
330:
329:
104:
100:
96:
1452:Ruxolitinib
1422:Oclacitinib
1417:Nemolizumab
1332:Crisaborole
1312:Brimonidine
1287:Abrocitinib
1235:Finasteride
1230:Dutasteride
1133:Finasteride
1128:Dutasteride
1123:Alfatradiol
1023:Monobenzone
908:Cyclosporin
826:Antifungals
732:Mepartricin
608:Finasteride
603:Epristeride
598:Dutasteride
515:AdisInsight
331:Izonsteride
282: g·mol
126:176975-26-1
79:Identifiers
41:Other names
21:Izonsteride
1477:Categories
1457:Tiratricol
1402:Lokivetmab
1392:Ivermectin
1352:Diclofenac
1198:Nepidermin
1084:Tacrolimus
942:Resorcinol
918:Tacrolimus
882:Xenysalate
867:Miconazole
852:Climbazole
832:Bifonazole
689:Oxendolone
646:Tamsulosin
612:+tadalafil
529:US 5622962
453:References
335:LY-320,236
287:3D model (
275:Molar mass
191:A5E8C36F34
162:ChemSpider
117:CAS Number
88:IUPAC name
44:LY-320,236
1366:estradiol
1362:Estrogens
1357:Dupilumab
1297:Androgens
1259:Flutamide
1186:Minoxidil
1162:Flutamide
1074:Oxaceprol
841:cetrimide
813:Flutamide
651:Terazosin
641:Silodosin
636:Doxazosin
631:Alfuzosin
388:Synthesis
383:Chemistry
342:inhibitor
339:selective
50:Routes of
1327:Collagen
1317:Caffeine
1018:Mequinol
937:Coal tar
436:See also
369:Fujisawa
357:isoforms
64:ATC code
57:By mouth
1444:(e.g.,
1364:(e.g.,
1299:(e.g.,
1095:(e.g.,
992:(e.g.,
402:enamine
359:of the
354:type II
344:of the
337:) is a
239:Formula
137:PubChem
1280:Others
1193:Others
952:Sulfur
773:Other
725:Others
535:
479:
425:lactam
361:enzyme
350:type I
313:SMILES
280:422.61
171:151061
151:172988
396:with
289:JSmol
107:)-one
957:Urea
581:G04C
477:ISBN
367:and
352:and
182:UNII
99:,10b
71:None
779:D11
207:EPA
141:CID
95:(4a
1479::
513:.
461:^
379:.
253:26
247:24
1448:)
1368:)
1303:)
1099:)
996:)
963:)
959:(
843:)
839:(
781:)
766:e
759:t
752:v
614:)
610:(
583:)
579:(
568:e
561:t
554:v
538:.
517:.
499:.
485:.
398:R
291:)
268:2
265:S
262:O
259:2
256:N
250:H
244:C
209:)
205:(
105:H
101:R
97:R
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
