Gestrinone
IUPAC 名称
(10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-1,6,16-trien-5-one
描述
Gestrinone was developed in the early 1970s and was tested clinically as a weekly oral contraceptive in European and North American countries. ]. Without significant advantages over other oral contraceptives and with its high price, gestrinone was no longer used after the Stage II clinical trial. However, from 1982 aroused widespread interest due to substantial therapeutic effects in treating endometriosis. Under different endocrine conditions, gestrinone possesses estrogenic, progestational, androgenic, antiestrogenic and antiprogesterone actions. Starting from gestrinone, chemists can synthesize tetrahydrogestrinone (THG) in one reaction step. THG is a real designer steroid; designer steroids (chemically modified steroids) pose a threat to the integrity of the sport community. These compounds have recently been detected in urine specimens from athletes, resulting in temporary or permanent suspension from amateur and/or professional competition. (PMID: 15934041, 17707720) [HMDB]
异构
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]
InChI标识符
InChI=1S/C21H24O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,9,11,13,18-19,23H,3,5-8,10,12H2,1H3/t18-,19+,20+,21+/m1/s1
键
BJJXHLWLUDYTGC-ANULTFPQSA-N