17α-Ethynyl-3α-androstanediol

Chemical compound (3R,5S,8R,9S,10S,13S,14S,17R)-17-ethynyl-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol Ethynylandrostanediol.svg skin-invert-image 250px By mouth Estrogen 183387-50-0 42611099 DB06307 32698509 891O182ZP5 Ethynylandrostanediol; HE3235; Apoptone; 17α-Ethynyl-5α-androstanediol; 17α-Ethynyl-5α-androstane-3α,17β-diol; 5α-Pregn-20-yne-3α,17α-diol 21 32 2 C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C)O 1S/C21H32O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,14-18,22-23H,5-13H2,2-3H3/t14-,15+,16+,17-,18-,19-,20-,21-/m0/s1 CKAXZOYFIHQCBN-JRRMKBMNSA-N 17α-Ethynyl-3α-androstanediol (developmental code names HE-3235, Apoptone), also known as 17α-ethynyl-5α-androstane-3α,17β-diol, is a synthetic androstane steroid and a 17α-substituted derivative of 3α-androstanediol which was never marketed. Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J 17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism Invest New Drugs 30 1 59–78 2012 20814732 10.1007/s10637-010-9517-0 24785562 Trauger R, Corey E, Bell D, White S, Garsd A, Stickney D, Reading C, Frincke J Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235) Br. J. Cancer 100 7 1068–72 2009 19337256 2669987 10.1038/sj.bjc.6604987 http://adisinsight.springer.com/drugs/800025305 Archived copy 2024-02-10 2025-04-15 https://web.archive.org/web/20250415182740/https://adisinsight.springer.com/drugs/800025305 dead It was under development for the treatment of prostate cancer but was discontinued. 17α-Ethynyl-3α-androstanediol itself shows very low affinity for steroid receptors, including the AR androgen receptor, ERα estrogen receptor alpha, ERβ estrogen receptor beta, PR progesterone receptor, and GR glucocorticoid receptor, and its mechanism of action is not well-characterized. Koreckij TD, Trauger RJ, Montgomery RB, Pitts TE, Coleman I, Nguyen H, Reading CL, Nelson PS, Vessella RL, Corey E HE3235 inhibits growth of castration-resistant prostate cancer Neoplasia 11 11 1216–25 2009 19881957 2767223 10.1593/neo.09960 It produces 5α-dihydroethisterone (5α-dihydro-17α-ethynyltestosterone), a ligand of several steroid hormone receptors, and 17α-ethynyl-3β-androstanediol, an estrogen, as active metabolites. These metabolites may contribute importantly to the biological activity of 17α-ethynyl-3α-androstanediol, with 17α-ethynyl-3α-androstanediol potentially serving as a prodrug. Beyler AL, Clinton RO Uterine growth stimulating and testicular growth suppressing activities of 17alpha-ethinylandrostane-3beta, 17beta-diol, its delta 5-analog and derivatives Proc. Soc. Exp. Biol. Med. 92 2 404–8 June 1956 13350363 10.3181/00379727-92-22493 87469965 Analogues of 17α-ethynyl-3α-androstanediol include 17α-ethynyl-3β-androstanediol, ethinylandrostenediol (17α-ethynyl-5-androstenediol), ethandrostate (17α-ethynyl-5-androstenediol 3β-cyclohexanepropionate), ethinylestradiol (17α-ethynylestradiol), ethisterone (17α-ethynyltestosterone), and 5α-dihydroethisterone (17α-ethynyldihydrotestosterone). References Category:5α-Reduced steroid metabolites Category:Abandoned drugs Category:Ethynyl compounds Category:Androgens Category:Androstanes Category:Antigonadotropins Category:Diols Category:Experimental cancer drugs Category:Sex hormone esters and conjugates Category:Synthetic estrogens