17α-Ethynyl-3β-androstanediol

Chemical compound (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 HE3235.svg skin-invert-image By mouth Estrogen 13611-96-6 45042186 HE-3539; HE3539; Ethinylandrostanediol; 17α-Ethynyl-5α-androstane-3β,17β-diol; 5α,17α-Pregn-20-yne-3β,17-diol 21 32 2 C[C@]12CCC(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-KVECEQEYSA-N 17α-Ethynyl-3β-androstanediol (developmental code HE-3539; also known as 17α-ethynyl-5α-androstane-3β,17β-diol) is a synthetic estrogen and a 17α-substituted derivative of 3β-androstanediol which was never marketed. Beyler AL, Clinton RO Uterine growth stimulating and testicular growth suppressing activities of 17alpha-ethinylandrostane-3beta, 17beta-diol, its delta 5-analog and derivatives Proceedings of the Society for Experimental Biology and Medicine 92 2 404–408 June 1956 13350363 10.3181/00379727-92-22493 87469965 Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J 6 17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism Investigational New Drugs 30 1 59–78 February 2012 20814732 10.1007/s10637-010-9517-0 24785562 17α-Ethynyl-3β-androstanediol shows high affinity for the estrogen receptors in vitro (IC50 Half-maximal inhibitory concentration values of 16 nM for ERα and 126 nM for ERβ relative to values of 8 nM at ERα and 7 nM at ERβ for estradiol), and activates the estrogen receptors in vitro (EC50 Half-maximal effective concentration value of 0.9 nM relative to 0.002 nM for estradiol). It also has weak affinity for the androgen receptor in vitro (IC50 = 277 nM relative to 15 nM for dihydrotestosterone), but doesn't appear to activate the receptor. 17α-Ethynyl-3β-androstanediol may produce 17α-ethynyl-3α-androstanediol and 5α-dihydroethisterone (5α-dihydro-17α-ethynyltestosterone) as active metabolites in vivo. In accordance with its in-vitro estrogenic activity, 17α-ethynyl-3β-androstanediol produces estrogenic effects like uterotrophy and testicular atrophy in animals. Esters of 17α-ethynyl-3β-androstanediol have been developed and studied. Clinton R, Neumann H, Laskowski S, Christiansen R Notes - Esters of 17α-Ethinyl-androstane-3β,17β-diol and 17 α-Ethinylandrost-5-ene-3β, 17β-diol The Journal of Organic Chemistry 22 4 1957 473–475 0022-3263 10.1021/jo01355a627 17α-Ethynyl-3β-androstanediol is a positional isomer of 17α-ethynyl-3α-androstanediol, and is a metabolite of this compound in vivo via metabolic inversion of the position of the C3 hydroxyl group. It may be involved in the biological activity of 17α-ethynyl-3α-androstanediol. Analogues Analogues of 17α-ethynyl-3β-androstanediol include 17α-ethynyl-3α-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:Androstanes Category:Antigonadotropins Category:Diols Category:Human drug metabolites Category:Synthetic estrogens