17α-ethynyl-5α-androstane-3α,17β-diol

Ethynylandrostanediol

Clinical data
Synonyms	HE3235; Apoptone; 17α-Ethynyl-5α-androstane-3α,17β-diol; 5α-Pregn-20-yne-3α,17α-diol
Identifiers
IUPAC name (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
CAS Number	183387-50-0
PubChem CID	42611099
ChemSpider	32698509
UNII	891O182ZP5
Chemical and physical data
Formula	C21H32O2
Molar mass	316.49 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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
InChI InChI=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 Key:CKAXZOYFIHQCBN-JRRMKBMNSA-N

Ethynylandrostanediol (developmental code name HE-3235), or 17α-ethynyl-5α-androstane-3α,17β-diol, also known as Apoptone, is a synthetic, orally active, 17α-substituted analogue of the androstanediols which was under development for the treatment of prostate cancer and breast cancer but was discontinued. It has very low affinity for steroid receptors, including the AR, ERα, ERβ, PR, and GR, and its mechanism of action is not well-characterized.