Chemistry:17α-Ethynyl-3α-androstanediol
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| Other names | Ethynylandrostanediol; HE3235; Apoptone; 17α-Ethynyl-5α-androstanediol; 17α-Ethynyl-5α-androstane-3α,17β-diol; 5α-Pregn-20-yne-3α,17α-diol |
| Routes of administration | By mouth |
| Drug class | Estrogen |
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| Formula | C21H32O2 |
| Molar mass | 316.485 g·mol−1 |
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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.[1][2][3] It was under development for the treatment of prostate cancer but was discontinued.[1][2][3]
17α-Ethynyl-3α-androstanediol itself shows very low affinity for steroid receptors, including the AR, ERα, ERβ, PR, and GR, and its mechanism of action is not well-characterized.[1][4] 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.[1][5] These metabolites may contribute importantly to the biological activity of 17α-ethynyl-3α-androstanediol, with 17α-ethynyl-3α-androstanediol potentially serving as a prodrug.[1][5]
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
- ↑ 1.0 1.1 1.2 1.3 1.4 "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs 30 (1): 59–78. 2012. doi:10.1007/s10637-010-9517-0. PMID 20814732.
- ↑ 2.0 2.1 "Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235)". Br. J. Cancer 100 (7): 1068–72. 2009. doi:10.1038/sj.bjc.6604987. PMID 19337256.
- ↑ 3.0 3.1 http://webcache.googleusercontent.com/search?q=cache:Jy1DYIHEUtQJ:adisinsight.springer.com/drugs/800025305[yes|permanent dead link|dead link}}]
- ↑ "HE3235 inhibits growth of castration-resistant prostate cancer". Neoplasia 11 (11): 1216–25. 2009. doi:10.1593/neo.09960. PMID 19881957.
- ↑ 5.0 5.1 "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. doi:10.3181/00379727-92-22493. PMID 13350363.
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