Chemistry:17α-Ethynyl-3β-androstanediol
 | |
| Clinical data | |
|---|---|
| Other names | HE-3539; HE3539; Ethinylandrostanediol; 17α-Ethynyl-5α-androstane-3β,17β-diol; 5α,17α-Pregn-20-yne-3β,17-diol |
| Routes of administration | By mouth |
| Drug class | Estrogen |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| Chemical and physical data | |
| Formula | C21H32O2 |
| Molar mass | 316.485 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
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.[1][2]
17α-Ethynyl-3β-androstanediol shows high affinity for the estrogen receptors in vitro (IC50 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 value of 0.9 nM relative to 0.002 nM for estradiol).[2] 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.[2] 17α-Ethynyl-3β-androstanediol may produce 17α-ethynyl-3α-androstanediol and 5α-dihydroethisterone (5α-dihydro-17α-ethynyltestosterone) as active metabolites in vivo.[2] In accordance with its in-vitro estrogenic activity, 17α-ethynyl-3β-androstanediol produces estrogenic effects like uterotrophy and testicular atrophy in animals.[1]
Esters of 17α-ethynyl-3β-androstanediol have been developed and studied.[3]
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.[2] It may be involved in the biological activity of 17α-ethynyl-3α-androstanediol.[2]
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
- ↑ 1.0 1.1 "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. doi:10.3181/00379727-92-22493. PMID 13350363.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Investigational New Drugs 30 (1): 59–78. February 2012. doi:10.1007/s10637-010-9517-0. PMID 20814732.
- ↑ "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): 473–475. 1957. doi:10.1021/jo01355a627. ISSN 0022-3263.
 |  |
