 | |
| Names | |
|---|---|
| IUPAC name 5α-Androstane-3α,17β-diol | |
| Systematic IUPAC name (1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-9a,11a-Dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-1,7-diol | |
| Other names Hombreol | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.015.862 |
| UNII | |
| |
| |
| Properties | |
| C19H32O2 | |
| Molar mass | 292.463 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
3α-Androstanediol also known as5α-androstane-3α,17β-diol and sometimes shortened in the literature to3α-diol, is anendogenoussteroid hormone andneurosteroid and ametabolite ofandrogens likedihydrotestosterone (DHT).[1][2][3]
3α-Androstanediol is aninhibitoryandrostaneneurosteroid and weakandrogen andestrogen.[1][2][3]
As a neurosteroid, it acts as a potentpositive allosteric modulator of theGABAA receptor,[4] and has been found to haverewarding,[5][6]anxiolytic,[7]pro-sexual,[8] andanticonvulsant effects.[9][10] As androgens such astestosterone and DHT are known to have many of the same effects as 3α-diol and are converted into itin vivo, it is thought that this compound may in part be responsible for said effects.[5][6][7][10]
Relative to its isomer3β-androstanediol, which is a potentestrogen, 3α-androstanediol has substantially lower, though still significantaffinity for theestrogen receptors, with a several-fold preference forERβ overERα.[11][12] It has approximately 0.07% and 0.3% of theaffinity ofestradiol at the ERα and ERβ, respectively.[13]
  |
3α-Androstanediol shows high affinity forsex hormone-binding globulin (SHBG), similar to that oftestosterone.[14]
3α-Androstanediol, also known as 5α-androstane-3α,17β-diol, is anaturally occurringandrostanesteroid and astructural analogue of DHT (5α-androstan-17β-ol-3-one). A notablepositional isomer of 3α-androstanediol is3β-androstanediol.
An orally active synthetic analogue of 3α-androstanediol,17α-ethynyl-3α-androstanediol (HE-3235, Apoptone), was formerly under investigation for the treatment ofprostate cancer andbreast cancer.[15]
