3α-androstanediol

3α-Androstanediol

Names
IUPAC name (3R,5S,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol
Other names Hombreol
Identifiers
CAS Number	1852-53-5
3D model (Jmol)	Interactive image
ChemSpider	15039
ECHA InfoCard	100.015.862
PubChem	15818
InChI InChI=1S/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1 Key: CBMYJHIOYJEBSB-KHOSGYARSA-N InChI=1/C19H32O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-17,20-21H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-/m0/s1 Key: CBMYJHIOYJEBSB-KHOSGYARBM
SMILES [H][C@]34[C@]2([H])CC[C@@]1([H])C[C@H](O)CC[C@@](C)1[C@]([H])2CC[C@@](C)3[C@@H](O)CC4
Properties
Chemical formula	C19H32O2
Molar mass	292.46 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3α-Androstanediol (often abbreviated as 3α-diol), also known as 5α-androstane-3α,17β-diol, is an endogenous inhibitory androstane neurosteroid and weak androgen, and a major metabolite of dihydrotestosterone (DHT). As a neurosteroid, it acts as a potent positive allosteric modulator of the GABA_A receptor, and has been found to have rewarding,anxiolytic,pro-sexual, and anticonvulsant effects. As androgens such as testosterone and DHT are known to have many of the same effects as 3α-diol and are converted into it in vivo, it is thought that this compound may in part be responsible for said effects. Relative to its isomer 3β-androstanediol, which is a potent estrogen, 3α-androstanediol has substantially lower, though still significant affinity for the estrogen receptors, with a several-fold preference for ERβ over ERα. It has approximately 0.07% and 0.3% of the affinity of estradiol at the ERα and ERβ, respectively.

An orally active synthetic analogue of 3α-androstanediol, 17α-ethynyl-5α-androstane-3α,17β-diol (HE-3235, Apoptone), was formerly under investigation for the treatment of prostate cancer and breast cancer.