Androsterone

Androsterone

Clinical data
ATC code	none
Identifiers
IUPAC name (3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-one
CAS Number	53-41-8 Y
PubChem CID	5879
ChemSpider	5668 Y
UNII	C24W7J5D5R
ChEBI	CHEBI:16032 Y
ChEMBL	CHEMBL87285 Y
ECHA InfoCard	100.000.159
Chemical and physical data
Formula	C19H30O2
Molar mass	290.440 g/mol
3D model (Jmol)	Interactive image
SMILES O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@H](O)CC[C@]34C)C
InChI InChI=1S/C19H30O2/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/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1 Y Key:QGXBDMJGAMFCBF-HLUDHZFRSA-N Y

Androsterone, or 5α-androstan-3α-ol-17-one, is an endogenous steroid hormone, neurosteroid, and putative pheromone. It is a weak androgen with a potency that is approximately 1/7th that of testosterone. Androsterone is a metabolite of testosterone and dihydrotestosterone (DHT). In addition, it can be converted back into DHT via 3α-hydroxysteroid dehydrogenase and 17β-hydroxysteroid dehydrogenase, bypassing conventional intermediates such as androstenedione and testosterone, and as such, can be considered to be a metabolic intermediate in its own right. Androsterone is also known to be an inhibitory androstane neurosteroid, acting as a positive allosteric modulator of the GABA_A receptor, and possesses anticonvulsant effects. The unnatural enantiomer of androsterone is more potent as a positive allosteric modulator of GABA_A receptors and as an anticonvulsant than the natural form. Androsterone's 3β-isomer is epiandrosterone, and its 5β-epimer is etiocholanolone. The 3β,5β-isomer is epietiocholanolone.