Etiocholanolone

Etiocholanolone
Clinical data


ATC code	none
Identifiers
IUPAC name (3R,5R,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
Synonyms	Aetiocholanolone 5-Isoandrosterone
CAS Number	53-42-9^Y
PubChem CID	5880
DrugBank	DB02854^N
ChemSpider	5669^N
UNII	97CGB1M48I
ChEBI	CHEBI:28195^N
ChEMBL	CHEMBL85799^N
Chemical and physical data
Formula	C₁₉H₃₀O₂
Molar mass	290.445 g/mol
3D model (Jmol)	Interactive image
SMILES [H][C@]12CC[C@@]3([H])[C@]4([H])CCC(=O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC[C@@H](O)C2
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+/m1/s1^N Key:QGXBDMJGAMFCBF-BNSUEQOYSA-N^N
^NY (what is this?)

Etiocholanolone, also known as 5β-androsterone, as well as 3α-hydroxy-5β-androstan-17-one or etiocholan-3α-ol-17-one, is an etiocholane (5β-androstane) steroid as well as an endogenous 17-ketosteroid that is produced from the metabolism of testosterone. It causes fever, immunostimulation, and leukocytosis, and is used to evaluate adrenal cortex function, bone marrow performance, and in neoplastic disease to stimulate the immune system. Etiocholanolone 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 etiocholanolone is more potent as a positive allosteric modulator of GABA_A receptors and as an anticonvulsant than the natural form.