Etiocholanolone

Etiocholanolone
Clinical data
Other names	Aetiocholanolone; 5-Isoandrosterone
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;
CAS Number	53-42-9 ;
PubChem CID	5880;
DrugBank	DB02854 ;
ChemSpider	5669 ;
UNII	97CGB1M48I;
ChEBI	CHEBI:28195 ;
ChEMBL	ChEMBL85799 ;
Chemical and physical data
Formula	C19H30O2
Molar mass	290.447 g·mol−1
3D model (JSmol)	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 ; Key:QGXBDMJGAMFCBF-BNSUEQOYSA-N ;
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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.

Etiocholanolone has been studied as a pyrogenic steroid in the so-called steroid fever (or etiocholanolone fever), a condiditon similar to familial mediterranean fever (FMF). Etiocholanolone (like pregnanolone) activates the pyrin inflammasome. It is not known whether these endogenous steroids play a role in triggering FMF flares but they may make a link between stress, menstrual cycle and disease flares.

Etiocholanolone is produced from 5β-dihydrotestosterone, with 3α,5β-androstanediol as an intermediate.

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