THC Science

Epietiocholanolone
Names
	IUPAC name 3β-Hydroxy-5β-androstan-17-one
	Systematic IUPAC name (3aS,3bR,5aR,7S,9aS,9bS,11aS)-7-Hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-one
	Other names 5β-Androstan-3β-ol-17-one; Etiocholan-3β-ol-17-one
Identifiers
CAS Number	571-31-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:89524;
ChEMBL	ChEMBL260526;
ChemSpider	216866;
PubChem CID	247732;
UNII	C1751JYC6P;
CompTox Dashboard (EPA)	DTXSID20289698 ;
	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-XRJZGPCZSA-N;
	SMILES C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O;
Properties
Chemical formula	C19H30O2
Molar mass	290.447 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

Epietiocholanolone, also known as 3β-hydroxy-5β-androstan-17-one or as etiocholan-3β-ol-17-one, is an etiocholane (5β-androstane) steroid as well as an inactive metabolite of testosterone that is formed in the liver.^[1]^[2]^[3] The metabolic pathway is testosterone to 5β-dihydrotestosterone (via 5β-reductase),^[1] 5β-dihydrotestosterone to 3β,5β-androstanediol (via 3β-hydroxysteroid dehydrogenase), and 3β,5β-androstanediol to epietiocholanolone (via 17β-hydroxysteroid dehydrogenase).^[3] Epietiocholanolone can also be formed directly from 5β-androstanedione (via 3β-hydroxysteroid dehydrogenase).^[3]^[4] It is glucuronidated and sulfated in the liver and excreted in urine.^[3]^[5]

References[edit]

^ ^a ^b Arun Nagrath; Narendra Malhotra; Seth Shikha (31 July 2012). Progress in Obstetrics & Gynecology. JP Medical Ltd. pp. 265–. ISBN 978-93-5025-779-1.
^ J. Horsky; J. Presl (6 December 2012). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 107–. ISBN 978-94-009-8195-9.
^ ^a ^b ^c ^d MORFIN Robert (20 December 2010). Les stéroïdes naturels de A à Z. Lavoisier. pp. 428–. ISBN 978-2-7430-1918-1.
^ Hugh L. J. Makin; D.B. Gower (4 June 2010). Steroid Analysis. Springer Science & Business Media. pp. 462–. ISBN 978-1-4020-9775-1.
^ Hauser B, Deschner T, Boesch C (2008). "Development of a liquid chromatography-tandem mass spectrometry method for the determination of 23 endogenous steroids in small quantities of primate urine". J. Chromatogr. B. 862 (1–2): 100–12. doi:10.1016/j.jchromb.2007.11.009. PMID 18054529.