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Epietiocholanolone

From Wikipedia, the free encyclopedia

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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • 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
  • C[C@]12CC[C@@H](C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O
Properties
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).

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]

See also

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ Hugh L. J. Makin; D.B. Gower (4 June 2010). Steroid Analysis. Springer Science & Business Media. pp. 462–. ISBN 978-1-4020-9775-1.
  5. ^ 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.


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This page was last edited on 9 December 2023, at 00:48
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