Epietiocholanolone
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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 | |
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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]
See also
References
- ^ 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.
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- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- 11β-Hydroxypregnenolone
- 17α-Hydroxypregnenolone
- 21-Hydroxypregnenolone
- 17α,21-Dihydroxypregnenolone
- 11β,17α,21-Trihydroxypregnenolone
- Cholestanes: 24S-Hydroxycholesterol
- Cholesterol
- Pregnanes: 3α-Dihydroprogesterone
- 3β-Dihydroprogesterone
- 5α-Dihydrocorticosterone
- 5α-Dihydroprogesterone
- 5β-Dihydroprogesterone
- Allopregnanolone
- Corticosterone
- DHC
- DHDOC
- 11-Deoxycorticosterone
- Epipregnanolone
- Isopregnanolone
- Pregnanolone
- Pregnenolone
- Pregnenolone sulfate
- Progesterone
- THB
- THDOC
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