Chemistry:5β-Dihydrotestosterone
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| IUPAC name
17β-Hydroxy-5β-androstan-3-one
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| Systematic IUPAC name
(1S,3aS,3bR,5aR,9aS,9bS,11aS)-1-Hydroxy-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one | |
| Other names
5β-Androstan-17β-ol-3-one; Etiocholan-17β-ol-3-one; 5β-Dihydrotestosterone; 5β-DHT
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| 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). | |
| Infobox references | |
5β-Dihydrotestosterone (5β-DHT), also known as 5β-androstan-17β-ol-3-one or as etiocholan-17β-ol-3-one, is an etiocholane (5β-androstane) steroid as well as an inactive metabolite of testosterone formed by 5β-reductase in the liver and bone marrow[1][2] and an intermediate in the formation of 3α,5β-androstanediol and 3β,5β-androstanediol (by 3α- and 3β-hydroxysteroid dehydrogenase) and, from them, respectively, etiocholanolone and epietiocholanolone (by 17β-hydroxysteroid dehydrogenase).[3][4] Unlike its isomer 5α-dihydrotestosterone (5α-DHT or simply DHT), 5β-DHT either does not bind to or binds only very weakly to the androgen receptor.[1] 5β-DHT is notable among metabolites of testosterone in that, due to the fusion of the A and B rings in the cis orientation, it has an extremely angular molecular shape, and this could be related to its lack of androgenic activity.[5] 5β-DHT, unlike 5α-DHT, is also inactive in terms of neurosteroid activity,[6][7] although its metabolite, etiocholanolone, does possess such activity.[8][9]
See also
References
- ↑ 1.0 1.1 Hormones, Brain and Behavior Online. Academic Press. 18 June 2002. pp. 2262–. ISBN 978-0-08-088783-8. https://books.google.com/books?id=CATnr24wGL4C&pg=PT2262.
- ↑ H.-J. Bandmann; R. Breit; E. Perwein (6 December 2012). Klinefelter's Syndrome. Springer Science & Business Media. pp. 293–. ISBN 978-3-642-69644-2. https://books.google.com/books?id=NGgrBgAAQBAJ&pg=PT293.
- ↑ Shlomo Melmed; Kenneth S. Polonsky; P. Reed Larsen; Henry M. Kronenberg (30 November 2015). Williams Textbook of Endocrinology. Elsevier Health Sciences. pp. 711–. ISBN 978-0-323-29738-7. https://books.google.com/books?id=YZ8_CwAAQBAJ&pg=PA711.
- ↑ Anita H. Payne; Matthew P. Hardy (28 October 2007). The Leydig Cell in Health and Disease. Springer Science & Business Media. pp. 186–. ISBN 978-1-59745-453-7. https://books.google.com/books?id=x4ttqKIAOg0C&pg=PA186.
- ↑ B.A. Cooke; H.J. Van Der Molen; R.J.B. King (1 November 1988). Hormones and their Actions. Elsevier. pp. 173–. ISBN 978-0-08-086077-0. https://books.google.com/books?id=bWUVADC74d8C&pg=PA173.
- ↑ Current Topics in Membranes and Transport. Academic Press. 1 February 1988. pp. 169–. ISBN 978-0-08-058502-4. https://books.google.com/books?id=ocWRusKe5WAC&pg=PA169.
- ↑ Abraham Weizman (1 February 2008). Neuroactive Steroids in Brain Function, Behavior and Neuropsychiatric Disorders: Novel Strategies for Research and Treatment. Springer Science & Business Media. pp. 210–. ISBN 978-1-4020-6854-6. https://books.google.com/books?id=uABKkFdPjhkC&pg=PA210.
- ↑ "Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor". Mol. Pharmacol. 71 (6): 1582–90. June 2007. doi:10.1124/mol.106.033407. PMID 17341652.
- ↑ "Anticonvulsant activity of androsterone and etiocholanolone". Epilepsia 46 (6): 819–27. June 2005. doi:10.1111/j.1528-1167.2005.00705.x. PMID 15946323.
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