From Wikipedia, the free encyclopedia
5β-Dihydrotestosterone
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Names
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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
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Other names
5β-Androstan-17β-ol-3-one; Etiocholan-17β-ol-3-one; 5β-Dihydrotestosterone; 5β-DHT
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Identifiers
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ChEBI
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ChEMBL
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ChemSpider
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ECHA InfoCard
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100.164.933
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UNII
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C[C@]12CCC(=O)C[C@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
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Properties
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C19H30O2
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Molar mass
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290.447 g·mol−1
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Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
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
- ^
a
b
Hormones, Brain and Behavior Online. Academic Press. 18 June 2002. pp. 2262–.
ISBN
978-0-08-088783-8.
-
^ 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.
-
^ 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.
-
^ 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.
-
^ 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.
-
^
Current Topics in Membranes and Transport. Academic Press. 1 February 1988. pp. 169–.
ISBN
978-0-08-058502-4.
-
^ 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.
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^ Li P, Bracamontes J, Katona BW, Covey DF, Steinbach JH, Akk G (June 2007).
"Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor". Mol. Pharmacol. 71 (6): 1582–90.
doi:
10.1124/mol.106.033407.
PMC
3788649.
PMID
17341652.
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^ Kaminski RM, Marini H, Kim WJ, Rogawski MA (June 2005).
"Anticonvulsant activity of androsterone and etiocholanolone". Epilepsia. 46 (6): 819–27.
doi:
10.1111/j.1528-1167.2005.00705.x.
PMC
1181535.
PMID
15946323.