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5β-Dihydrotestosterone


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 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 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 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 5β-DHT, unlike 5α-DHT, is also inactive in terms of neurosteroid activity, although its metabolite, etiocholanolone, does possess such activity

See also

  • 3α-Androstanediol
  • 3β-Androstanediol
  • Androsterone
  • Epiandrosterone

References

  1. ^ a b Hormones, Brain and Behavior Online Academic Press 18 June 2002 pp 2262– ISBN 978-0-08-088783-8 
  2. ^ 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 
  3. ^ 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 
  4. ^ 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 
  5. ^ BA Cooke; HJ Van Der Molen; RJB King 1 November 1988 Hormones and their Actions Elsevier pp 173– ISBN 978-0-08-086077-0 
  6. ^ Current Topics in Membranes and Transport Academic Press 1 February 1988 pp 169– ISBN 978-0-08-058502-4 
  7. ^ 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 
  8. ^ 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:101124/mol106033407 PMID 17341652 
  9. ^ Kaminski RM, Marini H, Kim WJ, Rogawski MA June 2005 "Anticonvulsant activity of androsterone and etiocholanolone" Epilepsia 46 6: 819–27 doi:101111/j1528-1167200500705x PMC 1181535  PMID 15946323 





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