5β-Dihydrotestosterone explained

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. 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

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

Notes and References

1. Book: Hormones, Brain and Behavior Online. 18 June 2002. Academic Press. 978-0-08-088783-8. 2262–.
2. Book: H.-J. Bandmann. R. Breit. E. Perwein. Klinefelter's Syndrome. 6 December 2012. Springer Science & Business Media. 978-3-642-69644-2. 293–.
3. Book: Shlomo Melmed. Kenneth S. Polonsky. P. Reed Larsen. Henry M. Kronenberg. Williams Textbook of Endocrinology. 30 November 2015. Elsevier Health Sciences. 978-0-323-29738-7. 711–.
4. Book: Anita H. Payne. Matthew P. Hardy. The Leydig Cell in Health and Disease. 28 October 2007. Springer Science & Business Media. 978-1-59745-453-7. 186–.
5. Book: B.A. Cooke. H.J. Van Der Molen. R.J.B. King. Hormones and their Actions. 1 November 1988. Elsevier. 978-0-08-086077-0. 173–.
6. Book: Current Topics in Membranes and Transport. 1 February 1988. Academic Press. 978-0-08-058502-4. 169–.
7. Book: Abraham Weizman. Neuroactive Steroids in Brain Function, Behavior and Neuropsychiatric Disorders: Novel Strategies for Research and Treatment. 1 February 2008. Springer Science & Business Media. 978-1-4020-6854-6. 210–.
8. Li P, Bracamontes J, Katona BW, Covey DF, Steinbach JH, Akk G . Natural and enantiomeric etiocholanolone interact with distinct sites on the rat alpha1beta2gamma2L GABAA receptor . Mol. Pharmacol. . 71 . 6 . 1582–90 . June 2007 . 17341652 . 10.1124/mol.106.033407 . 3788649 .
9. Kaminski RM, Marini H, Kim WJ, Rogawski MA . Anticonvulsant activity of androsterone and etiocholanolone . Epilepsia . 46 . 6 . 819–27 . June 2005 . 15946323 . 1181535 . 10.1111/j.1528-1167.2005.00705.x .