5α-Dihydrocorticosterone

5α-Dihydrocorticosterone (5α-DHC, 5α-DHB), also known as 11β,21-dihydroxy-5α-pregnane-3,20-dione, is a naturally occurring, endogenous glucocorticoid steroid hormone and neurosteroid.[1][2][3] It is biosynthesized from corticosterone by the enzyme 5α-reductase.[4][5][6] DHC has central depressant effects and impairs long-term potentiation in animals.[7][8]

5α-Dihydrocorticosterone
Names
IUPAC name
11β,21-Dihydroxy-5α-pregnane-3,20-dione
Systematic IUPAC name
(1S,3aS,3bS,5aS,9aS,9bS,10S,11aS)-10-Hydroxy-1-(hydroxyacetyl)-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C21H32O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h12,14-17,19,22,24H,3-11H2,1-2H3/t12-,14-,15-,16+,17-,19+,20-,21-/m0/s1
  • CC12CCC(=O)CC1CCC3C2C(CC4(C3CCC4C(=O)CO)C)O
Properties
C21H32O4
Molar mass 348.47638 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. R.A. Hill; H.L.J. Makin; D.N. Kirk; G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 218–. ISBN 978-0-412-27060-4.
  2. McInnes, K. J.; Kenyon, C. J.; Chapman, K. E.; Livingstone, D. E. W.; Macdonald, L. J.; Walker, B. R.; Andrew, R. (2004). "5 -Reduced Glucocorticoids, Novel Endogenous Activators of the Glucocorticoid Receptor". Journal of Biological Chemistry. 279 (22): 22908–22912. doi:10.1074/jbc.M402822200. ISSN 0021-9258. PMID 15044432.
  3. Magnaghi V (2007). "GABA and neuroactive steroid interactions in glia: new roles for old players?". Curr Neuropharmacol. 5 (1): 47–64. doi:10.2174/157015907780077132. PMC 2435342. PMID 18615153.
  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. 48–. ISBN 978-1-4020-6854-6.
  5. Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 147–. ISBN 978-0-08-054423-6.
  6. N. Kato; M. Kawata; R.K. Pitman (3 July 2007). PTSD: Brain Mechanisms and Clinical Implications. Springer Science & Business Media. pp. 125–. ISBN 978-4-431-29567-9.
  7. Dubrovsky, B.; Williams, D.; Kraulis, I. (1985). "Effects of corticosterone and 5?-dihydrocorticosterone on brain excitability in the rat". Journal of Neuroscience Research. 14 (1): 117–128. doi:10.1002/jnr.490140111. ISSN 0360-4012. PMID 4020896. S2CID 84291184.
  8. Dubrovsky, B.O.; Liquornik, M.S.; Noble, P.; Gijsbers, K. (1987). "Effects of 5α-dihydrocorticosterone on evoked responses and long-term potentiation". Brain Research Bulletin. 19 (6): 635–638. doi:10.1016/0361-9230(87)90049-9. ISSN 0361-9230. PMID 3440216. S2CID 54274436.


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