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5α-Dihydrocorticosterone

From Wikipedia, the free encyclopedia
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 mass348.47638 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

5α-Dihydrocorticosterone (5α-DHC,5α-DHB), also known as11β,21-dihydroxy-5α-pregnane-3,20-dione, is anaturally occurring,endogenousglucocorticoidsteroid hormone andneurosteroid.[1][2][3] It isbiosynthesized fromcorticosterone by theenzyme5α-reductase.[4][5][6] DHC hascentral depressant effects and impairslong-term potentiation in animals.[7][8]

See also

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References

[edit]
  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.
Precursors
Corticosteroids
Glucocorticoids
Mineralocorticoids
Sex steroids
Androgens
Estrogens
Progestogens
Neurosteroids
Others
GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
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