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
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
C21 H32 O4
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).
Chemical compound
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]
See also
References
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^
Neurosteroids and Brain Function . Academic Press. 12 December 2001. pp. 147–.
ISBN
978-0-08-054423-6 .
^ 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 .
^ 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 .
^ 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 .
GR Tooltip Glucocorticoid receptor