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Dihydrodeoxycorticosterone

Dihydrodeoxycorticosterone
Names
IUPAC name
21-Hydroxy-5α-pregnane-3,20-dione
Systematic IUPAC name
(1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-(Hydroxyacetyl)-9a,11a-dimethylhexadecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
5α-Dihydro-11-deoxycorticosterone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13,15-18,22H,3-12H2,1-2H3/t13-,15-,16-,17-,18+,20-,21-/m0/s1
    Key: USPYDUPOCUYHQL-KVHKMPIWSA-N
  • InChI=1/C21H32O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h13,15-18,22H,3-12H2,1-2H3/t13-,15-,16-,17-,18+,20-,21-/m0/s1
    Key: USPYDUPOCUYHQL-KVHKMPIWBY
  • C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CO)C
Properties
C21H32O3
Molar mass 332.484 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5α-Dihydrodeoxycorticosterone (abbreviated as DHDOC), also known as 21-hydroxy-5α-pregnan-20-one, is an endogenous progestogen and neurosteroid.[1] It is synthesized from the adrenal hormone deoxycorticosterone (DOC) by the enzyme 5α-reductase type I.[1] DHDOC is an agonist of the progesterone receptor, as well as a positive allosteric modulator of the GABAA receptor, and is known to have anticonvulsant effects.[1][2]

Chemistry

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See also: List of neurosteroids

See also

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References

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  1. ^ a b c Reddy DS, Rogawski MA (May 2002). "Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA(A) receptor function and seizure susceptibility". J. Neurosci. 22 (9): 3795–805. doi:10.1523/JNEUROSCI.22-09-03795.2002. PMC 6758375. PMID 11978855.
  2. ^ Edwards HE, Vimal S, Burnham WM (December 2005). "The acute anticonvulsant effects of deoxycorticosterone in developing rats: role of metabolites and mineralocorticoid-receptor responses". Epilepsia. 46 (12): 1888–97. doi:10.1111/j.1528-1167.2005.00295.x. PMID 16393154. S2CID 26030656.