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Names | |
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IUPAC name
21-Hydroxy-5α-pregnane-3,20-dione
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Systematic IUPAC name
(1S,3aS,3bR,5aS,9aS,9bS,11aS)-1-(Hydroxyacetyl)-9a,11a-dimethylhexadecahydro-7H-cyclopentaphenanthren-7-one | |
Other names
5α-Dihydro-11-deoxycorticosterone
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Identifiers | |
3D model (JSmol)
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ChEBI | |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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 , 100 kPa).
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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
See also
- Tetrahydrodeoxycorticosterone (THDOC)
- 5α-Dihydroprogesterone (DHP)
- Hydroxydione
References
- ^ 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.
- ^ 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.
PRTooltip Progesterone receptor |
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mPRTooltip Membrane progesterone receptor (PAQRTooltip Progestin and adipoQ receptor) |
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