Dihydrodeoxycorticosterone

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 GABA_A receptor, and is known to have anticonvulsant effects.[1][2]

Dihydrodeoxycorticosterone

Names
IUPAC name (5α)-21-Hydroxypregnane-3,20-dione
Other names 5α-Dihydro-11-deoxycorticosterone
Identifiers
CAS Number	298-36-2
3D model (JSmol)	Interactive image
ChemSpider	4953958
PubChem CID	6451493
CompTox Dashboard (EPA)	DTXSID40952236
InChI 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
SMILES 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
Chemical formula	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).
Infobox references

Chemistry

See also: List of neurosteroids

See also

• Tetrahydrodeoxycorticosterone (THDOC)
• 5α-Dihydroprogesterone (DHP)
• Hydroxydione

References

1. 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. 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.