5α-Dihydroprogesterone

5α-Dihydroprogesterone

Names
IUPAC name (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Identifiers
CAS Number	566-65-4
ChEBI	CHEBI:28952
Jmol 3D model	Interactive image
PubChem	24779611
SMILES [H][C@]34[C@]2([H])CC[C@@]1([H])CC(CC[C@@](C)1[C@]([H])2CC[C@@](C)3[C@@H]([C@@](C)=O)CC4)=O
Properties
Chemical formula	C21H32O2
Molar mass	316.48 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

5α-Dihydroprogesterone (5α-DHP), also known as 5α-pregnan-3,20-dione, is an endogenous progestogen and neurosteroid that is synthesized from progesterone. It is also an intermediate in the synthesis of allopregnanolone and isopregnanolone from progesterone. 5α-DHP is an agonist of the progesterone receptor and a positive allosteric modulator of the GABA_A receptor (albeit with an affinity for this receptor that is regarded as relatively low (in comparison to 3α-hydroxylated progesterone metabolites such as allopregnanolone and pregnanolone)). It has also been found to act as a negative allosteric modulator of the GABA_A-rho receptor. In addition, it is a weak agonist of the pregnane X receptor (PXR) (EC₅₀ >10,000 µM)), with approximately six-fold lower potency relative to its 5β-isomer, 5β-dihydroprogesterone.

See also

• 3α-Dihydroprogesterone
• Epipregnanolone
• 3β-Dihydroprogesterone