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
Other names Allopregnanedione; 5α-Pregnan-3,20-dione
Identifiers
CAS Number	566-65-4
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28952
ChemSpider	83782
ECHA InfoCard	100.008.453
PubChem CID	92810
InChI InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1 Key: XMRPGKVKISIQBV-BJMCWZGWSA-N
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
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 allopregnanedione, as well as 5α-pregnane-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.