5α-Dihydroprogesterone

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5α-Dihydroprogesterone
Skeletal formula of 5α-dihydroprogesterone
Ball-and-stick model of the 5α-dihydroprogesterone molecule
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
566-65-4
ChEBI CHEBI:28952
Jmol-3D images Image
PubChem 24779611
Properties
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-pregnan-3,20-dione; abbreviated as 5α-DHP) is an endogenous progestogen and neurosteroid that is synthesized from progesterone.[1][2] It is also an intermediate in the synthesis of allopregnanolone from progesterone. 5α-DHP is an agonist of the progesterone receptor, and a positive allosteric modulator of the GABAA receptor.[1][2][3]

See also[edit]

References[edit]

  1. ^ a b Mellon SH (October 2007). "Neurosteroid regulation of central nervous system development". Pharmacol. Ther. 116 (1): 107–24. doi:10.1016/j.pharmthera.2007.04.011. PMC 2386997. PMID 17651807. 
  2. ^ a b Guidotti A, Dong E, Matsumoto K, Pinna G, Rasmusson AM, Costa E (November 2001). "The socially-isolated mouse: a model to study the putative role of allopregnanolone and 5alpha-dihydroprogesterone in psychiatric disorders". Brain Res. Brain Res. Rev. 37 (1-3): 110–5. doi:10.1016/s0165-0173(01)00129-1. PMID 11744079. 
  3. ^ Rupprecht R, Reul JM, Trapp T et al. (September 1993). "Progesterone receptor-mediated effects of neuroactive steroids". Neuron 11 (3): 523–30. doi:10.1016/0896-6273(93)90156-l. PMID 8398145.