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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
3D model (JSmol)
ChEBI
ECHA InfoCard 100.008.453 Edit this at Wikidata
  • [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
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).

5α-Dihydroprogesterone (5α-DHP), also known as 5α-pregnan-3,20-dione, is an endogenous progestogen and neurosteroid that is synthesized from progesterone.[1][2] 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 GABAA 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)).[1][2][3][4] It has also been found to act as a negative allosteric modulator of the GABAA-rho receptor.[5] 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.[6]

See also

References

  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.
  4. ^ Ocvirk, Rok; Pearson Murphy, Beverley E.; Franklin, Keith B.J.; Abbott, Frances V. (2008). "Antinociceptive profile of ring A-reduced progesterone metabolites in the formalin test". Pain. 138 (2): 402–409. doi:10.1016/j.pain.2008.01.019. ISSN 0304-3959.
  5. ^ Johnston GA (2002). "Medicinal chemistry and molecular pharmacology of GABA(C) receptors" (PDF). Curr Top Med Chem. 2 (8): 903–13. PMID 12171579.
  6. ^ Lehmann JM, McKee DD, Watson MA, Willson TM, Moore JT, Kliewer SA (1998). "The human orphan nuclear receptor PXR is activated by compounds that regulate CYP3A4 gene expression and cause drug interactions". J. Clin. Invest. 102 (5): 1016–23. doi:10.1172/JCI3703. PMC 508967. PMID 9727070.



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