Allopregnanediol

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Allopregnanediol
Allopregnanediol.svg
Names
IUPAC name
(3R,5R,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-Hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Identifiers
  • 80-92-2
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:8387
ChEMBL
  • ChEMBL269897
PubChem CID
  • 219833
UNII
  • JR3JD1Y22C
Properties
C21H36O2
Molar mass 320.52 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

Allopregnanediol, or 5α-pregnane-3α,20α-diol, is an endogenous metabolite of progesterone and allopregnanolone and an isomer of pregnanediol (5β-pregnan-3α,20α-diol).[1] It has been found to act like a partial agonist of an allosteric site of the GABA receptor and hence might play a biological role as a neurosteroid.[2] It has also been found to act as an agonist of the human pregnane X receptor, albeit with an EC50 that is more than an order of magnitude lower than that of other endogenous pregnanes like pregnenolone, pregnanediol, allopregnanedione, and allopregnanolone.[3]

Chemistry

References

  1. ^ Finn, Deborah A.; Purdy, Robert H. (2007). "Neuroactive Steroids in Anxiety and Stress". doi:10.1002/9780470101001.hcn026.
  2. ^ Belelli D, Gee KW (1989). "5 alpha-pregnan-3 alpha,20 alpha-diol behaves like a partial agonist in the modulation of GABA-stimulated chloride ion uptake by synaptoneurosomes". Eur. J. Pharmacol. 167 (1): 173–6. doi:10.1016/0014-2999(89)90760-7. PMID 2550257.
  3. ^ Ekins, Sean; Reschly, Erica J; Hagey, Lee R; Krasowski, Matthew D (2008). "Evolution of pharmacologic specificity in the pregnane X receptor". BMC Evolutionary Biology. 8 (1): 103. doi:10.1186/1471-2148-8-103. ISSN 1471-2148.


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