Allopregnanediol
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| IUPAC name
5α-Pregnane-3α,20α-diol
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| Systematic IUPAC name
(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1-[(1S)-1-Hydroxyethyl]-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
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3D model (JSmol)
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| ChEMBL | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C21H36O2 | |
| Molar mass | 320.517 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]References
[edit]- ^ Finn, Deborah A.; Purdy, Robert H. (2007). "Neuroactive Steroids in Anxiety and Stress". Handbook of Contemporary Neuropharmacology. doi:10.1002/9780470101001.hcn026. ISBN 978-0470101001.
- ^ 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.
- ^ 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. Bibcode:2008BMCEE...8..103E. doi:10.1186/1471-2148-8-103. ISSN 1471-2148. PMC 2358886. PMID 18384689.
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