Allopregnanediol
Chemical compound
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Names | |
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IUPAC name
5α-Pregnane-3α,20α-diol
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Systematic IUPAC name
(1
S
,3a
S
,3b
R
,5a
S
,7
R
,9a
S
,9b
S
,11a
S
)-1-[(1
S
)-1-Hydroxyethyl]-9a,11a-dimethylhexadecahydro-1
H
-cyclopenta[
a
]phenanthren-7-ol
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Identifiers | |
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3D model (
JSmol
)
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ChEBI | |
ChEMBL | |
PubChem
CID
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UNII | |
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Properties | |
C 21 H 36 O 2 | |
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 EC 50 that is more than an order of magnitude lower than that of other endogenous pregnanes like pregnenolone , pregnanediol, allopregnanedione , and allopregnanolone. [3]
Chemistry
See also:
List of neurosteroids
References
- ↑ 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. doi : 10.1186/1471-2148-8-103 . ISSN 1471-2148 . PMC 2358886 . PMID 18384689 .
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