Names | |
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IUPAC name
3β-Hydoxy-5β-pregnan-20-one
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Systematic IUPAC name
1-[(1S,3aS,3bR,5aR,7S,9aS,9bS,11aS)-7-Hydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one | |
Other names
3β,5β-Tetrahydroprogesterone
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Identifiers | |
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3D model (JSmol)
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ChemSpider | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C21H34O2 | |
Molar mass | 318.501 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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Epipregnanolone, also known as 3β-hydroxy-5β-pregnan-20-one, 3β,5β-tetrahydroprogesterone, or 3β,5β-THP, is an endogenous neurosteroid.[1] It acts as a negative allosteric modulator of the GABAA receptor and reverses the effects of potentiators like allopregnanolone.[2][3] Epipregnanolone is biosynthesized from progesterone by the actions of 5β-reductase and 3β-hydroxysteroid dehydrogenase, with 5β-dihydroprogesterone as the intermediate in this two-step transformation.[2]
Epipregnanolone is not a progestogen itself, but via metabolization into other steroids, behaves indirectly as one.[4]
The sulfate of epipreganolone, epipregnanolone sulfate, is a negative allosteric modulator of the NMDA[5] and GABAA receptors[6] and also acts as a TRPM3 channel activator.[7][8]
See also: List of neurosteroids |
Ionotropic |
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Metabotropic |
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PRTooltip Progesterone receptor |
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mPRTooltip Membrane progesterone receptor (PAQRTooltip Progestin and adipoQ receptor) |
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