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Epipregnanolone

Epipregnanolone
Epipregnanolone.svg
Names
IUPAC name
3β-Hydoxy-5β-pregnan-20-one
Other names
3β,5β-tetrahydroprogesterone
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
Properties
C21H34O2
Molar mass 318.49 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Epipregnanolone, also known as 3β-hydoxy-5β-pregnan-20-one or 3β,5β-tetrahydroprogesterone (3β,5β-THP), is an endogenous neurosteroid. It acts as a negative allosteric modulator of the GABAA receptor and reverses the effects of potentiators like allopregnanolone. 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.

Epipregnanolone is not a progestogen itself, but via metabolization into other steroids, behaves indirectly as one.

The sulfate of epipreganolone, epipregnanolone sulfate, is a negative allosteric modulator of the NMDA receptor, and also acts as a TRPM3 channel activator.



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