Epipregnanolone

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Epipregnanolone
Epipregnanolone.svg
Names
IUPAC name
3β-Hydoxy-5β-pregnan-20-one
Other names
3β,5β-tetrahydroprogesterone
Identifiers
128-21-2
ChemSpider 198867
Jmol 3D model Interactive image
PubChem 228491
  • InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15+,16+,17-,18+,19+,20+,21-/m1/s1
    Key: AURFZBICLPNKBZ-GRWISUQFSA-N
  • CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
Properties
C21H34O2
Molar mass 318.49 g/mol
Vapor pressure {{{value}}}
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.[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 receptor,[5] and also acts as a TRPM3 channel activator.[6][7]

See also

References

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  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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