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Epipregnanolone
| Column 1 | Column 2 |
|---|---|
| IUPAC name | |
| 3β-Hydoxy-5β-pregnan-20-one | |
| 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 | |
| CAS Number | .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}128-21-2 Y |
| 3D model (JSmol) | Interactive image |
| ChemSpider | 198867 |
| PubChem CID | 228491 |
| UNII | 3KQ00893OL Y |
| CompTox Dashboard (EPA) | DTXSID00155766 |
| InChI | |
| 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/s1Key: AURFZBICLPNKBZ-GRWISUQFSA-N | |
| SMILES | |
| CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CCC@@HO)C)C | |
| Chemical formula | 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). |
Infobox references | |
Epipregnanolone, also known as 3β-hydroxy-5β-pregnan-20-one, 3β,5β-tetrahydroprogesterone, or 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 and GABAA receptors and also acts as a TRPM3 channel activator.
- Isopregnanolone
- 3β-Dihydroprogesterone
- Pregnanolone
- 5α-Dihydroprogesterone
- 3β-Androstanediol
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