Epipregnanolone
 | |
| Names | |
|---|---|
| IUPAC name
3β-Hydoxy-5β-pregnan-20-one | |
| Other names
3β,5β-tetrahydroprogesterone | |
| Identifiers | |
| 128-21-2 | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 198867 |
| PubChem | 228491 |
| |
| |
| 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.[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
- ↑ Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 18–. ISBN 978-0-08-054423-6.
- 1 2 Abraham Weizman (1 February 2008). Neuroactive Steroids in Brain Function, Behavior and Neuropsychiatric Disorders: Novel Strategies for Research and Treatment. Springer Science & Business Media. pp. 6–. ISBN 978-1-4020-6854-6.
- ↑ Jan Egebjerg; Arne Schousboe; Povl Krogsgaard-Larsen (4 October 2001). Glutamate and GABA Receptors and Transporters: Structure, Function and Pharmacology. CRC Press. pp. 248–. ISBN 978-0-7484-0881-8.
- ↑ Beyer, C.; González-Flores, O.; Ramı́rez-Orduña, J.M.; González-Mariscal, G. (1999). "Indomethacin Inhibits Lordosis Induced by Ring A-Reduced Progestins: Possible Role of 3α-Oxoreduction in Progestin-Facilitated Lordosis". Hormones and Behavior. 35 (1): 1–8. doi:10.1006/hbeh.1998.1457. ISSN 0018-506X.
- ↑ Norman G. Bowery (19 June 2006). Allosteric Receptor Modulation in Drug Targeting. CRC Press. pp. 112–. ISBN 978-1-4200-1618-5.
- ↑ Issues in Pharmacology, Pharmacy, Drug Research, and Drug Innovation: 2011 Edition. ScholarlyEditions. 9 January 2012. pp. 3260–. ISBN 978-1-4649-6342-1.
- ↑ Advances in Glutamic Acid Research and Application: 2013 Edition: ScholarlyBrief. ScholarlyEditions. 21 June 2013. pp. 104–. ISBN 978-1-4816-7049-4.