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]
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| 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 | |
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 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]
Chemistry
editSee also
editReferences
edit- ^ Neurosteroids and Brain Function. Academic Press. 12 December 2001. pp. 18–. ISBN 978-0-08-054423-6.
- ^ a b 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. PMID 10049597. S2CID 11520064.
- ^ Norman G. Bowery (19 June 2006). Allosteric Receptor Modulation in Drug Targeting. CRC Press. pp. 112–. ISBN 978-1-4200-1618-5.
- ^ Park-Chung M, Malayev A, Purdy RH, Gibbs TT, Farb DH (1999). "Sulfated and unsulfated steroids modulate gamma-aminobutyric acidA receptor function through distinct sites". Brain Res. 830 (1): 72–87. doi:10.1016/s0006-8993(99)01381-5. PMID 10350561. S2CID 44664830.
- ^ 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.