Chemistry:7β-Hydroxyepiandrosterone
From HandWiki
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| Names | |
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| IUPAC name
3β,7β-Dihydroxy-5α-androstan-17-one
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| Systematic IUPAC name
(3aS,3bR,4S,5aR,7S,9aS,9bS,11aS)-4,7-Dihydroxy-9a,11a-dihydroxyhexadecahydro-1H-cyclopenta[a]phenanthren-1-one | |
| Other names
7β-OH-EPIA; 5α-Androstan-3β,7β-diol-17-one
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C19H30O3 | |
| Molar mass | 306.446 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 | |
Tracking categories (test):
7β-Hydroxyepiandrosterone (7β-OH-EPIA), also known as 5α-androstan-3β,7β-diol-17-one, is an endogenous androgen, estrogen, and neurosteroid that is produced from dehydroepiandrosterone and epiandrosterone.[1][2][3] It has neuroprotective effects and, along with 7α-hydroxyepiandrosterone, may mediate the neuroprotective effects of DHEA.[1] 7β-OH-EPIA may act as a highly potent antagonist of the G protein-coupled estrogen receptor (GPER) (affinity of <1 nM).[4]
References
- ↑ 1.0 1.1 "Protection against inflammatory neurodegeneration and glial cell death by 7beta-hydroxy epiandrosterone, a novel neurosteroid". Neurobiol. Dis. 15 (2): 262–8. 2004. doi:10.1016/j.nbd.2003.11.001. PMID 15006696.
- ↑ "The DHEA metabolite 7β-hydroxy-epiandrosterone exerts anti-estrogenic effects on breast cancer cell lines". Steroids 77 (5): 542–51. 2012. doi:10.1016/j.steroids.2012.01.019. PMID 22342541. https://tel.archives-ouvertes.fr/tel-00727277/file/ThA_se_-_Sandra_-_NIRO.pdf.
- ↑ "DHEA metabolites activate estrogen receptors alpha and beta". Steroids 78 (1): 15–25. 2013. doi:10.1016/j.steroids.2012.10.002. PMID 23123738.
- ↑ "International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators". Pharmacol. Rev. 67 (3): 505–40. July 2015. doi:10.1124/pr.114.009712. PMID 26023144.
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