7β-Hydroxyepiandrosterone

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]

7β-Hydroxyepiandrosterone
Names
IUPAC name
3β,7β-Dihydroxy-5α-androstan-17-one
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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C19H30O3/c1-18-7-5-12(20)9-11(18)10-15(21)17-13-3-4-16(22)19(13,2)8-6-14(17)18/h11-15,17,20-21H,3-10H2,1-2H3/t11-,12+,13+,14+,15+,17+,18+,19+/m1/s1
    Key: VFPMCLQMAUVEHD-UCPSWNCLSA-N
  • C[C@]12CC[C@@H](C[C@@H]1C[C@@H]([C@@H]3[C@@H]2CC[C@]4([C@H]3CCC4=O)C)O)O
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

References
  1. Dudas B, Hanin I, Rose M, Wülfert E (2004). "Protection against inflammatory neurodegeneration and glial cell death by 7beta-hydroxy epiandrosterone, a novel neurosteroid". Neurobiol. Dis. 15 (2): 262–8. doi:10.1016/j.nbd.2003.11.001. PMID 15006696. S2CID 24078411.
  2. Sandra N, Ester P, Marie-Agnès P, Robert M, Olivier H (2012). "The DHEA metabolite 7β-hydroxy-epiandrosterone exerts anti-estrogenic effects on breast cancer cell lines" (PDF). Steroids. 77 (5): 542–51. doi:10.1016/j.steroids.2012.01.019. PMID 22342541. S2CID 140140008.
  3. Miller KK, Al-Rayyan N, Ivanova MM, Mattingly KA, Ripp SL, Klinge CM, Prough RA (2013). "DHEA metabolites activate estrogen receptors alpha and beta". Steroids. 78 (1): 15–25. doi:10.1016/j.steroids.2012.10.002. PMC 3529809. PMID 23123738.
  4. Prossnitz ER, Arterburn JB (July 2015). "International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators". Pharmacol. Rev. 67 (3): 505–40. doi:10.1124/pr.114.009712. PMC 4485017. PMID 26023144.



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