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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
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
C 19 H 30 O 3
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).
Chemical compound
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
^
a
b 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 .
^ 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 .
^ 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 .
^ 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 .
AR Tooltip Androgen receptor
Agonists
SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A