17-Phenylandrostenol

17-Phenylandrostenol (17-PA), or (3α,5α)-17-phenylandrost-16-en-3-ol, is a steroid drug which binds to GABAA receptors. It acts as an antagonist against the sedative effects of neuroactive steroids, but has little effect when administered by itself, and does not block the effects of benzodiazepines or barbiturates.[1][2]

17-Phenylandrostenol
Clinical data
Other names(3α,5α)-17-Phenyl-androst-16-en-3-ol
Identifiers
IUPAC name
  • (3R,5S,8R,9S,10S,13S,14S)-10,13-dimethyl-17-phenyl- 2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC25H34O
Molar mass350.546 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CC[C@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC=C4C5=CC=CC=C5)C)O
InChI
  • InChI=1S/C25H34O/c1-24-14-12-19(26)16-18(24)8-9-20-22-11-10-21(17-6-4-3-5-7-17)25(22,2)15-13-23(20)24/h3-7,10,18-20,22-23,26H,8-9,11-16H2,1-2H3/t18-,19+,20-,22-,23-,24-,25+/m0/s1 Y
  • Key:SINAMTXBCYKFDL-WBJZGETLSA-N Y
 NY (what is this?)  (verify)

Chemistry
See also: List of neurosteroids

See also
  • Androstenol

References
  1. Mennerick S, He Y, Jiang X, Manion BD, Wang M, Shute A, Benz A, Evers AS, Covey DF, Zorumski CF (May 2004). "Selective antagonism of 5alpha-reduced neurosteroid effects at GABA(A) receptors". Molecular Pharmacology. 65 (5): 1191–7. doi:10.1124/mol.65.5.1191. PMID 15102947.
  2. Kelley SP, Alan JK, O'Buckley TK, Mennerick S, Krishnan K, Covey DF, Leslie Morrow A (October 2007). "Antagonism of neurosteroid modulation of native γ-aminobutyric acid receptors by (3α,5α)-17-phenylandrost-16-en-3-ol". European Journal of Pharmacology. 572 (2–3): 94–101. doi:10.1016/j.ejphar.2007.06.028. PMC 2098702. PMID 17658511.



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