17-Phenylandrostenol

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	694438-95-4 ;
PubChem CID	25068278;
ChemSpider	21475142 ;
Chemical and physical data
Formula	C25H34O
Molar mass	350.546 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:SINAMTXBCYKFDL-WBJZGETLSA-N ;
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17-Phenylandrostenol (17-PA), or (3α,5α)-17-phenylandrost-16-en-3-ol, is a steroid drug which binds to GABA_A 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]

Chemistry

^ 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.
^ 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.