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Chemical compound
Pharmaceutical compound
17-Phenylandrostenol Other names (3α,5α)-17-Phenyl-androst-16-en-3-ol
(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 Formula C 25 H 34 O Molar mass −1 3D model (JSmol )
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=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 N Y (what is this?) (verify)
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]
^ 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 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see here for a full list): α-EMTBL Alcohols (e.g., drinking alcohol , 2M2B )Anabolic steroids Avermectins (e.g., ivermectin )Barbiturates (e.g., phenobarbital )Benzodiazepines (e.g., diazepam )Bromide compounds (e.g., potassium bromide )Carbamates (e.g., meprobamate )Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine) )Etazepine Etifoxine Fenamates (e.g., mefenamic acid )Flavonoids (e.g., apigenin , hispidulin )Fluoxetine Flupirtine Imidazoles (e.g., etomidate )Kava constituents (e.g., kavain )Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone , cholesterol , THDOC )Niacin Niacinamide Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil ), cyclopyrrolones (e.g., zopiclone ), imidazopyridines (e.g., zolpidem ), pyrazolopyrimidines (e.g., zaleplon ))Norfluoxetine Petrichloral Phenols (e.g., propofol )Phenytoin Piperidinediones (e.g., glutethimide )Propanidid Pyrazolopyridines (e.g., etazolate )Quinazolinones (e.g., methaqualone )Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin )Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal) )Topiramate Valerian constituents (e.g., valerenic acid )Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane )Negative modulators: 1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α3IA α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolic steroids Amiloride Anisatin β-Lactams (e.g., penicillins , cephalosporins , carbapenems )Basmisanil Bemegride Bicyclic phosphates (TBPS , TBPO , IPTBO )BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil )Flavonoids (e.g., amentoflavone , oroxylin A )Flumazenil Fluoroquinolones (e.g., ciprofloxacin )Flurothyl Furosemide Golexanolone Iomazenil (123 I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide )Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e., picrotin , picrotoxinin and dihydropicrotoxinin )Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426 GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
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