Phaclofen Names IUPAC name [3-amino-2-(4-chlorophenyl)propyl]phosphonic acid
Identifiers ChemSpider InChI=1S/C9H13ClNO3P/c10-9-3-1-7(2-4-9)8(5-11)6-15(12,13)14/h1-4,8H,5-6,11H2,(H2,12,13,14)
N Key: VSGNGLJPOGUDON-UHFFFAOYSA-N
N InChI=1/C9H13ClNO3P/c10-9-3-1-7(2-4-9)8(5-11)6-15(12,13)14/h1-4,8H,5-6,11H2,(H2,12,13,14)
Key: VSGNGLJPOGUDON-UHFFFAOYAO
C1=CC(=CC=C1C(CN)CP(=O)(O)O)Cl
Properties C9 H13 ClNO3 P Molar mass 249.631 g/mol Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Phaclofen , or phosphonobaclofen , is a selective antagonist for the GABAB receptor .[ 1] It was the first selective GABAB antagonist discovered, but its utility was limited by the fact that it does not cross the blood brain barrier.[ 2]
References ^ Kerrn D, Ong J, Prager R, Gynther B, Curtis D (3 March 1987). "Phaclofen: a peripheral and central baclofen antagonist". Brain Research . 405 (1): 150– 154. doi :10.1016/0006-8993(87)90999-1 . PMID 3032346 . S2CID 29595421 . ^ Froestl W, Mickel SJ, von Sprecher G, Diel PJ, Hall RG, Maier L, Strub D, Melillo V, Baumann PA, Bernasconi R, et al. (August 18, 1995). "Phosphinic acid analogues of GABA. 2. Selective, orally active GABAB antagonists". J Med Chem . 38 (17): 3313– 3331. doi :10.1021/jm00017a016 . PMID 7650685 .
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 Negative modulators: Compound 14
See also Receptor/signaling modulators GABAA receptor positive modulators GABA metabolism/transport modulators