GABAB receptor antagonist
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).
Chemical compound
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]
^ 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 .