Phaclofen

GABAB receptor antagonist
Phaclofen
Names
IUPAC name
[3-amino-2-(4-chlorophenyl)propyl]phosphonic acid
Identifiers
CAS Number
  • 108351-35-5 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 1579 ☒N
IUPHAR/BPS
  • 1091
PubChem CID
  • 1641
InChI
  • 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
Chemical formula
 C9H13ClNO3P
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).
☒N verify (what is checkY☒N ?)
Infobox references
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]

References

  1. ^ 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.
  2. ^ 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.
  • v
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GABA receptor modulators
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators
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