RWJ-51204

RWJ-51204 is an anxiolytic drug used in scientific research. It has similar effects to benzodiazepine drugs, but is structurally distinct and so is classed as a nonbenzodiazepine anxiolytic.

RWJ-51204
Identifiers
IUPAC name
  • 5-ethoxymethyl-7-fluoro-3-oxo-1,2,3,5-tetrahydrobenzo[4,5] imidazo[1,2a]pyridine-4-N-(2-fluorophenyl)carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H19F2N3O3
Molar mass399.398 g·mol−1
3D model (JSmol)
SMILES
  • Fc1ccccc1NC(=O)C=3C(=O)CCN4c2c(cc(F)cc2)N(C=34)COCC
InChI
  • InChI=1S/C21H19F2N3O3/c1-2-29-12-26-17-11-13(22)7-8-16(17)25-10-9-18(27)19(21(25)26)20(28)24-15-6-4-3-5-14(15)23/h3-8,11H,2,9-10,12H2,1H3,(H,24,28) Y
  • Key:VQOQDABVGWLROX-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

RWJ-51204 is a nonselective partial agonist at GABAA receptors.[1] It produces primarily anxiolytic effects at low doses, with sedative, ataxia and muscle relaxant effects only appearing at some 20x the effective anxiolytic dose.[2] It was discovered by researchers at the pharmaceutical company Johnson & Johnson,[3][4] but its development has been discontinued.

References
  1. Atack JR (August 2003). "Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site". Current Drug Targets. CNS and Neurological Disorders. 2 (4): 213–32. doi:10.2174/1568007033482841. PMID 12871032.
  2. Dubinsky B, Vaidya AH, Rosenthal DI, Hochman C, Crooke JJ, DeLuca S, DeVine A, Cheo-Isaacs CT, Carter AR, Jordan AD, Reitz AB, Shank RP (November 2002). "5-ethoxymethyl-7-fluoro-3-oxo-1,2,3,5-tetrahydrobenzo[4,5]imidazo[1,2a]pyridine-4-N-(2-fluorophenyl)carboxamide (RWJ-51204), a new nonbenzodiazepine anxiolytic". The Journal of Pharmacology and Experimental Therapeutics. 303 (2): 777–90. doi:10.1124/jpet.102.036954. PMID 12388665. S2CID 23880756.
  3. US 5817668, Reitz AB, Jordan AD, Sanfilippo PJ, Vavouyios-Smith A, issued 6 October 1998, assigned to Ortho Pharma Corp
  4. Cohen JH, Maryanoff CA, Stefanik SM, Sorgi KL, Villani FJ (1999). "Process research for the synthesis of RWJ-51204, a novel anxiolytic agent". Organic Process Research & Development. 3 (4): 260–265. doi:10.1021/op990182l.


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