RWJ-51204

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	205701-85-5
PubChem (CID)	9822240
ChemSpider	7997989
ChEMBL	CHEMBL80436
Chemical and physical data
Formula	C21H19F2N3O3
Molar mass	399.390 g/mol
3D model (Jmol)	Interactive image
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) Key:VQOQDABVGWLROX-UHFFFAOYSA-N
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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 is a nonselective partial agonist at GABA_A 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. Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site. Current Drug Targets. CNS and Neurological Disorders. 2003 Aug;2(4):213-32.
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. 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. Journal of Pharmacology and Experimental Therapeutics. 2002 Nov;303(2):777-90.
3. Reitz AB, Jordan AD, Sanfilippo PJ, and Vavouyios-Smith A (1998) U.S. Patent 5,817,668.
4. Cohen JH, Maryanoff CA, Stefanik SM, Sorgi KL, Villani FJ. Process research for the synthesis of RWJ-51204, a novel anxiolytic agent. Organic Process Research & Development. 1999; 3(4):260-265.