Bifeprunox

Title: Bifeprunox
CAS Registry Number: 350992-10-8
CAS Name: 7-[4-([1,1¢-Biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone
Molecular Formula: C24H23N3O2
Molecular Weight: 385.46
Percent Composition: C 74.78%, H 6.01%, N 10.90%, O 8.30%
Literature References: Exhibits partial agonist activity at dopamine D2 and serotonin 5-HT1A receptors. Prepn: R. W. Feenstra et al., WO 9736893; eidem, US 6225312 (1997, 2001 both to Duphar); and receptor binding studies: idem et al., Bioorg. Med. Chem. Lett. 11, 2345 (2001). Analysis of binding affinity vs in vitro efficacy: A. Newman-Tancredi et al., Int. J. Neuropsychopharmacol. 8, 341 (2005). Review of development: W. Wolf, Curr. Opin. Invest. Drugs 4, 72-76 (2003).
Derivative Type: Methanesulfonate
CAS Registry Number: 350992-13-1
Additional Names: Bifeprunox mesylate
Manufacturers' Codes: DU-127090
Molecular Formula: C24H23N3O2.CH4O3S
Molecular Weight: 481.56
Percent Composition: C 62.35%, H 5.65%, N 8.73%, O 16.61%, S 6.66%
Therap-Cat: Antipsychotic.
Keywords: Antipsychotic; Dopamine-Serotonin System Stabilizer.
Bifidus Factor Bifluranol Bifonazole BIGCHAP Biguanide

Bifeprunox
Bifeprunox.png
Systematic (IUPAC) name
7-[4-(biphenyl-3-ylmethyl)piperazin-1-yl]-1,3-benzoxazol-2(3H)-one
Clinical data
Legal status  ?
Identifiers
CAS number 350992-10-8 N
ATC code None
PubChem CID 208951
ChemSpider 181044 YesY
UNII AP69E83Z79 YesY
ChEMBL CHEMBL218166 YesY
Chemical data
Formula C24H23N3O2 
Mol. mass 385.458 g/mol
 N (what is this?)  (verify)

Bifeprunox (DU-127,090) is a novel atypical antipsychotic agent which, along with SLV313, aripiprazole, and SSR-181507 combines minimal D2 receptor agonism with 5-HT receptor agonism.[1]

Bifeprunox has a novel mechanism of action. Conventional antipsychotics are classed into typical and atypical. The typical antipsychotics, such as chlorpromazine and haloperidol are potent D2 receptor antagonists. The atypical antipsychotics started with clozapine, these are classified as multireceptor interacting compounds, acting as an agonist towards 5-HT1A and an antagonist towards D2 receptors among other 5-HT and DA receptors. Bifeprunox and other novel atypical antipsychotics will instead of antagonizing D2 receptors, will act as partial agonists, as well as partial agonists towards 5-HT1A receptors.[2]

In a multi-center, placebo-controlled study, 20 mg of bifeprunox was found to be significantly more effective than placebo at reducing symptoms of schizophrenia, with a low incidence of side effects.[3]

An NDA for Bifeprunox was filed with the U.S. Food and Drug Administration in January 2007. The FDA rejected the application in August 2007.[4] In June 2009, Solvay and Lundbeck decided to cease development because "efficacy data did not support pursuing the existing development strategy of stabilisation of non-acute patients with schizophrenia." [5]