bifeprunox

{{Short description|Experimental dopamine D2 receptor partial agonist researched as an antipsychotic agent}}

{{Infobox drug

| Verifiedfields = changed

| verifiedrevid = 459978705

| IUPAC_name = 7-[4-(biphenyl-3-ylmethyl)piperazin-1-yl]-1,3-benzoxazol-2(3H)-one

| image = Bifeprunox.png

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 350992-10-8

| ATC_prefix = none

| ATC_suffix =

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 218166

| PubChem = 208951

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 181044

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AP69E83Z79

| C=24 | H=23

| N=3 | O=2

| smiles = O=C2Oc1c(cccc1N2)N5CCN(Cc4cccc(c3ccccc3)c4)CC5

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C24H23N3O2/c28-24-25-21-10-5-11-22(23(21)29-24)27-14-12-26(13-15-27)17-18-6-4-9-20(16-18)19-7-2-1-3-8-19/h1-11,16H,12-15,17H2,(H,25,28)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CYGODHVAJQTCBG-UHFFFAOYSA-N

}}

Bifeprunox (INN; code name DU-127,090) is an atypical antipsychotic which, similarly to aripiprazole, combines minimal D₂ receptor agonism with serotonin receptor agonism.{{cite journal |vauthors=Cuisiat S, Bourdiol N, Lacharme V, Newman-Tancredi A, Colpaert F, Vacher B |title=Towards a new generation of potential antipsychotic agents combining D2 and 5-HT1A receptor activities |journal=J. Med. Chem. |volume=50 |issue=4 |pages=865–76 |year=2007 |pmid=17300168 |doi=10.1021/jm061180b}} It was under development for the treatment of schizophrenia, psychosis and Parkinson's disease.{{Cite web |title=Bifeprunox |url=https://go.drugbank.com/drugs/DB04888 |access-date=2023-11-16 |website=go.drugbank.com |language=en}}

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.{{cite journal

| vauthors=Casey DE, Sands EE, Heisterberg J, Yang HM

| title=Efficacy and safety of bifeprunox in patients with an acute exacerbation of schizophrenia: results from a randomized, double-blind, placebo-controlled, multicenter, dose-finding study

| journal=Psychopharmacology

| volume=200

| issue=3

| pages=317–31

| date=October 2008

| pmid=18597078

| doi=10.1007/s00213-008-1207-7

| s2cid=23291727

}} 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.[http://www.finanznachrichten.de/nachrichten-2007-08/artikel-8796651.asp Wyeth and Solvay say FDA rejects application for antipsychotic drug bifeprunox.] Thomson Financial, August 10, 2007. In June 2009, Solvay and Wyeth decided to cease development because "efficacy data did not support pursuing the existing development strategy of stabilisation of non-acute patients with schizophrenia."[http://www.lundbeck.com/investor/releases/ReleaseDetails/Release_1331489_EN.asp Pipeline update - following an interim analysis the studies with bifeprunox for the treatment of schizophrenia is discontinued] {{Webarchive|url=https://web.archive.org/web/20110714003443/http://www.lundbeck.com/investor/releases/ReleaseDetails/Release_1331489_EN.asp|date=2011-07-14}} Lundbeck Press Release.