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Details

Stereochemistry ACHIRAL
Molecular Formula C24H23N3O2
Molecular Weight 385.4583
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIFEPRUNOX

SMILES

O=C1NC2=CC=CC(N3CCN(CC4=CC=CC(=C4)C5=CC=CC=C5)CC3)=C2O1

InChI

InChIKey=CYGODHVAJQTCBG-UHFFFAOYSA-N
InChI=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)

HIDE SMILES / InChI

Molecular Formula C24H23N3O2
Molecular Weight 385.4583
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Bifeprunox, code name DU-127,090 is an atypical antipsychotic agent, which combines minimal D2 receptor agonism with 5-HT receptor agonism. Bifeprunox was in phase III of clinical trials for the treatment of schizophrenia, Bipolar Depression and in phase I for Parkinson's disease, but these studies were discontinued because efficacy data did not support pursuing the existing development strategy of stabilization of non-acute patients with schizophrenia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
8.0 null [pKi]
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
8.5 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
381.5 ng × h/mL
20 mg 1 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BIFEPRUNOX plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
825.1 ng × h/mL
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BIFEPRUNOX plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
20 mg 1 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BIFEPRUNOX plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1%
40 mg 1 times / day multiple, oral
dose: 40 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BIFEPRUNOX plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
New 1-aryl-4-(biarylmethylene)piperazines as potential atypical antipsychotics sharing dopamine D(2)-receptor and serotonin 5-HT(1A)-receptor affinities.
2001 Sep 3
DU-127090 Solvay/H Lundbeck.
2003 Jan
Novel antipsychotic agents with 5-HT(1A) agonist properties: role of 5-HT(1A) receptor activation in attenuation of catalepsy induction in rats.
2005 Aug
Molecule of the month. Bifeprunox mesilate.
2005 Oct
Contrasting contribution of 5-hydroxytryptamine 1A receptor activation to neurochemical profile of novel antipsychotics: frontocortical dopamine and hippocampal serotonin release in rat brain.
2005 Oct
Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia.
2005 Sep
Aripiprazole: the evidence of its therapeutic impact in schizophrenia.
2006
Differential profile of antipsychotics at serotonin 5-HT1A and dopamine D2S receptors coupled to extracellular signal-regulated kinase.
2006 Mar 18
Partial agonist properties of the antipsychotics SSR181507, aripiprazole and bifeprunox at dopamine D2 receptors: G protein activation and prolactin release.
2006 Mar 27
In vivo occupancy of dopamine D2 receptors by antipsychotic drugs and novel compounds in the mouse striatum and olfactory tubercles.
2006 Sep
Antipsychotic-like vs cataleptogenic actions in mice of novel antipsychotics having D2 antagonist and 5-HT1A agonist properties.
2006 Sep
Drug-drug interactions associated with second-generation antipsychotics: considerations for clinicians and patients.
2007
Discriminative stimulus properties of S32504, a novel D3/D2 receptor agonist and antiparkinson agent, in rats: attenuation by the antipsychotics, aripiprazole, bifeprunox, N-desmethylclozapine, and by selective antagonists at dopamine D2 but not D3 receptors.
2007 Apr
Action of novel antipsychotics at human dopamine D3 receptors coupled to G protein and ERK1/2 activation.
2007 Aug
Partial agonist actions of aripiprazole and the candidate antipsychotics S33592, bifeprunox, N-desmethylclozapine and preclamol at dopamine D(2L) receptors are modified by co-transfection of D(3) receptors: potential role of heterodimer formation.
2007 Aug
Neuropharmacological profile of bifeprunox: merits and limitations in comparison with other third-generation antipsychotics.
2007 Jul
Putative antipsychotics with pronounced agonism at serotonin 5-HT1A and partial agonist activity at dopamine D2 receptors disrupt basal PPI of the startle reflex in rats.
2007 Jul
Pharmacological profiles in rats of novel antipsychotics with combined dopamine D2/serotonin 5-HT1A activity: comparison with typical and atypical conventional antipsychotics.
2007 Mar
Differential agonist and inverse agonist profile of antipsychotics at D2L receptors coupled to GIRK potassium channels.
2007 Mar
Differences in agonist/antagonist properties at human dopamine D(2) receptors between aripiprazole, bifeprunox and SDZ 208-912.
2007 Nov 28
Pharmacological causes of hyperprolactinemia.
2007 Oct
Differential profile of typical, atypical and third generation antipsychotics at human 5-HT7a receptors coupled to adenylyl cyclase: detection of agonist and inverse agonist properties.
2007 Oct
Bipolar depression: trial-based insights to guide patient care.
2008
Partial agonist actions at dopamine D2L receptors are modified by co-transfection of D3 receptors: potential role of heterodimer formation.
2008
Dopamine D2(High) receptors moderately elevated by bifeprunox and aripiprazole.
2008 Dec
Antipsychotics differ in their ability to internalise human dopamine D2S and human serotonin 5-HT1A receptors in HEK293 cells.
2008 Feb 26
Atypical antipsychotic-induced metabolic side effects: insights from receptor-binding profiles.
2008 Jan
Actions of novel agonists, antagonists and antipsychotic agents at recombinant rat 5-HT6 receptors: a comparative study of coupling to G alpha s.
2008 Jul 7
Effects of antipsychotics and reference monoaminergic ligands on marble burying behavior in mice.
2008 Mar
Agonist and antagonist properties of antipsychotics at human dopamine D4.4 receptors: G-protein activation and K+ channel modulation in transfected cells.
2008 May
Characterization of aripiprazole partial agonist activity at human dopamine D3 receptors.
2008 Nov 12
Apomorphine-induced emesis in dogs: differential sensitivity to established and novel dopamine D2/5-HT(1A) antipsychotic compounds.
2008 Nov 12
The antipsychotics clozapine and olanzapine increase plasma glucose and corticosterone levels in rats: comparison with aripiprazole, ziprasidone, bifeprunox and F15063.
2008 Sep 11
Receptor reserve-dependent properties of antipsychotics at human dopamine D2 receptors.
2009 Apr 1
Effects of bifeprunox and aripiprazole on rat serotonin and dopamine neuronal activity and anxiolytic behaviour.
2009 Mar
Differences among conventional, atypical and novel putative D(2)/5-HT(1A) antipsychotics on catalepsy-associated behaviour in cynomolgus monkeys.
2009 Nov 5
Tetrabenazine is neuroprotective in Huntington's disease mice.
2010 Apr 26
Development and application of an LC-MS/MS method for measuring the effect of (partial) agonists on cAMP accumulation in vitro.
2010 Apr 30
Dopamine D2-D3 receptor heteromers: pharmacological properties and therapeutic significance.
2010 Feb
The importance of 5-HT1A receptor agonism in antipsychotic drug action: rationale and perspectives.
2010 Jul
The effect of metformin on anthropometrics and insulin resistance in patients receiving atypical antipsychotic agents: a meta-analysis.
2010 Oct
Not all partial dopamine D(2) receptor agonists are the same in treating schizophrenia. Exploring the effects of bifeprunox and aripiprazole using a computer model of a primate striatal dopaminergic synapse.
2010 Sep 7
Identification of N-propylnoraporphin-11-yl 5-(1,2-dithiolan-3-yl)pentanoate as a new anti-Parkinson's agent possessing a dopamine D2 and serotonin 5-HT1A dual-agonist profile.
2011 Jul 14
Patents

Sample Use Guides

Flex dose (20 or 30 mg)tablet, QD for 1 year
Route of Administration: Oral
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:38:33 UTC 2023
Edited
by admin
on Fri Dec 15 16:38:33 UTC 2023
Record UNII
AP69E83Z79
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BIFEPRUNOX
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
Bifeprunox [WHO-DD]
Common Name English
bifeprunox [INN]
Common Name English
7-[4-(Biphenyl-3-ylmethyl)piperazin-1-yl]benzoxazol-2(3H)-one
Systematic Name English
BIFEPRUNOX [MI]
Common Name English
BIFEPRUNOX [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
Code System Code Type Description
FDA UNII
AP69E83Z79
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
NCI_THESAURUS
C65262
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
INN
8266
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
SMS_ID
100000089783
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL218166
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
EVMPD
SUB20312
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
MESH
C509981
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
WIKIPEDIA
BIFEPRUNOX
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
MERCK INDEX
m2484
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB04888
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
CAS
350992-10-8
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
PUBCHEM
208951
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID80188592
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
USAN
RR-138
Created by admin on Fri Dec 15 16:38:33 UTC 2023 , Edited by admin on Fri Dec 15 16:38:33 UTC 2023
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY