BIFEPRUNOX

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15707540 | https://globenewswire.com/news-release/2009/07/30/130354/0/en/Pipeline-update-following-an-interim-analysis-the-studies-with-bifeprunox-for-the-treatment-of-schizophrenia-is-discontinued.html

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15707540	Agonist 2678		8.0 null [pKi]
D(2) dopamine receptor 58 Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15707540	Partial Agonist 290		8.5 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 298 Sources: https://clinicaltrials.gov/ct2/show/NCT00366327	Primary	Phase III 656	Unknown Approved Use Unknown
Bipolar depression 9 Sources: https://clinicaltrials.gov/ct2/show/NCT00245973	Primary	Phase III 656	Unknown Approved Use Unknown
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12625033	Primary	Phase I 428	Unknown Approved Use Unknown

AUC

Value	Dose	Co-administered	Analyte	Population
381.5 ng × h/mL REVIEW https://www.formularywatch.com/view/bifeprunox-partial-dopamine-receptor-agonist-treatment-schizophrenia	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 REVIEW https://www.formularywatch.com/view/bifeprunox-partial-dopamine-receptor-agonist-treatment-schizophrenia	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% REVIEW https://www.formularywatch.com/view/bifeprunox-partial-dopamine-receptor-agonist-treatment-schizophrenia	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% REVIEW https://www.formularywatch.com/view/bifeprunox-partial-dopamine-receptor-agonist-treatment-schizophrenia	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

Vendor/Aggregator	ID	URL
Alfa Chemistry	ACM350992131	http://www.alfa-chemistry.com/search.aspx?q=ACM350992131
Angene	AGN-PC-0WH1IE	http://www.angenechemical.com/productshow/AGN-PC-0WH1IE.html
Axon MedChem	1508	https://www.axonmedchem.com/product/1508
BOC Sciences	350992-10-8	http://www.bocsci.com/description.asp?cas=350992-10-8
BOC Sciences	350992-13-1	http://www.bocsci.com/description.asp?cas=350992-13-1
Lab Network	LN01346299	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01346299
MolPort	MolPort-003-845-039	https://www.molport.com/shop/molecule-link/MolPort-003-845-039
MolPort	MolPort-005-943-082	https://www.molport.com/shop/molecule-link/MolPort-005-943-082
MuseChem	R005333	https://www.musechem.com/product/R005333.html
Otava	7070707030	https://search.otavachemicals.com/#!/search?query=7070707030&type=code
ShangHai Biochempartner	BCP02133	http://www.biochempartner.com/search_BCP02133
Toronto Research Chemicals	B383200	https://www.trc-canada.com/product-detail/?CatNum=B383200
Toronto Research Chemicals	D473080	https://www.trc-canada.com/product-detail/?CatNum=D473080
Wonderchem	WD05YDO	http://www.wonder-chem.com/search.html?text=WD05YDO
eMolecules	11313129	https://orderbb.emolecules.com/search/#?query=11313129
eMolecules	300123197	https://orderbb.emolecules.com/search/#?query=300123197
eMolecules	50891881	https://orderbb.emolecules.com/search/#?query=50891881
mcule	MCULE-8263015928	https://mcule.com/MCULE-8263015928/
mcule	MCULE-8477820759	https://mcule.com/MCULE-8477820759/

PubMed

Title	Date	PubMed
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	15996562
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	15987834
Novel antipsychotics activate recombinant human and native rat serotonin 5-HT1A receptors: affinity, efficacy and potential implications for treatment of schizophrenia.	2005 Sep	15707540
Aripiprazole: the evidence of its therapeutic impact in schizophrenia.	2006	22496680
Drug-drug interactions associated with second-generation antipsychotics: considerations for clinicians and patients.	2007	17285099
Action of novel antipsychotics at human dopamine D3 receptors coupled to G protein and ERK1/2 activation.	2007 Aug	17588617
Neuropharmacological profile of bifeprunox: merits and limitations in comparison with other third-generation antipsychotics.	2007 Jul	17659474
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	17393144
Pharmacological profiles in rats of novel antipsychotics with combined dopamine D2/serotonin 5-HT1A activity: comparison with typical and atypical conventional antipsychotics.	2007 Mar	17351418
Differential agonist and inverse agonist profile of antipsychotics at D2L receptors coupled to GIRK potassium channels.	2007 Mar	17239906
Bipolar depression: trial-based insights to guide patient care.	2008	18689288
Agonist and antagonist properties of antipsychotics at human dopamine D4.4 receptors: G-protein activation and K+ channel modulation in transfected cells.	2008 May	17897483
Serotonergic approaches in the development of novel antipsychotics.	2008 Nov	18621404
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.	2008 Oct	18597078
Differences among conventional, atypical and novel putative D(2)/5-HT(1A) antipsychotics on catalepsy-associated behaviour in cynomolgus monkeys.	2009 Nov 5	19464324
Dopamine D2-D3 receptor heteromers: pharmacological properties and therapeutic significance.	2010 Feb	19896900
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	21591752

Patents

Sample Use Guides

In Vivo Use Guide

Flex dose (20 or 30 mg)tablet, QD for 1 year

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:38:33 GMT 2023` Edited by `admin` on `Fri Dec 15 16:38:33 GMT 2023`
Record UNII	AP69E83Z79
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIFEPRUNOX

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