BIFEPRUNOX MESYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H23N3O2.CH4O3S
Molecular Weight	481.564
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ONWKHSGOYGLGPO-UHFFFAOYSA-N

InChI=1S/C24H23N3O2.CH4O3S/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;1-5(2,3)4/h1-11,16H,12-15,17H2,(H,25,28);1H3,(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
DU-127090 Solvay/H Lundbeck.	2003 Jan	12625033
Drug-drug interactions associated with second-generation antipsychotics: considerations for clinicians and patients.	2007	17285099
Upcoming agents for the treatment of schizophrenia: mechanism of action, efficacy and tolerability.	2008	18973393
Partial agonist actions at dopamine D2L receptors are modified by co-transfection of D3 receptors: potential role of heterodimer formation.	2008	18585083
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	18511034

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 16:17:19 GMT 2023` Edited by `admin` on `Fri Dec 15 16:17:19 GMT 2023`
Record UNII	8F018D8L02
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BIFEPRUNOX MESYLATE

Official Name

English

7-(4-(BIPHENYL-3-YLMETHYL)PIPERAZIN-1-YL)BENZOXAZOL-2(3H)-ONE METHANESULPHONATE

Systematic Name

English

2(3H)-BENZOXAZOLONE, 7-(4-((1,1'-BIPHENYL)-3-YLMETHYL)-1-PIPERAZINYL)-, MONOMETHANESULFONATE

Systematic Name

English

7-[4-(Biphenyl-3-ylmethyl)piperazin-1-yl]benzoxazol-2(3H)-one methanesulfonate

Systematic Name

English

BIFEPRUNOX MESILATE

Common Name

English

BIFEPRUNOX METHANESULFONATE

Common Name

English

Bifeprunox mesylate [WHO-DD]

Common Name

English

DU127090

Code

English

BIFEPRUNOX MESYLATE [USAN]

Common Name

English

BIFEPRUNOX METHANESULFONATE [MI]

Common Name

English

DU-127090

Code

English

2(3H)-BENZOXAZOLONE, 7-(4-((1,1'-BIPHENYL)-3-YLMETHYL)-1-PIPERAZINYL)-, MONOMETHANESULPHONATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29710