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
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)
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 |
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15707540 |
8.0 null [pKi] | ||
Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15707540 |
8.5 null [pKi] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
|
Molecule of the month. Bifeprunox mesilate. | 2005 Oct |
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Aripiprazole: the evidence of its therapeutic impact in schizophrenia. | 2006 |
|
Partial agonist properties of the antipsychotics SSR181507, aripiprazole and bifeprunox at dopamine D2 receptors: G protein activation and prolactin release. | 2006 Mar 27 |
|
Antipsychotic-like vs cataleptogenic actions in mice of novel antipsychotics having D2 antagonist and 5-HT1A agonist properties. | 2006 Sep |
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Partial agonist actions at dopamine D2L receptors are modified by co-transfection of D3 receptors: potential role of heterodimer formation. | 2008 |
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Agonist and antagonist properties of antipsychotics at human dopamine D4.4 receptors: G-protein activation and K+ channel modulation in transfected cells. | 2008 May |
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Apomorphine-induced emesis in dogs: differential sensitivity to established and novel dopamine D2/5-HT(1A) antipsychotic compounds. | 2008 Nov 12 |
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Differences among conventional, atypical and novel putative D(2)/5-HT(1A) antipsychotics on catalepsy-associated behaviour in cynomolgus monkeys. | 2009 Nov 5 |
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Dopamine D2-D3 receptor heteromers: pharmacological properties and therapeutic significance. | 2010 Feb |
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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
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00366327
Flex dose (20 or 30 mg)tablet, QD for 1 year
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://dx.doi.org/10.1016/S0920-9964(03)80847-2
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:17:19 UTC 2023
by
admin
on
Fri Dec 15 16:17:19 UTC 2023
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Record UNII |
8F018D8L02
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C29710
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8F018D8L02
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RR-139
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C142956
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6918587
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m2484
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300000044496
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350992-13-1
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DBSALT002852
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CHEMBL218166
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |