Bifeprunox

Summary

Bifeprunox (CHEMBL218166) is a phase-3 clinical-stage small molecule; indicated across 6 conditions including depressive disorder and bipolar disorder.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Indications: 6 conditions
• Clinical trials: 19
• Chemistry: 385.5 Da · C24H23N3O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL218166
Name	Bifeprunox
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	208951
Molecular formula	C24H23N3O2
Molecular weight	385.5
InChIKey	CYGODHVAJQTCBG-UHFFFAOYSA-N

SMILES: C1CN(CCN1CC2=CC(=CC=C2)C3=CC=CC=C3)C4=CC=CC5=C4OC(=O)N5

IUPAC name: 7-[4-[(3-phenylphenyl)methyl]piperazin-1-yl]-3H-1,3-benzoxazol-2-one

Also known as: Bifeprunox, bifeprunox, BIFEPRUNOX, MMV1646880

Parent form; salt/anhydrous children: CHEMBL2107317

Patent coverage: 824 distinct patent families (3,394 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: 5-hydroxytryptamine receptor 1A, D(2) dopamine receptor, 5-hydroxytryptamine receptor 1A, 5-hydroxytryptamine receptor 2A, D(2) dopamine receptor.

Bioactivity

ChEMBL activities: 14 potent at pChembl ≥ 5 of 14 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
DRD2	10.4	Ki	0.04	nM	CHEMBL_ACT_3116210
DRD2	10	Ki	0.1	nM	CHEMBL_ACT_3116194
DRD2	9.22	Ki	0.6	nM	CHEMBL_ACT_12652732
P61169	8.81	Ki	1.55	nM	CHEMBL_ACT_1818632
DRD2	8.66	Ki	2.2	nM	CHEMBL_ACT_3113103
DRD2	8.66	Ki	2.2	nM	CHEMBL_ACT_852908
DRD2	8.64	Ki	2.3	nM	CHEMBL_ACT_14723047
DRD2	8.64	Ki	2.29	nM	CHEMBL_ACT_14723109
DRD2	8.54	IC50	2.9	nM	CHEMBL_ACT_12652704
HTR1A	8.03	Ki	9.3	nM	CHEMBL_ACT_3113106
HTR1A	8.03	Ki	9.3	nM	CHEMBL_ACT_852909
P19327	7.19	Ki	64.57	nM	CHEMBL_ACT_1818589
HTR1A	6.49	EC50	323.6	nM	CHEMBL_ACT_1818654
P14842	5.48	Ki	3311	nM	CHEMBL_ACT_1818610

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

6 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
depressive disorder	3	MONDO:0002050	MONDO:0002050
bipolar disorder	3	MONDO:0004985	EFO:0009963
Alzheimer disease	3	MONDO:0004975	MONDO:0004975
schizoaffective disorder	2	MONDO:0005487	EFO:0005411

2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 19.

Phase distribution

Phase	Trials
PHASE3	14
PHASE2	4
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00134459	PHASE3	COMPLETED	Study Evaluating Bifeprunox in Bipolar Depression
NCT00160147	PHASE3	TERMINATED	Treatment of Elderly Subjects With Psychosis and Behavioral Disturbances Associated With Dementia of the Alzheimer’s Type
NCT00193687	PHASE3	COMPLETED	Bifeprunox in the Treatment of Schizophrenia
NCT00193713	PHASE3	COMPLETED	Bifeprunox in the Treatment of Schizophrenia
NCT00230828	PHASE3	COMPLETED	Patient-reported Outcomes in the Treatment of Schizophrenia
NCT00245973	PHASE3	COMPLETED	Study Evaluating Bifeprunox in Bipolar Depression
NCT00366171	PHASE3	COMPLETED	Open Label Extension Study of Bifeprunox
NCT00366327	PHASE3	TERMINATED	Study Evaluating Bifeprunox in Patients With Schizophrenia.
NCT00366704	PHASE3	TERMINATED	Study Comparing Bifeprunox to Risperidone in Treatment of Outpatients With Schizophrenia With Weight as Primary Endpoint
NCT00380224	PHASE3	COMPLETED	Study Comparing the Affect of Bifeprunox Vs Olanzapine on Weight During the Treatment of Outpatients With Schizophrenia.
NCT00396214	PHASE3	TERMINATED	Compare the Effects of Bifeprunox and Quetiapine on Weight Changes in Stable Schizophrenic Patients
NCT00658645	PHASE3	TERMINATED	Efficacy of Bifeprunox in Patients With Schizophrenia
NCT00704509	PHASE3	TERMINATED	Efficacy of Bifeprunox in Patients With Schizophrenia
NCT00861497	PHASE3	TERMINATED	Bifeprunox Extension to Extension Study in Patients With Schizophrenia
NCT00139906	PHASE2	COMPLETED	Twice Daily Titration Study of Bifeprunox in Subjects With Schizophrenia
NCT00139919	PHASE2	COMPLETED	Progressively Decreasing Titration Schedules of Bifeprunox in Subjects With Schizophrenia or Bipolar Disorder
NCT00141479	PHASE2	COMPLETED	To Evaluate the Impact of Treatment Interruption on Re-initiation of Bifeprunox
NCT00141505	PHASE2	COMPLETED	PK Effects of Bifeprunox & Valproate in Bipolar I
NCT00581451	PHASE1	COMPLETED	Study Evaluating the Tolerability of Bifeprunox in Healthy Subjects

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).