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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL726
CHEMBL726
Compound Name FLUPHENAZINE
ChEMBL Synonyms PERMITIL | Permitil | FLUPHENAZINE HYDROCHLORIDE | PROLIXIN | MODITEN | Prolixin | FLUPHENAZINE
Max Phase 4 (Approved)
Trade Names MODITEN | PERMITIL | PROLIXIN | FLUPHENAZINE HYDROCHLORIDE
Molecular Formula C22H26F3N3OS

Additional synonyms for CHEMBL726 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES OCCN1CCN(CCCN2c3ccccc3Sc4ccc(cc24)C(F)(F)F)CC1
Standard InChI InChI=1S/C22H26F3N3OS/c23-22(24,25)17-6-7-21-19(16-17)28(18- ...
Download InChI
Standard InChI Key PLDUPXSUYLZYBN-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Drugs for Neglected Diseases Initiative (DNDi)
  • Gene Expression Atlas Compounds
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL726

Molecule Features

CHEMBL726 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:Y Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Dopamine D2 receptor antagonist Dopamine D2 receptor PubMed PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Psychotic DisordersD011618EFO:0005407psychosis4ATC
SchizophreniaD012559EFO:0000692schizophrenia3ClinicalTrials

Clinical Data

ClinicalTrials.gov FLUPHENAZINE
The Cochrane Collaboration FLUPHENAZINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL726. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 1.000
CHEMBL319 Alpha-1a adrenergic receptor Rattus norvegicus 1.000
CHEMBL217 Dopamine D2 receptor Homo sapiens 1.000
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 1.000
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 1.000
CHEMBL273 Serotonin 1a (5-HT1a) receptor Rattus norvegicus 1.000
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 1.000
CHEMBL223 Alpha-1d adrenergic receptor Homo sapiens 1.000
CHEMBL1850 Dopamine D5 receptor Homo sapiens 1.000
CHEMBL4892 Alpha-1a adrenergic receptor Bos taurus 1.000
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 1.000
CHEMBL225 Serotonin 2c (5-HT2c) receptor Homo sapiens 1.000
CHEMBL234 Dopamine D3 receptor Homo sapiens 1.000
CHEMBL224 Serotonin 2a (5-HT2a) receptor Homo sapiens 1.000
CHEMBL265 Dopamine D1 receptor Rattus norvegicus 1.000
CHEMBL3223 Serotonin 7 (5-HT7) receptor Rattus norvegicus 1.000
CHEMBL3998 Dopamine D2 receptor Bos taurus 0.999
CHEMBL1867 Alpha-2a adrenergic receptor Homo sapiens 0.998
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.997



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL231 Histamine H1 receptor Homo sapiens 1.000
CHEMBL315 Alpha-1b adrenergic receptor Rattus norvegicus 1.000
CHEMBL319 Alpha-1a adrenergic receptor Rattus norvegicus 1.000
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 1.000
CHEMBL217 Dopamine D2 receptor Homo sapiens 1.000
CHEMBL339 Dopamine D2 receptor Rattus norvegicus 1.000
CHEMBL5131 Trypanothione reductase Trypanosoma cruzi 1.000
CHEMBL4892 Alpha-1a adrenergic receptor Bos taurus 1.000
CHEMBL1850 Dopamine D5 receptor Homo sapiens 1.000
CHEMBL273 Serotonin 1a (5-HT1a) receptor Rattus norvegicus 1.000
CHEMBL322 Serotonin 2a (5-HT2a) receptor Rattus norvegicus 1.000
CHEMBL223 Alpha-1d adrenergic receptor Homo sapiens 1.000
CHEMBL234 Dopamine D3 receptor Homo sapiens 1.000
CHEMBL225 Serotonin 2c (5-HT2c) receptor Homo sapiens 1.000
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 1.000
CHEMBL265 Dopamine D1 receptor Rattus norvegicus 1.000
CHEMBL224 Serotonin 2a (5-HT2a) receptor Homo sapiens 1.000
CHEMBL3223 Serotonin 7 (5-HT7) receptor Rattus norvegicus 0.999
CHEMBL276 Muscarinic acetylcholine receptor M1 Rattus norvegicus 0.999
CHEMBL1867 Alpha-2a adrenergic receptor Homo sapiens 0.998

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
437.5 437.1749 4.31 6 29.95 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
5 1 0 4 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 7.39 3.92 3.58 2 30 0.73

Structural Alerts

There are no structural alerts for CHEMBL726

Compound Cross References

ATC N - NERVOUS SYSTEM
N05 - PSYCHOLEPTICS
N05A - ANTIPSYCHOTICS
N05AB - Phenothiazines with piperazine structure
N05AB02 - fluphenazine

ChemSpider ChemSpider:PLDUPXSUYLZYBN-UHFFFAOYSA-N
DailyMed fluphenazine hydrochloride
PubChem SID: 104171155 SID: 11111179 SID: 11111180 SID: 144203697 SID: 170465375 SID: 26751625 SID: 50100242 SID: 50104297 SID: 57287813 SID: 90341540
Wikipedia Fluphenazine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL726



ACToR 47646-09-3 69-23-8
Atlas fluphenazine
BindingDB 78433
Brenda 97943
ChEBI 5123
DrugBank DB00623
DrugCentral 1212
eMolecules 732810
EPA CompTox Dashboard DTXSID2023068
FDA SRS S79426A41Z
Guide to Pharmacology 204
Human Metabolome Database HMDB0014761
IBM Patent System 9117F7B792E3840B2DC507A0661D634B
KEGG Ligand C07010
LINCS LSM-3226
Mcule MCULE-7579992672
MolPort MolPort-001-727-938
Nikkaji J4.863A
PharmGKB PA449676
PubChem 3372
PubChem: Thomson Pharma 14832617
SureChEMBL SCHEMBL19221
ZINC ZINC000019203912

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/PLDUPXSUYLZYBN-UHFFFAOYSA-N spacer
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