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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL376488
CHEMBL376488
Compound Name BEDAQUILINE
ChEMBL Synonyms R-207910 | R403323 | BEDAQUILINE FUMARATE | BEDAQUILINE | SIRTURO | TMC207
Max Phase 4 (Approved)
Trade Names SIRTURO
Molecular Formula C32H31BrN2O2

Additional synonyms for CHEMBL376488 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1nc2ccc(Br)cc2cc1[C@@H](c3ccccc3)[C@@](O)(CCN(C)C)c4cccc5 ...
Download SMILES
Standard InChI InChI=1S/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7 ...
Download InChI
Standard InChI Key QUIJNHUBAXPXFS-XLJNKUFUSA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • MMV Pathogen Box
  • Orange Book
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL376488

Molecule Features

CHEMBL376488 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
ATP synthase inhibitor ATP synthase DailyMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
TuberculosisD014376Orphanet:3389Tuberculosis4DailyMed
ClinicalTrials
Liver DiseasesD008107EFO:0001421liver disease1ClinicalTrials
Tuberculosis, PulmonaryD014397EFO:1000049pulmonary tuberculosis3ClinicalTrials
LeprosyD007918EFO:0001054leprosy2ClinicalTrials
Tuberculosis, Multidrug-ResistantD018088EFO:0007381multidrug-resistant tuberculosis2ClinicalTrials

Clinical Data

ClinicalTrials.gov BEDAQUILINE
The Cochrane Collaboration BEDAQUILINE

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 CHEMBL376488. 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.


10uM


ChEMBL_ID Target Name Organism Score
CHEMBL289 Cytochrome P450 2D6 Homo sapiens 0.221

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
555.5 554.1569 7.13 8 45.59 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
4 1 2 4 1 2


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
13.05 9.31 7.71 6.17 5 37 0.22

Structural Alerts

There are 2 structural alerts for CHEMBL376488. To view alerts please click here.

Compound Cross References

ATC J - ANTIINFECTIVES FOR SYSTEMIC USE
J04 - ANTIMYCOBACTERIALS
J04A - DRUGS FOR TREATMENT OF TUBERCULOSIS
J04AK - Other drugs for treatment of tuberculosis
J04AK05 - bedaquiline

ChemSpider ChemSpider:QUIJNHUBAXPXFS-XLJNKUFUSA-N
DailyMed bedaquiline fumarate

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL376488



ACToR 654653-93-7
ChEBI 72292
DrugBank DB08903
DrugCentral 4741
FDA SRS 78846I289Y
IBM Patent System 9D79F800F152F800FE5501AF98029A39
KEGG Ligand C14122
MolPort MolPort-035-683-920
Nikkaji J2.291.406E
PDBe BQ1
PubChem 5388906
PubChem: Drugs of the Future 81044374
PubChem: Thomson Pharma 16896675
SureChEMBL SCHEMBL295482
ZINC ZINC000004655029

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