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CHEBI:72292 - bedaquiline

Default Structure
ChEBI IDCHEBI:72292
ChEBI Namebedaquiline
Stars
DefinitionA quinoline-based antimycobacterial drug used (as its fumarate salt) for the treatment of pulmonary multi-drug resistant tuberculosis by inhibition of ATP synthase, an enzyme essential for the replication of the mycobacteria.
Last Modified16 May 2024
SubmitterSteve
DownloadsMolfile
FormulaC32H31BrN2O2
Net Charge0
Average Mass555.516
Monoisotopic Mass554.15689
SMILESCOc1nc2ccc(Br)cc2cc1[C@@H](c1ccccc1)[C@@](O)(CCN(C)C)c1cccc2ccccc12
InChIInChI=1S/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1
InChIKeyQUIJNHUBAXPXFS-XLJNKUFUSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
ATP synthase inhibitor  A mitochondrial respiratory-chain inhibitor that interferes with the action of ATP synthase.
Application:
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
ChEBI Ontology
Outgoing Relation(s)
bedaquiline (CHEBI:72292) has role antitubercular agent (CHEBI:33231)
bedaquiline (CHEBI:72292) has role ATP synthase inhibitor (CHEBI:20854)
bedaquiline (CHEBI:72292) is a aromatic ether (CHEBI:35618)
bedaquiline (CHEBI:72292) is a naphthalenes (CHEBI:25477)
bedaquiline (CHEBI:72292) is a organobromine compound (CHEBI:37141)
bedaquiline (CHEBI:72292) is a quinolines (CHEBI:26513)
bedaquiline (CHEBI:72292) is a tertiary alcohol (CHEBI:26878)
bedaquiline (CHEBI:72292) is a tertiary amino compound (CHEBI:50996)
bedaquiline (CHEBI:72292) is conjugate base of bedaquiline(2+) (CHEBI:72706)
Incoming Relation(s)
bedaquiline(2+) (CHEBI:72706) is conjugate acid of bedaquiline (CHEBI:72292)
IUPAC Name 
(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol
INNs  Source
bedaquilinaWHO MedNet
bedaquilineKEGG DRUG
bédaquilineWHO MedNet
bedaquilinumWHO MedNet
Synonyms  Source
1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-olKEGG COMPOUND
R 207910ChemIDplus
R207910ChemIDplus
TMC 207ChemIDplus
TMC-207ChemIDplus
TMC207ChemIDplus
Manual XrefsDatabases
4741DrugCentral
BedaquilineWikipedia
BQ1PDBeChem
D09872KEGG DRUG
DB08903DrugBank
WO2005117875Patent
WO2006067048Patent
Registry NumbersSources
Reaxys:10733008Reaxys
CAS:654653-93-7KEGG COMPOUND
CAS:843663-66-1ChemIDplus
Citations