CHEBI:72292 - bedaquiline

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ChEBI Name bedaquiline
ChEBI ID CHEBI:72292
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C32H31BrN2O2
Net Charge 0
Average Mass 555.50500
Monoisotopic Mass 554.157
InChI InChI=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
InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N
SMILES COc1nc2ccc(Br)cc2cc1[C@@H](c1ccccc1)[C@@](O)(CCN(C)C)c1cccc2ccccc12
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): 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(s): antitubercular agent
A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Sources
bedaquilina WHO MedNet
bédaquiline WHO MedNet
bedaquiline KEGG DRUG
bedaquilinum WHO MedNet
Synonyms Sources
1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol KEGG COMPOUND
R 207910 ChemIDplus
R207910 ChemIDplus
TMC 207 ChemIDplus
TMC-207 ChemIDplus
TMC207 ChemIDplus
Manual Xrefs Databases
4741 DrugCentral
Bedaquiline Wikipedia
C14122 KEGG COMPOUND
D09872 KEGG DRUG
WO2005117875 Patent
WO2006067048 Patent
View more database links
Registry Numbers Types Sources
10733008 Reaxys Registry Number Reaxys
654653-93-7 CAS Registry Number KEGG COMPOUND
843663-66-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017