CHEBI:72295 - bedaquiline fumarate

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ChEBI Name bedaquiline fumarate
ChEBI ID CHEBI:72295
Definition A fumarate salt prepared from equimolar amounts of bedaquiline and fumaric acid. It is used in combination therapy 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 C36H35BrN2O6
Net Charge 0
Average Mass 671.57700
Monoisotopic Mass 670.16785
InChI InChI=1S/C32H31BrN2O2.C4H4O4/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;5-3(6)1-2-4(7)8/h4-17,20-21,30,36H,18-19H2,1-3H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t30-,32-;/m1./s1
InChIKey ZLVSPMRFRHMMOY-WWCCMVHESA-N
SMILES OC(=O)\C=C\C(O)=O.COc1nc2ccc(Br)cc2cc1[C@@H](c1ccccc1)[C@@](O)(CCN(C)C)c1cccc2ccccc12
Roles Classification
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 fumarate (CHEBI:72295) has part bedaquiline(2+) (CHEBI:72706)
bedaquiline fumarate (CHEBI:72295) has role antitubercular agent (CHEBI:33231)
bedaquiline fumarate (CHEBI:72295) has role ATP synthase inhibitor (CHEBI:20854)
bedaquiline fumarate (CHEBI:72295) is a fumarate salt (CHEBI:50921)
IUPAC Name
(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenylbutan-2-ol bis[(2Z)-but-2-enedioate]
Synonyms Sources
6-bromo-3-[(1R,2S)-4-(dimethylammonio)-2-hydroxy-2-(1-naphthyl)-1-phenylbutyl]-2-methoxyquinolinium (2E)-but-2-enedioate IUPAC
R403323 ChemIDplus
Brand Name Source
Sirturo ChEBI
Manual Xrefs Databases
D09873 KEGG DRUG
DBSALT000016 DrugBank
WO2008068231 Patent
View more database links
Registry Numbers Types Sources
18368422 Reaxys Registry Number Reaxys
845533-86-0 CAS Registry Number ChemIDplus
Last Modified
16 May 2024