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CHEBI:72295 - bedaquiline fumarate

ChEBI IDCHEBI:72295
ChEBI Namebedaquiline fumarate
Stars
DefinitionA 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.
Last Modified16 May 2024
SubmitterSteve
DownloadsMolfile
FormulaC32H31BrN2O2.C4H4O4
Net Charge0
Average Mass671.588
Monoisotopic Mass670.16785
SMILESCOc1nc2ccc(Br)cc2cc1[C@@H](c1ccccc1)[C@@](O)(CCN(C)C)c1cccc2ccccc12.O=C(O)/C=C/C(=O)O
InChIInChI=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
InChIKeyZLVSPMRFRHMMOY-WWCCMVHESA-N
Roles Classification
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 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  Source
R403323ChemIDplus
6-bromo-3-[(1R,2S)-4-(dimethylammonio)-2-hydroxy-2-(1-naphthyl)-1-phenylbutyl]-2-methoxyquinolinium (2E)-but-2-enedioateIUPAC
Brand Name  Source
SirturoChEBI
Manual XrefsDatabases
D09873KEGG DRUG
WO2008068231Patent
DBSALT000016DrugBank
Registry NumbersSources
Reaxys:18368422Reaxys
CAS:845533-86-0ChemIDplus