bedaquiline   Click here for help

GtoPdb Ligand ID: 11171

Synonyms: BDQ | compound 1a [PMID: 17496888] | R-207910 [1] | Sirturo® | TMC-207 | TMC207
Approved drug PDB Ligand
bedaquiline is an approved drug (FDA (2012), EMA (2014))
Compound class: Synthetic organic
Comment: Bedaquiline is a quinoline-based antimycobacterial drug that is used in the treatment of tuberculosis [1]. Functionally, it inhibits mycobacterial ATP synthase and enhances the antibacterial activity of second-line drug combinations.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 45.59
Molecular weight 554.16
XLogP 7.38
No. Lipinski's rules broken 1
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Canonical SMILES COc1nc2ccc(cc2cc1[C@H]([C@](c1cccc2c1cccc2)(CCN(C)C)O)c1ccccc1)Br
Isomeric SMILES COc1nc2ccc(cc2cc1[C@H]([C@](c1cccc2c1cccc2)(CCN(C)C)O)c1ccccc1)Br
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2014))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
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IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9316 bedaquiline
Synonyms Click here for help
BDQ | compound 1a [PMID: 17496888] | R-207910 [1] | Sirturo® | TMC-207 | TMC207
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Bedaquiline (Sirturo), R207910
Other databases
ChEMBL Ligand CHEMBL376488
DrugBank Ligand DB08903
DrugCentral Ligand 4741
GtoPdb PubChem SID 434122231
PubChem CID 5388906
Search Google for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N
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UniChem Compound Search for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N
UniChem Connectivity Search for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N