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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
InChI Key QUIJNHUBAXPXFS-XLJNKUFUSA-N
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.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol
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)
Other databases
ChEBI CHEBI:72292
ChEMBL Ligand CHEMBL376488
DrugBank Ligand DB08903
DrugCentral Ligand 4741
GtoPdb PubChem SID 434122231
PubChem CID 5388906
RCSB PDB Ligand BQ1
Search Google for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N
Search Google for chemicals with the same backbone QUIJNHUBAXPXFS
Search PubMed clinical trials bedaquiline
Search PubMed titles bedaquiline
Search PubMed titles/abstracts bedaquiline
UniChem Compound Search for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N
UniChem Connectivity Search for chemical match using the InChIKey QUIJNHUBAXPXFS-XLJNKUFUSA-N