Structure via PubChem · Public domain (PubChem)
bedaquiline
Sign in to saveAlso known as TMC207, 1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol, TMC-207, Bedaquilinum, Bedaquilina, R 207910, TMC 207, R207910
Bedaquiline, sometimes abbreviated as BDQ and sold under the brand name Sirturo, is a medication used for the treatment of active tuberculosis. Specifically, it is used to treat multi-drug-resistant tuberculosis along with other medications for tuberculosis. It is taken by mouth.
Key facts
- Drug.O
- 2
- Drug.Br
- 1
- Drug.N
- 2
- Drug.image
- Bedaquiline.svg
- Drug.image_class
- skin-invert-image
- Drug.caption
- Molecular structure of bedaquiline
- Drug.image2
- Bedaquiline 3D.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Sirturo
- Drug.MedlinePlus
- a613022
- Drug.DailyMedID
- Bedaquiline
- Drug.routes_of_administration
- By mouth
- Drug.caption2
- 3D representation of a bedaquiline molecule
- Drug.ATC_prefix
- J04
- Drug.ATC_suffix
- AK05
- Drug.legal_US
- Rx-only
- Drug.legal_EU
- Rx-only
- Drug.legal_status
- Rx-only
via Wikipedia infobox
Chemical data
- Formula
- C32H31BrN2O2
- Molecular weight
- 555.5 g/mol
- IUPAC name
- (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-naphthalen-1-yl-1-phenylbutan-2-ol
- SMILES
- CN(C)CC[C@@](C1=CC=CC2=CC=CC=C21)([C@H](C3=CC=CC=C3)C4=C(N=C5C=CC(=CC5=C4)Br)OC)O
- InChIKey
- QUIJNHUBAXPXFS-XLJNKUFUSA-N
- XLogP
- 7.2
- Polar surface area
- 45.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
2,026 papers- Bedaquiline: what might the future hold?The Lancet. Microbe · 2024
- Bedaquiline-Pretomanid-Linezolid Regimens for Drug-Resistant Tuberculosis.The New England journal of medicine · 2022
- Bedaquiline in Drug-Resistant Tuberculosis: A Mini-Review.Current molecular pharmacology · 2023
- Bedaquiline: Current status and future perspectives.Journal of global antimicrobial resistance · 2021
- Bedaquiline for treatment of non-tuberculous mycobacteria (NTM): a systematic review and meta-analysis.The Journal of antimicrobial chemotherapy · 2024
via PubMed
Wikidata facts
- Mass
- 554.157
- Has use
- medication
Show 9 more facts
- chemical formula
- C₃₂H₃₁BrN₂O₂
- subject has role
- bactericide
- isomeric SMILES
- CN(C)CC[C@@](C1=CC=CC2=CC=CC=C21)([C@H](C3=CC=CC=C3)C4=C(N=C5C=CC(=CC5=C4)Br)OC)O
- canonical SMILES
- CN(C)CCC(C1=CC=CC2=CC=CC=C21)(C(C3=CC=CC=C3)C4=C(N=C5C=CC(=CC5=C4)Br)OC)O
- World Health Organisation international non-proprietary name
- bedaquiline
- Commons category
- Bedaquiline
- defined daily dose
- 86
- medical condition treated
- multidrug-resistant tuberculosis
- significant drug interaction
- ketoconazole
Sources (7)
via Wikidata · CC0
~7 min read
Encyclopedic overview
10 sectionsContents
- Medical uses
- Side effects
- Drug interactions
- Mechanism of action
- Resistance
- History
- Society and culture
- Economics
- Research
- References
Bedaquiline, sometimes abbreviated as BDQ and sold under the brand name Sirturo, is a medication used for the treatment of active tuberculosis. Specifically, it is used to treat multi-drug-resistant tuberculosis along with other medications for tuberculosis. It is taken by mouth.
Common side effects include nausea, joint pains, headaches, and chest pain. Serious side effects include QT prolongation, liver dysfunction, and an increased risk of death. While harm during pregnancy has not been found, it has not been well studied in this population. It is in the diarylquinoline antimycobacterial class of medications. It works by blocking the ability of M.tuberculosis to make adenosine 5'-triphosphate (ATP).
Excerpted from Wikipedia’s “bedaquiline” article, available under the CC BY-SA 4.0 licence.