Bedaquiline fumarateProduct ingredient for Bedaquiline
- Name
- Bedaquiline fumarate
- Drug Entry
- Bedaquiline
Bedaquiline is a bactericidal antimycobacterial drug belonging to the class of diarylquinoline. The quinolinic central heterocyclic nucleus with alcohol and amine side chains is responsible for bedaquiline-mediated antimycobacterial activity.5 Although it is closely related to fluoroquinolones, bedaquiline does not affect DNA gyrase; instead, bedaquiline inhibits the c subunit of ATP synthase responsible for synthesizing ATP.5 Consequently, bedaquiline can be used to treat mycobacterial infection, particularly tuberculosis (TB).6 Although the current standard of TB treatment of anti-TB drugs for 2 months, including 2 key drugs isoniazid and rifampin, is highly effective, the emergence of multidrug-resistant TB (MDR-TB) to isoniazid and rifampin has substantially worsened patients outcome.4
Bedaquiline was approved by the FDA on December 28, 2012, to treat pulmonary MDR-TB, following favorable results in multiple pre-clinical and clinical studies.3,4 It is the first drug that was approved in the last 40 years by the FDA for TB unresponsive to current treatments on the market.3 Currently, bedaquiline is the last-line anti-TB drug and must only be used in an appropriate combination regimen.6,5
- Accession Number
- DBSALT000016
- Structure
Structure for Bedaquiline fumarate (DBSALT000016)
- Synonyms
- Not Available
- UNII
- P04QX2C1A5
- CAS Number
- 845533-86-0
- Weight
- Average: 671.577
Monoisotopic: 670.167849509 - Chemical Formula
- C36H35BrN2O6
- InChI Key
- ZLVSPMRFRHMMOY-WWCCMVHESA-N
- 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
- IUPAC Name
- (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol; (2E)-but-2-enedioic acid
- SMILES
- [H]\C(=C(\[H])C(O)=O)C(O)=O.[H][C@@](C1=CC=CC=C1)(C1=CC2=CC(Br)=CC=C2N=C1OC)[C@@](O)(CCN(C)C)C1=CC=CC2=CC=CC=C12
- External Links
- PubChem Compound
- 24812732
- ChemSpider
- 28528191
- ChEBI
- 72295
- ChEMBL
- CHEMBL2105700
- Wikipedia
- Bedaquiline
- Predicted Properties
Property Value Source Water Solubility 0.000193 mg/mL ALOGPS logP 6.37 ALOGPS logP 7.13 Chemaxon logS -6.5 ALOGPS pKa (Strongest Acidic) 13.61 Chemaxon pKa (Strongest Basic) 8.91 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 45.59 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 154.02 m3·mol-1 Chemaxon Polarizability 57.43 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon