Bedaquiline HCl

• CAT Number: I023138
• Molecular Formula: C32H32BrClN2O2
• Molecular Weight: 591.974
• Purity: 98%
• Synonyms: TMC-207;TMC 207; TMC207; R207910; AIDS222089; AIDS-222089; AIDS 222089; Bedaquiline fumarate
• Solubility: Soluble in DMSO
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: (1R,2S)-1-(6-Bromo-2-methoxy-3-quinolyl)-4-dimethylamino-2-(1-naphthyl)-1-phenyl-butan-2-ol hydrochloride
• InChI: InChI=1S/C32H31BrN2O2.ClH/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;1H/t30-,32-;/m1./s1
• InChIKey: AOJCUQGSVYCVQU-UNCJQMLCSA-N
• SMILES: O[C@](CCN(C)C)(C1=C2C=CC=CC2=CC=C1)[C@@H](C3=CC4=CC(Br)=CC=C4N=C3OC)C5=CC=CC=C5.[H]Cl

Bedaquiline, also known as TMC207 and R207910, is a diarylquinoline anti-tuberculosis drug, which was discovered by a team led by Koen Andries at Janssen Pharmaceutica. Bedaquiline blocks the proton pump for ATP synthase of mycobacteria. ATP production is required for cellular energy production and its loss leads to cell death, even in dormant or nonreplicating mycobacteria.It is the first member of a new class of drugs called the diarylquinolines. Bedaquiline is bactericidal.

Reference

1: Hussar DA, Polyak G. Lorcaserin, dimethyl fumarate, and bedaquiline fumarate. J Am Pharm Assoc (2003). 2013 May-Jun;53(3):328-30, 332, 334. doi: 10.1331/JAPhA.2013.13517. PubMed PMID: 23699683.
2: Centers for Disease Control and Prevention. Provisional CDC guidelines for the use and safety monitoring of bedaquiline fumarate (Sirturo) for the treatment of multidrug-resistant tuberculosis. MMWR Recomm Rep. 2013 Oct 25;62(RR-09):1-12. Erratum in: MMWR Recomm Rep. 2013 Nov 15;62(45):906. PubMed PMID: 24157696.