SML4007
TMC207
≥98% (HPLC)
Synonym(s):
(αS,βR)-6-Bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol, (1R, 2S)-1-(6-Bromo-2methoxy-3-quinolinyl)-4-(dimethylamino)-2-(1-naphthalenyl)-1-phenyl-2-butanol, Bedaquiline, R 207910, R-207910, R207910
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About This Item
Empirical Formula (Hill Notation):
C32H31BrN2O2
CAS Number:
Molecular Weight:
555.50
UNSPSC Code:
51111800
MDL number:
NACRES:
NA.21
Quality Level
assay
≥98% (HPLC)
form
powder
optical activity
[α]/D 195.0 to 155.0° (c = 0.5g/100mL in DMF)
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
-10 to -25°C
SMILES string
BrC(C=C1)=CC2=C1N=C(OC)C([C@@H](C3=CC=CC=C3)[C@](O)(C4=CC=CC5=C4C=CC=C5)CCN(C)C)=C2
InChI key
QUIJNHUBAXPXFS-XLJNKUFUSA-N
Biochem/physiol Actions
Potent and selective mycobacterial ATP synthase inhibitor with broad-spectrum anti-mycobacterial activity.
TMC207 (Bedaquiline; R207910) is an orally active, potent and selective mycobacterial ATP synthase inhibitor (M. smegmatis IC50 = 2.5 nM or 1.4 ng (non-salt form)/mL; human mitochondrial ATP syntase IC50 >200 uM) with broad-spectrum anti-mycobacterial activity (MIC 10-120 ng/mL), including M. bovis, avium complex (MAC), kansasii, marinum, fortuitum, abscessus, smegmatis, ulcerans, and both drug-susceptible and multiple drug-resistant M. tuberculosis strains (to rigampin, isoniazid, streptomycin, ethambutol, pyrazinamide, fluoroquinolone).
TMC207 (Bedaquiline; R207910) is an orally active, potent and selective mycobacterial ATP synthase inhibitor (M. smegmatis IC50 = 2.5 nM or 1.4 ng (non-salt form)/mL; human mitochondrial ATP syntase IC50 >200 uM) with broad-spectrum anti-mycobacterial activity (MIC 10-120 ng/mL), including M. bovis, avium complex (MAC), kansasii, marinum, fortuitum, abscessus, smegmatis, ulcerans, and both drug-susceptible and multiple drug-resistant M. tuberculosis strains (to rigampin, isoniazid, streptomycin, ethambutol, pyrazinamide, fluoroquinolone).
signalword
Warning
hcodes
pcodes
Hazard Classifications
Aquatic Chronic 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Anna C Haagsma et al.
Antimicrobial agents and chemotherapy, 53(3), 1290-1292 (2008-12-17)
The diarylquinoline TMC207 kills Mycobacterium tuberculosis by specifically inhibiting ATP synthase. We show here that human mitochondrial ATP synthase (50% inhibitory concentration [IC(50)] of >200 microM) displayed more than 20,000-fold lower sensitivity for TMC207 compared to that of mycobacterial ATP
Baohong Ji et al.
Antimicrobial agents and chemotherapy, 50(4), 1558-1560 (2006-03-30)
As measured by a proportional bactericidal technique in the mouse footpad system, the bactericidal activity against Mycobacterium leprae of R207910 was equal to that of rifapentine, rifampin, or moxifloxacin and significantly greater than those of minocycline, PA-824, and linezolid. These
Anil Koul et al.
Nature chemical biology, 3(6), 323-324 (2007-05-15)
The diarylquinoline R207910 (TMC207) is a promising candidate in clinical development for the treatment of tuberculosis. Though R207910-resistant mycobacteria bear mutations in ATP synthase, the compound's precise target is not known. Here we establish by genetic, biochemical and binding assays
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML4007-10MG | 04065271187399 |
| SML4007-50MG | 04065271189904 |