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SML4007

Sigma-Aldrich

TMC207

new

≥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:
843663-66-1
Molecular Weight:
555.50
MDL number:
MFCD22628872
UNSPSC Code:
51111800
UNSPSC Code:
12352200

Quality Level

100

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

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).

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

Hazard Classifications

Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Koen Andries et al.
Science (New York, N.Y.), 307(5707), 223-227 (2004-12-14)
The incidence of tuberculosis has been increasing substantially on a worldwide basis over the past decade, but no tuberculosis-specific drugs have been discovered in 40 years. We identified a diarylquinoline, R207910, that potently inhibits both drug-sensitive and drug-resistant Mycobacterium tuberculosis
M Ibrahim et al.
Antimicrobial agents and chemotherapy, 51(3), 1011-1015 (2006-12-21)
In previous studies, the diarylquinoline R207910 (also known as TMC207) was demonstrated to have high bactericidal activity when combined with first- or second-line antituberculous drugs. Here we extend the evaluation of R207910 in the curative model of murine tuberculosis by

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