Thiocarlide (isoxyl) is a thiourea derivative that was used in the 1960s to successfully treat tuberculosis (TB). It has considerable antimycobacterial activity in vitro and is effective against multi-drug resistant strains of Mycobacterium tuberculosis in the range of 1-10 µg/ml.1,2 At concentrations of 10 µM, isoxyl inhibits the synthesis of M. bovis during six hours of exposure which is similar to isoniazid (INH) and ethionamide (ETH), two other predominant anti-tuberculosis drugs. Unlike INH and ETH, isoxyl also partially inhibits the synthesis of fatty acids. Isoxyl shows no acute toxicity against primary macrophage cell cultures as demonstrated by diminution of redox activity.2
1
Phetsuksiri, B., Jackson, M., Scherman, H., et al. Unique mechanism of action of the thiourea drug isoxyl on mycobacterium tuberculosis. J Biol Chem278(52)53123-53130(2003).
2
Phetsuksiri, B., Baulard, A.R., Cooper, A.M., et al. Antimycobacterial activities of isoxyl and new derivatives through the inhibition of mycolic acid synthesis. Antimicrob Agents Chemother43(5)1042-1051(1999).
Synonyms
Isoxyl
Formal Name
N,N'-bis[4-(3-methylbutoxy)phenyl]-thiourea
CAS Number
910-86-1
Molecular Formula
C23H32N2O2S
Formula Weight
400.6
Formulation
A crystalline solid
Purity
>98%
λmax
273 nm
Stability
2 years
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
SMILES
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CC(C)CCOc1ccc(cc1)NC(=S)Nc1ccc(OCCC(C)C)cc1
Background Reading
Phetsuksiri, B., Jackson, M., Scherman, H., et al. Unique mechanism of action of the thiourea drug isoxyl on mycobacterium tuberculosis. J Biol Chem278(52)53123-53130(2003).
Phetsuksiri, B., Baulard, A.R., Cooper, A.M., et al. Antimycobacterial activities of isoxyl and new derivatives through the inhibition of mycolic acid synthesis. Antimicrob Agents Chemother43(5)1042-1051(1999).
Thiocarlide is available in the following screening
library: