Thiocarlide

Thiocarlide (or tiocarlide or isoxyl) is a thiourea drug used in the treatment of tuberculosis, inhibiting synthesis of oleic acid and tuberculostearic acid.[1]

Thiocarlide
Clinical data
ATC code
Identifiers
IUPAC name
  • 1,3-bis[4-(3-methylbutoxy)phenyl]thiourea
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.011.824
Chemical and physical data
FormulaC23H32N2O2S
Molar mass400.58 g·mol−1
3D model (JSmol)
SMILES
  • S=C(Nc1ccc(OCCC(C)C)cc1)Nc2ccc(OCCC(C)C)cc2
InChI
  • InChI=1S/C23H32N2O2S/c1-17(2)13-15-26-21-9-5-19(6-10-21)24-23(28)25-20-7-11-22(12-8-20)27-16-14-18(3)4/h5-12,17-18H,13-16H2,1-4H3,(H2,24,25,28) Y
  • Key:BWBONKHPVHMQHE-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Thiocarlide has considerable antimycobacterial activity in vitro and is effective against multi-drug resistant strains of Mycobacterium tuberculosis.[2] Isoxyl inhibits M. bovis with six hours of exposure, which is similar to isoniazid and ethionamide, two other prominent anti-TB drugs. Unlike these two drugs, however, isoxyl also partially inhibits the synthesis of fatty acids.

Thiocarlide was developed by a Belgian company, Continental Pharma S.A. Belgo-Canadienne in Brussels, Belgium. The head researcher was Professor N. P. Buu-Hoi, head of Continental Pharma's Research Division.

References
  1. Phetsuksiri B, Jackson M, Scherman H, et al. (December 2003). "Unique mechanism of action of the thiourea drug isoxyl on Mycobacterium tuberculosis". J. Biol. Chem. 278 (52): 53123–30. doi:10.1074/jbc.M311209200. PMC 4747054. PMID 14559907.
  2. Phetsuksiri B, Baulard AR, Cooper AM, et al. (May 1999). "Antimycobacterial activities of isoxyl and new derivatives through the inhibition of mycolic acid synthesis". Antimicrob. Agents Chemother. 43 (5): 1042–51. doi:10.1128/AAC.43.5.1042. PMC 89109. PMID 10223912.
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