Thiocarlide

Thiocarlide

Systematic (IUPAC) name
1,3-bis[4-(3-methylbutoxy)phenyl]thiourea
Identifiers
CAS Number	910-86-1
ATC code	J04AD02 (WHO)
PubChem	CID 3001386
ChemSpider	2272774
UNII	43M23X81Y2
ChEMBL	CHEMBL214920
Chemical data
Formula	C23H32N2O2S
Molar mass	400.578 g/mol
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) Key:BWBONKHPVHMQHE-UHFFFAOYSA-N
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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 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. 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. PMC 89109. PMID 10223912.