Thiocarlide

Thiocarlide
Clinical data
ATC code	J04AD02 (WHO) ;
Identifiers
	IUPAC name 1,3-bis[4-(3-methylbutoxy)phenyl]thiourea;
CAS Number	910-86-1 ;
PubChem CID	3001386;
ChemSpider	2272774 ;
UNII	43M23X81Y2;
KEGG	D07246;
ChEMBL	ChEMBL214920 ;
CompTox Dashboard (EPA)	DTXSID70238358 ;
ECHA InfoCard	100.011.824
Chemical and physical data
Formula	C23H32N2O2S
Molar mass	400.58 g·mol−1
3D model (JSmol)	Interactive image;
	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

↑ 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.
↑ 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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[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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