Thiocarlide

Thiocarlide

Clinical data
ATC code	J04AD02 ( WHO )
Identifiers
IUPAC name 1,3-bis[4-(3-methylbutoxy)phenyl]thiourea
CAS Number	910-86-1  N
PubChem CID	3001386
ChemSpider	2272774  Y
UNII	43M23X81Y2
KEGG	D07246
ChEMBL	ChEMBL214920  Y
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) Y Key:BWBONKHPVHMQHE-UHFFFAOYSA-N Y
NY  (what is this?)    (verify)

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.^{[ citation needed ]}

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.^{[ citation needed ]}

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.