Thiocarlide

Thiocarlide
Systematic (IUPAC) name


1,3-bis[4-(3-methylbutoxy)phenyl]thiourea
Identifiers
CAS Number	910-86-1^N
ATC code	J04AD02
PubChem	CID 3001386
ChemSpider	2272774^Y
UNII	43M23X81Y2^Y
ChEMBL	CHEMBL214920^Y
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)^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.

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. 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. PMC 89109. PMID 10223912.

Antimycobacterials, including tuberculosis treatment and leprostatic agents (J04)

Nucleic acid inhibitor

Rifamycins/ RNA polymerase inhibitor	Rifampicin^# Rifabutin Rifapentine Rifalazil^§

Antifolates/DSI	Dapsone^# Acedapsone Aldesulfone sodium

ASA	4-Aminosalicylic acid^# (Calcium aminosalicylate Sodium aminosalicylate)

Protein synthesis inhibitor

Aminoglycosides	Amikacin^# Capreomycin^# Kanamycin^# Streptomycin^#

Oxazolidone	Linezolid

Cell envelope antibiotic

Peptidoglycan layer	Alanine analogue: Cycloserine^#

Arabinogalactan layer	Ethylenediamine/arabinosyltransferase inhibitor: Ethambutol^# SQ109^†

Mycolic acid layer	Hydrazides/mycolic acid synth. inhibition: Isoniazid^# Thiocarbamides: Ethionamide^# Prothionamide Thiocarlide

Other/unknown

Combinations

Rifampicin/isoniazid/pyrazinamide

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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