View source for Thiocarlide

{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 470606991
| IUPAC_name = 1,3-bis[4-(3-methylbutoxy)phenyl]thiourea
| image = Thiocarlide.png
| alt = Structural formula of thiocarlide
| width = 250
| image2 = Thiocarlide 3D spacefill.png
| alt2 = Space-filling model of the thiocarlide molecule

<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status =
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 910-86-1
| ATC_prefix = J04
| ATC_suffix = AD02
| PubChem = 3001386
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| KEGG = D07246
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2272774
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 43M23X81Y2
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 214920

<!--Chemical data-->
| C=23 | H=32 | N=2 | O=2 | S=1
| smiles = S=C(Nc1ccc(OCCC(C)C)cc1)Nc2ccc(OCCC(C)C)cc2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = BWBONKHPVHMQHE-UHFFFAOYSA-N
}}

'''Thiocarlide''' (or '''tiocarlide''' or '''isoxyl''') is a [[thiourea]] drug used in the treatment of [[tuberculosis]], inhibiting synthesis of [[oleic acid]] and [[tuberculostearic acid]].<ref>{{cite journal  |vauthors=Phetsuksiri B, Jackson M, Scherman H, etal |title=Unique mechanism of action of the thiourea drug isoxyl on Mycobacterium tuberculosis |journal=J. Biol. Chem. |volume=278 |issue=52 |pages=53123–30 |date=December 2003 |pmid=14559907 |doi=10.1074/jbc.M311209200 |pmc=4747054 |doi-access=free }}</ref>

Thiocarlide has considerable anti[[mycobacteria]]l activity ''in vitro'' and is effective against multi-drug resistant strains of ''[[Mycobacterium tuberculosis]]''.<ref>{{cite journal  |vauthors=Phetsuksiri B, Baulard AR, Cooper AM, etal |title=Antimycobacterial activities of isoxyl and new derivatives through the inhibition of mycolic acid synthesis |journal=Antimicrob. Agents Chemother. |volume=43 |issue=5 |pages=1042–51 |date=May 1999 |pmid=10223912 |pmc=89109 |doi= 10.1128/AAC.43.5.1042}}</ref> 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.{{cn|date=August 2022}}

Thiocarlide was developed by a [[Belgium|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.{{cn|date=December 2022}}

==References==
{{reflist}}

{{Antimycobacterials}}

[[Category:Antibiotics]]
[[Category:Thioureas]]
[[Category:Phenol ethers]]
[[Category:Anti-tuberculosis drugs]]
[[Category:Isopentyl compounds]]

{{antiinfective-drug-stub}}