U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H32N2O2S
Molecular Weight 400.577
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIOCARLIDE

SMILES

CC(C)CCOC1=CC=C(NC(=S)NC2=CC=C(OCCC(C)C)C=C2)C=C1

InChI

InChIKey=BWBONKHPVHMQHE-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Thiocarlide (or tiocarlide or isoxyl) is a drug which was used in the treatment of tuberculosis. In addition was preclinical experiments, which showed, that it purely bacteriostatic against M. leprae. The precise mechanism is still unknown but was shown, that Delta9-desaturase could be a target for it. The more recent experiments have revealed, that Thiocarlide inhibits the dehydration step by the (3R)-hydroxyacyl dehydratases HadAB and HadBC.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P9WNZ3
Gene ID: 888821.0
Gene Symbol: desA3
Target Organism: Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
THE EFFECTIVENESS OF A THIOCARBANILIDE (ISOXYL) AS A THERAPEUTIC DRUG IN MOUSE TUBERCULOSIS.
1963 Nov
Absorption and excretion studies with thiocarlide (4'4-diisoamyloxythiocarbanilide) in man.
1966 Jun
Experimental studies on therapeutic effects of various combinations of antituberculosis drugs. II. Comparison of various regimens in treatment of experimental mouse tuberculosis infected with SM- and INH-resistant Schacht strain.
1967 Jul
[Simultaneous determination of double labelled isoxyl (3H and 35S) blood levels in man, by radio- and bio-assays].
1968
[Antitubercular agents. 44. N,N-dialkyldithiooxamide].
1988 Nov
The use of microarray analysis to determine the gene expression profiles of Mycobacterium tuberculosis in response to anti-bacterial compounds.
2004
Novel heteroarotinoids as potential antagonists of Mycobacterium bovis BCG.
2004 Feb 12
A common mechanism of inhibition of the Mycobacterium tuberculosis mycolic acid biosynthetic pathway by isoxyl and thiacetazone.
2012 Nov 9

Sample Use Guides

3 g in tablet form (6 tablets of 0.5 g) repeated after six hours.
Route of Administration: Oral
The specific inhibition of oleic acid synthesis by thiocarlide (ISO) suggested that the drug target is the aerobic desaturation system responsible for the synthesis of oleic acid from stearoyl-CoA in mycobacteria. To test this hypothesis Mycobacterium bovis BCG strain was grown in iron-supplemented medium, sonicated, and centrifuged at low speed, and both the cell wall pellet and the supernatant containing both cytosol and plasma membrane were assayed for Δ9 fatty acid desaturase activity. The assay was performed as originally described by Fulco and Bloch with minor modifications. Consistent with the findings of Fulco and Bloch in the absence of NADPH in the assay mixture, no oleic acid was detected. ISO consistently inhibited the incorporation of radioactivity into the oleic acid, but not into stearic acid, by 7% at 0.1 μg/ml and 61% at a concentration of 1.0 μg of ISO/ml in one typical experiment.
Name Type Language
TIOCARLIDE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
tiocarlide [INN]
Common Name English
TIOCARLIDE [MART.]
Common Name English
DATC
Code English
NSC-742400
Code English
TIOCARLIDE [MI]
Common Name English
4,4'-BIS(ISOPENTYLOXY)THIOCARBANILIDE
Common Name English
ISOXYL
Common Name English
THIOCARLIDE
Common Name English
Tiocarlide [WHO-DD]
Common Name English
DAT-C
Code English
Classification Tree Code System Code
WHO-ATC J04AD02
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
NCI_THESAURUS C280
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
WHO-VATC QJ04AD02
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
Code System Code Type Description
FDA UNII
43M23X81Y2
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
PRIMARY
CAS
910-86-1
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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WIKIPEDIA
THIOCARLIDE
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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EPA CompTox
DTXSID70238358
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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MERCK INDEX
m968
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2673
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ChEMBL
CHEMBL214920
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ECHA (EC/EINECS)
213-006-5
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NSC
742400
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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PUBCHEM
3001386
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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NCI_THESAURUS
C152637
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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DRUG BANK
DB13608
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
PRIMARY
MESH
C100189
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
PRIMARY
SMS_ID
100000077209
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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EVMPD
SUB11078MIG
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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INN
1597
Created by admin on Sat Dec 16 17:31:44 GMT 2023 , Edited by admin on Sat Dec 16 17:31:44 GMT 2023
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