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Details

Stereochemistry ACHIRAL
Molecular Formula C10H12N4OS
Molecular Weight 236.295
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AMITHIOZONE

SMILES

CC(=Nc1ccc(cc1)/C(/[H])=N/NC(=N)S)O

InChI

InChIKey=SRVJKTDHMYAMHA-WUXMJOGZSA-N
InChI=1S/C10H12N4OS/c1-7(15)13-9-4-2-8(3-5-9)6-12-14-10(11)16/h2-6H,1H3,(H,13,15)(H3,11,14,16)/b12-6+

HIDE SMILES / InChI

Molecular Formula C10H12N4OS
Molecular Weight 236.295
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Amithiozone, also known as thioacetazone, is an oral antibiotic, which is used in the treatment of tuberculosis. In 1991, the World Health Organization (WHO) recommended replacing thioacetazone with ethambutol in patients with known or suspected HIV infection. Thioacetazone is no longer included in WHO’s recommended first-line treatment for tuberculosis and is now reserved for uncommon situations in which treatment options have been compromised by resistance to other anti-tuberculosis medicines in HIV-negative individuals. Despite the increased recognition of this risk, thioacetazone remained in use mainly in low-income countries because of its low cost. Amithiozone has also been used in trials studying the treatment of Mycobacterium Avium-intracellular Infection. One of the possible mechanism action of the drug is interference with the metabolism of methionine of susceptible tubercle bacilli, which utilize methionine for nucleic acid synthesis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The chemical approach to the control of tuberculosis.
1952 Aug 8
Antibacterial nitrofuran derivatives. I. 5-nitro-2-furaldehyde semicarbazones and thiosemicarbazones.
1967 Jul
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.
1973 Sep
The early bactericidal activity of drugs in patients with pulmonary tuberculosis.
1980 Jun
Aplastic anaemia associated with anti-tuberculosis chemotherapy.
1982
Thiacetazone: in vitro activity against Mycobacterium avium and M. tuberculosis.
1990 Dec
The Garrod Lecture. Understanding the chemotherapy of tuberculosis--current problems.
1992 May
Antituberculosis activity of clarithromycin.
1995 Dec
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.
1997 May
Green fluorescent protein reporter microplate assay for high-throughput screening of compounds against Mycobacterium tuberculosis.
1998 Feb
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.
2000 Feb 1
In vitro activity of thiacetazone on mycobacterial species belonging to the Mycobacterium tuberculosis complex.
2002 Oct
Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice.
2003 Jan
Clinical concentrations of thioridazine kill intracellular multidrug-resistant Mycobacterium tuberculosis.
2003 Mar
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.
2005 Nov
EthA, a common activator of thiocarbamide-containing drugs acting on different mycobacterial targets.
2007 Mar
Preclinical pharmacokinetics of KBF611, a new antituberculosis agent in mice and rabbits, and comparison with thiacetazone.
2010 Mar
A common mechanism of inhibition of the Mycobacterium tuberculosis mycolic acid biosynthetic pathway by isoxyl and thiacetazone.
2012 Nov 9
Patents

Patents

Sample Use Guides

150 mg daily doses 6 days a week over the entire treatment period for a total of 8 months.
Route of Administration: Oral
Fifty-four strains of M. tuberculosis complex were characterised based on the minimum inhibitory concentration (MIC) of thiacetazone (amithiozone) and the growth pattern in the presence of different concentrations of the drug. The results showed that the MIC of thiacetazone to type II M. africanum strains was significantly higher than for other strains in the study (P < 0.01). Thiacetazone showed a paradoxical effect on 63% of strains where lower concentrations exhibited a better inhibiting activity than higher concentrations.
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:07:57 UTC 2021
Edited
by admin
on Sat Jun 26 03:07:57 UTC 2021
Record UNII
MMG78X7SSR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMITHIOZONE
Common Name English
N-(4-(((AMINO-THIOXOMETHYL)HYDRAZONO)METHYL)PHENYL)ACETAMIDE [WHO-IP]
Systematic Name English
CITAZONE
Brand Name English
THIOACETAZONE
INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
4'-FORMYLACETANILIDE THIOSEMICARBAZONE
Systematic Name English
THIOPARAMIZONE
Common Name English
THIOACETAZONUM [WHO-IP LATIN]
Common Name English
THIOACETAZONE [MART.]
Common Name English
THIOACETAZONE [WHO-IP]
Common Name English
THIOACETAZONE [INN]
Common Name English
THIOCARBAZIL
Brand Name English
THIOACETAZONE [WHO-DD]
Common Name English
THIACETAZONE
MI  
Common Name English
NSC-3550
Code English
THIBONE
Common Name English
SQ-2321
Code English
TB I-698
Code English
THIACETAZONE [MI]
Common Name English
4-ACETAMIDOBENZALDEHYDE THIOSEMICARBAZONE
Systematic Name English
P-ACETAMIDOBENZALDEHYDE THIOSEMICARBAZONE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C280
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
WHO-ATC J04AK07
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
WHO-VATC QJ04AM04
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
WHO-ATC J04AM04
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
Code System Code Type Description
EVMPD
SUB10975MIG
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
INN
252
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
ECHA (EC/EINECS)
203-170-6
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
PUBCHEM
9568512
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
CAS
104-06-3
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
WIKIPEDIA
THIOACETAZONE
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
MESH
D013828
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
FDA UNII
MMG78X7SSR
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
NCI_THESAURUS
C90769
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
MERCK INDEX
M10712
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL375492
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
DRUG CENTRAL
2631
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
EPA CompTox
104-06-3
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
DRUG BANK
DB12829
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
AMITHIOZONE
Created by admin on Sat Jun 26 03:07:57 UTC 2021 , Edited by admin on Sat Jun 26 03:07:57 UTC 2021
PRIMARY Description: Pale yellow crystals or a yellow, crystalline powder; almost odourless. Solubility: Very slightly soluble in water; slightly soluble in ethanol (~750 g/l) TS and methanol R; soluble in 10 parts of dimethylformamide R. Category: Antituberculosis drug. Storage: Thioacetazone should be kept in a tightly closed container, protected from light. Definition: Thioacetazone contains not less than 98.0% and not more than 102.0% of C10H12N4OS, calculated with reference to the dried substance.
Related Record Type Details
ACTIVE MOIETY