AMITHIOZONE

Possibly Marketed Outside US

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H12N4OS
Molecular Weight	236.293
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1

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	236.293
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25552777 | https://www.ncbi.nlm.nih.gov/pubmed/13838487

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

Primary Target	Pharmacology	Condition	Potency
Purine metabolism 1 Target ID: map00230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13838487	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25552777	Curative		Not Provided 511	Unknown Approved Use Unknown
Mycobacterium avium-intracellulare infection 1 Sources: https://clinicaltrials.gov/ct2/show/NCT00004689	Curative		Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	Disc. AE: Vomiting, Anorexia... Other AEs: Vomiting, Giddiness... AEs leading to discontinuation/dose reduction: Vomiting (2.7%) Anorexia (17%) Skin rash (1.3%) Stevens-Johnson syndrome (2.6%) Jaundice (3%) Diarrhoea (1.3%) Other AEs: Vomiting (23%) Giddiness (28%) Cutaneous hypersensitivity (7%) Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/

AEs

AE	Significance	Dose	Population
Diarrhoea	1.3% Disc. AE	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/
Skin rash	1.3% Disc. AE	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/
Anorexia	17% Disc. AE	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/
Stevens-Johnson syndrome	2.6% Disc. AE	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/
Vomiting	2.7% Disc. AE	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/
Vomiting	23%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/
Giddiness	28%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/
Jaundice	3% Disc. AE	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/
Cutaneous hypersensitivity	7%	150 mg 1 times / day multiple, oral Recommended Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/	unhealthy, CHILD\|ADOLESCENT\|ADULT Health Status: unhealthy Age Group: CHILD\|ADOLESCENT\|ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/4161578/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP4 290 BSEP 550 CYP19A1 429 MRP3 246 MRP2 499 CYP2C19 2057 CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9568512#section=Biological-Test-Results Page: 1.0	inconclusive [IC50 0.6918 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9568512#section=Biological-Test-Results Page: 7.0	inconclusive [IC50 27.5404 uM]
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9568512#section=Biological-Test-Results Page: 7.0	no [IC50 26.6032 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM3NTQ5MiJ9fQ==	no [IC50 >133 uM]
MRP2 625	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM3NTQ5MiJ9fQ==	no [IC50 >133 uM]
MRP3 326	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1OTE4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM3NTQ5MiJ9fQ==	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTI4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDM3NTQ5MiJ9fQ==	no [IC50 >133 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9568512#section=BioAssay-Results Page: 179.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9568512#section=BioAssay-Results Page: 172.0	no
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9568512#section=Biological-Test-Results Page: 147.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9568512#section=BioAssay-Results Page: 170.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/9568512#section=BioAssay-Results Page: 75.0

PubMed

Title	Date	PubMed
A common mechanism of inhibition of the Mycobacterium tuberculosis mycolic acid biosynthetic pathway by isoxyl and thiacetazone.	2012-11-09	23002234
Preclinical pharmacokinetics of KBF611, a new antituberculosis agent in mice and rabbits, and comparison with thiacetazone.	2010-03	20038272
EthA, a common activator of thiocarbamide-containing drugs acting on different mycobacterial targets.	2007-03	17220416
Differential antibiotic susceptibilities of starved Mycobacterium tuberculosis isolates.	2005-11	16251329
Clinical concentrations of thioridazine kill intracellular multidrug-resistant Mycobacterium tuberculosis.	2003-03	12604522
Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice.	2003-01	12499213
In vitro activity of thiacetazone on mycobacterial species belonging to the Mycobacterium tuberculosis complex.	2002-10	12365582
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.	2000-02-01	10609550
Green fluorescent protein reporter microplate assay for high-throughput screening of compounds against Mycobacterium tuberculosis.	1998-02	9527783
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.	1997-05	9145860
Antituberculosis activity of clarithromycin.	1995-12	8593004
The Garrod Lecture. Understanding the chemotherapy of tuberculosis--current problems.	1992-05	1624388
Thiacetazone: in vitro activity against Mycobacterium avium and M. tuberculosis.	1990-12	1702564
Aplastic anaemia associated with anti-tuberculosis chemotherapy.	1982	6184934
The early bactericidal activity of drugs in patients with pulmonary tuberculosis.	1980-06	6774638
Protein synthesis in Mycobacterium tuberculosis H37Rv and the effect of streptomycin in streptomycin-susceptible and -resistant strains.	1973-09	4202339
Antibacterial nitrofuran derivatives. I. 5-nitro-2-furaldehyde semicarbazones and thiosemicarbazones.	1967-07	4962510
The chemical approach to the control of tuberculosis.	1952-08-08	14950210

Patents

Sample Use Guides

In Vivo Use Guide

150 mg daily doses 6 days a week over the entire treatment period for a total of8 months.

Route of Administration: Oral

In Vitro Use Guide

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 `Mon Mar 31 18:45:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:45:28 GMT 2025`
Record UNII	MMG78X7SSR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOACETAZONE

Preferred Name

English

AMITHIOZONE

Common Name

English

N-(4-(((AMINO-THIOXOMETHYL)HYDRAZONO)METHYL)PHENYL)ACETAMIDE [WHO-IP]

Systematic Name

English

CITAZONE

Brand Name

English

4'-FORMYLACETANILIDE THIOSEMICARBAZONE

Systematic Name

English

THIOPARAMIZONE

Common Name

English

Thioacetazone [WHO-DD]

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

THIACETAZONE

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