Thiacetazone

Modify Date: 2024-01-02 17:06:56

Thiacetazone structure	Common Name	Thiacetazone
	CAS Number	104-06-3	Molecular Weight	236.294
	Density	1.3±0.1 g/cm3	Boiling Point	N/A
	Molecular Formula	C₁₀H₁₂N₄OS	Melting Point	225-230 â„ƒ
	MSDS	N/A	Flash Point	N/A

Use of Thiacetazone

Thiacetazone (Thioacetazone) is a thiourea-containing antitubercular agent and is an orally active antibiotic. Thiacetazone has antibacterial action, which inhibits growth of Mycobacterium tuberculosis H37Rv with a MIC value of 0.1 μg/mL[1].

Name	4-Acetylaminobenzaldehyde thiosemicarbazone
Synonym	More Synonyms

Description	Thiacetazone (Thioacetazone) is a thiourea-containing antitubercular agent and is an orally active antibiotic. Thiacetazone has antibacterial action, which inhibits growth of Mycobacterium tuberculosis H37Rv with a MIC value of 0.1 μg/mL[1].
Related Catalog	Research Areas >> Infection Signaling Pathways >> Anti-infection >> Bacterial
Target	MIC: 0.1 μg/mL (Mycobacterium tuberculosis H37Rv)[1]
In Vitro	Thiacetazone is a prodrug that is activated by the mycobacterial monooxygenase EthA, which is also the activator of two other anti-tuberculosis agents, Ethionamide and Isoxyl[3].
In Vivo	The Km and Vmax values for the N-deacetylation of Thiacetazone are 0.57 mM and 0.123 nmol of p-aminobenzaldehydethiosemicarbazone formed/min/mg cytosolic protein, respectively. The ability to metabolize Thiacetazone is the same in the livers of cat, mouse and human, but lagged significantly in that of rat[2].
References	[1]. J L Stigliani, et al. New Insights Into the Chemical Behavior of S-oxide Derivatives of Thiocarbonyl-Containing Antitubercular Drugs and the Influence on Their Mechanisms of Action and Toxicity. Ann Pharm Fr. 2019 Mar;77(2):126-135. [2]. P Khanna, et al. Characteristics of a Cytosolic Arylacylamidase Metabolizing Thiacetazone. J Pharmacol Exp Ther. 1992 Sep;262(3):1225-31. [3]. Anuradha Alahari, et al. Thiacetazone, an Antitubercular Drug That Inhibits Cyclopropanation of Cell Wall Mycolic Acids in Mycobacteria. PLoS One. 2007 Dec 19;2(12):e1343. [4]. C A Peloquin, et al. Pharmacokinetic Evaluation of Thiacetazone. Pharmacotherapy. Sep-Oct 1996;16(5):735-41.

Density	1.3±0.1 g/cm3
Melting Point	225-230 â„ƒ
Molecular Formula	C₁₀H₁₂N₄OS
Molecular Weight	236.294
Exact Mass	236.073181
PSA	111.60000
LogP	1.22
Index of Refraction	1.639

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AE3850000

CHEMICAL NAME :: Acetanilide, 4'-formyl-, 4'-(thiosemicarbazone)

CAS REGISTRY NUMBER :: 104-06-3

BEILSTEIN REFERENCE NO. :: 2810335

LAST UPDATED :: 199612

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C10-H12-N4-O-S

MOLECULAR WEIGHT :: 236.32

WISWESSER LINE NOTATION :: SUYZMNU1R DMV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 950 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - coma Lungs, Thorax, or Respiration - respiratory depression

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 3267 ug/kg

REFERENCE :: NULSAK Nucleus (Calcutta). (Dr. A.K. Sharma, Centre of Advanced Studies in Cell and Chromosome Research, Calcutta, 35 Baliygunge Circular Rd., Calcutta 700 019, India) V.1- 1958- Volume(issue)/page/year: 22,96,1979

Hazard Codes	Xn
Risk Phrases	22
Safety Phrases	36
WGK Germany	3
RTECS	AE3850000
HS Code	2930909090

4-Acetamidobenz...

CAS#:122-85-0

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CAS#:104-06-3

Literature: Journal of the American Chemical Society, , vol. 75, p. 1241

Hydrazinecarbot...

CAS#:6957-91-1

Ethanoic anhydride

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Thiacetazone

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Literature: Sb. Statei Obshch. Khim., , p. 1081,1083 Chem.Abstr., , p. 4572 Acta Physica et Chemica, , vol. 3, p. 54 US2530430 , ;

4-Acetamidobenz...

CAS#:122-85-0

Thiosemicarbazide

CAS#:79-19-6

Thiacetazone

CAS#:104-06-3

Literature: Bulletin de la Societe Chimique de France, , p. 48,53 DE852086 , ; DRP/DRBP Org.Chem.

HS Code	2930909090
Summary	2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

N-{4-[(E)-(2-carbamothioylhydrazinylidene)methyl]phenyl}acetamide

N-[4-[(E)-(carbamothioylhydrazinylidene)methyl]phenyl]acetamide

N-(4-{(E)-[(aminocarbonothioyl)hydrazono]methyl}phenyl)acetamide

N-(4-{(E)-[2-(aminocarbonothioyl)hydrazono]methyl}phenyl)acetamide

acetamide, N-[4-[(E)-[(aminothioxomethyl)hydrazono]methyl]phenyl]-

Acetamide, N-[4-[(E)-[2-(aminothioxomethyl)hydrazinylidene]methyl]phenyl]-

EINECS 203-170-6

THIACETAZONE

N-{4-[(E)-(Carbamothioylhydrazono)methyl]phenyl}acetamide

p-Acetamidobenzaldehyde thiosemicarbazon

thioacetazone

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Thiacetazone

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