Thiacetazone

Names

[ CAS No. ]:
104-06-3

[ Name ]:
Thiacetazone

[Synonym ]:
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

Biological Activity

[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.

Chemical & Physical Properties

[ 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

Toxicological Information

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

Safety Information

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
22

[ Safety Phrases ]:
36

[ WGK Germany ]:
3

[ RTECS ]:
AE3850000

[ HS Code ]:
2930909090

Synthetic Route

Click to get detail synthetic route

Customs

[ 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%