Introduction：Basic information about CAS 104-06-3|Thiacetazone, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Thiacetazone |
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| CAS Number | 104-06-3 | Molecular Weight | 236.294 |
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| Density | 1.3±0.1 g/cm3 | Boiling Point | / |
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| Molecular Formula | C10H12N4OS | Melting Point | 225-230 ℃ |
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| MSDS | / | Flash Point | / |
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Names
| Name | 4-Acetylaminobenzaldehyde thiosemicarbazone |
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| Synonym | More Synonyms |
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Thiacetazone BiologicalActivity
| 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]. |
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| Related Catalog | Research Areas >>InfectionSignaling Pathways >>Anti-infection >>Bacterial |
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| Target | MIC: 0.1 μg/mL (Mycobacterium tuberculosis H37Rv)[1] |
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| 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]. |
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| 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]. |
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| 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. |
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Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
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| Melting Point | 225-230 ℃ |
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| Molecular Formula | C10H12N4OS |
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| Molecular Weight | 236.294 |
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| Exact Mass | 236.073181 |
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| PSA | 111.60000 |
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| LogP | 1.22 |
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| Index of Refraction | 1.639 |
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| InChIKey | SRVJKTDHMYAMHA-WUXMJOGZSA-N |
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| SMILES | CC(=O)Nc1ccc(C=NNC(N)=S)cc1 |
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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 DATAACUTE 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
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Safety Information
| Hazard Codes | Xn |
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| Risk Phrases | 22 |
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| Safety Phrases | 36 |
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| WGK Germany | 3 |
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| RTECS | AE3850000 |
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| HS Code | 2930909090 |
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Customs
| HS Code | 2930909090 |
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| Summary | 2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0% |
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Synonyms
| 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 |
