| Size | Price | Stock | Qty |
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| 500mg |
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| Other Sizes |
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| ln Vitro |
The mycobacterial monooxygenase EthA, which also activates two more anti-tuberculosis medications, isoxyl and ethionamide, is responsible for the prodrug thiacetone [3].
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|---|---|
| ln Vivo |
The N-deacetylation of thiacetone exhibited Km and Vmax values of 0.57 mM and 0.123 nmol p-aminobenzaldehyde thiosemicarbazone formation/min/mg cytosolic protein, respectively. Rats' metabolism is much slower than that of cats, mice, or humans' livers when it comes to thioacetone metabolism [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. |
| Additional Infomation |
Thioacetazone is a member of acetamides and an anilide.
Amithiozone has been used in trials studying the treatment of Mycobacterium Avium-intracellulare Infection. Amithiozone is a thiosemicarbazone antimycobacterial agent with activity against isoniazid-resistant strains of Mycobacterium tuberculosis. Thioacetazone is a thiosemicarbazone prodrug with antitubercular activity. Although the exact mechanism by which thioacetazone exerts its effect has yet to be fully elucidated, this agent, upon activation by bacterial monooxygenase EtaA, appears to target and inhibit cyclopropane mycolic acid synthases (CMASs), a family of S-adenosyl-methionine-dependent methyl transferases responsible for cyclopropanation of mycolic acid. By inhibiting mycolic acid synthesis, the bacterial cell wall becomes more permeable and less resistant to injury which eventually leads to cell lysis. Mycolic acids, long-chain fatty acids, are essential mycobacterial cell wall components and play a key role in resistance to cell injury and mycobacterial virulence. A thiosemicarbazone that is used in association with other antimycobacterial agents in the initial and continuation phases of antituberculosis regimens. Thiacetazone containing regimens are less effective than the short-course regimen recommended by the International Union Against Tuberculosis and are used in some developing countries to reduce drug costs. (From Martindale, The Extra Pharmacopoeia, 30th ed, p217) |
| Molecular Formula |
C10H12N4OS
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|---|---|
| Molecular Weight |
236.29
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| Exact Mass |
236.073
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| CAS # |
104-06-3
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| PubChem CID |
9568512
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Melting Point |
225-230 ℃
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| Index of Refraction |
1.639
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| LogP |
1.22
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
16
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| Complexity |
285
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| Defined Atom Stereocenter Count |
0
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| SMILES |
S=C(N([H])[H])N([H])/N=C(\[H])/C1C([H])=C([H])C(=C([H])C=1[H])N([H])C(C([H])([H])[H])=O
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| InChi Key |
SRVJKTDHMYAMHA-WUXMJOGZSA-N
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| InChi Code |
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+
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| Chemical Name |
N-[4-[(E)-(carbamothioylhydrazinylidene)methyl]phenyl]acetamide
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| Synonyms |
Neotibil; Diazam; Thioacetazone
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~423.21 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.58 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (10.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (10.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.2321 mL | 21.1604 mL | 42.3209 mL | |
| 5 mM | 0.8464 mL | 4.2321 mL | 8.4642 mL | |
| 10 mM | 0.4232 mL | 2.1160 mL | 4.2321 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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