| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
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| Other Sizes |
| 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 |
Thioacetamide belongs to the acetamide and aniline classes of compounds. Thioacetamide has been used in clinical trials to study the treatment of intracellular infections of Mycobacterium avium. Thioacetamide is a thioaminourea anti-mycobacterial drug, active against isoniazid-resistant Mycobacterium tuberculosis strains. Thioacetamide is a thioaminourea prodrug with anti-tuberculosis activity. Although the exact mechanism of action of thioacetamide is not fully elucidated, it appears to target and inhibit cyclopropane mycoic acid synthases (CMASs) after activation by the bacterial monooxygenase EtaA. CMASs are a class of S-adenosylmethionine-dependent methyltransferases responsible for the cyclopropanelation of mycoic acids. By inhibiting mycoic acid synthesis, bacterial cell wall permeability increases, resistance to damage decreases, and ultimately cell lysis occurs. Mycoic acids are long-chain fatty acids and an important component of the mycobacterial cell wall, playing a crucial role in resisting cell damage and mycobacterial virulence. Thiazolone is a thioaminourea drug often used in combination with other antimycobacterial drugs in the initial and consolidation phases of anti-tuberculosis treatment regimens. Thiazolone-containing treatment regimens are less effective than the short-course regimens recommended by the International Union Against Tuberculosis (UITB), and some developing countries use these regimens to reduce drug costs. (Excerpt from Martindale Pharmacopoeia, 30th edition, page 217)
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| 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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