Thiacetazone
(Synonyms: 氨硫脲; Thioacetazone; Amithiozone) 目录号 : GC39822
An antitubercular agent
Cas No.:104-06-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Thioacetazone is an antitubercular agent.1 It is active against M. tuberculosis H37Rv, M. kansasii Bostrom, and M. avium serotype 2 (MICs = 0.3, 0.6, and 20 ?g/ml, respectively) but not M. simiae N29 or M. intracellulare serotype 16 (MICs = >40 ?g/ml for both). Formulations containing thioacetazone were previously used in the treatment of tuberculosis.
1.Collins, F.M., Klayman, D.L., and Morrison, N.E.Activity of 2-acetylpyridine and 2-acetylquinoline thiosemicarbazones tested in vitro in combination with other antituberculous drugsAm. Rev. Respir. Dis.125(1)58-60(1982)
| Cas No. | 104-06-3 | SDF | |
| 别名 | 氨硫脲; Thioacetazone; Amithiozone | ||
| Canonical SMILES | CC(NC1=CC=C(/C=N/NC(N)=S)C=C1)=O | ||
| 分子式 | C10H12N4OS | 分子量 | 236.29 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 | 2.116 mL | 4.2321 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Thiacetazone--avoid like poison or use with care?
Trans R Soc Trop Med Hyg 1993 Sep-Oct;87(5):578-82.PMID:7505496DOI:10.1016/0035-9203(93)90096-9.
Recent 5 reports of severe cutaneous hypersensitivity reactions in patients infected with human immunodeficiency virus (HIV) and with tuberculosis treated with Thiacetazone have prompted the World Health Organization to advise against the use of Thiacetazone in patients known, or suspected, to be infected with HIV. Because the poorest countries will have great difficulty in replacing Thiacetazone, the history, metabolism and possible mechanisms underlying the toxicity of this inexpensive, but problematic, drug are reviewed. Guidelines for National Tuberculosis Control Programme policies in response to Thiacetazone toxicity are discussed, taking into account the differing levels of resources available to developing countries.
NSC19723, a Thiacetazone-Like Benzaldehyde Thiosemicarbazone Improves the Efficacy of TB Drugs In Vitro and In Vivo
Microbiol Spectr 2022 Dec 21;10(6):e0259222.PMID:36314972DOI:10.1128/spectrum.02592-22.
The complexity and duration of tuberculosis (TB) treatment contributes to the emergence of drug resistant tuberculosis (DR-TB) and drug-associated side effects. Alternate chemotherapeutic agents are needed to shorten the time and improve efficacy of current treatment. In this study, we have assessed the antitubercular activity of NSC19723, a benzaldehyde thiosemicarbazone molecule. NSC19723 is structurally similar to Thiacetazone (TAC), a second-line anti-TB drug used to treat individuals with DR-TB. NSC19723 displayed better MIC values than TAC against Mycobacterium tuberculosis and Mycobacterium bovis BCG. In our checkerboard experiments, NSC19723 displayed better profiles than TAC in combination with known first-line and recently approved drugs. Mechanistic studies revealed that NSC19723 inhibits mycolic acid biosynthesis by targeting the HadABC complex. Computational studies revealed that the binding pocket of HadAB is similarly occupied by NSC19723 and TAC. NSC19723 also improved the efficacy of isoniazid in macrophages and mouse models of infection. Cumulatively, we have identified a benzaldehyde thiosemicarbazone scaffold that improved the activity of TB drugs in liquid cultures, macrophages, and mice. IMPORTANCE Mycobacterium tuberculosis, the causative agent of TB is among the leading causes of death among infectious diseases in humans. This situation has worsened due to the failure of BCG vaccines and the increased number of cases with HIV-TB coinfections and drug-resistant strains. Another challenge in the field is the lengthy duration of therapy for drug-sensitive and -resistant TB. Here, we have deciphered the mechanism of action of NSC19723, benzaldehyde thiosemicarbazone. We show that NSC19723 targets HadABC complex and inhibits mycolic acid biosynthesis. We also show that NSC19723 enhances the activity of known drugs in liquid cultures, macrophages, and mice. We have also performed molecular docking studies to identify the interacting residues of HadAB with NSC19723. Taken together, we demonstrate that NSC19723, a benzaldehyde thiosemicarbazone, has better antitubercular activity than Thiacetazone.
Adverse cutaneous reactions to Thiacetazone for tuberculosis treatment in Tanzania
Lancet 1995 Sep 9;346(8976):657-60.PMID:7544858DOI:10.1016/s0140-6736(95)92278-4.
Because Thiacetazone has been linked with serious adverse cutaneous reactions, we undertook 1 year of systematic surveillance for cutaneous thiacetazone-associated adverse reactions within the national tuberculosis programme of Tanzania. For individual cases, we collected information on age, sex, interval between commencing thiacetazone-containing treatment and occurrence of adverse reaction, most severe clinical presentation (toxic epidermal necrolysis, rash without necrolysis, itching without rash), and outcome (dead or alive) within 2 weeks of onset. Univariate and multivariate analyses were done of variables relevant to outcome. 1273 patients with adverse reactions were reported. The frequency of fatal outcome from any cutaneous reaction was 3.1 per 1000 among all tuberculosis patients, and 19.1% among patients with toxic epidermal necrolysis. About 60% of all adverse reactions and deaths occurred within 20 days of starting Thiacetazone. Case fatality from adverse cutaneous reactions was considerably less frequent than reported previously, suggesting that improved management might allow retention of Thiacetazone in the armamentarium of national tuberculosis programmes even where infection with HIV is prevalent.
A Coumarin-Based Analogue of Thiacetazone as Dual Covalent Inhibitor and Potential Fluorescent Label of HadA in Mycobacterium tuberculosis
ACS Infect Dis 2021 Mar 12;7(3):552-565.PMID:33617235DOI:10.1021/acsinfecdis.0c00325.
A novel coumarin-based molecule, designed as a fluorescent surrogate of a thiacetazone-derived antitubercular agent, was quickly and easily synthesized from readily available starting materials. This small molecule, coined Coum-TAC, exhibited a combination of appropriate physicochemical and biological properties, including resistance toward hydrolysis and excellent antitubercular efficiency similar to that of well-known Thiacetazone derivatives, as well as efficient covalent labeling of HadA, a relevant therapeutic target to combat Mycobacterium tuberculosis. More remarkably, Coum-TAC was successfully implemented as an imaging probe that is capable of labeling Mycobacterium tuberculosis in a selective manner, with an enrichment at the level of the poles, thus giving for the first time relevant insights about the polar localization of HadA in the mycobacteria.
Pharmacokinetic evaluation of Thiacetazone
Pharmacotherapy 1996 Sep-Oct;16(5):735-41.PMID:8888068doi
Study objective: To investigate the steady-state pharmacokinetics of Thiacetazone (TB-1), which is active in vitro against Mycobacterium avium complex (MAC). Design: Open-label phase I study. Setting: Specialized referral hospital. Patients: Twelve healthy men and women. Interventions: Oral TB-1 150 mg/day was administered for 7 days, followed by blood and urine collection over 48 hours. Measurements and main results: The serum concentration versus time curves of TB-1 showed sustained concentrations, with maximum values of 1.59 +/- 0.47 micrograms/ml, time to maximum 3.30 +/- 1.18 hours, and serum half-life of 15-16 hours. Less than 25% of TB-1 was recovered unchanged in the urine over 48 hours. Rashes occurred in two subjects at the end of the 7-day dosing period and resolved without progression or sequelae. Conclusions: Based on these data, we initiated a phase II study of TB-I in patients with pulmonary MAC infection who do not have the acquired immunodeficiency syndrome.