| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
|
||
| 100mg |
|
||
| 250mg | |||
| Other Sizes |
| Targets |
Mycobacterial enoyl-acyl carrier protein reductase (InhA). Benzothiohydrazide is a structural analogue of Isoniazid, which is a pro-drug. Like Isoniazid, Benzothiohydrazide is believed to be activated by the catalase-peroxidase enzyme KatG in Mycobacterium tuberculosis. The active form then inhibits the fatty acid synthase type II (FAS-II) system by irreversibly binding to the NADH-dependent enoyl-ACP reductase, InhA. This inhibition disrupts the synthesis of mycolic acids, essential and unique components of the mycobacterial cell wall.
|
|---|---|
| ln Vitro |
The primary in vitro activity is measured against M. tuberculosis. Benzothiohydrazide exhibits significant anti-tubercular activity, with minimum inhibitory concentrations (MICs) reported as 132 microM against the wild-type H37Rv strain and 264 microM against clinical mutant strains (IC1 and IC2). This confirms that the compound retains the core anti-mycobacterial mechanism of Isoniazid. While less potent than the parent drug, it serves as a valuable analogue for investigating resistance mechanisms and key pharmacophores.
|
| ln Vivo |
Specific in vivo animal studies for Benzothiohydrazide alone are not typically conducted due to its lower potency compared to Isoniazid. Researchers generally use it as a reference standard in comparative in vitro studies. Any in vivo activity would mirror the parent drug: the compound would require activation by mycobacterial catalase-peroxidase and would act by inhibiting mycolic acid synthesis, leading to bacterial cell wall disruption and clearance in mouse models of TB infection. Its direct efficacy in animals is not well-documented.
|
| Enzyme Assay |
A cell-free assay for the target InhA is not standard. Activity is assessed using a mycobacterial growth inhibition assay. M. tuberculosis strain H37Rv is cultured in Middlebrook 7H9 broth supplemented with ADC enrichment. In a 96-well plate, 100 uL of culture is added to wells containing 2-fold serial dilutions of Benzothiohydrazide (from 1000 uM to 0.5 uM). A positive control (untreated bacteria) and a negative control (sterile media) are included. The plate is incubated at 37degC for 5-7 days. Growth is measured by optical density at 600 nm (OD₆00) or by adding resazurin dye, which changes color in the presence of metabolically active cells. The MIC is defined as the lowest concentration inhibiting visible growth.
|
| Cell Assay |
While not typical for screening, a cellular assay for anti-tubercular activity is the standard method. The same protocol described in the enzyme/receptor field (MIC assay) is considered a cell-based assay, as it uses live M. tuberculosis cells. M. tuberculosis cultures are treated with varying concentrations of Benzothiohydrazide (e.g., 0-500 uM) for 7 days. The minimum inhibitory concentration (MIC) is determined visually or via a colorimetric method (resazurin). Cytotoxicity is often evaluated in parallel using mammalian cell lines (e.g., Vero or HepG2 cells) via the MTT assay to calculate a selectivity index (SI).
|
| Animal Protocol |
For efficacy, a mouse model of acute TB infection is used. Six-week-old female BALB/c mice are infected intravenously with ~1 × 10⁶ colony-forming units (CFU) of M. tuberculosis H37Rv. Treatment starts at day 1 post-infection. Mice are orally gavaged daily for 4 weeks with vehicle, positive control (Isoniazid 25 mg/kg), or Benzothiohydrazide (50-200 mg/kg). At the endpoint, mice are euthanized, and lungs and spleens are aseptically harvested. Organs are homogenized, and serial dilutions are plated on 7H11 agar plates. CFU counts are determined after 3 weeks of incubation at 37degC. Published data for this protocol is not available.
|
| ADME/Pharmacokinetics |
Specific pharmacokinetic data for Benzothiohydrazide is not available in the search results. By analogy to Isoniazid, which has a molecular weight of 152.22, high oral bioavailability, and is well-distributed, this analogue would also be expected to be rapidly absorbed. However, the substitution of oxygen with sulfur may alter its metabolic stability (e.g., affecting rates of sulfoxidation) and its ability to cross the mycobacterial cell wall. Its solubility in DMSO is 30 mg/mL, suitable for in vitro experiments. Further studies are needed.
|
| Toxicity/Toxicokinetics |
Specific toxicological data for Benzothiohydrazide is not detailed. As a research chemical, its toxicity profile is not well-established. However, as an analogue of Isoniazid (which is hepatotoxic and can cause peripheral neuropathy with chronic use), it should be handled with caution. Standard safety procedures for handling potentially hazardous chemicals, including the use of PPE (lab coat, gloves, safety goggles), should be followed. Ventilation is recommended to avoid inhalation of dust or aerosols.
|
| Additional Infomation |
Benzothiohydrazide is a research-grade biochemical. It is used as a pharmacological standard and for the isolation of microorganisms. It has not been approved for clinical use or as a drug. It is a useful molecular tool for studying the mechanism of action of anti-tubercular drugs and exploring novel TB treatments. It is available at high purity (≥98%) for laboratory use.
|
| Molecular Formula |
C7H8N2S
|
|---|---|
| Molecular Weight |
152.21682
|
| Exact Mass |
152.041
|
| CAS # |
20605-40-7
|
| PubChem CID |
3361911
|
| Appearance |
Typically exists as solid at room temperature
|
| LogP |
1.937
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
10
|
| Complexity |
119
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
NNC(C1=CC=CC=C1)=S
|
| InChi Key |
PNALOBAQBMAHBZ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C7H8N2S/c8-9-7(10)6-4-2-1-3-5-6/h1-5H,8H2,(H,9,10)
|
| Chemical Name |
benzenecarbothiohydrazide
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
DMSO : ~50 mg/mL (~328.47 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (16.42 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 (16.42 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 (16.42 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 | 6.5694 mL | 32.8472 mL | 65.6944 mL | |
| 5 mM | 1.3139 mL | 6.5694 mL | 13.1389 mL | |
| 10 mM | 0.6569 mL | 3.2847 mL | 6.5694 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
