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| Other Sizes |
| Targets |
Thiohydantoin acts by inhibiting enzymes or receptors involved in various biological processes. It has been shown to be an effective inhibitor of the mitochondrial membrane potential in rats and mice, suggesting it may work by inhibiting mitochondrial function. The compound's mechanism of action is not fully understood but is believed to involve interaction with specific molecular targets in cells. Thiohydantoin derivatives have been investigated as inhibitors of mutant isocitrate dehydrogenase 1 (IDH1) and other enzymes relevant to cancer metabolism. The compound's anticonvulsant activity suggests potential effects on neuronal ion channels or neurotransmitter systems.
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| ln Vitro |
In vitro, Thiohydantoin has demonstrated various biological activities in cell-based and biochemical assays. The compound acts as a corrosion inhibitor for mild steel in 0.1 M HCl, with inhibition efficiency dependent on both concentration and immersion time. In biological assays, Thiohydantoin has shown antimicrobial activity against various bacterial and fungal strains. The compound's antitumor activity has been evaluated in cancer cell lines, where it exhibits cytotoxic effects through mitochondrial inhibition. Its anticonvulsant activity has been demonstrated in neuronal cell models.
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| ln Vivo |
In vivo, Thiohydantoin has been evaluated in animal models for its anticonvulsant, antitumor, and antimicrobial activities. The compound has been shown to inhibit mitochondrial membrane potential in rats and mice, suggesting systemic biological activity. In seizure models, Thiohydantoin derivatives demonstrate protection against induced convulsions, supporting their potential as anticonvulsant agents. Antitumor activity has been evaluated in mouse xenograft models, where Thiohydantoin derivatives show inhibition of tumor growth. However, detailed in vivo efficacy data are limited and further studies are needed.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Thiohydantoin typically involve enzyme inhibition studies targeting specific enzymes such as IDH1 mutants or other metabolic enzymes. The compound is incubated with purified enzyme preparations at varying concentrations, and enzyme activity is measured using spectrophotometric or fluorometric substrates. Inhibition constants (IC50 or Ki) are calculated from dose-response curves. Receptor binding assays may be employed to identify potential molecular targets. Mitochondrial membrane potential assays using isolated mitochondria or cell-based systems are used to assess the compound's effects on mitochondrial function.
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| Cell Assay |
In vitro cellular assays for Thiohydantoin utilize various cancer cell lines (such as HeLa, MCF-7, or A549) to evaluate antitumor activity. Cells are treated with Thiohydantoin at concentrations ranging from 1 to 200 µM for 24-72 hours. Cell viability is assessed using MTT, CCK-8, or resazurin-based assays. Apoptosis is evaluated by Annexin V staining, caspase activity assays, or DNA fragmentation analysis. Mitochondrial membrane potential is measured using fluorescent dyes such as JC-1 or tetramethylrhodamine ethyl ester (TMRE). Antimicrobial activity is assessed using broth microdilution assays against bacterial and fungal strains.
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| Animal Protocol |
In vivo animal experiments for Thiohydantoin typically involve rodent models of epilepsy, cancer, or infection. In anticonvulsant studies, the compound is administered orally or intraperitoneally to mice or rats, followed by induction of seizures using pentylenetetrazole or maximal electroshock. Protection against seizures is recorded. In antitumor studies, immunodeficient mice bearing subcutaneous tumor xenografts are treated with Thiohydantoin, and tumor growth is monitored. Body weight, food intake, and general health are monitored throughout the study.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for Thiohydantoin are limited, as the compound is primarily used as a research chemical and corrosion inhibitor. The compound's small molecular weight (116.12 g/mol) suggests potential for oral absorption and tissue distribution. Its ability to affect mitochondrial membrane potential in rats and mice indicates systemic exposure following administration. However, detailed pharmacokinetic parameters including bioavailability, half-life, and metabolism have not been extensively characterized in the literature. Further studies would be needed to support therapeutic development.
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| Toxicity/Toxicokinetics |
Toxicity data for Thiohydantoin are limited. The compound is classified as a potential irritant, and standard safety precautions should be followed when handling. In animal studies, Thiohydantoin has been administered at various doses without reports of severe acute toxicity. However, comprehensive toxicology studies including repeat-dose, genotoxicity, and reproductive toxicity assessments have not been fully conducted. As with any experimental compound, careful handling and dose optimization are recommended. The compound's use as a corrosion inhibitor suggests it is handled as an industrial chemical.
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| References | |
| Additional Infomation |
Thio analogues of hydantoin, in which one or both carbonyl groups are replaced by thiocarbonyl groups.
Thiohydantoin (2-Thiohydantoin) is a heterocyclic compound with diverse biological activities including anticonvulsant, antitumor, and antimicrobial properties. It acts as a mitochondrial membrane potential inhibitor and has been studied as an inhibitor of mutant IDH1. The compound is also used as a corrosion inhibitor for mild steel. Thiohydantoin derivatives represent a class of compounds with potential therapeutic applications, though further research is needed to fully characterize their pharmacological properties and clinical potential. |
| Molecular Formula |
C3H4N2OS
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|---|---|
| Molecular Weight |
116.138
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| Exact Mass |
116.004
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| CAS # |
503-87-7
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| PubChem CID |
1274030
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| Appearance |
Light brown to brown solid powder
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| Density |
1.5±0.1 g/cm3
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| Melting Point |
229-231 °C (dec.)(lit.)
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| Index of Refraction |
1.655
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| LogP |
-0.62
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
7
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| Complexity |
122
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
UGWULZWUXSCWPX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C3H4N2OS/c6-2-1-4-3(7)5-2/h1H2,(H2,4,5,6,7)
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| Chemical Name |
2-sulfanylideneimidazolidin-4-one
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| Synonyms |
Thiohydantoin NSC 11772 2-Thiohydantoin
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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 : ~50 mg/mL (~430.51 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (21.53 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 (21.53 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 8.6103 mL | 43.0515 mL | 86.1030 mL | |
| 5 mM | 1.7221 mL | 8.6103 mL | 17.2206 mL | |
| 10 mM | 0.8610 mL | 4.3051 mL | 8.6103 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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