Thiabendazole
Overview
Description
Thiabendazole is a benzimidazole derivative first introduced in 1962. It is widely used as an antifungal and antiparasitic agent. This compound is effective against a variety of nematodes and is the drug of choice for strongyloidiasis. It also has applications as a fungicide in agriculture and as a preservative in the food industry .
Mechanism of Action
Target of Action
Thiabendazole, a benzimidazole derivative, primarily targets nematode worms, larval stages, and ova . It is particularly effective against a variety of nematodes, including Ascaris lumbricoides (common roundworm), Strongyloides stercoralis (threadworm), Necator americanus, Ancylostoma duodenale (hookworm), Trichuris trichiura (whipworm), Ancylostoma braziliense (dog and cat hookworm), Toxocara canis, Toxocara cati (ascarids), and Enterobius vermicularis (pinworm) .
Mode of Action
This enzyme is crucial for the energy production in these organisms. By inhibiting this enzyme, this compound disrupts the energy metabolism of the parasites, leading to their death . Additionally, this compound selectively binds to nematode β-tubulin, inhibiting polymerization, thus preventing the formation
Biochemical Analysis
Biochemical Properties
Thiabendazole plays a significant role in biochemical reactions by interacting with various enzymes, proteins, and other biomolecules. It primarily functions as an inhibitor of microtubule polymerization by binding to β-tubulin, a protein that is essential for the formation of microtubules. This interaction disrupts the normal function of microtubules, leading to the inhibition of cell division and growth. Additionally, this compound has been shown to interact with cytochrome P450 enzymes, which are involved in the metabolism of various endogenous and exogenous compounds .
Cellular Effects
This compound exerts several effects on different types of cells and cellular processes. It inhibits cell division by disrupting microtubule formation, leading to cell cycle arrest in the G2/M phase. This effect is particularly pronounced in rapidly dividing cells, such as cancer cells and parasitic worms. This compound also influences cell signaling pathways, including the Wnt/β-catenin pathway, which plays a crucial role in cell proliferation and differentiation. Furthermore, it affects gene expression by modulating the activity of transcription factors and other regulatory proteins .
Molecular Mechanism
The molecular mechanism of this compound involves its binding to β-tubulin, which prevents the polymerization of microtubules. This inhibition disrupts the mitotic spindle formation, leading to cell cycle arrest and apoptosis. This compound also inhibits the activity of cytochrome P450 enzymes, which can result in altered metabolism and detoxification processes. Additionally, it has been shown to modulate the expression of genes involved in cell proliferation, differentiation, and apoptosis .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound can vary over time. The compound is relatively stable under standard storage conditions, but it can degrade when exposed to light and heat. Long-term exposure to this compound has been shown to cause cumulative effects on cellular function, including increased oxidative stress and DNA damage. In vitro studies have demonstrated that prolonged treatment with this compound can lead to the development of resistance in certain cell lines .
Dosage Effects in Animal Models
The effects of this compound in animal models are dose-dependent. At low doses, it effectively inhibits the growth of parasitic worms and fungi without causing significant toxicity. At higher doses, this compound can cause adverse effects, including hepatotoxicity, nephrotoxicity, and neurotoxicity. Threshold effects have been observed, where the compound exhibits a narrow therapeutic window between effective and toxic doses .
Metabolic Pathways
This compound is metabolized primarily in the liver by cytochrome P450 enzymes. The major metabolic pathways include hydroxylation and conjugation with glucuronic acid, leading to the formation of water-soluble metabolites that are excreted in the urine. This compound can also affect metabolic flux by inhibiting the activity of key enzymes involved in energy production and detoxification processes .
Transport and Distribution
This compound is transported and distributed within cells and tissues through passive diffusion and active transport mechanisms. It can interact with various transporters and binding proteins, which influence its localization and accumulation. This compound has been shown to accumulate in the liver, kidneys, and gastrointestinal tract, where it exerts its therapeutic effects. The compound’s distribution is also influenced by its lipophilicity and protein-binding properties .
Subcellular Localization
This compound is primarily localized in the cytoplasm, where it interacts with microtubules and other cellular components. It can also be found in the nucleus, where it modulates gene expression and cell cycle progression. The subcellular localization of this compound is influenced by its chemical structure and post-translational modifications, which can direct it to specific compartments or organelles .
Preparation Methods
Synthetic Routes and Reaction Conditions: Thiabendazole can be synthesized through the condensation of ortho-phenylenediamine or ortho-nitroaniline with a carboxylic acid derivative. The cyclization process involves coupling at the ortho-phenylene nitrogen .
Industrial Production Methods: In industrial settings, this compound is produced using high-performance liquid chromatography (HPLC) and ultra-high-performance liquid chromatography (UHPLC) methods. These methods ensure the purity and quality of the compound .
Chemical Reactions Analysis
Types of Reactions: Thiabendazole undergoes various chemical reactions, including oxidation, reduction, and substitution.
Common Reagents and Conditions:
Oxidation: this compound can be oxidized using reagents like hydrogen peroxide under acidic conditions.
Reduction: Reduction reactions can be carried out using reducing agents such as sodium borohydride.
Substitution: Substitution reactions often involve halogenation using reagents like chlorine or bromine.
Major Products: The major products formed from these reactions include various substituted benzimidazole derivatives, which have diverse biological activities .
Scientific Research Applications
Thiabendazole has multiple applications across various fields:
Chemistry: It is used as a precursor for synthesizing new heterocyclic compounds with potential biological activities.
Biology: this compound is used in research to study its effects on fungal and parasitic organisms.
Medicine: It is employed in the treatment of infections caused by nematodes and fungi.
Industry: this compound is used as a fungicide to control mold, blight, and other fungal diseases in fruits and vegetables.
Comparison with Similar Compounds
Albendazole: Another benzimidazole derivative used as an antiparasitic agent.
Mebendazole: Similar to thiabendazole, it is used to treat nematode infections.
Fenbendazole: Used primarily in veterinary medicine for treating parasitic infections in animals.
Uniqueness of this compound: this compound is unique due to its dual role as both an antifungal and antiparasitic agent. Its ability to act as a chelating agent further distinguishes it from other similar compounds .
Properties
IUPAC Name |
4-(1H-benzimidazol-2-yl)-1,3-thiazole |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
WJCNZQLZVWNLKY-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1=CC=C2C(=C1)NC(=N2)C3=CSC=N3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C10H7N3S |
Source
|
| Record name | THIABENDAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/18232 | |
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| Record name | tiabendazole | |
| Source | Wikipedia | |
| URL | https://en.wikipedia.org/wiki/Tiabendazole | |
| Description | Chemical information link to Wikipedia. | |
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID0021337 |
Source
|
| Record name | Thiabendazole | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0021337 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
201.25 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Thiabendazole appears as white or cream-colored odorless, tasteless powder. Sublimes above 590 °F. Fluoresces in acidic solution. Formulated as a dust, flowable powder or wettable powder for use as a systemic fungicide and anthelmintic., Colorless, white, or tan odorless solid; [HSDB] Colorless solid; [EPA REDs] Off-white to yellow-tan solid; [CPSQ], Solid |
Source
|
| Record name | THIABENDAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/18232 | |
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| Record name | Thiabendazole | |
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| Record name | Thiabendazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014868 | |
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Solubility |
>30.2 [ug/mL] (The mean of the results at pH 7.4), less than 1 mg/mL at 70 °F (NTP, 1992), Max solubility in water at pH 2.2: 3.84%; slightly sol in alcohols, esters, chlorinated hydrocarbons, In n-heptane <0.1, xylene 0.13, methanol 8.28, 1,2-dichloroethane 0.81, acetone 2.43, ethyl acetate 1.49, n-octanol 3.91, all in g/L at 25 °C, Slightly soluble in ethanol, In water, 50 mg/L at 25 °C, 1.38e-01 g/L |
Source
|
| Record name | SID4262837 | |
| Source | Burnham Center for Chemical Genomics | |
| URL | https://pubchem.ncbi.nlm.nih.gov/bioassay/1996#section=Data-Table | |
| Description | Aqueous solubility in buffer at pH 7.4 | |
| Record name | THIABENDAZOLE | |
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| Record name | Thiabendazole | |
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| Record name | Thiabendazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014868 | |
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Density |
Amber liquid; density: 1.103 at 25 °C /Thiabendazole hypophosphite/ |
Source
|
| Record name | THIABENDAZOLE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2027 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Vapor Pressure |
Negligible (NTP, 1992), 4X10-9 mm Hg at 25 °C |
Source
|
| Record name | THIABENDAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/18232 | |
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Mechanism of Action |
The precise mode of action of thiabendazole on the parasite is unknown, but it most likely inhibits the helminth-specific enzyme fumarate reductase., Thiabendazole and other benzimidazole anthelmintics act by binding strongly to tubulin in the absorptive cells in the gut of parasitic worms. This interferes with the uptake of nutrients and the worms effectively starve to death. The host is less affected as the binding to mammalian tubulin is less strong and is reversible., Although the exact mechanism of anthelmintic activity of thiabendazole has not been fully elucidated, the drug has been shown to inhibit the helminth-specific enzyme, fumarate reductase. In animals, thiabendazole has anti-inflammatory, antipyretic, and analgesic effects. |
Source
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| Record name | Thiabendazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00730 | |
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Color/Form |
Colorless crystals, White crystals, Off-white powder, White to practically white powder, White to tan crystals | |
CAS No. |
148-79-8 |
Source
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| Record name | THIABENDAZOLE | |
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| URL | https://cameochemicals.noaa.gov/chemical/18232 | |
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Melting Point |
579 to 581 °F (NTP, 1992), 304-305 °C, 300 °C |
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| Record name | THIABENDAZOLE | |
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Retrosynthesis Analysis
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| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Q1: What is the chemical structure and properties of thiabendazole?
A1: this compound (2-(4-thiazolyl) benzimidazole) has the molecular formula C10H7N3S and a molecular weight of 201.25 g/mol. [] Spectroscopic data, including ultraviolet (UV) spectrophotometry, can be used for its identification and quantification. []
Q2: How does this compound perform under various conditions and in different applications?
A2: this compound is often applied as a post-harvest treatment for various fruits and vegetables to prevent fungal growth during storage. [, ] Studies demonstrate its efficacy against blue mold in apples caused by Penicillium expansum, even in this compound-resistant strains, highlighting its potential in resistance management strategies. [] Research has also explored its application via soil injection to protect peanut plants from fungal diseases. []
Q3: How stable is this compound under different storage conditions?
A3: While generally stable, this compound’s stability can be affected by factors such as temperature, humidity, and exposure to light. [] Specific formulation strategies, like encapsulation in nanoparticles, can enhance its stability and potentially improve its efficacy and bioavailability. []
Q4: How do modifications to the this compound structure affect its activity?
A4: Research suggests that the benzimidazole core of this compound is essential for its activity. [, ] Modifications to this core or the thiazole ring can significantly impact its potency, selectivity, and potential for resistance development. [, ] For example, studies on E. coli methionine aminopeptidase (MetAP) inhibition demonstrated that this compound analogs with metal-binding motifs exhibited higher inhibitory activity, emphasizing the importance of specific structural elements. []
Q5: How is this compound absorbed, distributed, metabolized, and excreted in animal models?
A5: Studies in animal models, such as laying hens, demonstrate that this compound is readily absorbed after oral administration and distributed to various tissues, including eggs. [] It is primarily metabolized in the liver, with 5-hydroxythis compound being a major metabolite. [, ] The excretion profile varies depending on the species and dosage. []
Q6: What in vitro and in vivo models have been used to study the efficacy of this compound?
A6: this compound’s efficacy has been extensively studied in both in vitro and in vivo models. Cell-based assays, such as those using Hn5 head and neck squamous carcinoma cells, have shown dose-dependent and time-dependent inhibition of cell proliferation. [] Animal models, including mice infected with parasites like Angiostrongylus cantonensis and Trichinella spiralis, have been used to evaluate its antiparasitic activity and compare it to other drugs like flubendazole. []
Q7: Are there concerns about resistance development to this compound?
A7: Yes, the development of resistance to this compound, particularly in fungal pathogens, is a significant concern. [, , ] Research has identified resistant strains of Fusarium sambucinum in potato tubers treated with this compound, emphasizing the need for alternative control measures and resistance management strategies. [, , ] Cross-resistance to other benzimidazole fungicides is also a possibility, necessitating careful monitoring and management. [, ]
Q8: What analytical methods are used to quantify this compound in different matrices?
A8: Various analytical methods have been employed to determine this compound levels in various matrices. High-performance liquid chromatography (HPLC) coupled with different detectors, such as UV or diode array detectors (DAD), is commonly used for its quantification in food samples, including apples, bananas, and wine. [, , ] More recently, advanced techniques like ultra-high-performance liquid chromatography coupled with high-resolution mass spectrometry (UPLC-HRMS) offer enhanced sensitivity and selectivity for trace analysis in complex matrices, such as water-pipe tobacco. []
Q9: What are the potential environmental impacts of this compound use?
A9: The persistence and fate of this compound in the environment are important considerations. [] Research has explored its degradation pathways in soil and water, as well as its potential effects on non-target organisms. [, ] Developing strategies to mitigate any negative environmental impacts and exploring alternative control methods are crucial for sustainable agriculture and environmental protection. []
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
