Mebendazole
Overview
Description
Mebendazole is a broad-spectrum anthelmintic compound used to treat various parasitic worm infestations. It was developed by Janssen Pharmaceutica in Belgium and came into use in 1971 . This compound is effective against a range of nematode infestations, including roundworm, hookworm, whipworm, and pinworm . It is poorly absorbed into the bloodstream, making it particularly effective for treating intestinal parasites .
Scientific Research Applications
Mebendazole has been repurposed for various scientific research applications beyond its original use as an anthelmintic. It has shown promise in the treatment of brain cancers, including glioma, by inhibiting malignant progression and increasing the sensitivity of glioma cells to conventional chemotherapy or radiotherapy . Additionally, this compound has been explored for its anticancer properties in multiple cancers, including acute myeloid leukemia, breast cancer, and gastrointestinal cancer .
Mechanism of Action
Target of Action
Mebendazole primarily targets helminths (parasitic worms) by interfering with their cellular processes. Specifically, it acts on the colchicine-sensitive site of tubulin , a protein involved in microtubule formation. By binding to this site, this compound inhibits tubulin polymerization or assembly into microtubules. These microtubules are essential for maintaining the structural integrity of the worm’s cells, including its tegument (outer covering) and intestinal cells .
Biochemical Analysis
Biochemical Properties
Mebendazole functions by interfering with the polymerization of tubulin, a protein essential for microtubule formation. This disruption leads to the loss of cytoplasmic microtubules, which are crucial for various cellular processes, including cell division and intracellular transport . This compound interacts with beta-tubulin, inhibiting its polymerization and thereby affecting the stability of microtubules . Additionally, this compound has been shown to inhibit glucose uptake in parasitic worms, leading to their death .
Cellular Effects
This compound exerts significant effects on various cell types and cellular processes. In cancer cells, this compound induces apoptosis by disrupting microtubule dynamics and causing cell cycle arrest at the G2/M phase . It also affects cell signaling pathways, including the hedgehog signaling pathway, which is involved in cell proliferation and survival . This compound has been shown to decrease the expression of genes associated with cell proliferation and increase the expression of pro-apoptotic genes . Furthermore, this compound influences cellular metabolism by inhibiting glucose uptake and disrupting mitochondrial function .
Molecular Mechanism
At the molecular level, this compound binds to beta-tubulin, inhibiting its polymerization and disrupting microtubule formation . This inhibition leads to the destabilization of microtubules, which are essential for cell division and intracellular transport . This compound also affects other molecular targets, including the Bcl-2 family of proteins, which regulate apoptosis . By inhibiting Bcl-2, this compound promotes the release of cytochrome c from mitochondria, triggering the apoptotic cascade . Additionally, this compound has been shown to inhibit angiogenesis by targeting vascular endothelial growth factor receptor 2 (VEGFR2) signaling .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of this compound have been observed to change over time. This compound is relatively stable, but its efficacy can decrease due to degradation . Long-term studies have shown that this compound can cause sustained inhibition of tumor growth and metastasis in in vivo models . The stability and degradation of this compound can vary depending on the experimental conditions and the presence of other compounds .
Dosage Effects in Animal Models
The effects of this compound vary with different dosages in animal models. At low doses, this compound effectively inhibits parasitic worm infections without causing significant toxicity . At higher doses, this compound can cause adverse effects, including bone marrow suppression and hepatotoxicity . In cancer models, higher doses of this compound have been shown to inhibit tumor growth and metastasis more effectively . The therapeutic window for this compound is relatively wide, but careful dose optimization is necessary to minimize toxicity .
Metabolic Pathways
This compound is metabolized primarily in the liver by cytochrome P450 enzymes . The major metabolic pathways involve oxidation and reduction reactions, leading to the formation of various metabolites . These metabolites can have different pharmacological activities and contribute to the overall efficacy and toxicity of this compound . The metabolic flux and levels of metabolites can vary depending on the dose and duration of treatment .
Transport and Distribution
This compound is poorly absorbed from the gastrointestinal tract, resulting in low systemic bioavailability . Once absorbed, this compound is extensively distributed in tissues, including the liver, lungs, and kidneys . It is transported in the bloodstream bound to plasma proteins, primarily albumin . This compound can also penetrate the blood-brain barrier, making it effective against central nervous system infections and tumors .
Subcellular Localization
This compound localizes primarily in the cytoplasm, where it interacts with microtubules . It does not have specific targeting signals or post-translational modifications that direct it to specific organelles . Its effects on microtubule dynamics can influence the distribution and function of other cellular components, including mitochondria and the endoplasmic reticulum . The disruption of microtubules by this compound can lead to changes in the organization and function of these organelles .
Preparation Methods
Synthetic Routes and Reaction Conditions
The preparation of mebendazole involves an acylation reaction followed by a Friedel-Crafts reaction. In the acylation reaction, trichlorotoluene is heated to 50-90°C, and a zinc chloride aqueous solution is added dropwise. After the reaction, reduced pressure distillation is carried out to obtain benzoyl chloride . In the Friedel-Crafts reaction, carbendazim, a solvent, and anhydrous aluminum chloride are mixed and stirred. Benzoyl chloride is then added dropwise, followed by continuous stirring and heat preservation reaction. Reduced pressure distillation is conducted to obtain this compound .
Industrial Production Methods
The industrial production of this compound typically follows the same synthetic route as described above. The process is optimized for high yield and efficiency, with a focus on simple flow, mild conditions, and high atom utilization rate .
Chemical Reactions Analysis
Types of Reactions
Mebendazole undergoes various chemical reactions, including oxidation, reduction, and substitution reactions.
Common Reagents and Conditions
Oxidation: Common oxidizing agents such as hydrogen peroxide or potassium permanganate can be used.
Reduction: Reducing agents like palladium-on-charcoal catalyst in the presence of hydrogen can be employed.
Substitution: Substitution reactions often involve the use of halogenating agents or nucleophiles.
Major Products
The major products formed from these reactions depend on the specific reagents and conditions used. For example, reduction of 4-amino-3-nitrobenzophenone with palladium-on-charcoal catalyst yields 3,4-diaminobenzophenone .
Comparison with Similar Compounds
Similar Compounds
Albendazole: Another benzimidazole anthelmintic used to treat a variety of parasitic worm infestations.
Pyrantel: An anthelmintic used to treat pinworm, hookworm, and roundworm infections.
Uniqueness
Mebendazole is unique in its ability to penetrate the blood-brain barrier, making it particularly effective for treating brain tumors . Its broad-spectrum activity and relatively low toxicity also distinguish it from other similar compounds .
Properties
IUPAC Name |
methyl N-(6-benzoyl-1H-benzimidazol-2-yl)carbamate |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
OPXLLQIJSORQAM-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C16H13N3O3 |
Source
|
| Record name | MEBENDAZOLE | |
| Source | CAMEO Chemicals | |
| URL | https://cameochemicals.noaa.gov/chemical/20586 | |
| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID4040682 |
Source
|
| Record name | Mebendazole | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID4040682 | |
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Molecular Weight |
295.29 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Mebendazole is a white to slightly yellow powder. Pleasant taste. Practically water insoluble. (NTP, 1992), Solid |
Source
|
| Record name | MEBENDAZOLE | |
| Source | CAMEO Chemicals | |
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| Description | CAMEO Chemicals is a chemical database designed for people who are involved in hazardous material incident response and planning. CAMEO Chemicals contains a library with thousands of datasheets containing response-related information and recommendations for hazardous materials that are commonly transported, used, or stored in the United States. CAMEO Chemicals was developed by the National Oceanic and Atmospheric Administration's Office of Response and Restoration in partnership with the Environmental Protection Agency's Office of Emergency Management. | |
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| Record name | Mebendazole | |
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Solubility |
Practically insoluble (NTP, 1992), Soluble in formic acid. Practically insoluble in ethanol, ether, chloroform, In water, 7.13X10+1 mg/L at 25 °C, 3.87e-02 g/L |
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|
| Record name | MEBENDAZOLE | |
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Mechanism of Action |
Mebendazole causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies., Although the exact mechanism of anthelmintic activity of mebendazole has not been fully elucidated, the drug appears to cause selective and irreversible inhibition of the uptake of glucose and other low molecular weight nutrients in susceptible helminths; inhibition of glucose uptake appears to result in endogenous depletion of glycogen stores in the helminth. Mebendazole does not inhibit glucose uptake in mammals. Mebendazole appears to cause degenerative changes in the intestine of nematodes and in the absorptive cells of cestodes. The principal anthelmintic effect of the drug appears to be degeneration of cytoplasmic microtubules within these intestinal and absorptive cells. Microtubular deterioration results in inhibition of organelle movement and interferes with the absorptive and secretory function. As a result of excessive accumulation of intracellular transport secretory granules, hydrolytic and proteolytic enzymes are released and cause cellular autolysis. This irreversible damage leads to death of the parasite., Vermicidal; may also be ovicidal for ova or most helminths; mebendazole causes degeneration of parasite's cytoplasmic microtubules and thereby selectively and irreversibly blocks glucose uptake in susceptible adult intestine-dwelling helminths and their tissue-dwelling larvae; inhibition of glucose uptake apparently results in depletion of the parasite's glycogen stores; this, in turn, results in reduced formation of adenosine triphosphate (ATP) required for survival and reproduction of the helminth; corresponding energy levels are gradually reduced until death of the parasite ensues; mebendazole does not appear to affect serum glucose concentrations in humans, however., Benzimidazoles produce many biochemical changes in susceptible nematodes, eg, inhibition of mitochondrial fumarate reductase, reduced glucose transport, and uncoupling of oxidative phosphorylation ... /but/ the primary action ... /should be/ to inhibit microtubule polymerization by binding to beta-tubulin. The selective toxicity of these agents derives from the fact that specific, high-affinity binding to parasite beta-tubulin occurs at much lower concn than does binding to the mammalian protein ... Benzimidazole-resistant Haemonchus contortus display reduced high-affinity drug binding to beta-tubulin and alterations in beta-tubulin isotype gene expression that correlate with drug resistance ... Two identified mechanisms of drug resistance in nematodes involve both a progressive loss of "susceptible" beta-tubulin gene isotypes together with emergence of a "resistant" isotype with a conserved point mutation that encodes a tyrosine instead of phenylalanine at position 200 of beta-tubulin. While this mutation may not be required for benzimidazole resistance in all parasites, eg, Giardia lamblia, benzimidazole resistance in parasitic nematodes is unlikely to be overcome by novel benzimidazole analogs, because tyrosine also is present at position 200 of human beta-tubulin. /Benzimidazoles/ |
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| Record name | Mebendazole | |
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Color/Form |
Off-white amorphous powder, Crystals from acetic acid and methanol | |
CAS No. |
31431-39-7 |
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| Record name | MEBENDAZOLE | |
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Melting Point |
551.3 °F (NTP, 1992), 288.5 °C |
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| Record name | MEBENDAZOLE | |
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Retrosynthesis Analysis
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| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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