Mebendazol
Descripción general
Descripción
El mebendazol es un compuesto antihelmíntico de amplio espectro utilizado para tratar diversas infestaciones de gusanos parásitos. Fue desarrollado por Janssen Pharmaceutica en Bélgica y entró en uso en 1971 . El this compound es efectivo contra una gama de infestaciones de nematodos, incluyendo ascárides, anquilostomas, tricocéfalos y oxiuros . Se absorbe mal en el torrente sanguíneo, lo que lo hace particularmente efectivo para tratar parásitos intestinales .
Mecanismo De Acción
El mebendazol funciona inhibiendo la polimerización de la tubulina en los parásitos, interrumpiendo la formación de microtúbulos e interfiriendo con la absorción de glucosa . Esto conduce en última instancia a la muerte del parásito. El compuesto se dirige a vías críticas implicadas en la proliferación celular, la apoptosis y la invasión/migración .
Aplicaciones Científicas De Investigación
El mebendazol se ha reutilizado para diversas aplicaciones de investigación científica más allá de su uso original como antihelmíntico. Ha mostrado promesa en el tratamiento de cánceres cerebrales, incluyendo el glioma, al inhibir la progresión maligna y aumentar la sensibilidad de las células gliomatosas a la quimioterapia o radioterapia convencionales . Además, se ha explorado el this compound por sus propiedades anticancerígenas en múltiples cánceres, incluyendo la leucemia mieloide aguda, el cáncer de mama y el cáncer gastrointestinal .
Análisis Bioquímico
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 . Mebendazole interacts with beta-tubulin, inhibiting its polymerization and thereby affecting the stability of microtubules . Additionally, Mebendazole has been shown to inhibit glucose uptake in parasitic worms, leading to their death .
Cellular Effects
Mebendazole exerts significant effects on various cell types and cellular processes. In cancer cells, Mebendazole 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 . Mebendazole has been shown to decrease the expression of genes associated with cell proliferation and increase the expression of pro-apoptotic genes . Furthermore, Mebendazole influences cellular metabolism by inhibiting glucose uptake and disrupting mitochondrial function .
Molecular Mechanism
At the molecular level, Mebendazole 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 . Mebendazole also affects other molecular targets, including the Bcl-2 family of proteins, which regulate apoptosis . By inhibiting Bcl-2, Mebendazole promotes the release of cytochrome c from mitochondria, triggering the apoptotic cascade . Additionally, Mebendazole 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 Mebendazole have been observed to change over time. Mebendazole is relatively stable, but its efficacy can decrease due to degradation . Long-term studies have shown that Mebendazole can cause sustained inhibition of tumor growth and metastasis in in vivo models . The stability and degradation of Mebendazole can vary depending on the experimental conditions and the presence of other compounds .
Dosage Effects in Animal Models
The effects of Mebendazole vary with different dosages in animal models. At low doses, Mebendazole effectively inhibits parasitic worm infections without causing significant toxicity . At higher doses, Mebendazole can cause adverse effects, including bone marrow suppression and hepatotoxicity . In cancer models, higher doses of Mebendazole have been shown to inhibit tumor growth and metastasis more effectively . The therapeutic window for Mebendazole is relatively wide, but careful dose optimization is necessary to minimize toxicity .
Metabolic Pathways
Mebendazole 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 Mebendazole . The metabolic flux and levels of metabolites can vary depending on the dose and duration of treatment .
Transport and Distribution
Mebendazole is poorly absorbed from the gastrointestinal tract, resulting in low systemic bioavailability . Once absorbed, Mebendazole is extensively distributed in tissues, including the liver, lungs, and kidneys . It is transported in the bloodstream bound to plasma proteins, primarily albumin . Mebendazole can also penetrate the blood-brain barrier, making it effective against central nervous system infections and tumors .
Subcellular Localization
Mebendazole 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 Mebendazole can lead to changes in the organization and function of these organelles .
Métodos De Preparación
Rutas sintéticas y condiciones de reacción
La preparación del mebendazol implica una reacción de acilación seguida de una reacción de Friedel-Crafts. En la reacción de acilación, el triclorotolueno se calienta a 50-90 °C, y se añade gota a gota una solución acuosa de cloruro de zinc. Después de la reacción, se realiza una destilación a presión reducida para obtener cloruro de benzoílo . En la reacción de Friedel-Crafts, se mezclan y agitan carbendazim, un disolvente y cloruro de aluminio anhidro. A continuación, se añade gota a gota cloruro de benzoílo, seguido de agitación continua y reacción de conservación del calor. Se realiza una destilación a presión reducida para obtener this compound .
Métodos de producción industrial
La producción industrial del this compound suele seguir la misma ruta sintética que se ha descrito anteriormente. El proceso se optimiza para obtener un alto rendimiento y eficiencia, con especial atención a un flujo simple, condiciones suaves y una alta tasa de utilización de átomos .
Análisis De Reacciones Químicas
Tipos de reacciones
El mebendazol experimenta diversas reacciones químicas, incluyendo reacciones de oxidación, reducción y sustitución.
Reactivos y condiciones comunes
Oxidación: Se pueden utilizar oxidantes comunes como el peróxido de hidrógeno o el permanganato de potasio.
Reducción: Se pueden emplear agentes reductores como el catalizador de paladio sobre carbón en presencia de hidrógeno.
Sustitución: Las reacciones de sustitución suelen implicar el uso de agentes halogenantes o nucleófilos.
Productos principales
Los productos principales que se forman a partir de estas reacciones dependen de los reactivos y las condiciones específicas que se utilicen. Por ejemplo, la reducción de la 4-amino-3-nitrobenzofenona con catalizador de paladio sobre carbón produce 3,4-diaminobenzofenona .
Comparación Con Compuestos Similares
Compuestos similares
Albendazol: Otro antihelmíntico benzimidazol utilizado para tratar una variedad de infestaciones de gusanos parásitos.
Pirantel: Un antihelmíntico utilizado para tratar infecciones por oxiuros, anquilostomas y ascárides.
Singularidad
El mebendazol es único en su capacidad para penetrar la barrera hematoencefálica, lo que lo hace particularmente efectivo para tratar tumores cerebrales . Su actividad de amplio espectro y su toxicidad relativamente baja también lo distinguen de otros compuestos similares .
Propiedades
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 | |
| 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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| Record name | Mebendazole | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014781 | |
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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 | |
| Source | DrugBank | |
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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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Strategy Settings
| 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
Descargo de responsabilidad e información sobre productos de investigación in vitro
Tenga en cuenta que todos los artículos e información de productos presentados en BenchChem están destinados únicamente con fines informativos. Los productos disponibles para la compra en BenchChem están diseñados específicamente para estudios in vitro, que se realizan fuera de organismos vivos. Los estudios in vitro, derivados del término latino "in vidrio", involucran experimentos realizados en entornos de laboratorio controlados utilizando células o tejidos. Es importante tener en cuenta que estos productos no se clasifican como medicamentos y no han recibido la aprobación de la FDA para la prevención, tratamiento o cura de ninguna condición médica, dolencia o enfermedad. Debemos enfatizar que cualquier forma de introducción corporal de estos productos en humanos o animales está estrictamente prohibida por ley. Es esencial adherirse a estas pautas para garantizar el cumplimiento de los estándares legales y éticos en la investigación y experimentación.
