甲苯达唑
描述
甲苯达唑是一种广谱驱虫药，用于治疗各种寄生虫感染。 它由比利时的杨森制药公司开发，并于 1971 年投入使用 。 甲苯达唑对多种线虫感染有效，包括蛔虫、钩虫、鞭虫和蛲虫 。 它几乎不被血液吸收，使其特别适用于治疗肠道寄生虫 .
作用机制
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, Mebendazole 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 .
科学研究应用
除了最初作为驱虫剂的用途外，甲苯达唑已被重新用于各种科学研究应用。 它在治疗脑癌（包括胶质瘤）方面显示出希望，通过抑制恶性进展并提高胶质瘤细胞对传统化疗或放疗的敏感性 。 此外，甲苯达唑因其在多种癌症中的抗癌特性而被研究，包括急性髓性白血病、乳腺癌和胃肠道癌 .
作用机理
甲苯达唑通过抑制寄生虫中微管蛋白的聚合来起作用，从而破坏微管的形成并干扰葡萄糖的摄取 。这最终导致寄生虫死亡。 该化合物靶向参与细胞增殖、凋亡和侵袭/迁移的关键途径 .
生化分析
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 .
准备方法
合成路线和反应条件
甲苯达唑的制备涉及酰化反应，然后进行傅-克反应。在酰化反应中，将三氯甲苯加热至 50-90°C，然后逐滴加入氯化锌水溶液。 反应结束后，进行减压蒸馏得到苯甲酰氯 。在傅-克反应中，将多菌灵、溶剂和无水三氯化铝混合并搅拌。然后逐滴加入苯甲酰氯，然后继续搅拌和热保存反应。 进行减压蒸馏得到甲苯达唑 .
工业生产方法
甲苯达唑的工业生产通常遵循与上述相同的合成路线。 该工艺针对高产率和效率进行了优化，重点关注流程简单、条件温和和原子利用率高 .
化学反应分析
反应类型
甲苯达唑会发生各种化学反应，包括氧化、还原和取代反应。
常用试剂和条件
氧化： 可以使用过氧化氢或高锰酸钾等常见的氧化剂。
还原： 可以使用钯碳催化剂在氢气存在下等还原剂.
取代： 取代反应通常涉及使用卤化剂或亲核试剂。
主要产物
从这些反应中形成的主要产物取决于所用试剂和条件的具体情况。 例如，用钯碳催化剂还原 4-氨基-3-硝基苯甲酮得到 3,4-二氨基苯甲酮 .
相似化合物的比较
类似化合物
阿苯达唑： 另一种苯并咪唑类驱虫药，用于治疗各种寄生虫感染.
吡喹酮： 一种驱虫药，用于治疗蛲虫、钩虫和蛔虫感染.
独特性
甲苯达唑独特的特点是能够穿透血脑屏障，使其特别适用于治疗脑肿瘤 。 其广谱活性及其相对较低的毒性也使其区别于其他类似化合物 .
属性
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 | |
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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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| 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/ |
Source
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| Record name | Mebendazole | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00643 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
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Color/Form |
Off-white amorphous powder, Crystals from acetic acid and methanol | |
CAS No. |
31431-39-7 |
Source
|
| Record name | MEBENDAZOLE | |
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Melting Point |
551.3 °F (NTP, 1992), 288.5 °C |
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| Record name | MEBENDAZOLE | |
| Source | CAMEO Chemicals | |
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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
体外研究产品的免责声明和信息
请注意，BenchChem 上展示的所有文章和产品信息仅供信息参考。 BenchChem 上可购买的产品专为体外研究设计，这些研究在生物体外进行。体外研究，源自拉丁语 "in glass"，涉及在受控实验室环境中使用细胞或组织进行的实验。重要的是要注意，这些产品没有被归类为药物或药品，他们没有得到 FDA 的批准，用于预防、治疗或治愈任何医疗状况、疾病或疾病。我们必须强调，将这些产品以任何形式引入人类或动物的身体都是法律严格禁止的。遵守这些指南对确保研究和实验的法律和道德标准的符合性至关重要。
