Mebendazole

CAS No:
31431-39-7 Category:
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Product Details:

  • CAS No: 31431-39-7
  • AHFC code: 08:08.0
  • Synonyms:
  • ATC Code: P02CA01
  • Chemical Formula: C12H21N
  • Molecular Weight: 295.2927
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00643 (APRD01086)
  • SMILES: COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C1=CC=CC=C1
  • InChl: OPXLLQIJSORQAM-UHFFFAOYSA-N
  • PubChem: 4030
  • IUPAC: methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate

Additional Details

Indication:
For the treatment of Enterobius vermicularis (pinworm), Trichuris trichiura (whipworm), Ascaris lumbricoides (common roundworm), Ancylostoma duodenale (common hookworm), Necator americanus (American hookworm) in single or mixed infections.
Pharmacodynamics:
Mebendazole is a (synthetic) broad-spectrum anthelmintic. The principal mode of action for Mebendazole is by its inhibitory effect on tubulin polymerization which results in the loss of cytoplasmic microtubules.
Mode 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.
Metabolism:
Primarily hepatic. Primary metabolite is 2-amino-5-benzoylbenzimidazole, but also metabolized to inactive hydroxy and hydroxyamino metabolites. All metabolites are devoid of anthelmintic activity.
Toxicity:
Acute oral toxicity (LD50): 620 mg/kg [Mouse]. Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching.
General Reference:
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