Mebendazole

Mebendazole
ATC Code P02CA01
Formula C16H13N3O3
Molar Mass (g·mol−1) 295,29
Physical State solid
Melting Point (°C) 288–289
PKS Value 6.6
CAS Number 31431-39-7
PUB Number 4030
Drugbank ID DB00643
Solubility sparingly soluble in water

Basics

Mebendazole belongs to the chemical group of benzimidazoles. It is used to treat diseases caused by worms.

Mebendazole shows effect on the following organisms:

  • Tapeworms
  • Hookworms
  • Whipworms
  • Trichinae
  • Pinworms
  • Roundworms

So it is an anthelmintic. Mebendazole is available by prescription and is usually given in tablet form.

Pharmacology

Pharmacodynamics

Mebendazole interferes with the cellular metabolism of worms. It binds to the protein β-tubulin. This disrupts the integrity of the worm cells and metabolic transport. It thereby prevents the absorption of glucose in the digestive tract of the worms. As a result, the parasite runs out of energy reserves after a certain time and dies. The substance has no effect on humans,

Pharmacokinetics

Only 5-10% of mebendazole is absorbed in the gastrointestinal tract. This percentage can be increased somewhat by fatty food. The active substance is present in the blood bound to proteins to 90-99%. It is primarily broken down in the cells of the liver by the enzymes of the CYP450 system. Only 2% of the ingested dose is metabolized and excreted in the urine. The majority is excreted unchanged in the stool. The elimination half-life is between 2 and 5 hours.

Drug Interactions

Carbamazepine, metronidazole and phenytoin should not be taken concurrently as they may increase or decrease plasma levels of Mebendazole. Therefore, drastic side effects or lack of effectiveness may occur.

Toxicity

Side effects

Mebendazole is usually well tolerated. Typical side effects after taking mebendazole are gastrointestinal symptoms such as abdominal pain, diarrhea and flatulence. Furthermore, dizziness, headache, nausea and vomiting may occur.

Signs of overdose include elevated liver enzyme levels, fever, hair loss, pruritus and neutropenia.

Toxicological data

(LD50): 620 mg/kg [Mouse, Oral]

Sources

  • Drugbank
  • PubChem
  • Aktories, Förstermann, Hofmann, Starke: Allgemeine und spezielle Pharmakologie und Toxikologie, Elsvier, 2017
Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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