Mebendazole
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| Systematic (IUPAC) name | |
| methyl (5-benzoyl-1H-benzimidazol-2-yl)carbamate | |
| Clinical data | |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a682315 |
| Pregnancy cat. | C |
| Legal status | ? |
| Routes | Oral |
| Pharmacokinetic data | |
| Bioavailability | ~2% |
| Metabolism | Hepatic |
| Half-life | 2.5 to 5.5 hours |
| Identifiers | |
| CAS number | 31431-39-7  |
| ATC code | P02CA01 QP52AC09 |
| PubChem | CID 4030 |
| DrugBank | APRD01086 |
| ChemSpider | 3890 |
| UNII | 81G6I5V05I |
| KEGG | D00368 |
| ChEBI | CHEBI:6704 |
| ChEMBL | CHEMBL685 |
| Chemical data | |
| Formula | C16H13N3O3 |
| Mol. mass | 295.293 g/mol |
| SMILES | eMolecules & PubChem |
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| Physical data | |
| Melt. point | 288.5 °C (551 °F) |
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Mebendazole or MBZ is a benzimidazole drug developed by Janssen Pharmaceutica and marketed as Vermox, Ovex, Antiox, and Pripsen. It is used to treat infestations by worms including pinworms, roundworms, tapeworms, hookworms, and whipworms.
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[edit] Medical use
The drug is a highly effective broad spectrum anthelmintic indicated for the treatment of nematode infestations, including round worm, whip worm, thread worm, and hook worm. It is poorly absorbed and has no systemic effects.
[edit] Mechanism
Mebendazole is thought to work by selectively inhibiting the synthesis of microtubules in parasitic worms, and by destroying extant cytoplasmic microtubes in their intestinal cells: thereby blocking the uptake of glucose and other nutrients, resulting in the gradual immobilization and eventual death of the helminths.
[edit] Dosage
Oral dosage for treatment of pinworms is 100 mg taken once. This regimen is repeated two weeks later if the infestation has not cleared up. Oral dosage for treatment of whipworm, common roundworm and hookworm is one 100-mg tablet morning and evening for 3 consecutive days. Dosage is the same for both adults and children.[1]
[edit] Adverse effects
Mebendazole is relatively free of toxic side effects or adverse reactions, although patients may complain of transient abdominal pain, diarrhea, slight headache, fever, dizziness, exanthema, urticaria and angioedema.
[edit] Contraindications
[edit] Pregnancy
Mebendazole is contraindicated in pregnant women because it has been shown to be embryotoxic and teratogenic in experimental animals.
[edit] Drug interactions
Carbamazepine and phenytoin lower serum levels of mebendazole. Cimetidine does not appreciably raise serum mebendazole, consistent with its poor systemic absorption.[2][3]
Stevens–Johnson syndrome (toxic epidermal necrolysis) can occur when mebendazole is combined with high doses of metronidazole.[4]
[edit] Discontinuation in United States
The last manufacturer of mebendazole in the United States, Teva Pharmaceuticals, announced on October 7, 2011, that they have ceased manufacture of this product. As of December, 2011, it is no longer available from any manufacturer in the USA. No reason was given for this discontinuation.[5]
[edit] See also
[edit] References
- ^ "Mebendazole". Drugs.com. http://www.drugs.com/pro/mebendazole.html. Retrieved 2011-10-29.
- ^ "Drug Interactions". Medicine chest. http://www.medicinechestonline.co.uk/static/professional2/drug_interactions.htm. Retrieved 2008-05-06.
- ^ Luder, P. J.; Siffert, B.; Witassek, F.; Meister, F.; Bircher, J. (1986). "Treatment of hydatid disease with high oral doses of mebendazole. Long-term follow-up of plasma mebendazole levels and drug interactions". European journal of clinical pharmacology 31 (4): 443–448. PMID 3816925.
- ^ Chen, K. T.; Twu, S. J.; Chang, H. J.; Lin, R. S. (2003). "Outbreak of Stevens-Johnson Syndrome/Toxic Epidermal Necrolysis Associated with Mebendazole and Metronidazole Use Among Filipino Laborers in Taiwan". American journal of public health 93 (3): 489–492. PMC 1447769. PMID 12604501. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1447769.
- ^ "Drug Shortages Bulletin 750". American Society of Health-System Pharmacists. http://www.ashp.org/DrugShortages/Current/bulletin.aspx?id=750. Retrieved 12/18/2011.
[edit] External links
- Vermox (UK manufacturer's website)
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