Mebendazole

Mebendazole

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 Y
ATC code	P02CA01 QP52AC09
PubChem	CID 4030
DrugBank	DB00643
ChemSpider	3890 Y
UNII	81G6I5V05I Y
KEGG	D00368 Y
ChEBI	CHEBI:6704 Y
ChEMBL	CHEMBL685 Y
Chemical data
Formula	C16H13N3O3
Mol. mass	295.293 g/mol
SMILES	eMolecules & 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) Y Key:OPXLLQIJSORQAM-UHFFFAOYSA-N Y
Physical data
Melt. point	288.5 °C (551 °F)
Y (what is this?)  (verify)

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.

Medical use

The drug is a highly effective broad spectrum antihelmintic indicated for the treatment of nematode infestations, including roundworm, whipworm, threadworm, and hookworm. It is poorly absorbed and has no systemic effects.^{[citation needed]}

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.

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]

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.

Contraindications

Pregnancy

Mebendazole is contraindicated in pregnant women because it has been shown to be embryotoxic and teratogenic in experimental animals.

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]

Oncologic treatment potential

Several studies show mebendazole exhibits a potent antitumor properties. MZ significantly inhibited cancer cell growth, migration and metastatic formation of adrenocortical carcinoma, both in vitro and in vivo.^[5] Treatment of lung cancer cell lines with MZ caused mitotic arrest, followed by apoptotic cell death with the feature of caspase activation and cytochrome c release.^[6] MZ induced a dose- and time-dependent apoptotic response in human lung cancer cell lines^[7], and apoptosis via Bcl-2 inactivation in chemoresistant melanoma cells.^[8]

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.^[9]

See also

• Metronidazole

References

External links

• Vermox (UK manufacturer's website)