|Trade names||Mintezol, others|
|AHFS/Drugs.com||International Drug Names|
|By mouth, topical|
|Bioavailability||Сmax 1–2 hours (oral administration)|
|Elimination half-life||8 hours|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||201.249 g/mol g·mol−1|
|3D model (JSmol)|
|Melting point||293 to 305 °C (559 to 581 °F)|
|(what is this?)|
Tiabendazole is also used as a food additive, a preservative with E number E233 (INS number 233). For example, it is applied to bananas to ensure freshness, and is a common ingredient in the waxes applied to the skins of citrus fruits. It is not approved as a food additive in the EU, Australia and New Zealand.
In dogs and cats, tiabendazole is used to treat ear infections.[clarification needed]
Genes responsible for the maintenance of cell walls in yeast have been shown to be responsible for angiogenesis in vertebrates. Tiabendazole serves to block angiogenesis in both frog embryos and human cells. It has also been shown to serve as a vascular disrupting agent to reduce newly established blood vessels. Tiabendazole has been shown to effectively do this in certain cancer cells.
Tiabendazole works by inhibition of the mitochondrial, helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone.
The substance appears to have a slight toxicity in higher doses, with effects such as liver and intestinal disorders at high exposure in test animals (just below LD50 level). Some reproductive disorders and decreasing weaning weight have been observed, also at high exposure. Effects on humans from use as a drug include nausea, vomiting, loss of appetite, diarrhea, dizziness, drowsiness, or headache; very rarely also ringing in the ears, vision changes, stomach pain, yellowing eyes and skin, dark urine, fever, fatigue, increased thirst and change in the amount of urine occur. Carcinogenic effects have been shown at higher doses.
Intermediate arylamidine 2 is prepared by HCl-catalyzed addition of aniline to the nitrile function of 4-cyanothiazole (1). The amidine (2) is then converted to its N-chloro analog 3 with sodium hypochlorite (NaOCl). Upon treatment with base, this undergoes a nitrene insertion reaction (4) to produce tiabendazole (5).
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