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| Trade names | Mintezol, others |
| AHFS/Drugs.com | International Drug Names |
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| Routes of administration | By mouth,topical |
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| Pharmacokinetic data | |
| Bioavailability | Сmax 1–2 hours (oral administration) |
| Metabolism | GI tract |
| Eliminationhalf-life | 8 hours |
| Excretion | Urine (90%) |
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| ECHA InfoCard | 100.005.206 |
| Chemical and physical data | |
| Formula | C10H7N3S |
| Molar mass | 201.25 g·mol−1 |
| 3D model (JSmol) | |
| Density | 1.103 g/cm3 |
| Melting point | 293 to 305 °C (559 to 581 °F) |
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Tiabendazole (INN,BAN), also known asthiabendazole (AAN,USAN) orTBZ and the trade names Mintezol, Tresaderm, and Arbotect, is a preservative,[1] an antifungal agent, and an antiparasitic agent.
Tiabendazole is used primarily to controlmold,blight, and other fungal diseases in fruits (e.g.oranges) and vegetables; it is also used as aprophylactic treatment forDutch elm disease.[citation needed]
Tiabendazole is also used as afood additive,[2][3] apreservative withE number E233 (INS number 233). For example, it is applied tobananas to ensure freshness, and is a common ingredient in thewaxes applied to the skins ofcitrus fruits. It is not approved as a food additive in the EU,[4] Australia and New Zealand.[5]
Use in treatment ofaspergillosis has been reported.[6]
It is also used in anti-fungalwallboards as a mixture withazoxystrobin.[citation needed]
As an antiparasitic, tiabendazole is able to controlroundworms (such as those causingstrongyloidiasis),[7]hookworms, and otherhelminth species which infect wild animals,livestock, and humans.[8] First approved for use in sheep in 1961 and horses in 1962, resistance to this drug was first found inHaemonchus contortus in 1964, and then in the two other major small ruminant nematode parasites,Teladorsagia circumcincta andTrichostrongylus colubriformis.[9]
Tiabendazole acts as a fungicide through binding fungal tubulin. ResistantAspergillus nidulans specimens were found to have a mutation in the gene coding for β-tubulin, which was reversible by a mutation in the gene for α-tubulin. This showed that thiabendazole binds to both α- and β-tubulin.[10]
This chemical is also used as a pesticide, including to treatBeech Leaf Disease.[11]
In dogs and cats, tiabendazole is used to treat ear infections.[clarification needed]
Tiabendazole is also achelating agent, which means it is used medicinally to bind metals in cases of metal poisoning, such aslead,mercury, orantimony poisoning.[medical citation needed]
Genes responsible for the maintenance of cell walls in yeast have been shown to be responsible forangiogenesis 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.[12]
Tiabendazole works by inhibition of the mitochondrial, helminth-specific enzyme,fumarate reductase, with possible interaction with endogenous quinone.[13]
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 belowLD50 level).[citation needed] 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.[citation needed] Carcinogenic effects have been shown at higher doses.[14]
Intermediate arylamidine (2) is prepared byaluminium trichloride-catalyzed addition ofaniline to the nitrile of 4-cyanothiazole (1).[15][16] The amidine (2) is then converted to itsN-chloro derivative3 withsodium hypochlorite (NaOCl). Upon treatment with base, this undergoes anitrene insertion reaction (4) to produce tiabendazole (5).
An alternative synthesis involves reacting 4-thiazolecarboxamide witho-phenylenediamine in polyphosphoric acid.[17]
A number ofderivatives of tiabendazole are also pharmaceutical drugs, includingalbendazole,cambendazole,fenbendazole,oxfendazole,mebendazole, andflubendazole.
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