Tiabendazole

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title: "Tiabendazole" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["antiparasitic-agents", "benzimidazoles", "fungicides", "preservatives", "thiazoles"] description: "Chemical compound" topic_path: "general/antiparasitic-agents" source: "https://en.wikipedia.org/wiki/Tiabendazole" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 457788234 | IUPAC_name = 4-(1H-1,3-Benzodiazol-2-yl)-1,3-thiazole | image = Thiabendazole.svg | image_class = skin-invert-image | width = 150 | image2 = Thiabendazole ball-and-stick.png | image_class2 = bg-transparent

| tradename = Mintezol, others | Drugs.com = | pregnancy_AU = B3 | pregnancy_category = | legal_AU = S4 | legal_UK = | legal_US = | legal_status = Rx-only | routes_of_administration = By mouth, topical

| bioavailability = Сmax 1–2 hours (oral administration) | protein_bound = | metabolism = GI tract | elimination_half-life = 8 hours | excretion = Urine (90%)

| IUPHAR_ligand = 7304 | CAS_number_Ref = | CAS_number = 148-79-8 | ATC_prefix = D01 | ATC_suffix = AC06 | ATC_supplemental =
| PubChem = 5430 | DrugBank_Ref = | DrugBank = DB00730 | UNII_Ref = | UNII = N1Q45E87DT | KEGG_Ref = | KEGG = D00372 | ChEMBL_Ref = | ChEMBL = 625 | NIAID_ChemDB = 007903 | ChemSpiderID_Ref = | ChemSpiderID = 5237 | StdInChI_Ref = | StdInChI = 1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13) | StdInChIKey_Ref = | StdInChIKey = WJCNZQLZVWNLKY-UHFFFAOYSA-N

| C=10 | H=7 | N=3 | S=1 | smiles = [nH]1c2ccccc2nc1c3cscn3 | density = 1.103 | melting_point = 293 | melting_high = 305

Tiabendazole (INN, BAN), also known as thiabendazole (AAN, USAN) or TBZ and the trade names Mintezol, Tresaderm, and Arbotect, is a preservative, an antifungal agent, and an antiparasitic agent.

Uses

Preservative

Tiabendazole is used primarily to control mold, blight, and other fungal diseases in fruits (e.g. oranges) and vegetables; it is also used as a prophylactic treatment for Dutch elm disease.

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.

Use in treatment of aspergillosis has been reported.

It is also used in anti-fungal wallboards as a mixture with azoxystrobin.

Parasiticide

As an antiparasitic, tiabendazole is able to control roundworms (such as those causing strongyloidiasis), hookworms, and other helminth species which infect wild animals, livestock, and humans. First approved for use in sheep in 1961 and horses in 1962, resistance to this drug was first found in Haemonchus contortus in 1964, and then in the two other major small ruminant nematode parasites, Teladorsagia circumcincta and Trichostrongylus colubriformis.

Fungicide

Tiabendazole acts as a fungicide through binding fungal tubulin. Resistant Aspergillus 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.

This chemical is also used as a pesticide, including to treat Beech Leaf Disease.

Other

In dogs and cats, tiabendazole is used to treat ear infections.

Tiabendazole is also a chelating agent, which means it is used medicinally to bind metals in cases of metal poisoning, such as lead, mercury, or antimony poisoning.

Research

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.

Pharmacodynamics

Tiabendazole works by inhibition of the mitochondrial, helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone.

Safety

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 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.

Synthesis

Intermediate aryl amidine (2) is prepared by aluminium trichloride-catalyzed addition of aniline to the nitrile of 4-cyanothiazole (1). The amidine (2) is then converted to its N-chloro derivative 3 with sodium hypochlorite (NaOCl). Upon treatment with base, this undergoes a nitrene insertion reaction (4) to produce tiabendazole (5).

::figure[src="https://upload.wikimedia.org/wikipedia/commons/8/89/Thiabendazole_synthesis.svg" caption="Tiabendazole synthesis"] ::

An alternative synthesis involves reacting 4-thiazolecarboxamide with o-phenylenediamine in polyphosphoric acid.

Derivatives

A number of derivatives of tiabendazole are also pharmaceutical drugs, including albendazole, cambendazole, fenbendazole, oxfendazole, mebendazole, and flubendazole.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/1/11/Cambendazole_synthesis.svg" caption="s2cid = 26567527 }}"] ::

References

References

1. "E233 : E Number: Preservative".
2. (March 1977). "Non-drug-related residues in tracer studies". Journal of Toxicology and Environmental Health.
3. (1989). "Dangerous Properties of Industrial Materials". Van Nostrand Reinhold.
4. "Current EU approved additives and their E Numbers".
5. (8 September 2011). "Standard 1.2.4 – Labelling of ingredients".
6. (January 1980). "Keratitis due to Aspergillus flavus successfully treated with thiabendazole". The British Journal of Ophthalmology.
7. (December 2004). "Efficacy and safety of ivermectin and thiabendazole in the treatment of strongyloidiasis". Expert Opinion on Pharmacotherapy.
8. (June 2002). "Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study". Haematologica.
9. Kaplan, Ray M.. (October 2004). "Drug resistance in nematodes of veterinary importance: a status report". Trends in Parasitology.
10. Wang, C. C.. (January 1984). "Parasite enzymes as potential targets for antiparasitic chemotherapy". Journal of Medicinal Chemistry.
11. "Beech Leaf Disease". University of Massachusetts Amherst.
12. (August 2012). "Evolutionarily repurposed networks reveal the well-known antifungal drug thiabendazole to be a novel vascular disrupting agent". PLOS Biology.
13. (1990). "Goodman and Gilman's The Pharmacological Basis of Therapeutics". Pergamon Press.
14. "Reregistration Eligibility Decision Thiabendazole". Environmental Protection Agency.
15. (1965). "Novel Preparation of Benzimidazoles from N-Arylamidines. New Synthesis of Thiabendazole". The Journal of Organic Chemistry.
16. "Anthelmintic substituted benzimidazole compositions".
17. (1961). "Antiparasitic Drugs. IV. 2-(4'-Thiazolyl)-Benzimidazole, A New Anthelmintic". Journal of the American Chemical Society.
18. "Anthelmintic 5-substituted aminobenzimidazoles".
19. (May 1970). "A new broad-spectrum anthelmintic: 2-(4-thiazolyl)-5-isopropoxycarbonylamino-benzimidazole". Experientia.

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