Tiabendazole

Overview

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.[1] WP

Uses, dosage and effects

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. WP⚠ Wikipedia itself has flagged this text: citation needed.

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.[2–5] WP

Use in treatment of aspergillosis has been reported.[6] WP

It is also used in anti-fungal wallboards as a mixture with azoxystrobin. WP⚠ Wikipedia itself has flagged this text: citation needed.

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.[7][8][9] WP

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.[10] WP

This chemical is also used as a pesticide, including to treat Beech Leaf Disease.[11] WP

Other

In dogs and cats, tiabendazole is used to treat ear infections. WP⚠ Wikipedia itself has flagged this text: clarification needed.

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. WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.

Risks and side effects

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 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.[12] WP⚠ Wikipedia itself has flagged this text: citation needed.

Pharmacology

Pharmacodynamics

Tiabendazole works by inhibition of the mitochondrial, helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone.[13] WP

Research

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.[14] WP

Chemistry

Formula

C10H7N3S PC

CAS number

148-79-8 PC

Molar mass (g/mol)

201.25 PC

IUPAC name (computed by PubChem)

4-(1H-benzimidazol-2-yl)-1,3-thiazole PC

SMILES

C1=CC=C2C(=C1)NC(=N2)C3=CSC=N3 PC

InChIKey

WJCNZQLZVWNLKY-UHFFFAOYSA-N PC

PubChem CID

5430

IUPAC name

4-(1H-1,3-Benzodiazol-2-yl)-1,3-thiazole WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other E233: E Number: Preservative
2. Journal / agency Rosenblum C. Non-drug-related residues in tracer studies. Journal of Toxicology and Environmental Health. March 1977. doi:10.1080/15287397709529480 · PMID 853540
3. Other Sax NI. Dangerous Properties of Industrial Materials. 1989
4. Other Current EU approved additives and their E Numbers
5. Other Standard 1.2.4 – Labelling of ingredients. 8 September 2011
6. Journal / agency Upadhyay MP, West EP, Sharma AP. Keratitis due to Aspergillus flavus successfully treated with thiabendazole. The British Journal of Ophthalmology. January 1980. doi:10.1136/bjo.64.1.30 · PMID 6766732 · PMC1039343
7. Journal / agency Igual-Adell R, Oltra-Alcaraz C, Soler-Company E, Sánchez-Sánchez P, Matogo-Oyana J, Rodríguez-Calabuig D. Efficacy and safety of ivermectin and thiabendazole in the treatment of strongyloidiasis. Expert Opinion on Pharmacotherapy. December 2004. doi:10.1517/14656566.5.12.2615 · PMID 15571478
8. Journal / agency Portugal R, Schaffel R, Almeida L, Spector N, Nucci M. Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study. Haematologica. June 2002. PMID 12031927
9. Journal / agency Kaplan, Ray M. Drug resistance in nematodes of veterinary importance: a status report. Trends in Parasitology. October 2004. doi:10.1016/j.pt.2004.08.001 · PMID 15363441
10. Journal / agency Wang, C. C. Parasite enzymes as potential targets for antiparasitic chemotherapy. Journal of Medicinal Chemistry. January 1984. doi:10.1021/jm00367a001 · PMID 6317859
11. Other Beech Leaf Disease
12. Other Reregistration Eligibility Decision Thiabendazole
13. Other Goodman and Gilman's The Pharmacological Basis of Therapeutics. 1990
14. Journal / agency Cha HJ, Byrom M, Mead PE, Ellington AD, Wallingford JB, Marcotte EM. Evolutionarily repurposed networks reveal the well-known antifungal drug thiabendazole to be a novel vascular disrupting agent. PLOS Biology. August 2012. doi:10.1371/journal.pbio.1001379 · PMID 22927795 · PMC3423972

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.