Tiabendazole

Tiabendazole

Systematic (IUPAC) name
4-(1H-1,3-benzodiazol-2-yl)-1,3-thiazole
Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	?
Legal status	?
Pharmacokinetic data
Metabolism	GI tract. Peak plasma 1-2 hours through oral admin.
Half-life	8 hours
Excretion	90% Urine
Identifiers
CAS number	148-79-8 Y
ATC code	D01AC06 P02CA02 QP52AC10
PubChem	CID 5430
DrugBank	APRD01252
UNII	N1Q45E87DT Y
KEGG	D00372 Y
ChEMBL	CHEMBL625 N
Chemical data
Formula	C10H7N3S
Mol. mass	201.249 g/mol
SMILES	eMolecules & PubChem
Physical data
Density	1.103 g/cm³
Melt. point	293–305 °C (559–581 °F)
N(what is this?)  (verify)

Tiabendazole (INN, other names include TBZ, thiabendazole and the trade names Mintezol, Tresaderm, and Arbotect) is a fungicide and parasiticide.

Uses

Fungicide

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

Use in treatment of Aspergillus has been reported.^[1]

Parasiticide

As an antiparasitic, it is able to control roundworms (such as Strongyloidiasis)^[2], hookworms, and other helminth species which attack wild animals, livestock and humans. ^[3]

Pharmacodynamics / Mode of Action

Inhibition of the mitochondrial helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone.^[4]

Other

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

In dogs and cats thiabendazole is also used to treat ear infections.

Thiabendazole is also used as a food additive^[5][6], 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 skin of citrus fruits. It is not approved for usage in the EU,^[7] Australia and New Zealand^[8] or the USA.

Safety

The substance appears to have a slight toxicity in higher doses, with effects such as liver and intestine disorder at high exposure in test animals (just below LD₅₀ level).^{[citation needed]} Some reproductive disorders and decreasing weanling weight have been observed, also at high exposure. Effects on humans from use as drug includes 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.^{[citation needed]} No mutagenic or carcinogenic effects have been shown.

See also

• Fungicide use in the United States
• List of fungicides
• Fungicide

References

1. ^ Upadhyay MP, West EP, Sharma AP (January 1980). "Keratitis due to Aspergillus flavus successfully treated with thiabendazole". Br J Ophthalmol 64 (1): 30–2. doi:10.1136/bjo.64.1.30. PMC 1039343. PMID 6766732. http://bjo.bmj.com/cgi/pmidlookup?view=long&pmid=6766732. 
2. ^ Igual-Adell R, Oltra-Alcaraz C, Soler-Company E, Sánchez-Sánchez P, Matogo-Oyana J, Rodríguez-Calabuig D (December 2004). "Efficacy and safety of ivermectin and thiabendazole in the treatment of strongyloidiasis". Expert Opin Pharmacother 5 (12): 2615–9. doi:10.1517/14656566.5.12.2615. PMID 15571478. http://www.informapharmascience.com/doi/abs/10.1517/14656566.5.12.2615. 
3. ^ Portugal R, Schaffel R, Almeida L, Spector N, Nucci M (June 2002). "Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study". Haematologica 87 (6): 663–4. PMID 12031927. http://www.haematologica.org/cgi/pmidlookup?view=long&pmid=12031927. 
4. ^ Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 970
5. ^ Rosenblum C (March 1977). "Non-drug-related residues in tracer studies". Journal of Toxicology and Environmental Health 2 (4): 803–14. doi:10.1080/15287397709529480. PMID 853540. 
6. ^ Sax, N.I. Dangerous Properties of Industrial Materials. Vol 1-3 7th ed. New York, NY: Van Nostrand Reinhold, 1989., p. 3251
7. ^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". http://www.food.gov.uk/safereating/chemsafe/additivesbranch/enumberlist. Retrieved 2011-10-27. 
8. ^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". http://www.comlaw.gov.au/Details/F2011C00827. Retrieved 2011-10-27. 

• Thiabendazole, Extension Toxicology Network
• Medicinenet: Thiabendazole - Oral