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__NOTOC__
{{Drugbox
{{Thiabendazole}}
| Verifiedfields = changed
{{CMG}}
| verifiedrevid = 457788234
| IUPAC_name = 4-(1''H''-1,3-benzodiazol-2-yl)-1,3-thiazole
| image =Thiabendazole.png
| width = 148
| image2 =Thiabendazole ball-and-stick.png


==Overview==
<!--Clinical data-->
| tradename = Mintezol
| Drugs.com = {{drugs.com|international|tiabendazole}}
| pregnancy_AU = B3
| pregnancy_category =
| legal_AU = S4
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = <!-- OTC / Rx-only -->
| legal_status =  rx only
| routes_of_administration =  oral, topical


Thiabendazole (or Tiabendazole) is a [[fungicide]] and parasiticide.
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = GI tract. Peak plasma 1-2 hours through oral administration
| elimination_half-life = 8 hours
| excretion = 90% I urine


==Category==
<!--Identifiers-->
 
| CASNo_Ref = {{cascite}}
Anthelmintic
| CAS_number_Ref = {{cascite|correct|??}}
 
| CAS_number = 148-79-8
==US Brand Names==
| ATC_prefix = D01
 
| ATC_suffix = AC06
MINTEZOL<sup>®</sup> (''DISCONTINUED'')
| ATC_supplemental = {{ATC|P02|CA02}} {{ATCvet|P52|AC10}}
 
| PubChem = 5430
==FDA Package Insert==
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
 
| DrugBank = DB00730
''' [[Thiabendazole description|Description]]'''
| UNII_Ref = {{fdacite|correct|FDA}}
'''| [[Thiabendazole clinical pharmacology|Clinical Pharmacology]]'''
| UNII = N1Q45E87DT
'''| [[Thiabendazole microbiology|Microbiology]]'''
| KEGG_Ref = {{keggcite|correct|kegg}}
'''| [[Thiabendazole indications and usage|Indications and Usage]]'''
| KEGG = D00372
'''| [[Thiabendazole contraindications|Contraindications]]'''
| ChEMBL_Ref = {{ebicite|changed|EBI}}
'''| [[Thiabendazole warnings and precautions|Warnings and Precautions]]'''
| ChEMBL = 625
'''| [[Thiabendazole adverse reactions|Adverse Reactions]]'''
| NIAID_ChemDB = 007903
'''| [[Thiabendazole drug interactions|Drug Interactions]]'''
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
'''| [[Thiabendazole overdosage|Overdosage]]'''
| ChemSpiderID = 5237
'''| [[Thiabendazole clinical studies|Clinical Studies]]'''
| InChI = 1/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)
'''| [[Thiabendazole dosage and administration|Dosage and Administration]]'''
|  InChIKey = WJCNZQLZVWNLKY-UHFFFAOYAV
'''| [[Thiabendazole how supplied|How Supplied]]'''
|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
'''| [[Thiabendazole labels and packages|Labels and Packages]]'''
| 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 = {{stdinchicite|changed|chemspider}}
==Mechanism of Action==
| StdInChIKey = WJCNZQLZVWNLKY-UHFFFAOYSA-N


<!--Chemical data-->
| C=10 | H=7 | N=3 | S=1
| molecular_weight = 201.249 g/mol
| smiles = [nH]1c2ccccc2nc1c3cscn3
| density = 1.103
| melting_point = 293
| melting_high = 305
}}
__NOTOC__
{{CMG}}


==Overview==
'''Tiabendazole''' ([[International Nonproprietary Name|INN]], [[British Approved Name|BAN]]), '''thiabendazole''' ([[Australian Approved Name|AAN]], [[United States Adopted Name|USAN]]), '''TBZ''' and the trade names Mintezol, Tresaderm, and Arbotect) is a [[fungicide]] and [[parasite|parasiticide]].


==Uses==
==Uses==


===Fungicide===
===Fungicide===
It is used primarily to control [[mold]], [[blight]], and other fungally caused diseases in fruits (e.g. [[Orange (fruit)|oranges]]) and vegetables; it is also used as a [[prophylaxis|prophylactic]] treatment for [[Dutch elm disease]].
It is used primarily to control [[mold]], [[blight]], and other fungal diseases in fruits (e.g. [[Orange (fruit)|oranges]]) and vegetables; it is also used as a [[prophylaxis|prophylactic]] treatment for [[Dutch elm disease]].


Use in treatment of [[aspergillosis]] has been reported.<ref name="pmid6766732">{{cite journal |author=Upadhyay MP, West EP, Sharma AP |title=Keratitis due to Aspergillus flavus successfully treated with thiabendazole |journal=Br J Ophthalmol |volume=64 |issue=1 |pages=30–2 |year=1980 |month=January |pmid=6766732 |pmc=1039343 |doi= 10.1136/bjo.64.1.30|url=http://bjo.bmj.com/cgi/pmidlookup?view=long&pmid=6766732}}</ref>
Use in treatment of [[aspergillosis]] has been reported.<ref name="pmid6766732">{{cite journal |author=Upadhyay MP, West EP, Sharma AP |title=Keratitis due to Aspergillus flavus successfully treated with thiabendazole |journal=Br J Ophthalmol |volume=64 |issue=1 |pages=30–2 |date=January 1980 |pmid=6766732 |pmc=1039343 |doi= 10.1136/bjo.64.1.30|url=http://bjo.bmj.com/cgi/pmidlookup?view=long&pmid=6766732}}</ref>


===Parasiticide===
===Parasiticide===
As an antiparasitic, it is able to control [[roundworm]]s (such as those causing  [[strongyloidiasis]]),<ref name="pmid15571478">{{cite journal |author=Igual-Adell R, Oltra-Alcaraz C, Soler-Company E, Sánchez-Sánchez P, Matogo-Oyana J, Rodríguez-Calabuig D |title=Efficacy and safety of ivermectin and thiabendazole in the treatment of strongyloidiasis |journal=Expert Opin Pharmacother |volume=5 |issue=12 |pages=2615–9 |year=2004 |month=December |pmid=15571478 |doi=10.1517/14656566.5.12.2615 |url=http://www.informapharmascience.com/doi/abs/10.1517/14656566.5.12.2615}}</ref> [[hookworm]]s, and other [[helminth]] species which attack wild animals, [[livestock]] and humans.<ref name="pmid12031927">{{cite journal |author=Portugal R, Schaffel R, Almeida L, Spector N, Nucci M |title=Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study |journal=Haematologica |volume=87 |issue=6 |pages=663–4 |year=2002 |month=June |pmid=12031927 |doi= |url=http://www.haematologica.org/cgi/pmidlookup?view=long&pmid=12031927}}</ref>
As an antiparasitic, it is able to control [[roundworm]]s (such as those causing  [[strongyloidiasis]]),<ref name="pmid15571478">{{cite journal |author=Igual-Adell R, Oltra-Alcaraz C, Soler-Company E, Sánchez-Sánchez P, Matogo-Oyana J, Rodríguez-Calabuig D |title=Efficacy and safety of ivermectin and thiabendazole in the treatment of strongyloidiasis |journal=Expert Opin Pharmacother |volume=5 |issue=12 |pages=2615–9 |date=December 2004 |pmid=15571478 |doi=10.1517/14656566.5.12.2615 |url=http://www.informapharmascience.com/doi/abs/10.1517/14656566.5.12.2615}}</ref> [[hookworm]]s, and other [[helminth]] species which attack wild animals, [[livestock]] and humans.<ref name="pmid12031927">{{cite journal |author=Portugal R, Schaffel R, Almeida L, Spector N, Nucci M |title=Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study |journal=Haematologica |volume=87 |issue=6 |pages=663–4 |date=June 2002 |pmid=12031927 |doi= |url=http://www.haematologica.org/cgi/pmidlookup?view=long&pmid=12031927}}</ref>


===Angiogenesis Inhibitor===
===Angiogenesis inhibitor===
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 <ref>{{cite journal|last=Cha|first=HJ|coauthors=Byrom M, Mead PE, Ellington AD, Wallingford JB, et al.|title=Evolutionarily Repurposed Networks Reveal the Well-Known Antifungal Drug Thiabendazole to Be a Novel Vascular Disrupting Agent|journal=PLoS Biology|year=2012|month=August|volume=10|issue=8|doi=10.1371/journal.pbio.1001379|url=http://www.plosbiology.org/article/info%3Adoi%2F10.1371%2Fjournal.pbio.1001379|accessdate=2012-08-21}}</ref>
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 <ref>{{cite journal|last=Cha|first=HJ|author2=Byrom M |author3=Mead PE |author4=Ellington AD |author5=Wallingford JB |author6=et al. |title=Evolutionarily Repurposed Networks Reveal the Well-Known Antifungal Drug Thiabendazole to Be a Novel Vascular Disrupting Agent|journal=PLoS Biology|date=August 2012|volume=10|issue=8|doi=10.1371/journal.pbio.1001379|url=http://www.plosbiology.org/article/info%3Adoi%2F10.1371%2Fjournal.pbio.1001379|accessdate=2012-08-21}}</ref>


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


In dogs and cats, thiabendazole is used to treat ear infections.
In dogs and cats, thiabendazole is used to treat ear infections.
Line 64: Line 94:
|issue=4
|issue=4
|pages=803–14
|pages=803–14
|year=1977
|date=March 1977
|month=March
|pmid=853540
|pmid=853540
|doi=
|doi=
Line 74: Line 103:


==Safety==
==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).{{Citation needed|date=June 2008}} 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.{{Citation needed|date=June 2008}} Carcinogenic effects have been shown at higher doses.<ref>{{cite web|title=Reregistration Eligibility Decision THIABENDAZOLE|url=http://www.epa.gov/oppsrrd1/REDs/thiabendazole_red.pdf|publisher=Environmental Protection Agency|accessdate=8 January 2013}}</ref>
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).{{Citation needed|date=June 2008}} 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|date=June 2008}} Carcinogenic effects have been shown at higher doses.<ref>{{cite web|title=Reregistration Eligibility Decision THIABENDAZOLE|url=http://www.epa.gov/oppsrrd1/REDs/thiabendazole_red.pdf|publisher=Environmental Protection Agency|accessdate=8 January 2013}}</ref>
 
==See also==
* [[Fungicide use in the United States]]
* [[List of fungicides]]
*[[Cambendazole]]


==References==
==References==
{{Reflist|2}}
{{reflist|2}}
* [http://pmep.cce.cornell.edu/profiles/extoxnet/pyrethrins-ziram/thiabendazole-ext.html Thiabendazole, Extension Toxicology Network]
* [http://www.medicinenet.com/thiabendazole-oral/article.htm Medicinenet: Thiabendazole - Oral]
 
{{Antifungals}}
{{Anthelmintics}}


[[Category:Antibiotics]]
[[Category:Antiparasitic agents]]
[[Category:Wikinfect]]
[[Category:Preservatives]]
[[Category:Fungicides]]
[[Category:Thiazoles]]
[[Category:Benzimidazoles]]
[[Category:Drug]]

Latest revision as of 19:29, 4 April 2015

Thiabendazole
Clinical data
Trade namesMintezol
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
Routes of
administration		oral, topical
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolismGI tract. Peak plasma 1-2 hours through oral administration
Elimination half-life8 hours
Excretion90% I urine
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
NIAID ChemDB
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC10H7N3S
Molar mass201.249 g/mol
3D model (JSmol)
Density1.103 g/cm3
Melting point293 to 305 °C (Expression error: Unrecognized word "to". °F)
 ☒N☑Y (what is this?)  (verify)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Tiabendazole (INN, BAN), thiabendazole (AAN, USAN), TBZ 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 fungal diseases in fruits (e.g. oranges) and vegetables; it is also used as a prophylactic treatment for Dutch elm disease.

Use in treatment of aspergillosis has been reported.[1]

Parasiticide

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

Angiogenesis inhibitor

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 [4]

Pharmacodynamics

TBZ works by inhibition of the mitochondrial, helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone.[5]

Other

Medicinally, thiabendazole 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.

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

Thiabendazole is also used as a food additive,[6][7] 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,[8] Australia and New Zealand.[9]

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 Template:LD50 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.[10]

See also

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.
  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.
  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.
  4. ↑ Cha, HJ; Byrom M; Mead PE; Ellington AD; Wallingford JB; et al. (August 2012). "Evolutionarily Repurposed Networks Reveal the Well-Known Antifungal Drug Thiabendazole to Be a Novel Vascular Disrupting Agent". PLoS Biology. 10 (8). doi:10.1371/journal.pbio.1001379. Retrieved 2012-08-21.
  5. ↑ 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
  6. ↑ 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. |access-date= requires |url= (help)
  7. ↑ Sax, N.I. Dangerous Properties of Industrial Materials. Vol 1-3 7th ed. New York, NY: Van Nostrand Reinhold, 1989., p. 3251
  8. ↑ UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
  9. ↑ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.
  10. ↑ "Reregistration Eligibility Decision THIABENDAZOLE" (PDF). Environmental Protection Agency. Retrieved 8 January 2013.

Template:Anthelmintics

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