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Identification
Name Thiabendazole
Accession Number DB00730 (APRD01252, DB08630)
Type small molecule
Groups approved
Description

2-Substituted benzimidazole first introduced in 1962. It is active against a variety of nematodes and is the drug of choice for strongyloidiasis. It has CNS side effects and hepatototoxic potential. (From Smith and Reynard, Textbook of Pharmacology, 1992, p919)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
2-(1,3-Thiazol-4-yl)-1H-benzimidazole
TBDZ
Thiabendazol
Thiabendole
Thiabenzazole
Thiabenzole
Tiabendazol
Tiabendazole
Salts Not Available
Brand names
Name Company
Apl-Luster
Arbotect
Bioguard
Bovizole
Chemviron TK 100
Cropasal
Drawipas
Eprofil
Equivet TZ
Equizole
Hokustar hp
Hymush
Lombristop
Mertec
Mertect
Mertect 160
Mertect 340f
Mertect lsp
Metasol TK 10
Metasol TK 100
Mintesol
Mintezol
Minzolum
Mycozol
Nemacin
Nemapan
Omnizole
Ormogal
Polival
RPH
Sanaizol 100
Sistesan
Storite
TBZ 6
TBZ 60W
Tebuzate
Tecto
Tecto 10P
Tecto 40F
Tecto 60
Tecto B
Tecto rph
Testo
Thiaben
Thibendole
Thibenzol
Thibenzole
Thibenzole 200
Thibenzole att
Thiprazole
Tiabenda
Tibimix 20
Tobaz
Top form wormer
Triasox
Tubazole
First Prev Next Last
Brand mixtures
Brand Name Ingredients
Tresaderm Dermatologic Solution Dexamethasone + Neomycin sulfate + Thiabendazole
Categories
  • Anthelmintics
  • Antinematodal Agents
CAS number 148-79-8
Weight Average: 201.248
Monoisotopic: 201.036067929
Chemical Formula C10H7N3S
InChI Key InChIKey=WJCNZQLZVWNLKY-UHFFFAOYSA-N
InChI
InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13)
Plain Text
IUPAC Name
2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
SMILES
N1C2=CC=CC=C2N=C1C1=CSC=N1
Plain Text
Mass Spec show (8.42 KB)
Taxonomy
Kingdom Organic
Classes
  • Benzimidazoles
Substructures
  • Benzimidazoles
  • Benzene and Derivatives
  • Imidazoles
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Imines
  • Cyanamides
Pharmacology
Indication For the treatment of strongyloidiasis (threadworm), cutaneous larva migrans (creeping eruption), visceral larva migrans, and trichinosis.
Pharmacodynamics Thiabendazole is a fungicide and parasiticide. 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. Thiabendazole is vermicidal and/or vermifugal against Ascaris lumbricoides ("common roundworm"), Strongyloides stercoralis (threadworm), Necator americanus, Ancylostoma duodenale (hookworm), Trichuris trichiura (whipworm), Ancylostoma braziliense (dog and cat hookworm), Toxocara canis, Toxocara cati (ascarids), and Enterobius vermicularis (pinworm). Thiabendazole also suppresses egg and/or larval production and may inhibit the subsequent development of those eggs or larvae which are passed in the feces.
Mechanism of action The precise mode of action of thiabendazole on the parasite is unknown, but it most likely inhibits the helminth-specific enzyme fumarate reductase.
Absorption Rapidly absorbed and peak plasma concentration is reached within 1 to 2 hours after the oral administration of a suspension. Some systemic absorption may occur from topical preparations applied to the skin.
Volume of distribution Not Available
Protein binding Not Available
Metabolism Hepatic. Metabolized almost completely to the 5-hydroxy form which appears in the urine as glucuronide or sulfate conjugates.
Route of elimination It is metabolized almost completely to the 5-hydroxy form which appears in the urine as glucuronide or sulfate conjugates.
Half life The half-life for thiabendazole in both normal and anephric patients is 1.2 hours (range 0.9 to 2 hours). The half-life for the 5-hydroxythiabendazole metabolite in both normal and anephric patients is 1.7 hours (range 1.4 to 2 hours).
Clearance Not Available
Toxicity Overdosage may be associated with transient disturbances of vision and psychic alterations. The oral LD 50 is 3.6 g/kg, 3.1 g/kg and 3.8 g/kg in the mouse, rat, and rabbit respectively.
Affected organisms
  • Roundworms, hookworms, and other helminth species
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Merck and co inc
Packagers
Dosage forms
Form Route Strength
Suspension Oral
Tablet, chewable Oral
Prices
Unit description Cost Unit
Thiabendazole powder 1.27 USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 300 °C PhysProp
water solubility 50 mg/L (at 25 °C) WAUCHOPE,RD ET AL. (1991A)
logP 2.47 NIELSEN,LS ET AL. (1992)
pKa 4.64 (at 25 °C) CHAMBERLAIN,K ET AL. (1996)
Predicted Properties
Property Value Source
water solubility 1.38e-01 g/l ALOGPS
logP 2.47 ALOGPS
logP 2.33 ChemAxon
logS -3.2 ALOGPS
pKa (strongest acidic) 10.28 ChemAxon
pKa (strongest basic) 4.08 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 41.57 ChemAxon
rotatable bond count 1 ChemAxon
refractivity 64.91 ChemAxon
polarizability 21.02 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00372 Link_out
PubChem Compound 5430 Link_out
PubChem Substance 46505131 Link_out
ChemSpider 5237 Link_out
ChEBI 45979 Link_out
ChEMBL 45979 Link_out
Therapeutic Targets Database DAP000664 Link_out
PharmGKB PA164746466 Link_out
HET TMG Link_out
Drug Product Database 140228 Link_out
RxList http://www.rxlist.com/cgi/generic2/thiabendazole.htm Link_out
Drugs.com http://www.drugs.com/cdi/thiabendazole.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Thiabendazole Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (428 KB)
MSDS show (73.1 KB)
Interactions
Drug Interactions
Drug Interaction
Acenocoumarol The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Acenocoumarol by decreasing Acenocoumarol metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Acenocoumarol if Thiabendazole is initiated, discontinued or dose changed.
Alosetron The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Alosetron by decreasing Alosetron metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Alosetron if Thiabendazole is initiated, discontinued or dose changed.
Aminophylline The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Aminophylline by decreasing Aminophylline metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Aminophylline if Thiabendazole is initiated, discontinued or dose changed.
Betaxolol The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Betaxolol by decreasing Betaxolol metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Betaxolol if Thiabendazole is initiated, discontinued or dose changed
Caffeine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Caffeine by decreasing Caffeine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Caffeine if Thiabendazole is initiated, discontinued or dose changed.
Clomipramine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Clomipramine by decreasing Clomipramine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Clomipramine if Thiabendazole is initiated, discontinued or dose changed.
Clozapine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Clozapine by decreasing Clozapine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Clozapine if Thiabendazole is initiated, discontinued or dose changed.
Cyclobenzaprine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Cyclobenzaprine by decreasing Cyclobenzaprine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Cyclobenzaprine if Thiabendazole is initiated, discontinued or dose changed.
Dacarbazine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Dacarbazine by decreasing Dacarbazine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Dacarbazine if Thiabendazole is initiated, discontinued or dose changed.
Doxepin The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Doxepin by decreasing Doxepin metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Doxepin if Thiabendazole is initiated, discontinued or dose changed.
Duloxetine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Duloxetine by decreasing Duloxetine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Duloxetine if Thiabendazole is initiated, discontinued or dose changed.
Flutamide The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Flutamide by decreasing Flutamide metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Flutamide if Thiabendazole is initiated, discontinued or dose changed.
Fluvoxamine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Fluvoxamine by decreasing Fluvoxamine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Fluvoxamine if Thiabendazole is initiated, discontinued or dose changed.
Guanabenz The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Guanabenz by decreasing Guanabenz metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Guanabenz if Thiabendazole is initiated, discontinued or dose changed.
Oxtriphylline Thiabendazole increases the effect and toxicity of theophylline
Ramelteon Thiabendazole increases levels/toxicity of ramelteon
Tacrine The metabolism of Tacrine, a CYP1A2 substrate, may be reduced by strong CYP1A2 inhibitors such as Thiabendazole. Consider modifying therapy to avoid Tacrine toxicity. Monitor the efficacy and toxicity of Tacrine if Thiabendazole is initiated, discontinued or if the dose is changed.
Theophylline The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Theophylline by decreasing Theophylline metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Theophylline if Thiabendazole is initiated, discontinued or dose changed.
Thiothixene The strong CYP1A2 inhibitor, Thiobendazole, may decrease the metabolism and clearance of Thiothixene, a CYP1A2 substrate. Consider alternate therapy or monitor for changes in Thiothixene therapeutic and adverse effects if Thiobendazole is initiated, discontinued or dose changed.
Tizanidine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Tizanidine by decreasing Tizanidine metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Tizanidine if Thiabendazole is initiated, discontinued or dose changed.
Trifluoperazine The strong CYP1A2 inhibitor, Thiabendazole, may increase the effects and toxicity of Trifluoperazine by decreasing Trifluoperazine metabolism and clearance. Monitor for changes in the therapeutic and adverse effects of Trifluoperazine if Thiabendazole is initiated, discontinued or dose changed.
Food Interactions Not Available
Targets

1. Fumarate reductase flavoprotein subunit

Pharmacological action: yes
Actions: inhibitor

Two distinct, membrane-bound, FAD-containing enzymes are responsible for the catalysis of fumarate and succinate interconversion; the fumarate reductase is used in anaerobic growth, and the succinate dehydrogenase is used in aerobic growth

Organism class: bacterial
UniProt ID: P00363 Link_out
Gene: frdA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Ge Z, Feng Y, Dangler CA, Xu S, Taylor NS, Fox JG: Fumarate reductase is essential for Helicobacter pylori colonization of the mouse stomach. Microb Pathog. 2000 Nov;29(5):279-87. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 1A2

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. Pubmed
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 1A1

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics

UniProt ID: P04798 Link_out
Gene: CYP1A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19