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Identification
NameThiabendazole
Accession NumberDB00730  (APRD01252, DB08630)
Typesmall molecule
Groupsapproved
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
Synonyms
SynonymLanguageCode
2-(1,3-THIAZOL-4-yl)-1H-benzimidazoleNot AvailableNot Available
4-(2-Benzimidazolyl)thiazoleNot AvailableNot Available
EquizoleNot AvailableNot Available
MintezolNot AvailableNot Available
MK 360Not AvailableNot Available
TBDZNot AvailableNot Available
TBZNot AvailableNot Available
ThiabendazoleNot AvailableNot Available
ThibenzoleNot AvailableNot Available
TiabendazoleNot AvailableINN
SaltsNot Available
Brand names
NameCompany
MintezolNot Available
Brand mixtures
Brand NameIngredients
Tresaderm Dermatologic SolutionDexamethasone + Neomycin sulfate + Thiabendazole
Categories
CAS number148-79-8
WeightAverage: 201.248
Monoisotopic: 201.036067929
Chemical FormulaC10H7N3S
InChI KeyWJCNZQLZVWNLKY-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)
IUPAC Name
2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
SMILES
N1C2=CC=CC=C2N=C1C1=CSC=N1
Mass Specshow(8.42 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassBenzimidazoles
SubclassNot Available
Direct parentBenzimidazoles
Alternative parentsBenzene and Substituted Derivatives; Thiazoles; Imidazoles; Polyamines
Substituentsbenzene; imidazole; azole; thiazole; polyamine; organonitrogen compound
Classification descriptionThis compound belongs to the benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
Pharmacology
IndicationFor the treatment of strongyloidiasis (threadworm), cutaneous larva migrans (creeping eruption), visceral larva migrans, and trichinosis.
PharmacodynamicsThiabendazole 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 actionThe precise mode of action of thiabendazole on the parasite is unknown, but it most likely inhibits the helminth-specific enzyme fumarate reductase.
AbsorptionRapidly 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 distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic. Metabolized almost completely to the 5-hydroxy form which appears in the urine as glucuronide or sulfate conjugates.

Route of eliminationIt is metabolized almost completely to the 5-hydroxy form which appears in the urine as glucuronide or sulfate conjugates.
Half lifeThe 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).
ClearanceNot Available
ToxicityOverdosage 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9473
Caco-2 permeable - 0.6733
P-glycoprotein substrate Non-substrate 0.7174
P-glycoprotein inhibitor I Non-inhibitor 0.9299
P-glycoprotein inhibitor II Non-inhibitor 0.9317
Renal organic cation transporter Non-inhibitor 0.8624
CYP450 2C9 substrate Non-substrate 0.8768
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.8103
CYP450 1A2 substrate Inhibitor 0.9106
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.5658
CYP450 2C19 substrate Inhibitor 0.8994
CYP450 3A4 substrate Non-inhibitor 0.8216
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6773
Ames test AMES toxic 0.9107
Carcinogenicity Non-carcinogens 0.9331
Biodegradation Not ready biodegradable 0.9814
Rat acute toxicity 2.0170 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9838
hERG inhibition (predictor II) Non-inhibitor 0.9321
Pharmacoeconomics
Manufacturers
  • Merck and co inc
Packagers
Dosage forms
FormRouteStrength
SuspensionOral
Tablet, chewableOral
Prices
Unit descriptionCostUnit
Thiabendazole powder1.27USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point300 °CPhysProp
water solubility50 mg/L (at 25 °C)WAUCHOPE,RD ET AL. (1991A)
logP2.47NIELSEN,LS ET AL. (1992)
pKa4.64 (at 25 °C)CHAMBERLAIN,K ET AL. (1996)
Predicted Properties
PropertyValueSource
water solubility1.38e-01 g/lALOGPS
logP2.47ALOGPS
logP2.33ChemAxon
logS-3.2ALOGPS
pKa (strongest acidic)10.28ChemAxon
pKa (strongest basic)4.08ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area41.57ChemAxon
rotatable bond count1ChemAxon
refractivity64.91ChemAxon
polarizability21.02ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Lynn E. Applegate, Carl A. Renner, “Preparation of high purity thiabendazole.” U.S. Patent US5310923, issued October, 1977.

US5310923
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00372
PubChem Compound5430
PubChem Substance46505131
ChemSpider5237
ChEBI45979
ChEMBLCHEMBL625
Therapeutic Targets DatabaseDAP000664
PharmGKBPA164746466
HETTMG
Drug Product Database140228
RxListhttp://www.rxlist.com/cgi/generic2/thiabendazole.htm
Drugs.comhttp://www.drugs.com/cdi/thiabendazole.html
WikipediaThiabendazole
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(428 KB)
MSDSshow(73.1 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe 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.
AlosetronThe 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.
AminophyllineThe 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.
BetaxololThe 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
CaffeineThe 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.
ClomipramineThe 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.
ClozapineThe 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.
CyclobenzaprineThe 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.
DacarbazineThe 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.
DoxepinThe 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.
DuloxetineThe 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.
FlutamideThe 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.
FluvoxamineThe 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.
GuanabenzThe 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.
OxtriphyllineThiabendazole increases the effect and toxicity of theophylline
RamelteonThiabendazole increases levels/toxicity of ramelteon
TacrineThe 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.
TheophyllineThe 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.
ThiothixeneThe 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.
TizanidineThe 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.
TrifluoperazineThe 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 InteractionsNot Available

Targets

1. Fumarate reductase flavoprotein subunit

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Fumarate reductase flavoprotein subunit P00363 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11