Identification
- Summary
Thiabendazole is a benzimidazole used in the treatment of strongyloides, cutaneous larva migrans, visceral larva migrans, and trichinosis infections.
- Generic Name
- Thiabendazole
- DrugBank Accession Number
- DB00730
- Background
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)
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Thiabendazole (DB00730)
- Weight
- Average: 201.248
Monoisotopic: 201.036067929 - Chemical Formula
- C10H7N3S
- Synonyms
- 2-(1,3-thiazole-4-yl)-1H-benzimidazole
- 2-(4-thiazolyl)-1H-benzimidazole
- 2-(thiazol-4-yl)benzimidazole
- 4-(2-benzimidazolyl)thiazole
- TBDZ
- Thiabendazole
- Tiabendazol
- Tiabendazole
- Tiabendazolum
- External IDs
- MK 360
- MK-360
- NSC-525040
- NSC-90507
Pharmacology
- Indication
For the treatment of strongyloidiasis (threadworm), cutaneous larva migrans (creeping eruption), visceral larva migrans, and trichinosis.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AFumarate reductase flavoprotein subunit inhibitorEscherichia coli (strain K12) - 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.
Hover over products below to view reaction partners
- 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Thiabendazole may decrease the excretion rate of Abacavir which could result in a higher serum level. Abametapir The serum concentration of Thiabendazole can be increased when it is combined with Abametapir. Abatacept The metabolism of Thiabendazole can be increased when combined with Abatacept. Abiraterone The serum concentration of Thiabendazole can be increased when it is combined with Abiraterone. Aceclofenac Aceclofenac may decrease the excretion rate of Thiabendazole which could result in a higher serum level. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Equizole / Thibenzole
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mintezol Suspension 500 mg/5mL Oral Merck Sharp & Dohme Limited 1967-04-21 2003-03-31 US 
Mintezol Tablet, chewable 500 mg/1 Oral Merck Sharp & Dohme Limited 1967-04-07 2008-10-31 US Mintezol Chewable Tab 500mg Tablet 500 mg / tab Oral Merck Sharp & Dohme Limited 1969-12-31 2000-08-03 Canada 
Categories
- ATC Codes
- D01AC06 — Tiabendazole
- D01AC — Imidazole and triazole derivatives
- D01A — ANTIFUNGALS FOR TOPICAL USE
- D01 — ANTIFUNGALS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- Drug Categories
- Anthelmintics
- Anti-Infective Agents
- Antifungals for Dermatological Use
- Antifungals for Topical Use
- Antihelminthic
- Antinematodal Agents
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Benzimidazole Derivatives
- Benzimidazoles
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Dermatologicals
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Imidazole and Triazole Derivatives
- Sulfur Compounds
- Thiazoles
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 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).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzimidazoles
- Sub Class
- Not Available
- Direct Parent
- Benzimidazoles
- Alternative Parents
- Benzenoids / Thiazoles / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
- Substituents
- Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Organic nitrogen compound / Organonitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 1,3-thiazole, ring assembly, benzimidazoles, benzimidazole fungicide (CHEBI:45979) / Thiazole fungicides (C07131) / a small molecule (THIABENDAZOLE)
- Affected organisms
- Roundworms, hookworms, and other helminth species
Chemical Identifiers
- UNII
- N1Q45E87DT
- CAS number
- 148-79-8
- InChI Key
- 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)
- IUPAC Name
- 2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
- SMILES
- N1C2=CC=CC=C2N=C1C1=CSC=N1
References
- Synthesis Reference
Lynn E. Applegate, Carl A. Renner, "Preparation of high purity thiabendazole." U.S. Patent US5310923, issued October, 1977.
US5310923- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014868
- KEGG Drug
- D00372
- KEGG Compound
- C07131
- PubChem Compound
- 5430
- PubChem Substance
- 46505131
- ChemSpider
- 5237
- BindingDB
- 50121347
- 10450
- ChEBI
- 45979
- ChEMBL
- CHEMBL625
- ZINC
- ZINC000000073711
- Therapeutic Targets Database
- DAP000664
- PharmGKB
- PA164746466
- PDBe Ligand
- TMG
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Tiabendazole
- PDB Entries
- 1yvm / 3sfe
- FDA label
- Download (428 KB)
- MSDS
- Download (73.1 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Merck and co inc
- Packagers
- Dept Health Central Pharmacy
- Medisca Inc.
- Merck & Co.
- Mississippi State Dept Health
- Dosage Forms
Form Route Strength Suspension Auricular (otic) Suspension Oral 500 mg/5mL Tablet, chewable Oral 500 mg/1 Tablet Oral 500 mg / tab Tablet Oral - Prices
Unit description Cost Unit Thiabendazole powder 1.27USD 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 (°C) 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 0.138 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 64.91 m3·mol-1 Chemaxon Polarizability 21.02 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.5658 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Download (8.42 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 141.6303605 predictedDarkChem Lite v0.1.0 [M-H]- 141.7619605 predictedDarkChem Lite v0.1.0 [M-H]- 146.2169364 predictedDarkChem Lite v0.1.0 [M-H]- 141.9030605 predictedDarkChem Lite v0.1.0 [M-H]- 132.93706 predictedDeepCCS 1.0 (2019) [M+H]+ 142.9450605 predictedDarkChem Lite v0.1.0 [M+H]+ 142.4532605 predictedDarkChem Lite v0.1.0 [M+H]+ 146.5590844 predictedDarkChem Lite v0.1.0 [M+H]+ 142.5615605 predictedDarkChem Lite v0.1.0 [M+H]+ 135.33263 predictedDeepCCS 1.0 (2019) [M+Na]+ 142.3650605 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.2612605 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.5907006 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.1265605 predictedDarkChem Lite v0.1.0 [M+Na]+ 142.787 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Succinate dehydrogenase activity
- Specific Function
- 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 succina...
- Gene Name
- frdA
- Uniprot ID
- P00363
- Uniprot Name
- Fumarate reductase flavoprotein subunit
- Molecular Weight
- 65971.215 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- 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 un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- 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. [Article]
- Bapiro TE, Sayi J, Hasler JA, Jande M, Rimoy G, Masselle A, Masimirembwa CM: Artemisinin and thiabendazole are potent inhibitors of cytochrome P450 1A2 (CYP1A2) activity in humans. Eur J Clin Pharmacol. 2005 Nov;61(10):755-61. doi: 10.1007/s00228-005-0037-3. Epub 2005 Oct 29. [Article]
- Bapiro TE, Egnell AC, Hasler JA, Masimirembwa CM: Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5. [Article]
- Coulet M, Dacasto M, Eeckhoutte C, Larrieu G, Sutra JF, Alvinerie M, Mace K, Pfeifer AM, Galtier P: Identification of human and rabbit cytochromes P450 1A2 as major isoforms involved in thiabendazole 5-hydroxylation. Fundam Clin Pharmacol. 1998;12(2):225-35. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- 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 un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Delescluse C, Ledirac N, Li R, Piechocki MP, Hines RN, Gidrol X, Rahmani R: Induction of cytochrome P450 1A1 gene expression, oxidative stress, and genotoxicity by carbaryl and thiabendazole in transfected human HepG2 and lymphoblastoid cells. Biochem Pharmacol. 2001 Feb 15;61(4):399-407. [Article]
- Backlund M, Weidolf L, Ingelman-Sundberg M: Structural and mechanistic aspects of transcriptional induction of cytochrome P450 1A1 by benzimidazole derivatives in rat hepatoma H4IIE cells. Eur J Biochem. 1999 Apr;261(1):66-71. doi: 10.1046/j.1432-1327.1999.00225.x. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:54