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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:30:22 UTC
HMDB IDHMDB14868
Secondary Accession Numbers
  • HMDB29712
Metabolite Identification
Common NameThiabendazole
DescriptionThiabendazole 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)The precise mode of action of thiabendazole on the parasite is unknown, but it most likely inhibits the helminth-specific enzyme fumarate reductase. Thiabendazole is also used as a postharvest treatment for bananas, plantains and oranges. Registered in Canada for control of silver scurf in stored potatoes 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. Thiabendazole has been shown to exhibit analgesic, anti-mycotic and emetic functions (PMID 4050451 , 311456 , 2295264 ). Thiabendazole belongs to the family of 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).
Structure
Thumb
Synonyms
ValueSource
2-(1,3-THIAZOL-4-yl)-1H-benzimidazoleChEBI
2-(1,3-Thiazol-4-yl)benzimidazoleChEBI
2-(4-Thiazolyl)-1H-benzimidazoleChEBI
2-(Thiazol-4-yl)benzimidazoleChEBI
4-(2-Benzimidazolyl)thiazoleChEBI
EquizoleChEBI
MintezolChEBI
MK 360ChEBI
TBZChEBI
ThibenzoleChEBI
1YvmHMDB
2-(4'-Thiazolyl)benzimidazoleHMDB
2-(4-Thiazolyl)-benzimidazoleHMDB
2-(4-Thiazolyl)benzimidazoleHMDB
2-Thiazol-4-yl-1H-benzoimidazoleHMDB
2-Thiazole-4-ylbenzimidazoleHMDB
2-[4-Thiazoly]benzimidazoleHMDB
5-(4-Thiazolyl)benzimidazoleHMDB
Apl-lusterHMDB
ArbotectHMDB
BiogardHMDB
BioguardHMDB
BovizoleHMDB
Captan tHMDB
Chemviron TK 100HMDB
CropasalHMDB
DrawipasHMDB
e-Z-ExHMDB
EprofilHMDB
Equivet TZHMDB
Equizole aHMDB
Helmindrax octelminHMDB
Hokustar HPHMDB
HymushHMDB
LombristopHMDB
MertecHMDB
MertectHMDB
Mertect 160HMDB
Mertect 340FHMDB
Mertect LSPHMDB
Metasol TK 10HMDB
Metasol TK 100HMDB
Metasol TK-100HMDB
MintesolHMDB
MintezoleHMDB
MinzolumHMDB
MycozolHMDB
NemacinHMDB
NemapanHMDB
OmnizoleHMDB
OrmogalHMDB
PitrizetHMDB
PolivalHMDB
RPHHMDB
Sanaizol 100HMDB
SistesanHMDB
StoriteHMDB
Syntol m100HMDB
TBDZHMDB
TBZ 6HMDB
TBZ 60WHMDB
TebuzateHMDB
TectoHMDB
tecto 10PHMDB
tecto 40FHMDB
tecto 60HMDB
tecto bHMDB
tecto RPHHMDB
TestoHMDB
ThiabenHMDB
ThiabendazolHMDB
ThiabendazoleHMDB
Thiabendazole(usan)HMDB
Thiabendazole, ban, bsi, iso, jmaf, usanHMDB
ThiabendazolumHMDB
ThiabendoleHMDB
ThiabenzazoleHMDB
ThiabenzoleHMDB
ThibendoleHMDB
ThibenzolHMDB
Thibenzole 200HMDB
Thibenzole attHMDB
ThiprazoleHMDB
TiabendaHMDB
TiabendazolHMDB
Tiabendazole, innHMDB
TiabendazolumHMDB
Tibimix 20HMDB
TMGHMDB
TobazHMDB
Top form wormerHMDB
TresadermHMDB
TriasoxHMDB
TubazoleHMDB
Chemical FormulaC10H7N3S
Average Molecular Weight201.248
Monoisotopic Molecular Weight201.036067929
IUPAC Name2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
Traditional Nametesto
CAS Registry Number148-79-8
SMILES
N1C2=CC=CC=C2N=C1C1=CSC=N1
InChI Identifier
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)
InChI KeyInChIKey=WJCNZQLZVWNLKY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassNot Available
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Benzenoid
  • Heteroaromatic compound
  • Thiazole
  • Imidazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
  • Food
Biofunction
  • Ametic
  • Analgesic
  • Anthelmintics
  • Anti-mycotic
  • Antinematodal Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.38e-01 g/LNot Available
LogP2.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
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 Area41.57 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity64.91 m3·mol-1ChemAxon
Polarizability21.02 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
MSMass Spectrum (Electron Ionization)splash10-0uk9-6960000000-9a4ba4c366b41681668eView in MoNA
1D NMR13C NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00730
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00730
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-5 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00730
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000906
KNApSAcK IDNot Available
Chemspider ID5237
KEGG Compound IDC07131
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThiabendazole
NuGOwiki LinkHMDB14868
Metagene LinkHMDB14868
METLIN IDNot Available
PubChem Compound5430
PDB IDTMG
ChEBI ID45979
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Gomaa AA: The effect of thiabendazole on pain threshold. Acta Pharmacol Toxicol (Copenh). 1985 Jul;57(1):18-22. [4050451 ]
  2. Miller GR, Rebell G, Magoon RC, Kulvin SM, Forster RK: Intravitreal antimycotic therapy and the cure of mycotic endophthalmitis caused by a Paecilomyces lilacinus contaminated pseudophakos. Ophthalmic Surg. 1978 Dec;9(6):54-63. [311456 ]
  3. Schneider D, Gannon R, Sweeney K, Shore E: Theophylline and antiparasitic drug interactions. A case report and study of the influence of thiabendazole and mebendazole on theophylline pharmacokinetics in adults. Chest. 1990 Jan;97(1):84-7. [2295264 ]
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Enzymes

General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
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. [19934256 ]
General function:
Involved in monooxygenase 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 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. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
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. [19754423 ]
  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. [19934256 ]