Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2013-05-29 19:49:11 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
  1. 1yvm
  2. 2-(1,3-Thiazol-4-yl)-1H-benzimidazole
  3. 2-(1,3-Thiazol-4-yl)benzimidazole
  4. 2-(4'-Thiazolyl)benzimidazole
  5. 2-(4-Thiazolyl)-1H-Benzimidazole
  6. 2-(4-Thiazolyl)-Benzimidazole
  7. 2-(4-Thiazolyl)benzimidazole
  8. 2-(Thiazol-4-yl)benzimidazole
  9. 2-Thiazol-4-yl-1H-benzoimidazole
  10. 2-Thiazole-4-ylbenzimidazole
  11. 2-[4-Thiazoly]benzimidazole
  12. 4-(2-benzimidazolyl)thiazole
  13. 5-(4-Thiazolyl)benzimidazole
  14. Apl-luster
  15. Arbotect
  16. Biogard
  17. Bioguard
  18. Bovizole
  19. Captan t
  20. Chemviron TK 100
  21. Cropasal
  22. Drawipas
  23. E-z-Ex
  24. Eprofil
  25. Equivet TZ
  26. Equizole
  27. Equizole a
  28. Helmindrax octelmin
  29. Hokustar HP
  30. Hymush
  31. Lombristop
  32. Mertec
  33. Mertect
  34. Mertect 160
  35. Mertect 340f
  36. Mertect LSP
  37. Metasol tk 10
  38. Metasol TK 100
  39. Metasol TK-100
  40. Mintesol
  41. Mintezol
  42. Mintezol (TN)
  43. Mintezole
  44. Minzolum
  45. MK 360
  46. Mycozol
  47. Nemacin
  48. Nemapan
  49. Omnizole
  50. Ormogal
  51. Pitrizet
  52. Polival
  53. RPH
  54. Sanaizol 100
  55. Sistesan
  56. Storite
  57. Syntol M100
  58. TBDZ
  59. TBZ
  60. TBZ 6
  61. TBZ 60W
  62. Tebuzate
  63. Tecto
  64. Tecto 10P
  65. Tecto 40F
  66. Tecto 60
  67. Tecto b
  68. Tecto RPH
  69. Testo
  70. Thiaben
  71. Thiabendazol
  72. Thiabendazole (usp)
  73. Thiabendazole [bsi:iso]
  74. Thiabendazole [usan:ban]
  75. Thiabendazole(usan)
  76. Thiabendazole, BAN, BSI, ISO, JMAF, USAN
  77. Thiabendazolum
  78. Thiabendole
  79. Thiabenzazole
  80. Thiabenzole
  81. Thibendole
  82. Thibenzol
  83. Thibenzole
  84. Thibenzole 200
  85. Thibenzole att
  86. Thiprazole
  87. Tiabenda
  88. Tiabendazol
  89. Tiabendazole
  90. Tiabendazole (jan/inn)
  91. Tiabendazole, INN
  92. Tiabendazolum
  93. Tibimix 20
  94. TMG
  95. Tobaz
  96. Top form wormer
  97. Tresaderm
  98. Triasox
  99. Tubazole
Chemical FormulaC10H7N3S
Average Molecular Weight201.248
Monoisotopic Molecular Weight201.036067929
IUPAC Name2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
Traditional IUPAC Namethiabendazole
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 KeyWJCNZQLZVWNLKY-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassBenzimidazoles
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Thiazole fungicides(KEGG)
  • a small molecule(Cyc)
  • benzimidazoles(ChEBI)
Substituents
  • Imidazole
  • Thiazole
Direct ParentBenzimidazoles
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
  • Endogenous
  • 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 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
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00730
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00730
  • Not Applicable
Abnormal Concentrations
Not Available
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. Pubmed: 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. Pubmed: 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. Pubmed: 2295264
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Enzymes

Gene Name:
CYP1A1
Uniprot ID:
P04798
Gene Name:
CYP1A2
Uniprot ID:
P05177