Human Metabolome Database Version 3.5

Showing metabocard for Thiabendazole (HMDB14868)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-05-29 13:49:11 -0600
HMDB ID HMDB14868
Secondary Accession Numbers
  • HMDB29712
Metabolite Identification
Common Name Thiabendazole
Description Thiabendazole 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 Link_out, 311456 Link_out, 2295264 Link_out). 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C10H7N3S
Average Molecular Weight 201.248
Monoisotopic Molecular Weight 201.036067929
IUPAC Name 2-(1,3-thiazol-4-yl)-1H-1,3-benzodiazole
Traditional IUPAC Name thiabendazole
CAS Registry Number 148-79-8
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 Key WJCNZQLZVWNLKY-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Benzimidazoles
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Thiazole fungicides(KEGG)
  • a small molecule(Cyc)
  • benzimidazoles(ChEBI)
Substituents
  • Imidazole
  • Thiazole
Direct Parent Benzimidazoles
Ontology
Status Expected and Not Quantified
Origin
  • Drug
  • Endogenous
  • Food
Biofunction
  • Ametic
  • Analgesic
  • Anthelmintics
  • Anti-mycotic
  • Antinematodal Agents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 300 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.38e-01 g/L Not Available
LogP 2.2 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.14 g/L ALOGPS
LogP 2.47 ALOGPS
LogP 2.33 ChemAxon
LogS -3.16 ALOGPS
pKa (strongest acidic) 10.28 ChemAxon
pKa (strongest basic) 4.08 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 41.57 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 64.91 ChemAxon
Polarizability 21.02 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00730
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00730
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00730 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB000906
KNApSAcK ID Not Available
Chemspider ID 5237 Link_out
KEGG Compound ID C07131 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Thiabendazole Link_out
NuGOwiki Link HMDB14868 Link_out
Metagene Link HMDB14868 Link_out
METLIN ID Not Available
PubChem Compound 5430 Link_out
PDB ID TMG Link_out
ChEBI ID 45979 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  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 Link_out
  4. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.

Enzymes
Name: Cytochrome P450 1A1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: P04798 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA