Human Metabolome Database Version 3.5

Showing metabocard for Fenbendazole (HMDB29745)

Record Information
Version 3.5
Creation Date 2012-09-11 11:32:22 -0600
Update Date 2013-06-29 22:46:08 -0600
Secondary Accession Numbers None
Metabolite Identification
Common Name Fenbendazole
Description Veterinary anthelmintic. Fenbendazole is a fda approved for use in cattle, pigs and goats Fenbendazole (Hoechst brand names Panacur and Safe-Guard, Intervet Panacur and Panacur Rabbit) is a broad spectrum benzimidazole anthelmintic used against gastrointestinal parasites including roundworms, hookworms, whipworms, the taenia species of tapeworms, pinworms, aelurostrongylus, paragonimiasis, strongyles and strongyloides and can be administered to sheep, cattle, horses, fish, dogs, cats, rabbits and seals. Drug interactions may occur if using bromsalan flukicides (Dibromsalan, Tribromsalan). Abortions in cattle and death in sheep have been reported after using these medications together. (Plumb's Veterinary Drug Handbook, Fifth Edition. 2005) Fenbendazole has been shown to exhibit antibiotic function (PMID 12708591 Link_out). Fenbendazole 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
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Display: 2D Structure | 3D Structure
  1. 2-(Methoxycarbonylamino)-5-(phenylthio)benzimidazole
  2. 2-Benzimidazolecarbamic acid, 5-(phenylthio)-, methyl ester
  3. Axilur
  4. Fenbendazol
  5. Fenbendazole (usp/inn)
  6. Fenbendazole [usan:ban:inn]
  7. Fenbendazolum
  8. Hoe 881
  9. Methyl (5-(phenylthio)-1H-benzimidazol-2-yl)carbamate
  10. Methyl 5-(phenylthio)-2-benzimidazolecarbamate
  11. Methyl 5-phenylthio-1H-benzimidazol-2-ylcarbamate
  12. Methyl [5-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate
  13. Panacur
  14. Panacur (TN)
  15. Pancacur
  16. Phenbendasol
  17. Safe-Guard
  18. Worm-A-Rest
Chemical Formula C15H13N3O2S
Average Molecular Weight 299.348
Monoisotopic Molecular Weight 299.072847365
IUPAC Name methyl N-[5-(phenylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
Traditional IUPAC Name fenbendazole
CAS Registry Number 43210-67-9
InChI Identifier InChI=1S/C15H13N3O2S/c1-20-15(19)18-14-16-12-8-7-11(9-13(12)17-14)21-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Benzimidazoles
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Aminoimidazole
  • Carbamic Acid Ester (Urethane)
  • Imidazole
  • Thioether
Direct Parent Benzimidazoles
Status Expected and Not Quantified
  • Endogenous
  • Food
Biofunction Not Available
  • Nutrient
Cellular locations
  • Membrane
Physical Properties
State Not Available
Experimental Properties
Property Value Reference
Melting Point 233 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0061 g/L ALOGPS
LogP 3.33 ALOGPS
LogP 3.99 ChemAxon
LogS -4.69 ALOGPS
pKa (strongest acidic) 9.59 ChemAxon
pKa (strongest basic) 4.06 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 67.01 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 83.61 ChemAxon
Polarizability 31.76 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Not Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB000946
KNApSAcK ID Not Available
Chemspider ID 3217 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Fenbendazole Link_out
NuGOwiki Link HMDB29745 Link_out
Metagene Link HMDB29745 Link_out
METLIN ID Not Available
PubChem Compound 3334 Link_out
PDB ID Not Available
ChEBI ID 151961 Link_out
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Harcourt-Brown FM, Holloway HK: Encephalitozoon cuniculi in pet rabbits. Vet Rec. 2003 Apr 5;152(14):427-31. Pubmed: 12708591 Link_out
  2. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.