Fenbendazole (CED0005825)

Record Information
Version1.0
Creation Date2016-05-22 04:28:12 UTC
Update Date2026-08-19 09:33:19 UTC
Accession NumberCHEM017571
Identification
Common NameFenbendazole
ClassSmall Molecule
Description
Fenbendazole is an organic compound with the chemical formula C15H13N3O2S and an average molecular weight of 299.35 g/mol. Fenbendazole belongs to the 2-benzimidazolylcarbamic acid esters, a subclass of benzimidazoles within the organic compounds. Within the broader classification of chemical substances, it is categorized as an organoheterocyclic compound. The compound has been identified in or released from 29 recorded sources. In the realm of healthcare, pharmaceuticals, and veterinary products, it is used as an anthelmintic. Other recorded sources include food preservation within food, food processing, and cookware. It is also found in household items such as credit card holders, as well as household cleaning and consumer products, including pipe accessories, tobacco smoke filters, and non-electric simulated smoking devices. Within the building and construction sector, it is associated with floors, roofs, fencing, and tents or canopies. Additionally, it is linked to electrical and electronic equipment, including antennas, amplifiers, conductors or conductive bodies characterized by the conductive materials, discharge tubes with liquid pool cathodes, and discharge lamps, among 14 other sources. Recorded exposure routes for fenbendazole include oral and oropharyngeal pathways.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2-(Methoxycarbonylamino)-5-(phenylthio)benzimidazoleChEBI
5-(Phenylthio)-2-benzimidazolecarbamic acid methyl esterChEBI
[5-(Phenylthio)-1H-benzimidazol-2-yl]carbamic acid methyl esterChEBI
FenbendazolChEBI
FenbendazolumChEBI
Hoe 881VChEBI
Methyl 5-(phenylthio)-2-benzimidazolecarbamateChEBI
Methyl [5-(phenylthio)-1H-benzimidazol-2-yl]carbamateChEBI
PanacurChEBI
Safe-quardChEBI
5-(Phenylthio)-2-benzimidazolecarbamate methyl esterGenerator
[5-(Phenylthio)-1H-benzimidazol-2-yl]carbamate methyl esterGenerator
Methyl 5-(phenylthio)-2-benzimidazolecarbamic acidGenerator
Methyl [5-(phenylthio)-1H-benzimidazol-2-yl]carbamic acidGenerator
2-Benzimidazolecarbamic acid, 5-(phenylthio)-, methyl esterHMDB
AxilurHMDB
Hoe 881HMDB
Methyl (5-(phenylthio)-1H-benzimidazol-2-yl)carbamateHMDB
Methyl 5-phenylthio-1H-benzimidazol-2-ylcarbamateHMDB
Methyl [5-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamateHMDB
PancacurHMDB
PhenbendasolHMDB
Safe-guardHMDB
Worm-a-restHMDB
Chemical FormulaC15H13N3O2S
Average Molecular Mass299.348 g/mol
Monoisotopic Mass299.073 g/mol
CAS Registry Number43210-67-9
IUPAC Namemethyl N-[5-(phenylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
Traditional Namefenbendazole
SMILESCOC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2
InChI IdentifierInChI=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)
InChI KeyHDDSHPAODJUKPD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub Class2-benzimidazolylcarbamic acid esters
Direct Parent2-benzimidazolylcarbamic acid esters
Alternative Parents
Substituents
  • 2-benzimidazolylcarbamic acid ester
  • Diarylthioether
  • Aryl thioether
  • Thiophenol ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Carbamic acid ester
  • Carbonic acid derivative
  • Thioether
  • Azacycle
  • Sulfenyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0061 g/LALOGPS
logP3.33ALOGPS
logP3.99ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.59ChemAxon
pKa (Strongest Basic)4.06ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area67.01 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.61 m³·mol⁻¹ChemAxon
Polarizability31.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-03dl-1590000000-b1bdde740346b5e86169Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-c52f281023614ea62183Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gb9-0095000000-aaa3ee589638ab95694bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0190000000-542ec3d7c28deadb2a86Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-0950000000-ca845f292ef10ba06084Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-1a2be36ab88deab8ea4bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-74437145eda13588d093Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0091000000-372a453c1125eba23231Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066r-0790000000-d29f6f0177872af1decfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-772531394a7b47426d88Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a59-0900000000-14444c086a0cdeba7497Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066r-2950000000-c7869e27c483ff82b599Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-399f6be99867d442c079Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a59-0900000000-5907f0139e02ca29f43aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-772531394a7b47426d88Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-c52f281023614ea62183Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0gb9-0095000000-aaa3ee589638ab95694bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-0950000000-9c6037ec83f1156a6e89Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0190000000-542ec3d7c28deadb2a86Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0091000000-372a453c1125eba23231Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-066r-0790000000-d29f6f0177872af1decfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0009000000-74437145eda13588d093Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-7a4d3a65aef233181655Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a59-0900000000-14444c086a0cdeba7497Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0269000000-1dbacf97c14ccb6e6d2cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-0191000000-073f08323851b13a48c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-2920000000-260a80378a37148914a6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066s-2090000000-eb8b842b3c805178f94eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-2290000000-388e3fb832b0ad04f98dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1930000000-f2170079121987663840Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0029000000-70af035d607265739e0aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0091000000-2f97e775d6b06a7d62efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02dl-1790000000-477c4bc058fa9eff3e3dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-a78fa7d0727321ae905aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1090000000-7178ee19dbeedbfbc36eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-3940000000-136b564313a1e25f7958Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2198.0Log mg/kg[1200:3900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
386AnthelminticsHealthcare, pharmaceuticals & veterinary productsNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
499RoofsBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
515Discharge Tubes With Liquid Pool CathodesElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
533Sparking PlugsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
572Credit Card HoldersHousehold itemsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
590Lifeboat EquipmentMarine, shipping & aquacultureNot Available
591LifeboatsMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
621Chutes And SlidesRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
635ButtonsTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
649Pins ClothesTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
651Purses Money Bags WalletsTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
661UmbrellasTextiles, leather & furnishingsNot Available
663Sanitary EquipmentWastewater, sanitation & biosolidsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Methionine aminopeptidase structureClick to view 3D structureMethionine aminopeptidaseP0AE18Escherichia coli (strain K12)Predicted (SEA)0.155698
Mitogen-activated protein kinase 14 structureClick to view 3D structureMitogen-activated protein kinase 14Q16539HumansPredicted (SEA)92.1735
Tyrosine-protein kinase ABL1 structureClick to view 3D structureTyrosine-protein kinase ABL1P00519HumansPredicted (SEA)160.603
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)8.87481
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)360.909
Click to view 3D structureCasein kinase I isoform alphaP67827Bos taurusPredicted (SEA)1.71268
Proto-oncogene tyrosine-protein kinase Src structureClick to view 3D structureProto-oncogene tyrosine-protein kinase SrcP12931HumansPredicted (SEA)366.281
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)96.4552
Click to view 3D structureLuciferin 4-monooxygenaseP08659Photinus pyralisPredicted (SEA)25.0674
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.700643
Aurora kinase B structureClick to view 3D structureAurora kinase BQ96GD4HumansPredicted (SEA)718.626
Hepatocyte growth factor receptor structureClick to view 3D structureHepatocyte growth factor receptorP08581HumansPredicted (SEA)716.057
Photoreceptor-specific nuclear receptor structureClick to view 3D structurePhotoreceptor-specific nuclear receptorQ9Y5X4HumansPredicted (SEA)17.1268
Cyclin-dependent kinase 9 structureClick to view 3D structureCyclin-dependent kinase 9P50750HumansPredicted (SEA)411.044
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)868.797
Casein kinase I isoform epsilon structureClick to view 3D structureCasein kinase I isoform epsilonP49674HumansPredicted (SEA)173.604
Click to view 3D structureCalmodulin-domain protein kinase 1Q9BJF5Toxoplasma gondiiPredicted (SEA)29.8941
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)1649.94
Click to view 3D structureMetabotropic glutamate receptor 5Q3UVX5Mus musculusPredicted (SEA)1.32344
Click to view 3D structureCasein kinase I isoform deltaQ06486Rattus norvegicusPredicted (SEA)5.44945
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)776.079
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)1288.17
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)1151.23
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)378.425
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)236.35
Concentrations
Not Available
External Links
DrugBank IDDB11410
HMDB IDHMDB0029745
FooDB IDFDB000946
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFenbendazole
Chemspider ID3217
ChEBI ID77092
PubChem Compound ID3334
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22048645
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23488766
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23959307
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24183965
5. Harcourt-Brown FM, Holloway HK: Encephalitozoon cuniculi in pet rabbits. Vet Rec. 2003 Apr 5;152(14):427-31.
6. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.