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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:22 UTC
Update Date2022-03-07 02:52:16 UTC
HMDB IDHMDB0029745
Secondary Accession Numbers
  • HMDB29745
Metabolite Identification
Common NameFenbendazole
DescriptionVeterinary 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
Structure
Data?1582753458
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 Weight299.348
Monoisotopic Molecular Weight299.072847365
IUPAC Namemethyl N-[5-(phenylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
Traditional Namefenbendazole
CAS Registry Number43210-67-9
SMILES
COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2
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)
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point233 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available170.835http://allccs.zhulab.cn/database/detail?ID=AllCCS00000954
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.07331661259
DarkChem[M-H]-171.74631661259
DeepCCS[M+H]+169.32830932474
DeepCCS[M-H]-166.9730932474
DeepCCS[M-2H]-199.85730932474
DeepCCS[M+Na]+175.42230932474
AllCCS[M+H]+167.032859911
AllCCS[M+H-H2O]+163.732859911
AllCCS[M+NH4]+170.032859911
AllCCS[M+Na]+170.932859911
AllCCS[M-H]-167.032859911
AllCCS[M+Na-2H]-166.032859911
AllCCS[M+HCOO]-164.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FenbendazoleCOC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C23774.7Standard polar33892256
FenbendazoleCOC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C22523.5Standard non polar33892256
FenbendazoleCOC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C23067.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fenbendazole,1TMS,isomer #1COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2[NH]1)[Si](C)(C)C2747.9Semi standard non polar33892256
Fenbendazole,1TMS,isomer #1COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2[NH]1)[Si](C)(C)C2630.0Standard non polar33892256
Fenbendazole,1TMS,isomer #2COC(=O)NC1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C2795.1Semi standard non polar33892256
Fenbendazole,1TMS,isomer #2COC(=O)NC1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C2542.7Standard non polar33892256
Fenbendazole,2TMS,isomer #1COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C)[Si](C)(C)C2773.1Semi standard non polar33892256
Fenbendazole,2TMS,isomer #1COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C)[Si](C)(C)C2640.0Standard non polar33892256
Fenbendazole,1TBDMS,isomer #1COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2[NH]1)[Si](C)(C)C(C)(C)C2930.3Semi standard non polar33892256
Fenbendazole,1TBDMS,isomer #1COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2[NH]1)[Si](C)(C)C(C)(C)C2835.0Standard non polar33892256
Fenbendazole,1TBDMS,isomer #2COC(=O)NC1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C(C)(C)C2994.4Semi standard non polar33892256
Fenbendazole,1TBDMS,isomer #2COC(=O)NC1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C(C)(C)C2773.9Standard non polar33892256
Fenbendazole,2TBDMS,isomer #1COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3106.3Semi standard non polar33892256
Fenbendazole,2TBDMS,isomer #1COC(=O)N(C1=NC2=CC(SC3=CC=CC=C3)=CC=C2N1[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3032.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fenbendazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-1590000000-b1bdde740346b5e861692017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenbendazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-0udi-0009000000-c52f281023614ea621832017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-0gb9-0095000000-aaa3ee589638ab95694b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-014i-0190000000-542ec3d7c28deadb2a862017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-0aor-0950000000-ca845f292ef10ba060842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0900000000-1a2be36ab88deab8ea4b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-0udi-0009000000-74437145eda13588d0932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-014i-0091000000-372a453c1125eba232312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-066r-0790000000-d29f6f0177872af1decf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0900000000-772531394a7b47426d882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole LC-ESI-QTOF , positive-QTOFsplash10-0a59-0900000000-14444c086a0cdeba74972017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole , positive-QTOFsplash10-066r-2950000000-c7869e27c483ff82b5992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole 50V, Positive-QTOFsplash10-0a4i-0900000000-399f6be99867d442c0792021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole 50V, Positive-QTOFsplash10-0a59-0900000000-5907f0139e02ca29f43a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole 40V, Positive-QTOFsplash10-0a4i-0900000000-772531394a7b47426d882021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole 10V, Positive-QTOFsplash10-0udi-0009000000-c52f281023614ea621832021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole 20V, Positive-QTOFsplash10-0gb9-0095000000-aaa3ee589638ab95694b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole 40V, Positive-QTOFsplash10-0aor-0950000000-9c6037ec83f1156a6e892021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole 30V, Positive-QTOFsplash10-014i-0190000000-542ec3d7c28deadb2a862021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Fenbendazole 20V, Positive-QTOFsplash10-014i-0091000000-372a453c1125eba232312021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenbendazole 10V, Positive-QTOFsplash10-0udi-0269000000-1dbacf97c14ccb6e6d2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenbendazole 20V, Positive-QTOFsplash10-00kf-0191000000-073f08323851b13a48c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenbendazole 40V, Positive-QTOFsplash10-0a4i-2920000000-260a80378a37148914a62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenbendazole 10V, Negative-QTOFsplash10-066s-2090000000-eb8b842b3c805178f94e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenbendazole 20V, Negative-QTOFsplash10-014i-2290000000-388e3fb832b0ad04f98d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenbendazole 40V, Negative-QTOFsplash10-0a4i-1930000000-f21700791219876638402016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11410
Phenol Explorer Compound IDNot Available
FooDB IDFDB000946
KNApSAcK IDNot Available
Chemspider ID3217
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenbendazole
METLIN IDNot Available
PubChem Compound3334
PDB IDNot Available
ChEBI ID77092
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .