NAV

Fenbendazole

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Fenbendazole
DrugBank Accession Number
DB11410
Background

Fenbendazole is a benzimidazole that presents a wide spectrum anthelmintic effect. It is used against a number of gastrointestinal parasites including giardia, roundworms, hookworms, whipworms, the Taenia genus of tapeworms, pinworms, aelurostrongylus, paragonimiasis, strongyles, and Strongyloides. Fenbendazole is approved to be administered under veterinary to sheep, cattle, horses, fish, dogs, cats, rabbits and seals.

Type
Small Molecule
Groups
Vet approved
Structure
3D
Similar Structures
Weight
Average: 299.348
Monoisotopic: 299.072847365
Chemical Formula
C15H13N3O2S
Synonyms
  • [5-(phenylthio)-1H-benzimidazol-2-yl]carbamic acid methyl ester
  • 2-(methoxycarbonylamino)-5-(phenylthio)benzimidazole
  • 5-(phenylthio)-2-benzimidazolecarbamic acid methyl ester
  • Fenbendazol
  • Fenbendazole
  • Fenbendazolum
  • Methyl [5-(phenylthio)-1H-benzimidazol-2-yl]carbamate
  • methyl 5-(phenylthio)-2-benzimidazolecarbamate
External IDs
  • HOE 881V
  • LSM-3134
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
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MethotrexateThe excretion of Methotrexate can be decreased when combined with Fenbendazole.
Food Interactions
Not Available

Products

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International/Other Brands
Panacur / Safe-quard

Categories

ATC Codes
P02CA06 — Fenbendazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
2-benzimidazolylcarbamic acid esters
Direct Parent
2-benzimidazolylcarbamic acid esters
Alternative Parents
Diarylthioethers / Thiophenol ethers / Benzene and substituted derivatives / Imidazoles / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Sulfenyl compounds / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
2-benzimidazolylcarbamic acid ester / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azole / Benzenoid / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Diarylthioether
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carbamate ester, organic sulfide, benzimidazoles (CHEBI:77092)
Affected organisms
Not Available

Chemical Identifiers

UNII
621BVT9M36
CAS number
43210-67-9
InChI Key
HDDSHPAODJUKPD-UHFFFAOYSA-N
InChI
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)
IUPAC Name
methyl N-[5-(phenylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
SMILES
COC(=O)NC1=NC2=C(N1)C=CC(SC1=CC=CC=C1)=C2

References

General References
  1. Duwel D, Hajdu P, Damm D: [Pharmacokinetics of fenbendazole. 2]. Berl Munch Tierarztl Wochenschr. 1975 Nov 1;88(21):418-9. [Article]
  2. Duwel D, Hajdu P, Damm D: [Pharmacokinetics of fenbendazole]. Berl Munch Tierarztl Wochenschr. 1975 Apr 1;88(7):131-4. [Article]
  3. Marriner SE, Bogan JA: Pharmacokinetics of fenbendazole in sheep. Am J Vet Res. 1981 Jul;42(7):1146-8. [Article]
  4. Paul JW, Muser RK: Use of fenbendazole in horses. Mod Vet Pract. 1981 Jul;62(7):557-61. [Article]
  5. McKellar QA, Harrison P, Galbraith EA, Inglis H: Pharmacokinetics of fenbendazole in dogs. J Vet Pharmacol Ther. 1990 Dec;13(4):386-92. [Article]
  6. Hayes RH, Oehme FW, Leipold H: Safety of fenbendazole in swine. Am J Vet Res. 1983 Jun;44(6):1112-6. [Article]
  7. Kalita CC, Gautam OP, Banerjee DP: Fenbendazole against haemonchosis in sheep. Indian Vet J. 1978 Aug;55(8):660-2. [Article]
  8. Short CR, Barker SA, Hsieh LC, Ou SP, McDowell T, Davis LE, Neff-Davis CA, Koritz G, Bevill RF, Munsiff IJ: Disposition of fenbendazole in cattle. Am J Vet Res. 1987 Jun;48(6):958-61. [Article]
  9. Bhandari B, Singhi A: Fenbendazole (Hoe 881) in enterobiasis. Trans R Soc Trop Med Hyg. 1980;74(5):691. [Article]
  10. Malan FS, Reinecke RK, Scialdo RC: Anthelmintic efficacy fenbendazole paste in equines. J S Afr Vet Assoc. 1981 Jun;52(2):127-30. [Article]
  11. Harcourt-Brown FM, Holloway HK: Encephalitozoon cuniculi in pet rabbits. Vet Rec. 2003 Apr 5;152(14):427-31. [Article]
  12. Gardner CR, Mishin V, Laskin JD, Laskin DL: Exacerbation of acetaminophen hepatotoxicity by the anthelmentic drug fenbendazole. Toxicol Sci. 2012 Feb;125(2):607-12. doi: 10.1093/toxsci/kfr301. Epub 2011 Nov 1. [Article]
  13. Forwood JM, Harris JO, Deveney MR: Efficacy of bath and orally administered praziquantel and fenbendazole against Lepidotrema bidyana Murray, a monogenean parasite of silver perch, Bidyanus bidyanus (Mitchell). J Fish Dis. 2013 Nov;36(11):939-47. doi: 10.1111/jfd.12089. Epub 2013 Mar 11. [Article]
  14. Wu Z, Lee D, Joo J, Shin JH, Kang W, Oh S, Lee do Y, Lee SJ, Yea SS, Lee HS, Lee T, Liu KH: CYP2J2 and CYP2C19 are the major enzymes responsible for metabolism of albendazole and fenbendazole in human liver microsomes and recombinant P450 assay systems. Antimicrob Agents Chemother. 2013 Nov;57(11):5448-56. doi: 10.1128/AAC.00843-13. Epub 2013 Aug 19. [Article]
  15. Yu CG, Singh R, Crowdus C, Raza K, Kincer J, Geddes JW: Fenbendazole improves pathological and functional recovery following traumatic spinal cord injury. Neuroscience. 2014 Jan 3;256:163-9. doi: 10.1016/j.neuroscience.2013.10.039. Epub 2013 Oct 30. [Article]
  16. Yannai, Shmuel (2003). Dictionary of Food Compounds with : Additives, Flavors, and Ingredients. CRC Press LLC. [ISBN:1584884169]
Human Metabolome Database
HMDB0029745
KEGG Drug
D04140
ChemSpider
3217
BindingDB
31047
RxNav
4325
ChEBI
77092
ChEMBL
CHEMBL37161
ZINC
ZINC000000402911
Wikipedia
Fenbendazole

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00609 mg/mLALOGPS
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 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity83.61 m3·mol-1Chemaxon
Polarizability31.76 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03dl-1590000000-b1bdde740346b5e86169
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-c52f281023614ea62183
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0gb9-0095000000-aaa3ee589638ab95694b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0190000000-542ec3d7c28deadb2a86
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0aor-0950000000-ca845f292ef10ba06084
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-1a2be36ab88deab8ea4b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0009000000-74437145eda13588d093
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0091000000-372a453c1125eba23231
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-066r-0790000000-d29f6f0177872af1decf
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0900000000-772531394a7b47426d88
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a59-0900000000-14444c086a0cdeba7497
MS/MS Spectrum - , positiveLC-MS/MSsplash10-066r-2950000000-c7869e27c483ff82b599
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0109000000-8b3a050fb1930c97e4d4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-310834f2c66b7c52a744
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0091000000-d805dd248c99b89754a7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-a2655baa9520d3d84f10
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0w93-0590000000-ad0fa24b871b8d2f0aab
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053i-0930000000-d5b5eab27e763fc4b001
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-186.0460928
predicted
DarkChem Lite v0.1.0
[M-H]-185.6218928
predicted
DarkChem Lite v0.1.0
[M-H]-183.9791928
predicted
DarkChem Lite v0.1.0
[M-H]-166.97044
predicted
DeepCCS 1.0 (2019)
[M+H]+185.8461928
predicted
DarkChem Lite v0.1.0
[M+H]+185.7268928
predicted
DarkChem Lite v0.1.0
[M+H]+184.1863928
predicted
DarkChem Lite v0.1.0
[M+H]+169.32845
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.1345928
predicted
DarkChem Lite v0.1.0
[M+Na]+186.0372928
predicted
DarkChem Lite v0.1.0
[M+Na]+184.1442928
predicted
DarkChem Lite v0.1.0
[M+Na]+175.42159
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:29 / Updated at February 21, 2021 18:53