Mebendazole

Basic Info

Common NameMebendazole(F06054)
2D Structure
FRCD IDF06054
CAS Number31431-39-7
PubChem CID4030
FormulaC16H13N3O3
IUPAC Name

methyl N-(6-benzoyl-1H-benzimidazol-2-yl)carbamate

InChI Key

OPXLLQIJSORQAM-UHFFFAOYSA-N

InChI

InChI=1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21)

Canonical SMILES

COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3

Isomeric SMILES

COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3

Synonyms
        
            Mebenvet
        
            mebendazole
        
            31431-39-7
        
            Vermox
        
            Telmin
        
            Pantelmin
        
            Vermirax
        
            Mebenoazole
        
            Ovitelmin
        
            Bantenol
Classifies
                

                  
                    Predicted: Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzophenones
Intermediate Tree NodesNot available
Direct ParentBenzophenones
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents2-benzimidazolylcarbamic acid ester - Benzophenone - Aryl-phenylketone - Benzimidazole - Benzoyl - Aryl ketone - Azole - Imidazole - Heteroaromatic compound - Carbamic acid ester - Ketone - Carbonic acid derivative - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organopnictogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Properties

Property NameProperty Value
Molecular Weight295.298
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity423
Monoisotopic Mass295.096
Exact Mass295.096
XLogP2.8
Formal Charge0
Heavy Atom Count22
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9261
Human Intestinal AbsorptionHIA+0.9932
Caco-2 PermeabilityCaco2+0.7261
P-glycoprotein SubstrateNon-substrate0.6073
P-glycoprotein InhibitorInhibitor0.5844
Inhibitor0.7534
Renal Organic Cation TransporterNon-inhibitor0.8464
Distribution
Subcellular localizationMitochondria0.7218
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7490
CYP450 2D6 SubstrateNon-substrate0.9116
CYP450 3A4 SubstrateNon-substrate0.6532
CYP450 1A2 InhibitorInhibitor0.9107
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8308
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6779
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9515
Non-inhibitor0.8028
AMES ToxicityAMES toxic0.7212
CarcinogensNon-carcinogens0.9102
Fish ToxicityHigh FHMT0.9300
Tetrahymena Pyriformis ToxicityHigh TPT0.9481
Honey Bee ToxicityLow HBT0.6462
BiodegradationNot ready biodegradable0.9940
Acute Oral ToxicityIII0.7825
Carcinogenicity (Three-class)Non-required0.4713
Model Value Unit
Absorption
Aqueous solubility-3.8171LogS
Caco-2 Permeability1.0985LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5855LD50, mol/kg
Fish Toxicity1.3713pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5203pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HoneyJapan0.02ppm
Other Aquatic AnimalJapan0.02ppm
CrustaceansJapan0.02ppm
Shelled MolluscasJapan0.02ppm
Other FishJapan0.02ppm
PerciformesJapan0.02ppm
AnguilliformesJapan0.02ppm
SalmoniformesJapan0.02ppm
Other Poultry,EggsJapan0.02ppm
Chicken,EggsJapan0.02ppm
Other Poultry Animals,Edible OffalJapan0.02ppm
Chicken,Edible OffalJapan0.02ppm
Other Poultry Animals,KidneyJapan0.02ppm
Chicken,KidneyJapan0.02ppm
Other Poultry Animals,LiverJapan0.02ppm
Chicken,LiverJapan0.02ppm
Other Poultry Animals,FatJapan0.02ppm
Chicken,FatJapan0.02ppm
Other Poultry Animals,MuscleJapan0.02ppm
Chicken,MuscleJapan0.02ppm

References

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Chitosan from shrimp shells: A renewable sorbent applied to the clean-up step of the QuEChERS method in order to determine multi-residues of veterinary drugs indifferent types of milk.Food Chem2018 Feb 128946249
A Liquid Chromatography - Tandem Mass Spectrometry Approach for theIdentification of Mebendazole Residue in Pork, Chicken, and Horse.PLoS One2017 Jan 1328085912
Outbreak of trichinellosis due to wild boar meat and evaluation of theeffectiveness of post exposure prophylaxis, Germany, 2013.Clin Infect Dis2015 Jun 1525770171
Antiparasitic efficacy of a novel plant-based functional food using an Ascarissuum model in pigs.Acta Trop2014 Nov24979686
Development of high performance liquid chromatography-ultraviolet detectionmethod for screening mebendazole, clorsulon, diaveridine, and tolfenamic acid in animal-based food samples.Drug Test Anal2014 Mar23576386
Analysis of veterinary drug residues in cheese by ultra-high-performance LCcoupled to triple quadrupole MS/MS.J Sep Sci2013 Apr23576365
Development and validation of a multiclass method for the determination ofveterinary drug residues in chicken by ultra high performance liquidchromatography-tandem mass spectrometry.Talanta2012 Jan 3022284481
Stability during cooking of anthelmintic veterinary drug residues in beef.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Feb21240825
Development of a liquid chromatography-tandem mass spectrometry with pressurized liquid extraction method for the determination of benzimidazole residues inedible tissues.J Chromatogr B Analyt Technol Biomed Life Sci2011 Jun 121543271
Development of a high-performance liquid chromatography method to monitor theresidues of benzimidazoles in bovine milk.J Chromatogr B Analyt Technol Biomed Life Sci2010 Oct 1520863770
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A large-scale outbreak of trichinellosis caused by Trichinella britovi in Turkey.Zoonoses Public Health2009 Mar18705658
Treatment response to iron and folic acid alone is the same as with multivitaminsand/or anthelminthics in severely anemic 6- to 24-month-old children.J Nutr2009 Aug19535425
The effect of iron fortification and de-worming on anaemia and iron status ofVietnamese schoolchildren.Br J Nutr2007 May17381970
Benzimidazole drugs and modulation of biotransformation enzymes.Res Vet Sci2004 Apr14672851
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Multiresidue method for isolation and liquid chromatographic determination ofseven benzimidazole anthelmintics in milk.J Assoc Off Anal Chem1989 Sep-Oct2808233
A field evaluation of benzimidazole and nonbenzimidazole drugs in a herd of dairygoats.J Vet Intern Med1988 Jul-Sep3225804
Toxicological significance of covalently-bound residues.Food Addit Contam1984 Apr-Jun6536527