ContaminantDB: Fenbendazole

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:28:12 UTC

Update Date

2016-11-09 01:15:37 UTC

Accession Number

CHEM017571

Identification

Common Name

Fenbendazole

Class

Small Molecule

Description

A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted at positons 2 and 5 by (methoxycarbonyl)amino and phenylsulfanediyl groups, respectively. A broad-spectrum anthelmintic, it is used, particularly in veterinary medicine, for the treatment of nematodal infections.

Contaminant Sources

FooDB Chemicals
STOFF IDENT Compounds
Suspected Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-(Methoxycarbonylamino)-5-(phenylthio)benzimidazole	ChEBI
5-(Phenylthio)-2-benzimidazolecarbamic acid methyl ester	ChEBI
[5-(Phenylthio)-1H-benzimidazol-2-yl]carbamic acid methyl ester	ChEBI
Fenbendazol	ChEBI
Fenbendazolum	ChEBI
Hoe 881V	ChEBI
Methyl 5-(phenylthio)-2-benzimidazolecarbamate	ChEBI
Methyl [5-(phenylthio)-1H-benzimidazol-2-yl]carbamate	ChEBI
Panacur	ChEBI
Safe-quard	ChEBI
5-(Phenylthio)-2-benzimidazolecarbamate methyl ester	Generator
[5-(Phenylthio)-1H-benzimidazol-2-yl]carbamate methyl ester	Generator
Methyl 5-(phenylthio)-2-benzimidazolecarbamic acid	Generator
Methyl [5-(phenylthio)-1H-benzimidazol-2-yl]carbamic acid	Generator
2-Benzimidazolecarbamic acid, 5-(phenylthio)-, methyl ester	HMDB
Axilur	HMDB
Hoe 881	HMDB
Methyl (5-(phenylthio)-1H-benzimidazol-2-yl)carbamate	HMDB
Methyl 5-phenylthio-1H-benzimidazol-2-ylcarbamate	HMDB
Methyl [5-(phenylsulfanyl)-1H-benzimidazol-2-yl]carbamate	HMDB
Pancacur	HMDB
Phenbendasol	HMDB
Safe-guard	HMDB
Worm-a-rest	HMDB

Chemical Formula

C₁₅H₁₃N₃O₂S

Average Molecular Mass

299.348 g/mol

Monoisotopic Mass

299.073 g/mol

CAS Registry Number

43210-67-9

IUPAC Name

methyl N-[5-(phenylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate

Traditional Name

fenbendazole

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 Key

HDDSHPAODJUKPD-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

2-benzimidazolylcarbamic acid esters

Direct Parent

2-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

carbamate ester (CHEBI:77092 )
organic sulfide (CHEBI:77092 )
benzimidazoles (CHEBI:77092 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0061 g/L	ALOGPS
logP	3.33	ALOGPS
logP	3.99	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	4.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.01 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	83.61 m³·mol⁻¹	ChemAxon
Polarizability	31.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-1590000000-b1bdde740346b5e86169	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-c52f281023614ea62183	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0gb9-0095000000-aaa3ee589638ab95694b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0190000000-542ec3d7c28deadb2a86	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0aor-0950000000-ca845f292ef10ba06084	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-1a2be36ab88deab8ea4b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-74437145eda13588d093	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-014i-0091000000-372a453c1125eba23231	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-066r-0790000000-d29f6f0177872af1decf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-772531394a7b47426d88	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a59-0900000000-14444c086a0cdeba7497	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-066r-2950000000-c7869e27c483ff82b599	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-0900000000-399f6be99867d442c079	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a59-0900000000-5907f0139e02ca29f43a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-772531394a7b47426d88	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-c52f281023614ea62183	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-0095000000-aaa3ee589638ab95694b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-0950000000-9c6037ec83f1156a6e89	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0190000000-542ec3d7c28deadb2a86	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0091000000-372a453c1125eba23231	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0269000000-1dbacf97c14ccb6e6d2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-0191000000-073f08323851b13a48c5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-2920000000-260a80378a37148914a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-066s-2090000000-eb8b842b3c805178f94e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2290000000-388e3fb832b0ad04f98d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-1930000000-f2170079121987663840	Spectrum