Human Metabolome Database Version 3.5

Showing metabocard for Mebendazole (HMDB14781)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-02-08 17:32:18 -0700
HMDB ID HMDB14781
Secondary Accession Numbers None
Metabolite Identification
Common Name Mebendazole
Description Mebendazole is only found in individuals that have used or taken this drug. It is a benzimidazole that acts by interfering with carbohydrate metabolism and inhibiting polymerization of microtubules. [PubChem]Mebendazole causes degenerative alterations in the tegument and intestinal cells of the worm by binding to the colchicine-sensitive site of tubulin, thus inhibiting its polymerization or assembly into microtubules. The loss of the cytoplasmic microtubules leads to impaired uptake of glucose by the larval and adult stages of the susceptible parasites, and depletes their glycogen stores. Degenerative changes in the endoplasmic reticulum, the mitochondria of the germinal layer, and the subsequent release of lysosomes result in decreased production of adenosine triphosphate (ATP), which is the energy required for the survival of the helminth. Due to diminished energy production, the parasite is immobilized and eventually dies.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C16H13N3O3
Average Molecular Weight 295.2927
Monoisotopic Molecular Weight 295.095691297
IUPAC Name methyl N-(6-benzoyl-1H-1,3-benzodiazol-2-yl)carbamate
Traditional IUPAC Name mebendazole
CAS Registry Number 31431-39-7
SMILES COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C1=CC=CC=C1
InChI Identifier 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)
InChI Key OPXLLQIJSORQAM-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Diphenylmethanes
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • benzimidazoles(ChEBI)
Substituents
  • Aminoimidazole
  • Benzimidazole
  • Benzoyl
  • Carbamic Acid Ester (Urethane)
  • Imidazole
  • Ketone
Direct Parent Diphenylmethanes
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Antinematodal Agents
  • Tubulin Modulators
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 288.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.87e-02 g/L Not Available
LogP 2.8 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.039 g/L ALOGPS
LogP 2.95 ALOGPS
LogP 3.26 ChemAxon
LogS -3.88 ALOGPS
pKa (strongest acidic) 8.44 ChemAxon
pKa (strongest basic) 3.93 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 84.08 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 81.5 ChemAxon
Polarizability 31.1 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00643
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00643
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00643 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 3890 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Mebendazole Link_out
NuGOwiki Link HMDB14781 Link_out
Metagene Link HMDB14781 Link_out
METLIN ID Not Available
PubChem Compound 4030 Link_out
PDB ID Not Available
ChEBI ID 6704 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Wikipedia Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: P04798 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Tubulin beta-2C chain
Reactions: Not Available
Gene Name: TUBB2C
Uniprot ID: P68371 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Tubulin alpha-1A chain
Reactions: Not Available
Gene Name: TUBA1A
Uniprot ID: Q71U36 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Multidrug resistance protein 1
Reactions: Not Available
Gene Name: ABCB1
Uniprot ID: P08183 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA