Human Metabolome Database Version 3.5

Showing metabocard for Albendazole (HMDB14659)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-02-08 17:32:02 -0700
HMDB ID HMDB14659
Secondary Accession Numbers None
Metabolite Identification
Common Name Albendazole
Description Albendazole is only found in individuals that have used or taken this drug. It is a benzimidazole broad-spectrum anthelmintic structurally related to mebendazole that is effective against many diseases. (From Martindale, The Extra Pharmacopoeia, 30th ed, p38)Albendazole 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 C12H15N3O2S
Average Molecular Weight 265.331
Monoisotopic Molecular Weight 265.088497429
IUPAC Name methyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
Traditional IUPAC Name albendazole
CAS Registry Number 54965-21-8
SMILES CCCSC1=CC2=C(C=C1)N=C(NC(=O)OC)N2
InChI Identifier InChI=1S/C12H15N3O2S/c1-3-6-18-8-4-5-9-10(7-8)14-11(13-9)15-12(16)17-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
InChI Key HXHWSAZORRCQMX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Benzimidazoles
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • a small molecule(Cyc)
  • benzimidazoles(ChEBI)
  • carbamate ester(ChEBI)
Substituents
  • Aminoimidazole
  • Carbamic Acid Ester (Urethane)
  • Imidazole
  • Thioether
Direct Parent Benzimidazoles
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Anthelmintics
  • Anticestodal Agents
  • Antiprotozoal Agents
  • Tubulin Modulators
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 209 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 2.28e-02 g/L Not Available
LogP 2.7 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.023 g/L ALOGPS
LogP 3.22 ALOGPS
LogP 3.2 ChemAxon
LogS -4.07 ALOGPS
pKa (strongest acidic) 9.51 ChemAxon
pKa (strongest basic) 4.27 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 67.01 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 73.01 ChemAxon
Polarizability 29.3 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • 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 DB00518
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00518
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00518 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 1998 Link_out
KEGG Compound ID C01779 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Albendazole Link_out
NuGOwiki Link HMDB14659 Link_out
Metagene Link HMDB14659 Link_out
METLIN ID Not Available
PubChem Compound 2082 Link_out
PDB ID Not Available
ChEBI ID 16664 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. Pubmed: 8228321 Link_out
  2. Oxberry ME, Reynoldson JA, Thompson RC: The binding and distribution of albendazole and its principal metabolites in Giardia duodenalis. J Vet Pharmacol Ther. 2000 Jun;23(3):113-20. Pubmed: 11110097 Link_out
  3. Ramirez T, Benitez-Bribiesca L, Ostrosky-Wegman P, Herrera LA: In vitro effects of albendazole and its metabolites on the cell proliferation kinetics and micronuclei frequency of stimulated human lymphocytes. Arch Med Res. 2001 Mar-Apr;32(2):119-22. Pubmed: 11343808 Link_out
  4. Molina AJ, Merino G, Prieto JG, Real R, Mendoza G, Alvarez AI: Absorption and metabolism of albendazole after intestinal ischemia/reperfusion. Eur J Pharm Sci. 2007 May;31(1):16-24. Epub 2007 Feb 6. Pubmed: 17350811 Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions:
Albendazole + NADPH + Oxygen unknown albendazole S-oxide + NADP + Water details
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: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 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