Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2013-02-09 00:32:02 UTC
HMDB IDHMDB14659
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlbendazole
DescriptionAlbendazole 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
SynonymsNot Available
Chemical FormulaC12H15N3O2S
Average Molecular Weight265.331
Monoisotopic Molecular Weight265.088497429
IUPAC Namemethyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
Traditional IUPAC Namealbendazole
CAS Registry Number54965-21-8
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 KeyHXHWSAZORRCQMX-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassBenzimidazoles
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • a small molecule(Cyc)
  • benzimidazoles(ChEBI)
  • carbamate ester(ChEBI)
Substituents
  • Aminoimidazole
  • Carbamic Acid Ester (Urethane)
  • Imidazole
  • Thioether
Direct ParentBenzimidazoles
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Anthelmintics
  • Anticestodal Agents
  • Antiprotozoal Agents
  • Tubulin Modulators
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point209 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.28e-02 g/LNot Available
LogP2.7Not Available
Predicted Properties
PropertyValueSource
water solubility0.023 g/LALOGPS
logP3.22ALOGPS
logP3.2ChemAxon
logS-4.1ALOGPS
pKa (strongest acidic)9.51ChemAxon
pKa (strongest basic)4.27ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count2ChemAxon
polar surface area67.01ChemAxon
rotatable bond count5ChemAxon
refractivity73.01ChemAxon
polarizability29.3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00518
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00518
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00518
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1998
KEGG Compound IDC01779
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlbendazole
NuGOwiki LinkHMDB14659
Metagene LinkHMDB14659
METLIN IDNot Available
PubChem Compound2082
PDB IDNot Available
ChEBI ID16664
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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
  2. Haque A, Hollister WS, Willcox A, Canning EU: The antimicrosporidial activity of albendazole. J Invertebr Pathol. 1993 Sep;62(2):171-7. Pubmed: 8228321
  3. 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
  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

Enzymes

Gene Name:
CYP3A4
Uniprot ID:
P08684
Reactions
Albendazole + NADPH + Oxygen unknown albendazole S-oxide + NADP + Waterdetails
Gene Name:
CYP1A1
Uniprot ID:
P04798
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
TUBB2C
Uniprot ID:
P68371
Gene Name:
TUBA1A
Uniprot ID:
Q71U36

Transporters

Gene Name:
ABCB1
Uniprot ID:
P08183