Showing metabocard for Albendazole (BMDB0109650)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2020-05-05 15:49:08 UTC
Update Date2020-05-05 18:38:56 UTC
BMDB IDBMDB0109650
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlbendazole
DescriptionAlbendazole, also known as albenza or SK and F62979, 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. Albendazole is a drug which is used for the treatment of parenchymal neurocysticercosis due to active lesions caused by larval forms of the pork tapeworm, taenia solium and for the treatment of cystic hydatid disease of the liver, lung, and peritoneum, caused by the larval form of the dog tapeworm, echinococcus granulosus. Albendazole is a strong basic compound (based on its pKa). Albendazole exists in all living organisms, ranging from bacteria to humans. In humans, albendazole is involved in tamoxifen metabolism pathway. Albendazole is a potentially toxic compound. Symptoms of overdose include elevated liver enzymes, headaches, hair loss, low levels of white blood cells (neutropenia), fever, and itching. Albendazole causes degenerative alterations in the tegument and intestinal cells of the worm by diminishing its energy production, ultimately leading to immobilization and death of the parasite. 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. Route of Elimination: Albendazole is rapidly converted in the liver to the primary metabolite, albendazole sulfoxide, which is further metabolized to albendazole sulfone and other primary oxidative metabolites that have been identified in human urine.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(5-(Propylthio)-1H-benzimidazol-2-yl)carbamic acid methyl esterChEBI
5-(Propylthio)-2-carbomethoxyaminobenzimidazoleChEBI
AlbenzaChEBI
EskazoleChEBI
O-Methyl N-(5-(propylthio)-2-benzimidazolyl)carbamateChEBI
ProftrilChEBI
ValbazenChEBI
ZentelChEBI
(5-(Propylthio)-1H-benzimidazol-2-yl)carbamate methyl esterGenerator
O-Methyl N-(5-(propylthio)-2-benzimidazolyl)carbamic acidGenerator
Albendazole armstrong brandHMDB
Albendazole diba brandHMDB
Albendazole pfizer brandHMDB
AlbendoralHMDB
Armstrong brand OF albendazoleHMDB
SK And F62979HMDB
Albendazole sanicoopa brandHMDB
Albendazole valdecasas brandHMDB
BendaparHMDB
DigezanolHMDB
EndoplusHMDB
Fustery brand OF albendazoleHMDB
Hormona brand OF albendazoleHMDB
Liferpal brand OF albendazoleHMDB
LurdexHMDB
Mediamix V disthelmHMDB
MetiazolHMDB
Monohydrochloride, albendazoleHMDB
SK And F-62979HMDB
Sanicoopa brand OF albendazoleHMDB
Albendazole fustery brandHMDB
GascopHMDB
Noé-socopharm brand OF albendazoleHMDB
Pfizer brand OF albendazoleHMDB
SmithKline beecham brand OF albendazoleHMDB
V Disthelm, mediamixHMDB
Albendazole hormona brandHMDB
Albendazole liferpal brandHMDB
Albendazole monohydrochlorideHMDB
Albendazole noé-socopharm brandHMDB
BilutacHMDB
Diba brand OF albendazoleHMDB
DisthelmHMDB
Disthelm, mediamix VHMDB
Noé socopharm brand OF albendazoleHMDB
SK And F 62979HMDB
Valdecasas brand OF albendazoleHMDB
AndazolMeSH
Chemical FormulaC12H15N3O2S
Average Molecular Weight265.331
Monoisotopic Molecular Weight265.088497429
IUPAC Namemethyl N-[6-(propylsulfanyl)-1H-1,3-benzodiazol-2-yl]carbamate
Traditional Namealbendazol
CAS Registry NumberNot Available
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
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub Class2-benzimidazolylcarbamic acid esters
Direct Parent2-benzimidazolylcarbamic acid esters
Alternative Parents
Substituents
  • 2-benzimidazolylcarbamic acid ester
  • Aryl thioether
  • Thiophenol ether
  • Alkylarylthioether
  • Benzenoid
  • Azole
  • Imidazole
  • Carbamic acid ester
  • Heteroaromatic compound
  • Carbonic acid derivative
  • Thioether
  • Azacycle
  • Sulfenyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 Area67.01 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.01 m³·mol⁻¹ChemAxon
Polarizability29.3 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0014659
DrugBank IDDB00518
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1998
KEGG Compound IDC01779
BioCyc IDALBENDAZOLE
BiGG IDNot Available
Wikipedia LinkAlbendazole
METLIN IDNot Available
PubChem Compound2082
PDB IDNot Available
ChEBI ID16664
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available