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Record Information
Version3.6
Creation Date2013-06-15 16:49:43 UTC
Update Date2017-03-02 22:05:12 UTC
HMDB IDHMDB60560
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlbendazole sulfoxide
DescriptionAlbendazole sulfoxide is a metabolite of albendazole. Albendazole, marketed as Albenza, Eskazole, Zentel, Andazol and Alworm, is a member of the benzimidazole compounds used as a drug indicated for the treatment of a variety of worm infestations. Although this use is widespread in the United States, the U.S. Food and Drug Administration (FDA) has not approved albendazole for this indication. It is marketed by Amedra Pharmaceuticals. Albendazole was first discovered at the SmithKline Animal Health Laboratories in 1972. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
(+-)-Albendazole sulfoxideChEBI
Albendazole oxideChEBI
Albendazole sulfoxideChEBI
RicobendazoleChEBI
RycobendazoleChEBI
(+-)-Albendazole sulphoxideGenerator
Albendazole sulphoxideGenerator
Albendazole sulfoxide, monohydrochlorideMeSH
Chemical FormulaC12H15N3O3S
Average Molecular Weight281.331
Monoisotopic Molecular Weight281.083412051
IUPAC NameN-[6-(propane-1-sulfinyl)-1H-1,3-benzodiazol-2-yl]methoxycarboximidic acid
Traditional NameN-[5-(propane-1-sulfinyl)-3H-1,3-benzodiazol-2-yl]methoxycarboximidic acid
CAS Registry NumberNot Available
SMILES
CCCS(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC
InChI Identifier
InChI=1S/C12H15N3O3S/c1-3-6-19(17)8-4-5-9-10(7-8)14-11(13-9)15-12(16)18-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
InChI KeyVXTGHWHFYNYFFV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzimidazoles
Direct ParentBenzimidazoles
Alternative Parents
Substituents
  • Benzimidazole
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Sulfoxide
  • Carboximidic acid derivative
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfinyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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
Water Solubility4.45 mg/mLALOGPS
logP1.17ALOGPS
logP2.26ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.07ChemAxon
pKa (Strongest Basic)1.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.57 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.56 m3·mol-1ChemAxon
Polarizability29.33 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0090000000-4f8faf80d5525c831f61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0090000000-e552a43e2f05f7fd3a52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0390000000-4daf753348e11cbca5d9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0940000000-be363233970a009f5c67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-19ee9c1374c824bdde53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00791
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60560
Metagene LinkHMDB60560
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available