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Record Information
Version4.0
Creation Date2013-06-15 16:49:43 UTC
Update Date2017-09-27 08:43:50 UTC
HMDB IDHMDB0060560
Secondary Accession Numbers
  • HMDB60560
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
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Industrial application:

  Pharmaceutical industry:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.56 m³·mol⁻¹ChemAxon
Polarizability29.33 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
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, Positivesplash10-00e9-1090000000-e150095a8f96d26a5f0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2190000000-95bc61e0d527da36378fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9450000000-880977de0008e20d5883View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0532-3090000000-8b0222ac217c5e4b2b61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2190000000-a555b482ba6eed51876fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-9680000000-b24eefc0024e732c7ed6View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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
      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