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Record Information
Version3.6
Creation Date2013-06-15 16:49:46 UTC
Update Date2017-03-02 22:05:12 UTC
HMDB IDHMDB60561
Secondary Accession NumbersNone
Metabolite Identification
Common NameAlbendazole sulfone
DescriptionAlbendazole sulfone 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
SynonymsNot Available
Chemical FormulaC12H15N3O4S
Average Molecular Weight297.33
Monoisotopic Molecular Weight297.078326673
IUPAC NameN-[6-(propane-1-sulfonyl)-1H-1,3-benzodiazol-2-yl]methoxycarboximidic acid
Traditional Namealbendazole sulfone
CAS Registry NumberNot Available
SMILES
CCCS(=O)(=O)C1=CC2=C(C=C1)N=C(N2)N=C(O)OC
InChI Identifier
InChI=1S/C12H15N3O4S/c1-3-6-20(17,18)8-4-5-9-10(7-8)14-11(13-9)15-12(16)19-2/h4-5,7H,3,6H2,1-2H3,(H2,13,14,15,16)
InChI KeyCLSJYOLYMZNKJB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzimidazoles
Direct Parent2-benzimidazolylcarbamic acid esters
Alternative Parents
Substituents
  • 2-benzimidazolylcarbamic acid ester
  • Benzenoid
  • Azole
  • Imidazole
  • Sulfone
  • Sulfonyl
  • Heteroaromatic compound
  • Carbamic acid ester
  • Carbonic acid derivative
  • Azacycle
  • 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
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 Solubility0.18 mg/mLALOGPS
logP0.86ALOGPS
logP2.37ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.88ChemAxon
pKa (Strongest Basic)1.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.64 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.15 m3·mol-1ChemAxon
Polarizability30 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-QFT , negativesplash10-01ot-0090000000-b3afb8dad582be0beeb2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0090000000-5a1d69ed89637bb24f52View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0690000000-5ef27baadffc6d2e54b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-8a289e6c98ff7e198fa5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-14e3ece0959c3970ed68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-3d7314457228b1500e09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-05r0-0900000000-547cf67f0eabc7f7c663View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-4900000000-fdf89b0b89e5b9a2db78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03xr-9400000000-36b83cc4358c036b82ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0190000000-9925e91cfa0767b775c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0920000000-0096cb747826bf7247c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-a9108d509d15ab62519dView 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 IDDBMET00790
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC16626
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB60561
Metagene LinkHMDB60561
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