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Record Information
Version3.6
Creation Date2013-06-18 17:42:26 UTC
Update Date2017-03-02 22:05:17 UTC
HMDB IDHMDB60654
Secondary Accession NumbersNone
Metabolite Identification
Common NameCitalopram N-oxide
DescriptionCitalopram N-oxide is a metabolite of citalopram. Citalopram is an antidepressant drug of the selective serotonin reuptake inhibitor (SSRI) class. It has U.S. Food and Drug Administration (FDA) approval to treat major depression, and is prescribed off-label for a number of anxiety conditions. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H21FN2O2
Average Molecular Weight340.3913
Monoisotopic Molecular Weight340.158706131
IUPAC Name3-[5-cyano-1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-1-yl]-N,N-dimethylpropanamine oxide
Traditional Namecitalopram N-oxide
CAS Registry NumberNot Available
SMILES
CN(C)(=O)CCCC1(OCC2=C1C=CC(=C2)C#N)C1=CC=C(F)C=C1
InChI Identifier
InChI=1S/C20H21FN2O2/c1-23(2,24)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-25-20/h4-9,12H,3,10-11,14H2,1-2H3
InChI KeyDIOGFDCEWUUSBQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylbutylamines
Alternative Parents
Substituents
  • Phenylbutylamine
  • Isocoumaran
  • Fluorobenzene
  • Halobenzene
  • Aryl fluoride
  • Aryl halide
  • Trialkyl amine oxide
  • N-oxide
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Trisubstituted n-oxide
  • Carbonitrile
  • Nitrile
  • Organic nitrogen compound
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.002 mg/mLALOGPS
logP1.2ALOGPS
logP2.64ChemAxon
logS-5.2ALOGPS
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.9 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.07 m3·mol-1ChemAxon
Polarizability36.04 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot 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 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 IDDBMET00195
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16607
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60654
      Metagene LinkHMDB60654
      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