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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 16:58:09 UTC
Update Date2017-12-07 17:18:07 UTC
HMDB IDHMDB0060573
Secondary Accession Numbers
  • HMDB60573
Metabolite Identification
Common NameChlorpromazine-N-oxide
DescriptionChlorpromazine-N-oxide is a metabolite of chlorpromazine. Chlorpromazine (as chlorpromazine hydrochloride, abbreviated CPZ; marketed in the United States as Thorazine and elsewhere as Largactil) is a typical antipsychotic. First synthesized on December 11, 1950, chlorpromazine was the first drug developed with specific antipsychotic action, and would serve as the prototype for the phenothiazine class of drugs, which later grew to comprise several other agents. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
2-chloro-10-(3'-Dimethyloxidoaminopropyl)phenothiazineChEBI
Chemical FormulaC17H19ClN2OS
Average Molecular Weight334.864
Monoisotopic Molecular Weight334.090661637
IUPAC Name3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropanamine oxide
Traditional Namechlorpromazine n-oxide
CAS Registry NumberNot Available
SMILES
CN(C)(=O)CCCN1C2=CC=CC=C2SC2=C1C=C(Cl)C=C2
InChI Identifier
InChI=1S/C17H19ClN2OS/c1-20(2,21)11-5-10-19-14-6-3-4-7-16(14)22-17-9-8-13(18)12-15(17)19/h3-4,6-9,12H,5,10-11H2,1-2H3
InChI KeyLFDFWIIFGRXCFR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Para-thiazine
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Trialkyl amine oxide
  • Tertiary amine
  • N-oxide
  • Azacycle
  • Trisubstituted n-oxide
  • Thioether
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • 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:

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 Solubility0.00058 g/LALOGPS
logP1.84ALOGPS
logP3.41ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)4.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.12 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.8 m³·mol⁻¹ChemAxon
Polarizability36.1 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-0002-3192000000-b58a61a04eff14215133View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0139000000-30e61f6508e6c1c508ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fe0-2598000000-5c9185020bd700a12cb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7x-9350000000-f6eecad2761081125fe3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-bb74226afd9b458ad76cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1069000000-47ec271b54f6c21c513eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-0190000000-ef93452eac6268285bd9View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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 IDDBMET00815
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC10966
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound443037
      PDB IDNot Available
      ChEBI ID3648
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available