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Record Information
Version3.6
Creation Date2013-06-15 16:58:09 UTC
Update Date2016-02-11 08:08:31 UTC
HMDB IDHMDB60573
Secondary Accession NumbersNone
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 KeyInChIKey=LFDFWIIFGRXCFR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Benzenoid
  • Aryl halide
  • Aryl chloride
  • Para-thiazine
  • Tertiary amine
  • Azacycle
  • Trisubstituted n-oxide
  • Thioether
  • N-oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Organic cation
  • 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 Solubility0.000583 mg/mLALOGPS
logP1.84ALOGPS
logP3.41ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)4.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.12 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.8 m3·mol-1ChemAxon
Polarizability36.1 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 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 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
NuGOwiki LinkHMDB60573
Metagene LinkHMDB60573
METLIN IDNot Available
PubChem Compound443037
PDB IDNot Available
ChEBI ID3648
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available