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Record Information
Version3.6
Creation Date2013-07-09 16:06:05 UTC
Update Date2016-02-11 08:15:05 UTC
HMDB IDHMDB60900
Secondary Accession NumbersNone
Metabolite Identification
Common NameClozapine N-oxide
DescriptionClozapine N-oxide is a metabolite of clozapine. Clozapine (sold as Clozaril, Gen-Clozapine in Canada, Azaleptin, Leponex, Fazaclo, Froidir; Denzapine, Zaponex in the UK; Klozapol in Poland, Clopine in Australia and New Zealand) is an atypical antipsychotic medication used in the treatment of schizophrenia, and is also used off-label in the treatment of bipolar disorder. Wyatt. R and Chew. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
Clozapine-N-oxideChEMBL
4-{6-chloro-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl}-1-methylpiperazin-1-ium-1-olic acidGenerator
Chemical FormulaC18H19ClN4O
Average Molecular Weight342.823
Monoisotopic Molecular Weight342.124738957
IUPAC Name4-{6-chloro-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl}-1-methylpiperazin-1-ium-1-olate
Traditional Name4-{6-chloro-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-10-yl}-1-methylpiperazin-1-ium-1-olate
CAS Registry NumberNot Available
SMILES
C[N+]1([O-])CCN(CC1)C1=NC2=C(NC3=CC=CC=C13)C=CC(Cl)=C2
InChI Identifier
InChI=1S/C18H19ClN4O/c1-23(24)10-8-22(9-11-23)18-14-4-2-3-5-15(14)20-16-7-6-13(19)12-17(16)21-18/h2-7,12,20H,8-11H2,1H3
InChI KeyInChIKey=OGUCZBIQSYYWEF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dibenzodiazepines. These are compounds containing a dibenzodiazepine moiety, which consists of two benzene connected by a diazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub ClassDibenzodiazepines
Direct ParentDibenzodiazepines
Alternative Parents
Substituents
  • Dibenzodiazepine
  • 1,4-benzodiazepine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Imidolactam
  • Benzenoid
  • Piperazine
  • 1,4-diazinane
  • Aryl halide
  • Aryl chloride
  • Tertiary amine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Trisubstituted n-oxide
  • Secondary amine
  • Carboxylic acid amidine
  • N-oxide
  • Amidine
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Organic zwitterion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.058 mg/mLALOGPS
logP1.5ALOGPS
logP2.28ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.9ChemAxon
pKa (Strongest Basic)3.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.51 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity99.4 m3·mol-1ChemAxon
Polarizability36.27 Å3ChemAxon
Number of Rings4ChemAxon
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 IDDBMET00101
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
NuGOwiki LinkHMDB60900
Metagene LinkHMDB60900
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