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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:32:34 UTC
Update Date2019-07-23 07:14:33 UTC
HMDB IDHMDB0060536
Secondary Accession Numbers
  • HMDB60536
Metabolite Identification
Common NameNorclozapine
DescriptionNorclozapine is the major metabolite of Clozapine. Clozapine is an atypical antipsychotic medication used in the treatment of schizophrenia, and is also sometimes used off-label for the treatment of bipolar disorder. Clozapine is extensively metabolized in the liver, via the cytochrome P450 system, to polar metabolites suitable for elimination in the urine and feces. The major metabolite, norclozapine (desmethyl-clozapine), is pharmacologically active. (Wikipedia )
Structure
Thumb
Synonyms
ValueSource
8-Chloro-11-(1-piperazinyl)-5H-dibenzo(b,e)(1,4)diazepineChEBI
DemethylclozapineChEBI
DesmethylclozapineChEBI
N-Desmethyl clozapineChEBI
NDMCChEBI
8-Chloro-11-piperazin-1-yl-5H-dibenzo(b,e)(1,4)diazepineMeSH
NorclozapineChEBI
Chemical FormulaC17H17ClN4
Average Molecular Weight312.797
Monoisotopic Molecular Weight312.114174271
IUPAC Name6-chloro-10-(piperazin-1-yl)-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaene
Traditional NameNDMC
CAS Registry NumberNot Available
SMILES
ClC1=CC=C2NC3=CC=CC=C3C(=NC2=C1)N1CCNCC1
InChI Identifier
InChI=1S/C17H17ClN4/c18-12-5-6-15-16(11-12)21-17(22-9-7-19-8-10-22)13-3-1-2-4-14(13)20-15/h1-6,11,19-20H,7-10H2
InChI KeyJNNOSTQEZICQQP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzodiazepines. Dibenzodiazepines are compounds containing a dibenzodiazepine moiety, which consists of two benzene connected by diazepine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodiazepines
Sub ClassDibenzodiazepines
Direct ParentDibenzodiazepines
Alternative Parents
Substituents
  • Dibenzodiazepine
  • 1,4-benzodiazepine
  • Aryl chloride
  • Aryl halide
  • 1,4-diazinane
  • Imidolactam
  • Piperazine
  • Benzenoid
  • Amidine
  • Carboxylic acid amidine
  • Secondary aliphatic amine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Secondary amine
  • Propargyl-type 1,3-dipolar organic compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesmethylclozapine
METLIN IDNot Available
PubChem Compound135409468
PDB IDNot Available
ChEBI ID64050
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ekstrom J, Godoy T, Riva A: N-Desmethylclozapine exerts dual and opposite effects on salivary secretion in the rat. Eur J Oral Sci. 2010 Feb;118(1):1-8. doi: 10.1111/j.1600-0722.2009.00696.x. [PubMed:20156258 ]
  2. Couchman L, Morgan PE, Spencer EP, Flanagan RJ: Plasma clozapine, norclozapine, and the clozapine:norclozapine ratio in relation to prescribed dose and other factors: data from a therapeutic drug monitoring service, 1993-2007. Ther Drug Monit. 2010 Aug;32(4):438-47. doi: 10.1097/FTD.0b013e3181dad1fb. [PubMed:20463634 ]
  3. Ertugrul A, Ozdemir H, Vural A, Dalkara T, Meltzer HY, Saka E: The influence of N-desmethylclozapine and clozapine on recognition memory and BDNF expression in hippocampus. Brain Res Bull. 2011 Feb 1;84(2):144-50. doi: 10.1016/j.brainresbull.2010.11.014. Epub 2010 Dec 4. [PubMed:21134422 ]
  4. Godoy T, Riva A, Ekstrom J: Clozapine-induced salivation: interaction with N-desmethylclozapine and amisulpride in an experimental rat model. Eur J Oral Sci. 2011 Aug;119(4):275-81. doi: 10.1111/j.1600-0722.2011.00832.x. [PubMed:21726287 ]
  5. Heusler P, Bruins Slot L, Tourette A, Tardif S, Cussac D: The clozapine metabolite N-desmethylclozapine displays variable activity in diverse functional assays at human dopamine D(2) and serotonin 5-HT(1)A receptors. Eur J Pharmacol. 2011 Nov 1;669(1-3):51-8. doi: 10.1016/j.ejphar.2011.07.031. Epub 2011 Aug 5. [PubMed:21835172 ]
  6. Humbert-Claude M, Davenas E, Gbahou F, Vincent L, Arrang JM: Involvement of histamine receptors in the atypical antipsychotic profile of clozapine: a reassessment in vitro and in vivo. Psychopharmacology (Berl). 2012 Mar;220(1):225-41. doi: 10.1007/s00213-011-2471-5. Epub 2011 Sep 13. [PubMed:21912901 ]