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Record Information
Version3.6
Creation Date2013-06-18 18:42:36 UTC
Update Date2017-03-02 22:05:18 UTC
HMDB IDHMDB60675
Secondary Accession NumbersNone
Metabolite Identification
Common NameCarbamazepine iminoquinone
DescriptionCarbamazepine iminoquinone is a metabolite of carbamazepine. Carbamazepine (CBZ) is an anticonvulsant and mood-stabilizing drug used primarily in the treatment of epilepsy and bipolar disorder, as well as trigeminal neuralgia. (Wikipedia) Conversion of the carbamazepine metabolite, 2-hydroxycarbamazepine, to the potentially reactive species, carbamazepine iminoquinone (CBZ-IQ), has been proposed as a possible bioactivation pathway in the pathogenesis of carbamazepine-induced hypersensitivity. (PMID: 16135660 )
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H9NO
Average Molecular Weight207.2274
Monoisotopic Molecular Weight207.068413915
IUPAC Name2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),2,4,7,9,11,13-heptaen-6-one
Traditional Name2H-dibenz[b,f]azepin-2-one
CAS Registry NumberNot Available
SMILES
O=C1C=CC2=NC3=CC=CC=C3C=CC2=C1
InChI Identifier
InChI=1S/C14H9NO/c16-12-7-8-14-11(9-12)6-5-10-3-1-2-4-13(10)15-14/h1-9H
InChI KeyCVKDTTCYQAJIAC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Azepine
  • Benzenoid
  • Heteroaromatic compound
  • Cyclic ketone
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen 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
  • 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 Solubility0.028 mg/mLALOGPS
logP2.35ALOGPS
logP2.66ChemAxon
logS-3.9ALOGPS
pKa (Strongest Basic)3.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.49 m3·mol-1ChemAxon
Polarizability22.28 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Carbamazepine Metabolism PathwaySMP00634Not 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 IDNot Available
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDC16605
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB60675
      Metagene LinkHMDB60675
      METLIN IDNot Available
      PubChem Compound276457
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Ju C, Uetrecht JP: Detection of 2-hydroxyiminostilbene in the urine of patients taking carbamazepine and its oxidation to a reactive iminoquinone intermediate. J Pharmacol Exp Ther. 1999 Jan;288(1):51-6. [PubMed:9862752 ]
      2. Pearce RE, Uetrecht JP, Leeder JS: Pathways of carbamazepine bioactivation in vitro: II. The role of human cytochrome P450 enzymes in the formation of 2-hydroxyiminostilbene. Drug Metab Dispos. 2005 Dec;33(12):1819-26. Epub 2005 Aug 31. [PubMed:16135660 ]