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Record Information
Version3.6
Creation Date2013-06-18 18:42:36 UTC
Update Date2016-02-11 08:10:53 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
Synonyms
ValueSource
2H-Dibenz[b,F]azepin-2-oneHMDB
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 KeyInChIKey=CVKDTTCYQAJIAC-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Azepine
  • Benzenoid
  • Heteroaromatic compound
  • Cyclic ketone
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • 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
  • 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
SpectraNot 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 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 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. [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. [16135660 ]