Oxcarbazepine (CHEM002270)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (14)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:37 UTC
Update Date2026-05-14 16:48:34 UTC
Accession NumberCHEM002270
Identification
Common NameOxcarbazepine
ClassSmall Molecule
DescriptionOxcarbazepine is structurally a derivative of carbamazepine, adding an extra oxygen atom to the benzylcarboxamide group. This difference helps reduce the impact on the liver of metabolizing the drug, and also prevents the serious forms of anemia occasionally associated with carbamazepine. Aside from this reduction in side effects, it is thought to have the same mechanism as carbamazepine - sodium channel inhibition - and is generally used to treat partial seizures in epileptic children and adults.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Anticonvulsant
  • Drug
  • Ester
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
10,11-Dihydro-10-oxo-5H-dibenz(b,F)azepine-5-carboxamideChEBI
OxcarbazepinaChEBI
OxcarbazepinumChEBI
OxtellarKegg
TrileptalKegg
OxcarbamazepineHMDB
Desitin brand OF oxcarbazepineHMDB
Novartis brand OF oxcarbazepineHMDB
TimoxHMDB
Chemical FormulaC15H12N2O2
Average Molecular Mass252.268 g/mol
Monoisotopic Mass252.090 g/mol
CAS Registry Number28721-07-5
IUPAC Name9-oxo-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide
Traditional Nameoxcarbazepine
SMILESNC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C12
InChI IdentifierInChI=1S/C15H12N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8H,9H2,(H2,16,19)
InChI KeyCTRLABGOLIVAIY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines 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
  • Aryl ketone
  • Aryl alkyl ketone
  • Azepine
  • Benzenoid
  • Vinylogous amide
  • Isourea
  • Ketone
  • Carboximidic acid derivative
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Imine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point215.5°C
Boiling PointNot Available
Solubility308 mg/L at 25°C (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP1.76ALOGPS
logP1.82ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)12.92ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.4 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.56 m³·mol⁻¹ChemAxon
Polarizability25.72 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3490000000-e819f3deb2b8c87b4232Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0f8i-1790000000-cd62672e7fa7c39f0be1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0kar-0690000000-cbc95a31913165d691a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-2910000000-d1242af6b8148ffac3a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0pb9-0090000000-46d01e1171f998679d03Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f8i-1790000000-cd62672e7fa7c39f0be1Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0kar-0690000000-cbc95a31913165d691a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-2910000000-d1242af6b8148ffac3a9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-053r-0790000000-1538838440ac9de0764bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0pb9-0090000000-7003f419893f7314126cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-fe8a28b607ec5dddd195Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ik9-0090000000-4536652e48c7784201c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-3950000000-4981fd5d2c607be060c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pbc-5090000000-5d40809535b419b6b2deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2090000000-d016d9db20537c45eaaeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-4e53a0698392fe26965dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0090000000-d2b279fe7e26771148aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-3f6fe55807c0254e0b44Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-0790000000-ca89b030e1d26b804a84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-229652fa3e4351b39559Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-9f12ac38c8faae87e87fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0090000000-296de1c6f0c6cab3a7f1Spectrum
Toxicity Profile
Route of ExposureCompletely absorbed following oral administration. Food has no effect on the rate and extent of absorption of oxcarbazepine. After single-dose administration of Trileptal tablets to healthy male volunteers under fasted conditions, the median tmax was 4.5 (range 3 to 13) hours. After single-dose administration of Trileptal oral suspension to healthy male volunteers under fasted conditions, the median tmax was six hours. Steady-state plasma concentrations of MHD are reached within 2-3 days in patients when Trileptal is given twice a day.
Mechanism of ToxicityThe exact mechanism by which oxcarbazepine exerts its anticonvulsant effect is unknown. It is known that the pharmacological activity of oxcarbazepine occurs primarily through its 10-monohydroxy metabolite (MHD). In vitro studies indicate an MHD-induced blockade of voltage-sensitive sodium channels, resulting in stabilization of hyperexcited neuronal membranes, inhibition of repetitive neuronal discharges, and diminution of propagation of synaptic impulses.
MetabolismOxcarbazepine is completely absorbed and extensively metabolized to its pharmacologically active 10-monohydroxy metabolite (MHD) by cytosolic enzymes. MHD is metabolized further by conjugation with glucuronic acid. Route of Elimination: Oxcarbazepine is cleared from the body mostly in the form of metabolites which are predominantly excreted by the kidneys. Fecal excretion accounts for less than 4% of the administered dose. Half Life: The half-life of the parent is about 2 hours, while the half-life of MHD is about 9 hours, so that MHD is responsible for most anti-epileptic activity.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor use as monotherapy or adjunctive therapy in the treatment of partial seizures in adults with epilepsy and as adjunctive therapy in the treatment of partial seizures in children ages 4-16 with epilepsy.
Minimum Risk LevelNot Available
Health EffectsMay cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.
SymptomsNot Available
TreatmentThere is no specific antidote. Symptomatic and supportive treatment should be administered as appropriate. Removal of the drug by gastric lavage and/or inactivation by administering activated charcoal should be considered. (2)
Concentrations
Not Available
DrugBank IDDB00776
HMDB IDHMDB0014914
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkOxcarbazepine
Chemspider ID31608
ChEBI ID7824
PubChem Compound ID34312
Kegg Compound IDC07492
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Judith Aronhime, “New crystal forms of oxcarbazepine and processes for their preparation.” U.S. Patent US20030004154, issued January 02, 2003.

MSDSNot Available
General References
1. Mazza M, Della Marca G, Di Nicola M, Martinotti G, Pozzi G, Janiri L, Bria P, Mazza S: Oxcarbazepine improves mood in patients with epilepsy. Epilepsy Behav. 2007 May;10(3):397-401. Epub 2007 Feb 14.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21924464