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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:35 UTC
HMDB IDHMDB0014914
Secondary Accession Numbers
  • HMDB14914
Metabolite Identification
Common NameOxcarbazepine
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.
Structure
Data?1582753235
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 Weight252.268
Monoisotopic Molecular Weight252.089877638
IUPAC Name9-oxo-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide
Traditional Nameoxcarbazepine
CAS Registry Number28721-07-5
SMILES
NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C12
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.16 g/LNot Available
LogP1.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM153.830932474
[M+H]+Not Available152.743http://allccs.zhulab.cn/database/detail?ID=AllCCS00001027
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP10(1.76) g/LALOGPS
logP10(1.82) g/LChemAxon
logS10(-3.2) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+157.06831661259
DarkChem[M-H]-155.61431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OxcarbazepineNC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C123826.6Standard polar33892256
OxcarbazepineNC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C122274.4Standard non polar33892256
OxcarbazepineNC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C122474.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Oxcarbazepine,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C212320.1Semi standard non polar33892256
Oxcarbazepine,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C212392.8Standard non polar33892256
Oxcarbazepine,1TMS,isomer #1C[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C213233.0Standard polar33892256
Oxcarbazepine,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C2401.5Semi standard non polar33892256
Oxcarbazepine,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C2609.6Standard non polar33892256
Oxcarbazepine,2TMS,isomer #1C[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C3146.5Standard polar33892256
Oxcarbazepine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C212531.4Semi standard non polar33892256
Oxcarbazepine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C212613.4Standard non polar33892256
Oxcarbazepine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C213337.6Standard polar33892256
Oxcarbazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C2798.1Semi standard non polar33892256
Oxcarbazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C2995.0Standard non polar33892256
Oxcarbazepine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3240.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Oxcarbazepine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-3490000000-e819f3deb2b8c87b42322017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxcarbazepine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Oxcarbazepine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine LC-ESI-qTof , Positive-QTOFsplash10-0f8i-1790000000-cd62672e7fa7c39f0be12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine LC-ESI-qTof , Positive-QTOFsplash10-0kar-0690000000-cbc95a31913165d691a72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine LC-ESI-qTof , Positive-QTOFsplash10-001i-2910000000-d1242af6b8148ffac3a92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine LC-ESI-QFT , negative-QTOFsplash10-0pb9-0090000000-46d01e1171f998679d032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine , positive-QTOFsplash10-0f8i-1790000000-cd62672e7fa7c39f0be12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine , positive-QTOFsplash10-0kar-0690000000-cbc95a31913165d691a72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine , positive-QTOFsplash10-001i-2910000000-d1242af6b8148ffac3a92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine 35V, Positive-QTOFsplash10-053r-0790000000-1538838440ac9de0764b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Oxcarbazepine 35V, Negative-QTOFsplash10-0pb9-0090000000-7003f419893f7314126c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 10V, Positive-QTOFsplash10-0udi-0090000000-fe8a28b607ec5dddd1952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 20V, Positive-QTOFsplash10-0ik9-0090000000-4536652e48c7784201c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 40V, Positive-QTOFsplash10-0006-3950000000-4981fd5d2c607be060c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 10V, Negative-QTOFsplash10-0pbc-5090000000-5d40809535b419b6b2de2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 20V, Negative-QTOFsplash10-0a4i-2090000000-d016d9db20537c45eaae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 40V, Negative-QTOFsplash10-0006-9220000000-4e53a0698392fe26965d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 10V, Positive-QTOFsplash10-0udi-0090000000-d2b279fe7e26771148aa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 20V, Positive-QTOFsplash10-03di-0090000000-3f6fe55807c0254e0b442021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 40V, Positive-QTOFsplash10-0a59-0790000000-ca89b030e1d26b804a842021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 10V, Negative-QTOFsplash10-0udi-0090000000-229652fa3e4351b395592021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 20V, Negative-QTOFsplash10-0a4i-0090000000-9f12ac38c8faae87e87f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Oxcarbazepine 40V, Negative-QTOFsplash10-0a4i-0090000000-296de1c6f0c6cab3a7f12021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00776 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00776 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00776
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID31608
KEGG Compound IDC07492
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxcarbazepine
METLIN IDNot Available
PubChem Compound34312
PDB IDNot Available
ChEBI ID7824
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. 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. [PubMed:17300991 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Vohora D, Saraogi P, Yazdani MA, Bhowmik M, Khanam R, Pillai KK: Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs. Drugs Today (Barc). 2010 Apr;46(4):265-77. doi: 10.1358/dot.2010.46.4.1445795. [PubMed:20502724 ]