Identification
- Summary
Oxcarbazepine is an anti-epileptic used in the treatment of partial-onset seizures.
- Brand Names
- Oxtellar, Trileptal
- Generic Name
- Oxcarbazepine
- DrugBank Accession Number
- DB00776
- Background
Oxcarbazepine is an anti-epileptic medication used in the treatment of partial onset seizures that was first approved for use in the United States in 2000.10,11,12 It is a structural derivative of carbamazepine8 and exerts a majority of its activity via a pharmacologically active metabolite, MHD, which exists as a racemate in the blood - a pro-drug of the more active (S)-enantiomer is also marketed as a separate anti-epileptic under the name eslicarbazepine.1 Compared to other anti-epileptic drugs, which are generally metabolized via the cytochrome P450 system, oxcarbazepine has a reduced propensity for involvement in drug-drug interactions owing to its primarily reductive metabolism.6
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Oxcarbazepine (DB00776)
- Weight
- Average: 252.268
Monoisotopic: 252.089877638 - Chemical Formula
- C15H12N2O2
- Synonyms
- 10,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carboxamide
- OCBZ
- Oxcarbamazepine
- Oxcarbazepina
- Oxcarbazepine
- Oxcarbazepinum
- External IDs
- GP 47680
- GP-47680
- KIN-493
- SPN-804
Pharmacology
- Indication
In the United States, oxcarbazepine is indicated for use as monotherapy or adjunctive therapy in the treatment of partial-onset seizures in adults and as monotherapy in the treatment of partial-onset seizures in pediatric patients aged 4 years and above, and as adjunctive therapy in pediatric patients aged 2 years and above with partial-onset seizures.10
In Canada, oxcarbazepine is indicated for use as monotherapy or adjunctive therapy in the treatment of partial-onset seizures in patients 6 years of age and older.11
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Partial-onset seizures •••••••••••• Adjunct therapy in management of Partial-onset seizures •••••••••••• Adjunct therapy in management of Partial-onset seizures •••••••••••• ••••• Management of Partial-onset seizures •••••••••••• ••••• Management of Partial-onset seizures •••••••••••• ••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Oxcarbazepine is an anticonvulsant drug that reduces the incidence of seizures in epilepsy by inhibiting abnormal electrical activity in the brain.10,11,12
There have been rare reports of oxcarbazepine resulting in the development of hematologic abnormalities, including agranulocytosis and aplastic anemia. Patients should be undergo frequent laboratory testing and should be monitored closely for signs and symptoms of blood dyscrasias. Oxcarbazepine has also been associated with the development of dermatologic reactions which can progress from a simple rash to potentially fatal reactions such as toxic epidermal necrolysis (TEN) or Stevens-Johnson Syndrome (SJS). Patients with the HLA-A 3101 and/or HLA-B 1502 alleles may be at higher risk of this reaction. Oxcarbazepine should be discontinued at the first sign of a drug-induced skin reaction.10,11,12
- Mechanism of action
The exact mechanism through which oxcarbazepine and its active metaoblite, MHD, exert their anti-epileptic effects is unclear, but is thought to primarily involve the blockade of voltage-gated sodium channels.10,11,12,9 The opening and closing of sodium channels allows for the propagation of action potentials along neurons - in epilepsy, these action potentials can occur in excess of that required for normal function, and the repetitive and pathological firing of these action potentials leads to seizure activity. Both oxcarbazepine and MHD are thought to inhibit seizure activity by binding to the inactive state of voltage-gated sodium channels, thus prolonging the period in which the receptor is unavailable for action potential propagation.8 This helps to stabilize hyperexcited neuronal membranes, inhibit repetitive neuron firing, and prevent the spread of seizure activity within the CNS without affecting normal neuronal transmission.10,11,12
Increased potassium conductance and modulation of voltage-activated calcium channels is also thought to play a role in the anti-seizure activity of oxcarbazepine.10,11,12 Inhibition of glutamatergic activity was thought to contribute to oxcarbazepine's activity5, but this effect could not be replicated in vivo.9
Target Actions Organism USodium channel protein inhibitorHumans - Absorption
Oxcarbazepine is completely absorbed following oral administration. A single 600mg dose of oxcarbazepine resulted in an MHD Cmax of 34 μmol/L and a median Tmax of 4.5 hours.10,11,12 When administered twice daily, steady-state levels of MHD are attained within 2-3 days. The rate and extent of absorption of oxcarbazepine is not affected by food intake.10,11,12
- Volume of distribution
The apparent volume of distribution of oxcarbazepine is 49 L.10,11,12 The apparent volumes of distribution of (S)- and (R)-MHD were found to be 23.6 L and 31.7 L, respectively.2
- Protein binding
The pharmacologically active metabolite of oxcarbazepine, MHD, is approximately 40% bound to plasma proteins, predominantly albumin.10,11,12
- Metabolism
Oxcarbazepine is rapidly and extensively metabolized to its primary metabolite, MHD, which is responsible for the bulk of its anti-epileptic activity and exists in much higher concentrations in the plasma than the parent drug.10,11,12 MHD is formed via reduction by several members of the aldo-keto reductase family of cytosolic liver enzymes and exists as a racemate in plasma in an approximate ratio of 80% (S)-MHD to 20% (R)-MHD.1 MHD is further metabolized to glucuronide conjugate metabolites for excretion, and small amounts are oxidized to 10-,11-dihydro-10,11-dihydroxycarbamazepine (DHD) which is pharmacologically inactive.10,11,12,7 Only 10% of an administered dose of oxcarbazepine will remain as either the parent drug or glucuronide conjugates of the parent drug.2
Hover over products below to view reaction partners
- Route of elimination
Following oral administration, more than 95% of the administered dose of oxcarbazepine is found in the urine. Of this, approximately 49% is MHD glucuronide metabolites, 27% is unchanged MHD, 3% is inactive DHD metabolites, 13% is conjugated oxcarbazepine, and less than 1% is unchanged parent drug. Fecal elimination accounts for only 4% of the administered dose.10,11,12
- Half-life
The plasma half-life of oxcarbazepine is approximately 2 hours and the plasma half-life of MHD is approximately 9 hours.10,11,12
- Clearance
Plasma clearance of oxcarbazepine has been estimated to be approximately 84.9 L/h, whereas plasma clearance of its active metabolite, MHD, was estimated to be 2.0 L/h.2 Rapid metabolic clearance appears to be the main pathway for oxcarbazepine, while clearance of its metabolites occurs mainly via renal excretion.6
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
The oral LD50 of oxcarbazepine in mammals is 1240 mg/kg and the oral TDLo in children has been reported to be 73 mg/kg.13 Isolated cases of oxcarbazepine overdose have been reported - patients who ingested up to 24,000mg recovered with symptomatic treatment.10,11 Symptoms may include respiratory and CNS depression, movement-related disorders (e.g. dyskinesia, ataxia), nausea/vomiting, hyponatremia, or QTc prolongation. There is no antidote for oxcarbazepine overdose - management should consist of supportive and symptomatic treatment, and consideration should be given to the use of gastric lavage or activated charcoal.10,11
- Pathways
Pathway Category Carbamazepine Metabolism Pathway Drug metabolism - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details HLA class I histocompatibility antigen, B-15 alpha chain HLA-B*15:02 Not Available HLA-B*15 ADR Directly Studied Patients who carry this allele may be at an increased risk of Stevens-Johnson Syndrome and toxic epidermal necrolysis when treated with oxcarbazepine. Details
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Oxcarbazepine is combined with 1,2-Benzodiazepine. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Oxcarbazepine. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Oxcarbazepine. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Oxcarbazepine. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Oxcarbazepine. - Food Interactions
- Avoid alcohol. Oxcarbazepine has CNS depressant properties that may be potentiated by co-administration with alcohol.
- Take with or without food. Co-administration with food does not significantly affect absorption.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Actinium / Barzepin / Carbox / Deprectal / Lonazet / Oxalepsy / Oxetol / Oxpin / Oxrate / Oxypine / Pharozepine / Prolepsi / Timox / Trexapin / Trileptin
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxcarbazepine Tablet 150 mg Oral Jubilant Generics Limited Not applicable Not applicable Canada 
Oxcarbazepine Tablet 600 mg Oral Jubilant Generics Limited Not applicable Not applicable Canada Oxcarbazepine Tablet 300 mg Oral Jubilant Generics Limited Not applicable Not applicable Canada Oxtellar XR Tablet 150 mg/1 Oral Supernus Pharmaceuticals, Inc. 2013-01-17 Not applicable US 
Oxtellar XR Tablet 600 mg/1 Oral Supernus Pharmaceuticals, Inc. 2013-01-17 Not applicable US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-oxcarbazepine Tablet 300 mg Oral Apotex Corporation 2006-08-01 Not applicable Canada Apo-oxcarbazepine Tablet 150 mg Oral Apotex Corporation 2006-08-01 Not applicable Canada Apo-oxcarbazepine Tablet 600 mg Oral Apotex Corporation 2006-08-01 Not applicable Canada Jamp-oxcarbazepine Tablet 300 mg Oral Jamp Pharma Corporation 2015-06-08 2022-09-06 Canada Jamp-oxcarbazepine Tablet 150 mg Oral Jamp Pharma Corporation 2015-06-08 2022-09-06 Canada
Categories
- ATC Codes
- N03AF02 — Oxcarbazepine
- Drug Categories
- Anti-epileptic Agent
- Anticonvulsants
- Carboxamide Derivatives
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Inducers
- Cytochrome P-450 CYP3A5 Inducers (strength unknown)
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Decreased Central Nervous System Disorganized Electrical Activity
- Dibenzazepines
- Drugs causing inadvertant photosensitivity
- Enzyme Inducing Antiepileptic Drugs
- Heterocyclic Compounds, Fused-Ring
- Membrane Transport Modulators
- Miscellaneous Anticonvulsants
- Nervous System
- P-glycoprotein inducers
- P-glycoprotein substrates
- Photosensitizing Agents
- Sodium Channel Blockers
- Voltage-Gated Sodium Channel Blockers
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzazepines
- Sub Class
- Dibenzazepines
- Direct Parent
- Dibenzazepines
- Alternative Parents
- Aryl alkyl ketones / Azepines / Benzenoids / Vinylogous amides / Isoureas / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Imines / Hydrocarbon derivatives
- Substituents
- Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azepine / Benzenoid / Carboximidic acid derivative / Dibenzazepine / Hydrocarbon derivative / Imine
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cyclic ketone, dibenzoazepine (CHEBI:7824)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- VZI5B1W380
- CAS number
- 28721-07-5
- InChI Key
- CTRLABGOLIVAIY-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 9-oxo-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide
- SMILES
- NC(=O)N1C2=CC=CC=C2CC(=O)C2=C1C=CC=C2
References
- Synthesis Reference
Judith Aronhime, "New crystal forms of oxcarbazepine and processes for their preparation." U.S. Patent US20030004154, issued January 02, 2003.
US20030004154- General References
- Malatkova P, Havlikova L, Wsol V: The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7. doi: 10.1016/j.cbi.2014.07.005. Epub 2014 Jul 22. [Article]
- Antunes NJ, van Dijkman SC, Lanchote VL, Wichert-Ana L, Coelho EB, Alexandre Junior V, Takayanagui OM, Tozatto E, van Hasselt JGC, Della Pasqua O: Population pharmacokinetics of oxcarbazepine and its metabolite 10-hydroxycarbazepine in healthy subjects. Eur J Pharm Sci. 2017 Nov 15;109S:S116-S123. doi: 10.1016/j.ejps.2017.05.034. Epub 2017 May 17. [Article]
- Zhang C, Zuo Z, Kwan P, Baum L: In vitro transport profile of carbamazepine, oxcarbazepine, eslicarbazepine acetate, and their active metabolites by human P-glycoprotein. Epilepsia. 2011 Oct;52(10):1894-904. doi: 10.1111/j.1528-1167.2011.03140.x. Epub 2011 Jun 21. [Article]
- Thomas AM, Atkinson TJ: Old Friends With New Faces: Are Sodium Channel Blockers the Future of Adjunct Pain Medication Management? J Pain. 2018 Jan;19(1):1-9. doi: 10.1016/j.jpain.2017.08.001. Epub 2017 Aug 24. [Article]
- Shorvon S: Oxcarbazepine: a review. Seizure. 2000 Mar;9(2):75-9. doi: 10.1053/seiz.2000.0391. [Article]
- Schmidt D, Sachdeo R: Oxcarbazepine for Treatment of Partial Epilepsy: A Review and Recommendations for Clinical Use. Epilepsy Behav. 2000 Dec;1(6):396-405. doi: 10.1006/ebeh.2000.0126. [Article]
- Schutz H, Feldmann KF, Faigle JW, Kriemler HP, Winkler T: The metabolism of 14C-oxcarbazepine in man. Xenobiotica. 1986 Aug;16(8):769-78. doi: 10.3109/00498258609043567. [Article]
- Abou-Khalil BW: Antiepileptic Drugs. Continuum (Minneap Minn). 2016 Feb;22(1 Epilepsy):132-56. doi: 10.1212/CON.0000000000000289. [Article]
- Czapinski P, Blaszczyk B, Czuczwar SJ: Mechanisms of action of antiepileptic drugs. Curr Top Med Chem. 2005;5(1):3-14. doi: 10.2174/1568026053386962. [Article]
- DailyMed Label: TRILEPTAL (oxcarbazepine) film-coated tablets or suspension, for oral use [Link]
- DPD Approved Drugs: Oxcarbazepine [Link]
- MedSafe NZ: Oxcarbazepine [Link]
- CaymenChem: Oxcarbazepine MSDS [Link]
- DailyMed Label: OXTELLAR XR (oxcarbazepine) extended-release tablets, for oral use [Link]
- External Links
- Human Metabolome Database
- HMDB0014914
- KEGG Drug
- D00533
- KEGG Compound
- C07492
- PubChem Compound
- 34312
- PubChem Substance
- 46507580
- ChemSpider
- 31608
- BindingDB
- 34179
- 32624
- ChEBI
- 7824
- ChEMBL
- CHEMBL1068
- ZINC
- ZINC000000004724
- Therapeutic Targets Database
- DAP000528
- PharmGKB
- PA450732
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Oxcarbazepine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Bipolar Disorder (BD) 2 4 Completed Treatment Bronchial Asthma 1 4 Completed Treatment Defiant Disorder, Oppositional 1 4 Completed Treatment Epilepsy 1 4 Completed Treatment Epilepsy, Partial Seizures 2
Pharmacoeconomics
- Manufacturers
- Ranbaxy laboratories ltd
- Novartis pharmaceuticals corp
- Apotex inc
- Breckenridge pharmaceutical inc
- Cadista pharmaceuticals inc
- Glenmark generics ltd
- Roxane laboratories inc
- Sun pharmaceutical industries ltd
- Taro pharmaceutical industries ltd
- Teva pharmaceuticals usa
- Packagers
- Amerisource Health Services Corp.
- Apotex Inc.
- Ascend Laboratories LLC
- Atlantic Biologicals Corporation
- Breckenridge Pharmaceuticals
- Bryant Ranch Prepack
- Cardinal Health
- Glenmark Generics Ltd.
- Innoviant Pharmacy Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Nexgen Pharma Inc.
- Novartis AG
- Nucare Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Remedy Repack
- Resource Optimization and Innovation LLC
- Roxane Labs
- Sandoz
- Southwood Pharmaceuticals
- Sun Pharmaceutical Industries Ltd.
- Taro Pharmaceuticals USA
- Teva Pharmaceutical Industries Ltd.
- Vangard Labs Inc.
- Dosage Forms
Form Route Strength Tablet Oral 600.000 mg Tablet, film coated Oral 150 mg Tablet, film coated Oral 300 MG Tablet, film coated Oral 600 MG Suspension Oral 6.00 g Tablet Oral 150.000 mg Tablet, extended release Oral 150 mg Tablet, extended release Oral 600 mg Tablet, delayed release Oral 300 mg Suspension Oral 300 mg/5mL Suspension Oral 60 mg/1mL Tablet Oral 150 mg/1 Tablet Oral 600 mg/1 Tablet, film coated Oral 150 mg/1 Tablet, film coated Oral 300 mg/1 Tablet, film coated Oral 600 mg/1 Tablet Oral 300.000 mg Suspension Oral 6.000 g Tablet Oral 300 mg/1 Tablet, coated Oral 300 mg Tablet, coated Oral 600 mg Tablet Oral 150 mg Tablet, film coated Oral Tablet Oral 300 mg Tablet Oral Suspension Oral Suspension Oral 60 mg/ml Tablet Oral 600 mg Suspension Oral 60 mg / mL Suspension Oral 60 mg - Prices
Unit description Cost Unit OXcarbazepine 300 mg/5ml Suspension 250ml Bottle 162.03USD bottle Trileptal 600 mg tablet 7.05USD tablet Oxcarbazepine 600 mg tablet 5.06USD tablet Trileptal 300 mg tablet 3.84USD tablet Oxcarbazepine 300 mg tablet 2.75USD tablet Trileptal 150 mg tablet 2.1USD tablet Oxcarbazepine 150 mg tablet 1.53USD tablet Trileptal 300 mg/5ml Suspension 0.79USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2277791 No 2008-11-18 2018-02-12 Canada US7037525 Yes 2006-05-02 2018-08-12 US US8119148 Yes 2012-02-21 2021-06-19 US US7910131 No 2011-03-22 2027-04-13 US US9119791 No 2015-09-01 2027-04-13 US US8821930 No 2014-09-02 2027-04-13 US US8617600 No 2013-12-31 2027-04-13 US US7722898 No 2010-05-25 2027-04-13 US US9370525 No 2016-06-21 2027-04-13 US US9351975 No 2016-05-31 2027-04-13 US US9855278 No 2018-01-02 2027-04-13 US US10220042 No 2019-03-05 2027-04-13 US US11166960 No 2021-11-09 2027-04-13 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 1.5 Not Available pKa 13.73 Canadian label - Predicted Properties
Property Value Source Water Solubility 0.16 mg/mL ALOGPS logP 1.76 ALOGPS logP 1.82 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 13.18 Chemaxon pKa (Strongest Basic) -4.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 63.4 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 71.56 m3·mol-1 Chemaxon Polarizability 25.72 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9894 Blood Brain Barrier + 0.9975 Caco-2 permeable + 0.6299 P-glycoprotein substrate Non-substrate 0.7157 P-glycoprotein inhibitor I Non-inhibitor 0.7193 P-glycoprotein inhibitor II Non-inhibitor 0.9348 Renal organic cation transporter Non-inhibitor 0.8176 CYP450 2C9 substrate Non-substrate 0.773 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6022 CYP450 1A2 substrate Non-inhibitor 0.7266 CYP450 2C9 inhibitor Non-inhibitor 0.7371 CYP450 2D6 inhibitor Non-inhibitor 0.9329 CYP450 2C19 inhibitor Non-inhibitor 0.7428 CYP450 3A4 inhibitor Non-inhibitor 0.8819 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8034 Ames test Non AMES toxic 0.5078 Carcinogenicity Non-carcinogens 0.9118 Biodegradation Not ready biodegradable 0.8977 Rat acute toxicity 1.9871 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9327 hERG inhibition (predictor II) Non-inhibitor 0.869
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 162.4072765 predictedDarkChem Lite v0.1.0 [M-H]- 162.5297765 predictedDarkChem Lite v0.1.0 [M-H]- 162.5079765 predictedDarkChem Lite v0.1.0 [M-H]- 150.75444 predictedDeepCCS 1.0 (2019) [M-H]- 162.4072765 predictedDarkChem Lite v0.1.0 [M-H]- 162.5297765 predictedDarkChem Lite v0.1.0 [M-H]- 162.5079765 predictedDarkChem Lite v0.1.0 [M-H]- 150.75444 predictedDeepCCS 1.0 (2019) [M+H]+ 162.9563765 predictedDarkChem Lite v0.1.0 [M+H]+ 163.2062765 predictedDarkChem Lite v0.1.0 [M+H]+ 163.1917765 predictedDarkChem Lite v0.1.0 [M+H]+ 153.15001 predictedDeepCCS 1.0 (2019) [M+H]+ 162.9563765 predictedDarkChem Lite v0.1.0 [M+H]+ 163.2062765 predictedDarkChem Lite v0.1.0 [M+H]+ 163.1917765 predictedDarkChem Lite v0.1.0 [M+H]+ 153.15001 predictedDeepCCS 1.0 (2019) [M+Na]+ 162.7183765 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.6331765 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.9390765 predictedDarkChem Lite v0.1.0 [M+Na]+ 159.07927 predictedDeepCCS 1.0 (2019) [M+Na]+ 162.7183765 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.6331765 predictedDarkChem Lite v0.1.0 [M+Na]+ 162.9390765 predictedDarkChem Lite v0.1.0 [M+Na]+ 159.07927 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- The specific voltage-sensitive sodium channel(s) responsible for oxcarbazepine's activity have not been elucidated.
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- 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...
Components:
References
- Thomas AM, Atkinson TJ: Old Friends With New Faces: Are Sodium Channel Blockers the Future of Adjunct Pain Medication Management? J Pain. 2018 Jan;19(1):1-9. doi: 10.1016/j.jpain.2017.08.001. Epub 2017 Aug 24. [Article]
- Shorvon S: Oxcarbazepine: a review. Seizure. 2000 Mar;9(2):75-9. doi: 10.1053/seiz.2000.0391. [Article]
- Schmidt D, Sachdeo R: Oxcarbazepine for Treatment of Partial Epilepsy: A Review and Recommendations for Clinical Use. Epilepsy Behav. 2000 Dec;1(6):396-405. doi: 10.1006/ebeh.2000.0126. [Article]
- DPD Approved Drugs: Oxcarbazepine [Link]
- DailyMed Label: TRILEPTAL (oxcarbazepine) film-coated tablets or suspension, for oral use [Link]
- MedSafe NZ: Oxcarbazepine [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Converts progesterone to its inactive form, 20-alpha-dihydroxyprogesterone (20-alpha-OHP). In the liver and intestine, may have a role in the transport of bile. May have a role in monitoring the in...
- Gene Name
- AKR1C1
- Uniprot ID
- Q04828
- Uniprot Name
- Aldo-keto reductase family 1 member C1
- Molecular Weight
- 36788.02 Da
References
- Malatkova P, Havlikova L, Wsol V: The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7. doi: 10.1016/j.cbi.2014.07.005. Epub 2014 Jul 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Works in concert with the 5-alpha/5-beta-steroid reductases to convert steroid hormones into the 3-alpha/5-alpha and 3-alpha/5-beta-tetrahydrosteroids. Catalyzes the inactivation of the most potent...
- Gene Name
- AKR1C2
- Uniprot ID
- P52895
- Uniprot Name
- Aldo-keto reductase family 1 member C2
- Molecular Weight
- 36734.97 Da
References
- Malatkova P, Havlikova L, Wsol V: The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7. doi: 10.1016/j.cbi.2014.07.005. Epub 2014 Jul 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
- Gene Name
- AKR1C3
- Uniprot ID
- P42330
- Uniprot Name
- Aldo-keto reductase family 1 member C3
- Molecular Weight
- 36852.89 Da
References
- Malatkova P, Havlikova L, Wsol V: The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7. doi: 10.1016/j.cbi.2014.07.005. Epub 2014 Jul 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinal dehydrogenase activity
- Specific Function
- Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid...
- Gene Name
- AKR1C4
- Uniprot ID
- P17516
- Uniprot Name
- Aldo-keto reductase family 1 member C4
- Molecular Weight
- 37066.52 Da
References
- Malatkova P, Havlikova L, Wsol V: The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7. doi: 10.1016/j.cbi.2014.07.005. Epub 2014 Jul 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Prostaglandin-e2 9-reductase activity
- Specific Function
- NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. ...
- Gene Name
- CBR1
- Uniprot ID
- P16152
- Uniprot Name
- Carbonyl reductase [NADPH] 1
- Molecular Weight
- 30374.73 Da
References
- Malatkova P, Havlikova L, Wsol V: The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7. doi: 10.1016/j.cbi.2014.07.005. Epub 2014 Jul 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Nadph binding
- Specific Function
- Has low NADPH-dependent oxidoreductase activity towards 4-benzoylpyridine and menadione (in vitro).
- Gene Name
- CBR3
- Uniprot ID
- O75828
- Uniprot Name
- Carbonyl reductase [NADPH] 3
- Molecular Weight
- 30849.97 Da
References
- Malatkova P, Havlikova L, Wsol V: The role of carbonyl reducing enzymes in oxcarbazepine in vitro metabolism in man. Chem Biol Interact. 2014 Sep 5;220:241-7. doi: 10.1016/j.cbi.2014.07.005. Epub 2014 Jul 22. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase 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 im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- General Function
- Vitamin d3 25-hydroxylase 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- InhibitorInducer
- General Function
- Oxygen binding
- 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 un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Antunes NJ, van Dijkman SC, Lanchote VL, Wichert-Ana L, Coelho EB, Alexandre Junior V, Takayanagui OM, Tozatto E, van Hasselt JGC, Della Pasqua O: Population pharmacokinetics of oxcarbazepine and its metabolite 10-hydroxycarbazepine in healthy subjects. Eur J Pharm Sci. 2017 Nov 15;109S:S116-S123. doi: 10.1016/j.ejps.2017.05.034. Epub 2017 May 17. [Article]
- Zhang C, Zuo Z, Kwan P, Baum L: In vitro transport profile of carbamazepine, oxcarbazepine, eslicarbazepine acetate, and their active metabolites by human P-glycoprotein. Epilepsia. 2011 Oct;52(10):1894-904. doi: 10.1111/j.1528-1167.2011.03140.x. Epub 2011 Jun 21. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55