Identification

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Name
Oxcarbazepine
Accession Number
DB00776  (APRD01308)
Type
Small Molecule
Groups
Approved
Description

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 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

Structure
Thumb
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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
OxcarbazepineTablet300 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
OxcarbazepineTablet150 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
OxcarbazepineTablet600 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
Oxtellar XRTablet300 mg/1OralSupernus Pharmaceuticals, Inc.2013-01-17Not applicableUs
Oxtellar XRTablet150 mg/1OralSupernus Pharmaceuticals, Inc.2013-01-17Not applicableUs
Oxtellar XRTablet600 mg/1OralSupernus Pharmaceuticals, Inc.2013-01-17Not applicableUs17772 0123 01 nlmimage10 bf3cdfd6
TrileptalTablet, film coated150 mg/1OralPhysicians Total Care, Inc.2003-07-07Not applicableUs00078 0456 05 nlmimage10 d5126a83
TrileptalTablet, film coated150 mg/1OralNovartis Pharmaceuticals Corporation2000-01-30Not applicableUs0078 045620180814 13942 7sk4b8
TrileptalTablet, film coated300 mg/1OralREMEDYREPACK INC.2018-08-07Not applicableUs
TrileptalTablet, film coated600 mg/1OralNovartis Pharmaceuticals Corporation2006-05-102006-05-10Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-oxcarbazepineTabletOralApotex Corporation2006-08-01Not applicableCanada
Apo-oxcarbazepineTabletOralApotex Corporation2006-08-01Not applicableCanada
Apo-oxcarbazepineTabletOralApotex Corporation2006-08-01Not applicableCanada
Jamp-oxcarbazepineTabletOralJamp Pharma Corporation2015-06-08Not applicableCanada
Jamp-oxcarbazepineTabletOralJamp Pharma Corporation2015-06-08Not applicableCanada
Jamp-oxcarbazepineTabletOralJamp Pharma Corporation2015-06-08Not applicableCanada
Novo-oxcarbazepineTabletOralNovopharm LimitedNot applicableNot applicableCanada
Novo-oxcarbazepineTabletOralNovopharm LimitedNot applicableNot applicableCanada
Novo-oxcarbazepineTabletOralNovopharm LimitedNot applicableNot applicableCanada
OxcarbazepineSuspension300 mg/5mLOralWest-Ward Pharmaceuticals Corp.2012-10-03Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands
Actinium / Barzepin / Carbox / Deprectal / Lonazet / Oxalepsy / Oxetol / Oxpin / Oxrate / Oxypine / Pharozepine / Prolepsi / Timox / Trexapin / Trileptin
Categories
UNII
VZI5B1W380
CAS number
28721-07-5
Weight
Average: 252.268
Monoisotopic: 252.089877638
Chemical Formula
C15H12N2O2
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

Pharmacology

Indication

In the United States, oxcarbazepine is indicated as monotherapy in the treatment of partial-onset seizures in patients 4 years of age and older, and as adjunctive therapy in the treatment of partial-onset seizures in patients 2 years of age and older.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

Associated Conditions
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-A3101 and/or HLA-B1502 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

TargetActionsOrganism
USodium channel protein
inhibitor
Humans
Additional Data Available
Adverse Effects

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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 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.10,11,7 Only 10% of an administered dose of oxcarbazepine will remain as either the parent drug or glucuronide conjugates of the parent drug.2

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

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

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Carbamazepine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
HLA class I histocompatibility antigen, B-15 alpha chainHLA-B*15:02Not AvailableHLA-B*15ADR Directly StudiedPatients 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
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.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Oxcarbazepine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Oxcarbazepine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Oxcarbazepine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineOxcarbazepine may increase the excretion rate of 3-isobutyl-1-methyl-7H-xanthine which could result in a lower serum level and potentially a reduction in efficacy.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Oxcarbazepine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Oxcarbazepine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Oxcarbazepine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Oxcarbazepine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineOxcarbazepine may increase the excretion rate of 6-O-benzylguanine which could result in a lower serum level and potentially a reduction in efficacy.
7-DeazaguanineOxcarbazepine may increase the excretion rate of 7-Deazaguanine which could result in a lower serum level and potentially a reduction in efficacy.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
  • Take without regard to meals. Avoid alcohol.

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
  1. 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. [PubMed:25063510]
  2. 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. [PubMed:28528287]
  3. 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. [PubMed:21692796]
  4. 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. [PubMed:28842369]
  5. Shorvon S: Oxcarbazepine: a review. Seizure. 2000 Mar;9(2):75-9. doi: 10.1053/seiz.2000.0391. [PubMed:10845729]
  6. 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. [PubMed:12737829]
  7. 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. [PubMed:3765657]
  8. Abou-Khalil BW: Antiepileptic Drugs. Continuum (Minneap Minn). 2016 Feb;22(1 Epilepsy):132-56. doi: 10.1212/CON.0000000000000289. [PubMed:26844734]
  9. 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. [PubMed:15638774]
  10. FDA Approved Drugs: Oxcarbazepine [Link]
  11. DPD Approved Drugs: Oxcarbazepine [Link]
  12. MedSafe NZ: Oxcarbazepine [Link]
  13. CaymenChem: Oxcarbazepine MSDS [Link]
  14. FDA Approved Drug Products: Oxtellar XR extended-release oral tablets [Link]
External Links
Human Metabolome Database
HMDB0014914
KEGG Drug
D00533
KEGG Compound
C07492
PubChem Compound
34312
PubChem Substance
46507580
ChemSpider
31608
BindingDB
34179
ChEBI
7824
ChEMBL
CHEMBL1068
Therapeutic Targets Database
DAP000528
PharmGKB
PA450732
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Oxcarbazepine
ATC Codes
N03AF02 — Oxcarbazepine
AHFS Codes
  • 28:12.92 — Miscellaneous Anticonvulsants

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers2
1CompletedBasic ScienceEpilepsies1
1CompletedTreatmentEpilepsies2
1CompletedTreatmentEpilepsies / Epilepsy, Localization Related1
1CompletedTreatmentEpilepsy, Localization Related1
1CompletedTreatmentSeizures2
1TerminatedSupportive CareMalignancies1
2CompletedTreatmentDisseminated Sclerosis1
2, 3CompletedTreatmentPartial-Onset Seizures1
2, 3CompletedTreatmentSchizophrenic Disorders1
3Active Not RecruitingTreatmentAdverse Effects / Epilepsy, Localization Related1
3CompletedTreatmentAgitation Aggression in Dementia1
3CompletedTreatmentEpilepsies2
3CompletedTreatmentEpilepsies / Epilepsy, Localization Related1
3CompletedTreatmentEpilepsy, Localization Related2
3Not Yet RecruitingTreatmentPediatric Chronic Neuropathic Pain1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3TerminatedTreatmentEpilepsy, Localization Related1
4CompletedTreatmentBipolar Disorder (BD)2
4CompletedTreatmentBronchial Asthma1
4CompletedTreatmentEpilepsies1
4CompletedTreatmentEpilepsy, Partial Seizures2
4CompletedTreatmentMetabolic Clearance Rate1
4CompletedTreatmentNeuralgia / Spinal Cord Injuries (SCI)1
4CompletedTreatmentOppositional Defiant Disorder1
4CompletedTreatmentPeripheral Nerve Injury (PNI) / Polyneuropathies / Postherpetic Neuralgia1
4CompletedTreatmentSeizures, Focal1
4Enrolling by InvitationTreatmentDepression, Bipolar / Measure-based Guidance / Treatment Effectiveness1
4Not Yet RecruitingTreatmentBenign Childhood Epilepsy With Centrotemporal Spikes1
4Not Yet RecruitingTreatmentEpilepsy, Localization Related1
4RecruitingTreatmentBipolar Disorder (BD)1
4WithdrawnTreatmentTrigeminal Neuralgia (TN)1
Not AvailableCompletedNot AvailableEpilepsies1
Not AvailableCompletedNot AvailableHealthy Volunteers2
Not AvailableCompletedTreatmentAutism, Early Infantile1
Not AvailableCompletedTreatmentEpilepsies / Seizures3
Not AvailableEnrolling by InvitationNot AvailableBipolar Disorder (BD)1
Not AvailableRecruitingNot AvailableEpilepsies1

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
FormRouteStrength
SuspensionOral300 mg/5mL
SuspensionOral60 mg/1mL
TabletOral150 mg/1
TabletOral150 mg
TabletOral300 mg/1
TabletOral300 mg
TabletOral600 mg/1
TabletOral600 mg
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral600 mg/1
TabletOral
SuspensionOral
Prices
Unit descriptionCostUnit
OXcarbazepine 300 mg/5ml Suspension 250ml Bottle162.03USD bottle
Trileptal 600 mg tablet7.05USD tablet
Oxcarbazepine 600 mg tablet5.06USD tablet
Trileptal 300 mg tablet3.84USD tablet
Oxcarbazepine 300 mg tablet2.75USD tablet
Trileptal 150 mg tablet2.1USD tablet
Oxcarbazepine 150 mg tablet1.53USD tablet
Trileptal 300 mg/5ml Suspension0.79USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2277791No2008-11-182018-02-12Canada
US7037525Yes2006-05-022018-08-12Us
US8119148Yes2012-02-212021-06-19Us
US7910131No2011-03-222027-04-13Us
US9119791No2015-09-012027-04-13Us
US8821930No2014-09-022027-04-13Us
US8617600No2013-12-312027-04-13Us
US7722898No2010-05-252027-04-13Us
US9370525No2016-06-212027-04-13Us
US9351975No2016-05-312027-04-13Us
US9855278No2018-01-022027-04-13Us
US10220042No2019-03-052027-04-13Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
logP1.5Not Available
pKa13.73Canadian label
Predicted Properties
PropertyValueSource
Water Solubility0.16 mg/mLALOGPS
logP1.76ALOGPS
logP1.82ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.18ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.4 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.56 m3·mol-1ChemAxon
Polarizability25.72 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9894
Blood Brain Barrier+0.9975
Caco-2 permeable+0.6299
P-glycoprotein substrateNon-substrate0.7157
P-glycoprotein inhibitor INon-inhibitor0.7193
P-glycoprotein inhibitor IINon-inhibitor0.9348
Renal organic cation transporterNon-inhibitor0.8176
CYP450 2C9 substrateNon-substrate0.773
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6022
CYP450 1A2 substrateNon-inhibitor0.7266
CYP450 2C9 inhibitorNon-inhibitor0.7371
CYP450 2D6 inhibitorNon-inhibitor0.9329
CYP450 2C19 inhibitorNon-inhibitor0.7428
CYP450 3A4 inhibitorNon-inhibitor0.8819
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8034
Ames testNon AMES toxic0.5078
CarcinogenicityNon-carcinogens0.9118
BiodegradationNot ready biodegradable0.8977
Rat acute toxicity1.9871 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9327
hERG inhibition (predictor II)Non-inhibitor0.869
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0pb9-0090000000-46d01e1171f998679d03
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f8i-1790000000-cd62672e7fa7c39f0be1
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0kar-0690000000-cbc95a31913165d691a7
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-2910000000-d1242af6b8148ffac3a9

Taxonomy

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
Dibenzazepine / Aryl ketone / Aryl alkyl ketone / Azepine / Benzenoid / Vinylogous amide / Isourea / Ketone / Carboximidic acid derivative / Azacycle
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cyclic ketone, dibenzoazepine (CHEBI:7824)

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
  1. 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. [PubMed:28842369]
  2. Shorvon S: Oxcarbazepine: a review. Seizure. 2000 Mar;9(2):75-9. doi: 10.1053/seiz.2000.0391. [PubMed:10845729]
  3. 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. [PubMed:12737829]
  4. DPD Approved Drugs: Oxcarbazepine [Link]
  5. FDA Approved Drugs: Oxcarbazepine [Link]
  6. 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
  1. 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. [PubMed:25063510]
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
  1. 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. [PubMed:25063510]
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
  1. 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. [PubMed:25063510]
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
  1. 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. [PubMed:25063510]
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
  1. 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. [PubMed:25063510]
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
  1. 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. [PubMed:25063510]
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
  1. Flockhart Table of Drug Interactions [Link]
  2. FDA Approved Drugs: Oxcarbazepine [Link]
  3. DPD Approved Drugs: Oxcarbazepine [Link]
  4. MedSafe NZ: Oxcarbazepine [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
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
  1. FDA Approved Drugs: Oxcarbazepine [Link]
  2. DPD Approved Drugs: Oxcarbazepine [Link]
  3. MedSafe NZ: Oxcarbazepine [Link]
  4. Trileptal (Oxcarbazepine) FDA Label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Inducer
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
  1. Flockhart Table of Drug Interactions [Link]
  2. FDA Approved Drugs: Oxcarbazepine [Link]
  3. DPD Approved Drugs: Oxcarbazepine [Link]
  4. MedSafe NZ: Oxcarbazepine [Link]

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
  1. FDA Approved Drugs: Oxcarbazepine [Link]
  2. DPD Approved Drugs: Oxcarbazepine [Link]
  3. MedSafe NZ: Oxcarbazepine [Link]

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
  1. 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. [PubMed:28528287]
  2. 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. [PubMed:21692796]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2019 15:54