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Identification
NameOxcarbazepine
Accession NumberDB00776  (APRD01308)
TypeSmall Molecule
GroupsApproved
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
Thumb
Synonyms
10,11-Dihydro-10-oxo-5H-dibenz(b,F)azepine-5-carboxamide
OCBZ
Oxcarbamazepine
Oxcarbazepina
Oxcarbazepine
Oxcarbazepinum
External Identifiers
  • GP 47680
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jamp-oxcarbazepineTablet300 mgOralJamp Pharma Corporation2015-06-08Not applicableCanada
Jamp-oxcarbazepineTablet600 mgOralJamp Pharma Corporation2015-06-08Not applicableCanada
Jamp-oxcarbazepineTablet150 mgOralJamp Pharma Corporation2015-06-08Not applicableCanada
Novo-oxcarbazepineTablet600 mgOralNovopharm LimitedNot applicableNot applicableCanada
Novo-oxcarbazepineTablet150 mgOralNovopharm LimitedNot applicableNot applicableCanada
Novo-oxcarbazepineTablet300 mgOralNovopharm LimitedNot applicableNot applicableCanada
OxcarbazepineTablet600 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
OxcarbazepineSuspension60 mg/mLOralSandoz Inc2001-05-30Not applicableUs
OxcarbazepineTablet150 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
OxcarbazepineTablet300 mgOralJubilant Generics LimitedNot applicableNot applicableCanada
Oxtellar XRTablet600 mg/1OralSupernus2013-01-17Not applicableUs
Oxtellar XRTablet150 mg/1OralSupernus2013-01-17Not applicableUs
Oxtellar XRTablet300 mg/1OralSupernus2013-01-17Not applicableUs
TrileptalTablet, film coated300 mg/1OralNovartis Pharmaceuticals Corporation2000-01-30Not applicableUs
TrileptalTablet, film coated300 mg/1OralPd Rx Pharmaceuticals, Inc.2000-01-30Not applicableUs
TrileptalTablet, film coated150 mg/1OralPhysicians Total Care, Inc.2003-07-07Not applicableUs
TrileptalSuspension60 mg/mLOralNovartis Pharmaceuticals Corporation2001-05-30Not applicableUs
TrileptalTablet, film coated300 mg/1OralPhysicians Total Care, Inc.2003-07-02Not applicableUs
TrileptalTablet, film coated150 mg/1OralNovartis Pharmaceuticals Corporation2000-01-30Not applicableUs
TrileptalTablet, film coated600 mg/1OralNovartis Pharmaceuticals Corporation2000-01-30Not applicableUs
Trileptal 150 mgTablet150 mgOralNovartis Pharmaceuticals Canada Inc2002-04-01Not applicableCanada
Trileptal 300 mgTablet300 mgOralNovartis Pharmaceuticals Canada Inc2002-04-01Not applicableCanada
Trileptal 600 mgTablet600 mgOralNovartis Pharmaceuticals Canada Inc2002-04-01Not applicableCanada
Trileptal Oral SuspensionSuspension60 mgOralNovartis Pharmaceuticals Canada Inc2002-09-05Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-oxcarbazepineTablet300 mgOralApotex Inc2006-08-01Not applicableCanada
Apo-oxcarbazepineTablet600 mgOralApotex Inc2006-08-01Not applicableCanada
Apo-oxcarbazepineTablet150 mgOralApotex Inc2006-08-01Not applicableCanada
OxcarbazepineTablet, film coated300 mg/1OralAidarex Pharmaceuticals LLC2007-10-09Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralGolden State Medical Supply2013-04-11Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralBreckenridge Pharmaceutical, Inc.2008-01-11Not applicableUs
OxcarbazepineTablet, film coated150 mg/1Oralbryant ranch prepack2008-01-11Not applicableUs
OxcarbazepineTablet300 mg/1OralWest Ward Pharmaceticals Corp.2007-10-09Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-10-09Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralCardinal Health2008-01-11Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralREMEDYREPACK INC.2011-05-202016-11-30Us
OxcarbazepineTablet, film coated150 mg/1OralAmerican Health Packaging2007-11-092016-10-25Us
OxcarbazepineTablet, film coated150 mg/1OralGlenmark Pharmaceuticals Inc., Usa2007-10-09Not applicableUs
OxcarbazepineTablet300 mg/1OralREMEDYREPACK INC.2009-12-09Not applicableUs
OxcarbazepineTablet150 mg/1OralCardinal Health2007-10-09Not applicableUs
OxcarbazepineTablet150 mg/1OralREMEDYREPACK INC.2010-11-20Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralApotex Corp.2008-04-09Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralREMEDYREPACK INC.2014-06-27Not applicableUs
OxcarbazepineSuspension300 mg/5mLOralAmneal Pharmaceuticals of New York, LLC2012-06-04Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralRebel Distributors Corp2007-10-09Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralJUBILANT CADISTA PHARMACEUTICALS, INC.2015-01-15Not applicableUs
OxcarbazepineTablet600 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2007-11-15Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralSun Pharmaceutical Industries Limited2007-10-09Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralAidarex Pharmaceuticals LLC2007-10-09Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralGolden State Medical Supply, Inc.2008-04-09Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralREMEDYREPACK INC.2013-02-212016-04-05Us
OxcarbazepineTablet, film coated300 mg/1Oralbryant ranch prepack2007-10-09Not applicableUs
OxcarbazepineTablet600 mg/1OralWest Ward Pharmaceticals Corp.2007-10-09Not applicableUs
OxcarbazepineTablet300 mg/1OralREMEDYREPACK INC.2012-01-31Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-10-09Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralClinical Solutions Wholesale, Llc2008-01-11Not applicableUs
OxcarbazepineTablet600 mg/1OralREMEDYREPACK INC.2011-08-222016-11-09Us
OxcarbazepineTablet, film coated300 mg/1OralAmerican Health Packaging2007-11-092016-10-25Us
OxcarbazepineTablet, film coated300 mg/1OralGlenmark Pharmaceuticals Inc., Usa2007-10-09Not applicableUs
OxcarbazepineTablet300 mg/1OralCardinal Health2007-10-09Not applicableUs
OxcarbazepineTablet150 mg/1OralREMEDYREPACK INC.2011-04-082016-10-13Us
OxcarbazepineTablet, film coated300 mg/1OralApotex Corp.2008-04-09Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralPhysicians Total Care, Inc.2007-11-14Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralAmerican Health Packaging2014-11-13Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralRebel Distributors Corp2007-10-09Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralGolden State Medical Supply2013-04-11Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralBreckenridge Pharmaceutical, Inc.2008-01-11Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralSun Pharmaceutical Industries Limited2007-10-09Not applicableUs
OxcarbazepineSuspension300 mg/5mLOralWest Ward Pharmaceuticals Corp.2012-10-03Not applicableUs
OxcarbazepineSuspension300 mg/5mLOralAv Kare, Inc.2014-01-232016-04-05Us
OxcarbazepineTablet, film coated300 mg/1OralGolden State Medical Supply, Inc.2008-04-09Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralREMEDYREPACK INC.2013-12-31Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralTYA Pharmaceuticals2007-10-09Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralGlenmark Pharmaceuticals Inc., Usa2007-10-09Not applicableUs
OxcarbazepineTablet150 mg/1OralREMEDYREPACK INC.2011-09-27Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-10-09Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralJUBILANT CADISTA PHARMACEUTICALS, INC.2015-01-15Not applicableUs
OxcarbazepineTablet150 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2007-11-15Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralAmerican Health Packaging2007-11-092016-06-30Us
OxcarbazepineTablet, film coated150 mg/1OralREMEDYREPACK INC.2008-11-03Not applicableUs
OxcarbazepineTablet600 mg/1OralREMEDYREPACK INC.2011-08-182016-11-08Us
OxcarbazepineTablet, film coated600 mg/1OralApotex Corp.2008-04-09Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralPhysicians Total Care, Inc.2009-10-16Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralAmerican Health Packaging2014-11-13Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralBreckenridge Pharmaceutical, Inc.2008-01-11Not applicableUs
OxcarbazepineSuspension60 mg/mLOralRanbaxy Pharmaceuticals Inc.2009-12-14Not applicableUs
OxcarbazepineTablet150 mg/1OralWest Ward Pharmaceticals Corp.2007-10-09Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralAidarex Pharmaceuticals LLC2007-10-09Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralGolden State Medical Supply2013-04-11Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralREMEDYREPACK INC.2010-10-12Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralMedsource Pharmaceuticals2007-10-09Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralGolden State Medical Supply, Inc.2008-04-09Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralREMEDYREPACK INC.2014-03-12Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralTYA Pharmaceuticals2008-01-11Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralREMEDYREPACK INC.2016-11-17Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralRebel Distributors Corp2007-10-09Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralJUBILANT CADISTA PHARMACEUTICALS, INC.2015-01-15Not applicableUs
OxcarbazepineTablet300 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2007-11-15Not applicableUs
OxcarbazepineTablet, film coated150 mg/1OralSun Pharmaceutical Industries Limited2007-10-09Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralREMEDYREPACK INC.2015-03-20Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralPhysicians Total Care, Inc.2010-06-23Not applicableUs
OxcarbazepineTablet, film coated600 mg/1OralAmerican Health Packaging2014-11-13Not applicableUs
OxcarbazepineTablet, film coated300 mg/1OralREMEDYREPACK INC.2011-05-202016-11-29Us
TrileptalTablet300 mg/1OralDIRECT RX2016-05-25Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Actinium Not Available
BarzepinNot Available
CarboxNot Available
DeprectalNot Available
LonazetNot Available
OxalepsyNot Available
OxetolNot Available
OxpinNot Available
OxrateNot Available
Oxypine Not Available
PharozepineNot Available
ProlepsiNot Available
Timox Not Available
TrexapinNot Available
Trileptin Not Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIVZI5B1W380
CAS number28721-07-5
WeightAverage: 252.268
Monoisotopic: 252.089877638
Chemical FormulaC15H12N2O2
InChI KeyCTRLABGOLIVAIY-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[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide
SMILES
NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C12
Pharmacology
IndicationFor 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.
Structured Indications
PharmacodynamicsOxcarbazepine 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 the same conditions.
Mechanism of actionThe 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium channel protein type 5 subunit alphaProteinyes
inhibitor
HumanQ14524 details
Related Articles
AbsorptionCompletely 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.
Volume of distribution
  • 49 L
Protein bindingApproximately 40% of the active 10-monohydroxy metabolite (MHD) is bound to serum proteins, predominantly to albumin. Neither oxcarbazepine nor its MHD binds with alpha-1-acid glycoprotein.
Metabolism

Oxcarbazepine 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.

SubstrateEnzymesProduct
Oxcarbazepine
Not Available
MHDDetails
Oxcarbazepine
Not Available
10-HydroxycarbazepineDetails
10-Hydroxycarbazepine
Not Available
10,11-DihydroxycarbamazepineDetails
Route of eliminationOxcarbazepine 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 lifeThe 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.
ClearanceNot Available
ToxicityIsolated cases of overdose with oxcarbazepine have been reported. The maximum dose taken was approximately 24,000 mg. All patients recovered with symptomatic treatment.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Carbamazepine Metabolism PathwayDrug metabolismSMP00634
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Oxcarbazepine.Approved
CarbamazepineThe serum concentration of the active metabolites of Oxcarbazepine can be reduced when Oxcarbazepine is used in combination with Carbamazepine resulting in a loss in efficacy.Approved, Investigational
ChlorothiazideThe risk or severity of adverse effects can be increased when Chlorothiazide is combined with Oxcarbazepine.Approved, Vet Approved
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Oxcarbazepine.Withdrawn
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Oxcarbazepine.Approved
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Oxcarbazepine.Approved
CobicistatThe serum concentration of Cobicistat can be decreased when it is combined with Oxcarbazepine.Approved
Conjugated Equine EstrogensThe serum concentration of Conjugated Equine Estrogens can be decreased when it is combined with Oxcarbazepine.Approved
DesogestrelThe serum concentration of Desogestrel can be decreased when it is combined with Oxcarbazepine.Approved
DienestrolThe serum concentration of Dienestrol can be decreased when it is combined with Oxcarbazepine.Approved
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Oxcarbazepine.Approved
DiethylstilbestrolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Oxcarbazepine.Approved
DolutegravirThe serum concentration of Dolutegravir can be decreased when it is combined with Oxcarbazepine.Approved
DrospirenoneThe serum concentration of Drospirenone can be decreased when it is combined with Oxcarbazepine.Approved
ElvitegravirThe serum concentration of Elvitegravir can be decreased when it is combined with Oxcarbazepine.Approved
Eslicarbazepine acetateThe risk or severity of adverse effects can be increased when Eslicarbazepine acetate is combined with Oxcarbazepine.Approved
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Oxcarbazepine.Approved, Investigational, Vet Approved
EstramustineThe serum concentration of Estramustine can be decreased when it is combined with Oxcarbazepine.Approved
Estrogens, esterifiedThe serum concentration of Estrogens, esterified can be decreased when it is combined with Oxcarbazepine.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be decreased when it is combined with Oxcarbazepine.Approved
EthanolEthanol may increase the central nervous system depressant (CNS depressant) activities of Oxcarbazepine.Approved
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Oxcarbazepine.Approved
Ethynodiol diacetateThe serum concentration of Ethynodiol diacetate can be decreased when it is combined with Oxcarbazepine.Approved
EtonogestrelThe serum concentration of Etonogestrel can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
FosphenytoinThe serum concentration of the active metabolites of Oxcarbazepine can be reduced when Oxcarbazepine is used in combination with Fosphenytoin resulting in a loss in efficacy.Approved
GestodeneThe serum concentration of Gestodene can be decreased when it is combined with Oxcarbazepine.Approved
HexestrolThe serum concentration of Hexestrol can be decreased when it is combined with Oxcarbazepine.Withdrawn
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Oxcarbazepine.Approved, Vet Approved
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Oxcarbazepine.Approved, Illicit
HydroflumethiazideThe risk or severity of adverse effects can be increased when Hydroflumethiazide is combined with Oxcarbazepine.Approved
IndapamideThe risk or severity of adverse effects can be increased when Indapamide is combined with Oxcarbazepine.Approved
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Oxcarbazepine.Approved
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
LynestrenolThe serum concentration of Lynestrenol can be decreased when it is combined with Oxcarbazepine.Investigational
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone acetate can be decreased when it is combined with Oxcarbazepine.Approved, Investigational
MefloquineThe therapeutic efficacy of Oxcarbazepine can be decreased when used in combination with Mefloquine.Approved
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Oxcarbazepine.Approved
MethallenestrilThe serum concentration of Methallenestril can be decreased when it is combined with Oxcarbazepine.Experimental
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Oxcarbazepine.Approved
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Oxcarbazepine.Approved
MianserinThe therapeutic efficacy of Oxcarbazepine can be decreased when used in combination with Mianserin.Approved
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Oxcarbazepine.Approved
NorelgestrominThe serum concentration of Norelgestromin can be decreased when it is combined with Oxcarbazepine.Approved
NorgestimateThe serum concentration of Norgestimate can be decreased when it is combined with Oxcarbazepine.Approved
NorgestrelThe serum concentration of Norgestrel can be decreased when it is combined with Oxcarbazepine.Approved
OrlistatThe serum concentration of Oxcarbazepine can be decreased when it is combined with Orlistat.Approved, Investigational
PerampanelThe serum concentration of Oxcarbazepine can be increased when it is combined with Perampanel.Approved
PhenobarbitalThe serum concentration of the active metabolites of Oxcarbazepine can be reduced when Oxcarbazepine is used in combination with Phenobarbital resulting in a loss in efficacy.Approved
PhenytoinThe serum concentration of the active metabolites of Oxcarbazepine can be reduced when Oxcarbazepine is used in combination with Phenytoin resulting in a loss in efficacy.Approved, Vet Approved
PolythiazideThe risk or severity of adverse effects can be increased when Polythiazide is combined with Oxcarbazepine.Approved
QuinethazoneThe risk or severity of adverse effects can be increased when Quinethazone is combined with Oxcarbazepine.Approved
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Oxcarbazepine.Approved
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Oxcarbazepine.Approved
SelegilineOxcarbazepine may increase the serotonergic activities of Selegiline.Approved, Investigational, Vet Approved
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Oxcarbazepine.Approved
Synthetic Conjugated Estrogens, AThe serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Oxcarbazepine.Approved
TrichlormethiazideThe risk or severity of adverse effects can be increased when Trichlormethiazide is combined with Oxcarbazepine.Approved, Vet Approved
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Oxcarbazepine.Approved
Valproic AcidThe serum concentration of Oxcarbazepine can be decreased when it is combined with Valproic Acid.Approved, Investigational
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. 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 ]
External Links
ATC CodesN03AF02
AHFS Codes
  • 28:12.92
PDB EntriesNot Available
FDA labelDownload (195 KB)
MSDSNot Available
ADMET
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 )
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
Dosage forms
FormRouteStrength
SuspensionOral300 mg/5mL
TabletOral150 mg/1
TabletOral300 mg/1
TabletOral600 mg/1
SuspensionOral60 mg/mL
Tablet, film coatedOral150 mg/1
Tablet, film coatedOral300 mg/1
Tablet, film coatedOral600 mg/1
TabletOral150 mg
TabletOral300 mg
TabletOral600 mg
SuspensionOral60 mg
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)
CA2277791 No2008-11-182018-02-12Canada
US7037525 Yes1998-08-122018-08-12Us
US7722898 No2007-04-132027-04-13Us
US7910131 No2007-04-132027-04-13Us
US8119148 Yes2001-06-192021-06-19Us
US8617600 No2007-04-132027-04-13Us
US8821930 No2007-04-132027-04-13Us
US9119791 No2007-04-132027-04-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point215.5 °CPhysProp
water solubility308 mg/L at 25 °C (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))Not Available
logP1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.56 m3·mol-1ChemAxon
Polarizability25.72 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
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
  • Aryl alkyl ketone
  • Aryl ketone
  • Azepine
  • Benzenoid
  • Vinylogous amide
  • Urea
  • Tertiary amine
  • Ketone
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity involved in sa node cell action potential
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 respon...
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
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 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
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 ]

Carriers

Kind
Protein
Organism
Human
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 04, 2016 04:00