Oxcarbazepine - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)Enzymes (3)Carriers (1)

Targets (1)Enzymes (3)Carriers (1)Biointeractions (4)

Identification

Name

Oxcarbazepine

Accession Number

DB00776 (APRD01308)

Type

Small Molecule

Groups

Approved

Description

Oxcarbazepine 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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 Ingredients

Not Available

Product Images

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Jamp-oxcarbazepine	Tablet	300 mg	Oral	Jamp Pharma Corporation	2015-06-08	Not applicable	Canada
Jamp-oxcarbazepine	Tablet	600 mg	Oral	Jamp Pharma Corporation	2015-06-08	Not applicable	Canada
Jamp-oxcarbazepine	Tablet	150 mg	Oral	Jamp Pharma Corporation	2015-06-08	Not applicable	Canada
Novo-oxcarbazepine	Tablet	600 mg	Oral	Novopharm Limited	Not applicable	Not applicable	Canada
Novo-oxcarbazepine	Tablet	300 mg	Oral	Novopharm Limited	Not applicable	Not applicable	Canada
Novo-oxcarbazepine	Tablet	150 mg	Oral	Novopharm Limited	Not applicable	Not applicable	Canada
Oxcarbazepine	Suspension	60 mg/mL	Oral	Sandoz	2001-05-30	Not applicable	US
Oxcarbazepine	Tablet	600 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable	Canada
Oxcarbazepine	Tablet	150 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	600 mg/1	Oral	Supernus	2013-01-17	Not applicable	US
Oxtellar XR	Tablet	150 mg/1	Oral	Supernus	2013-01-17	Not applicable	US
Oxtellar XR	Tablet	300 mg/1	Oral	Supernus	2013-01-17	Not applicable	US
Trileptal	Tablet, film coated	300 mg/1	Oral	Novartis	2000-01-30	Not applicable	US
Trileptal	Tablet, film coated	600 mg/1	Oral	Novartis	2000-01-30	Not applicable	US
Trileptal	Suspension	60 mg/mL	Oral	Novartis	2001-05-30	Not applicable	US
Trileptal	Tablet, film coated	300 mg/1	Oral	Pd Rx Pharmaceuticals, Inc.	2000-01-30	Not applicable	US
Trileptal	Tablet, film coated	150 mg/1	Oral	Physicians Total Care, Inc.	2003-07-07	Not applicable	US
Trileptal	Tablet, film coated	150 mg/1	Oral	Novartis	2000-01-30	Not applicable	US
Trileptal	Tablet, film coated	300 mg/1	Oral	Physicians Total Care, Inc.	2003-07-02	Not applicable	US
Trileptal 150 mg	Tablet	150 mg	Oral	Novartis	2002-04-01	Not applicable	Canada
Trileptal 300 mg	Tablet	300 mg	Oral	Novartis	2002-04-01	Not applicable	Canada
Trileptal 600 mg	Tablet	600 mg	Oral	Novartis	2002-04-01	Not applicable	Canada
Trileptal Oral Suspension	Suspension	60 mg	Oral	Novartis	2002-09-05	Not applicable	Canada

Approved Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-oxcarbazepine	Tablet	600 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	300 mg	Oral	Apotex Corporation	2006-08-01	Not applicable	Canada
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Ncs Health Care Of Ky, Inc Dba Vangard Labs	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet	150 mg/1	Oral	Remedy Repack	2011-04-08	2016-10-13	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Remedy Repack	2014-03-12	2016-12-21	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Golden State Medical Supply	2008-04-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	TYA Pharmaceuticals	2008-01-11	Not applicable	US
Oxcarbazepine	Tablet	150 mg/1	Oral	Cardinal Health	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet	300 mg/1	Oral	A S Medication Solutions	2007-10-09	2017-06-20	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Aidarex Pharmaceuticals LLC	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Breckenridge Pharmaceutical, Inc.	2008-01-11	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Jubilant Cadista Pharmaceuticals Inc.	2015-01-15	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Amerincan Health Packaging	2007-11-09	2016-06-30	US
Oxcarbazepine	Tablet	300 mg/1	Oral	West Ward Pharmaceutical	2007-10-09	Not applicable	US
Oxcarbazepine	Suspension	300 mg/5mL	Oral	Amneal Pharmaceuticals	2012-06-04	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Sun Pharmaceutical Industries Limited	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Amerincan Health Packaging	2014-11-13	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	bryant ranch prepack	2008-01-11	Not applicable	US
Oxcarbazepine	Tablet	150 mg/1	Oral	Remedy Repack	2010-11-20	2017-03-02	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Remedy Repack	2013-02-21	2016-04-05	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Golden State Medical Supply	2013-04-11	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	TYA Pharmaceuticals	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Remedy Repack	2010-10-12	Not applicable	US
Oxcarbazepine	Tablet	300 mg/1	Oral	Remedy Repack	2017-01-10	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Rebel Distributors	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Remedy Repack	2011-05-20	2016-11-30	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Physicians Total Care, Inc.	2010-06-23	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Apotex Corporation	2008-04-09	2017-04-14	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Aidarex Pharmaceuticals LLC	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet	300 mg/1	Oral	Taro Pharmaceuticals U.S.A., Inc.	2007-11-15	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Jubilant Cadista Pharmaceuticals Inc.	2015-01-15	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Amerincan Health Packaging	2007-11-09	2016-10-25	US
Oxcarbazepine	Tablet	150 mg/1	Oral	Remedy Repack	2011-09-27	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Glenmark Pharmaceuticals Inc.,Usa	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet	600 mg/1	Oral	West Ward Pharmaceutical	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Remedy Repack	2014-06-27	2017-12-12	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Sun Pharmaceutical Industries Limited	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Ncs Health Care Of Ky, Inc Dba Vangard Labs	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet	600 mg/1	Oral	Remedy Repack	2011-08-18	2016-11-08	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Physicians Total Care, Inc.	2007-11-14	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Golden State Medical Supply	2008-04-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Amerincan Health Packaging	2014-11-13	Not applicable	US
Oxcarbazepine	Tablet	300 mg/1	Oral	Cardinal Health	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Remedy Repack	2015-03-18	Not applicable	US
Oxcarbazepine	Suspension	300 mg/5mL	Oral	Av Kare, Inc.	2014-01-23	2016-04-05	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Breckenridge Pharmaceutical, Inc.	2008-01-11	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Golden State Medical Supply	2013-04-11	Not applicable	US
Oxcarbazepine	Suspension	60 mg/mL	Oral	Ranbaxy Inc.	2009-12-14	Not applicable	US
Oxcarbazepine	Tablet	600 mg/1	Oral	Remedy Repack	2011-08-22	2016-11-09	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Cardinal Health	2008-01-11	2017-05-10	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Apotex Corporation	2008-04-09	2017-04-14	US
Oxcarbazepine	Tablet	300 mg/1	Oral	Remedy Repack	2009-12-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Glenmark Pharmaceuticals Inc.,Usa	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Rebel Distributors	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Aidarex Pharmaceuticals LLC	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet	600 mg/1	Oral	Taro Pharmaceuticals U.S.A., Inc.	2007-11-15	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Jubilant Cadista Pharmaceuticals Inc.	2015-01-15	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Amerincan Health Packaging	2007-11-09	2016-10-25	US
Oxcarbazepine	Tablet	150 mg/1	Oral	West Ward Pharmaceutical	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Remedy Repack	2016-11-17	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Sun Pharmaceutical Industries Limited	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Mesource Pharmaceuticals	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Breckenridge Pharmaceutical, Inc.	2008-01-11	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Golden State Medical Supply	2013-04-11	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	bryant ranch prepack	2008-01-11	Not applicable	US
Oxcarbazepine	Suspension	300 mg/5mL	Oral	West Ward Pharmaceutical	2012-10-03	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Remedy Repack	2013-12-30	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Ncs Health Care Of Ky, Inc Dba Vangard Labs	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Remedy Repack	2011-05-20	2016-11-29	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Physicians Total Care, Inc.	2009-10-16	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Golden State Medical Supply	2008-04-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Amerincan Health Packaging	2014-11-13	Not applicable	US
Oxcarbazepine	Tablet, film coated	150 mg/1	Oral	Remedy Repack	2008-11-03	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	bryant ranch prepack	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Rebel Distributors	2007-10-09	Not applicable	US
Oxcarbazepine	Tablet	150 mg/1	Oral	Taro Pharmaceuticals U.S.A., Inc.	2007-11-15	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Clinical Solutions Wholsesale	2008-01-11	2017-06-20	US
Oxcarbazepine	Tablet, film coated	600 mg/1	Oral	Apotex Corporation	2008-04-09	2017-04-14	US
Oxcarbazepine	Tablet	300 mg/1	Oral	Remedy Repack	2012-01-31	Not applicable	US
Oxcarbazepine	Tablet, film coated	300 mg/1	Oral	Glenmark Pharmaceuticals Inc.,Usa	2007-10-09	Not applicable	US
Trileptal	Tablet	300 mg/1	Oral	Directrx	2016-05-25	Not applicable	US

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Actinium	Not Available
Barzepin	Not Available
Carbox	Not Available
Deprectal	Not Available
Lonazet	Not Available
Oxalepsy	Not Available
Oxetol	Not Available
Oxpin	Not Available
Oxrate	Not Available
Oxypine	Not Available
Pharozepine	Not Available
Prolepsi	Not Available
Timox	Not Available
Trexapin	Not Available
Trileptin	Not Available

Brand mixtures

Not Available

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[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaene-2-carboxamide

SMILES

NC(=O)N1C2=CC=CC=C2CC(=O)C2=CC=CC=C12

Pharmacology

Indication

For 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

Pharmacodynamics

Mechanism of action

The 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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Sodium channel protein type 5 subunit alpha	Protein	yes	inhibitor	Human	Q14524	details

Absorption

Completely 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 binding

Approximately 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.

Substrate	Enzymes	Product
Oxcarbazepine	Not Available	MHD	Details
Oxcarbazepine	Not Available	10-Hydroxycarbazepine	Details
10-Hydroxycarbazepine	Not Available	10,11-Dihydroxycarbamazepine	Details

Route of elimination

Oxcarbazepine is cleared from the body mostly in the form of metabolites which are predominantly excreted by the kidneys. Fecal excretion accounts for less than 4% of the administered dose.

Half life

The half-life of the parent is about 2 hours, while the half-life of MHD is about 9 hours, so that MHD is responsible for most anti-epileptic activity.

Clearance

Not Available

Toxicity

Isolated 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

Pathway	Category	SMPDB ID
Carbamazepine Metabolism Pathway	Drug metabolism	SMP00634

Pharmacogenomic Effects/ADRs

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*15:02	ADR Directly Studied	Increased risk of Stevens–Johnson syndrome and toxicepidermal necrolysis.	Details

Interactions

Drug Interactions

Drug	Interaction	Drug group
Aripiprazole	The serum concentration of Aripiprazole can be decreased when it is combined with Oxcarbazepine.	Approved, Investigational
Bendroflumethiazide	The risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Oxcarbazepine.	Approved
Carbamazepine	The 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
Chlorothiazide	The risk or severity of adverse effects can be increased when Chlorothiazide is combined with Oxcarbazepine.	Approved, Vet Approved
Chlorotrianisene	The serum concentration of Chlorotrianisene can be decreased when it is combined with Oxcarbazepine.	Withdrawn
Chlorthalidone	The risk or severity of adverse effects can be increased when Chlorthalidone is combined with Oxcarbazepine.	Approved
Cilostazol	The serum concentration of Cilostazol can be increased when it is combined with Oxcarbazepine.	Approved
Cobicistat	The serum concentration of Cobicistat can be decreased when it is combined with Oxcarbazepine.	Approved
Conjugated estrogens	The serum concentration of Conjugated Equine Estrogens can be decreased when it is combined with Oxcarbazepine.	Approved
Desogestrel	The serum concentration of Desogestrel can be decreased when it is combined with Oxcarbazepine.	Approved
Dienestrol	The serum concentration of Dienestrol can be decreased when it is combined with Oxcarbazepine.	Approved
Dienogest	The serum concentration of Dienogest can be decreased when it is combined with Oxcarbazepine.	Approved
Diethylstilbestrol	The serum concentration of Diethylstilbestrol can be decreased when it is combined with Oxcarbazepine.	Approved
Dolutegravir	The serum concentration of Dolutegravir can be decreased when it is combined with Oxcarbazepine.	Approved
Drospirenone	The serum concentration of Drospirenone can be decreased when it is combined with Oxcarbazepine.	Approved
Elvitegravir	The serum concentration of Elvitegravir can be decreased when it is combined with Oxcarbazepine.	Approved
Eslicarbazepine acetate	The risk or severity of adverse effects can be increased when Eslicarbazepine acetate is combined with Oxcarbazepine.	Approved
Estradiol	The serum concentration of Estradiol can be decreased when it is combined with Oxcarbazepine.	Approved, Investigational, Vet Approved
Estramustine	The serum concentration of Estramustine can be decreased when it is combined with Oxcarbazepine.	Approved
Estrogens, esterified	The serum concentration of Estrogens, esterified can be decreased when it is combined with Oxcarbazepine.	Approved
Estrone sulfate	The serum concentration of Estrone sulfate can be decreased when it is combined with Oxcarbazepine.	Approved
Ethanol	Ethanol may increase the central nervous system depressant (CNS depressant) activities of Oxcarbazepine.	Approved
Ethinyl Estradiol	The serum concentration of Ethinyl Estradiol can be decreased when it is combined with Oxcarbazepine.	Approved
Ethynodiol diacetate	The serum concentration of Ethynodiol diacetate can be decreased when it is combined with Oxcarbazepine.	Approved
Etonogestrel	The serum concentration of Etonogestrel can be decreased when it is combined with Oxcarbazepine.	Approved, Investigational
Fosphenytoin	The 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
Gestodene	The serum concentration of Gestodene can be decreased when it is combined with Oxcarbazepine.	Approved
Hexestrol	The serum concentration of Hexestrol can be decreased when it is combined with Oxcarbazepine.	Withdrawn
Hydrochlorothiazide	The risk or severity of adverse effects can be increased when Hydrochlorothiazide is combined with Oxcarbazepine.	Approved, Vet Approved
Hydrocodone	The serum concentration of Hydrocodone can be decreased when it is combined with Oxcarbazepine.	Approved, Illicit
Hydroflumethiazide	The risk or severity of adverse effects can be increased when Hydroflumethiazide is combined with Oxcarbazepine.	Approved
Indapamide	The risk or severity of adverse effects can be increased when Indapamide is combined with Oxcarbazepine.	Approved
Ledipasvir	The serum concentration of Ledipasvir can be decreased when it is combined with Oxcarbazepine.	Approved
Levonorgestrel	The serum concentration of Levonorgestrel can be decreased when it is combined with Oxcarbazepine.	Approved, Investigational
Lynestrenol	The serum concentration of Lynestrenol can be decreased when it is combined with Oxcarbazepine.	Investigational
Medroxyprogesterone acetate	The serum concentration of Medroxyprogesterone acetate can be decreased when it is combined with Oxcarbazepine.	Approved, Investigational
Mefloquine	The therapeutic efficacy of Oxcarbazepine can be decreased when used in combination with Mefloquine.	Approved
Mestranol	The serum concentration of Mestranol can be decreased when it is combined with Oxcarbazepine.	Approved
Methallenestril	The serum concentration of Methallenestril can be decreased when it is combined with Oxcarbazepine.	Experimental
Methyclothiazide	The risk or severity of adverse effects can be increased when Methyclothiazide is combined with Oxcarbazepine.	Approved
Metolazone	The risk or severity of adverse effects can be increased when Metolazone is combined with Oxcarbazepine.	Approved
Mianserin	The therapeutic efficacy of Oxcarbazepine can be decreased when used in combination with Mianserin.	Approved
Nimodipine	The serum concentration of Nimodipine can be decreased when it is combined with Oxcarbazepine.	Approved
Norelgestromin	The serum concentration of Norelgestromin can be decreased when it is combined with Oxcarbazepine.	Approved
Norgestimate	The serum concentration of Norgestimate can be decreased when it is combined with Oxcarbazepine.	Approved
Norgestrel	The serum concentration of Norgestrel can be decreased when it is combined with Oxcarbazepine.	Approved
Orlistat	The serum concentration of Oxcarbazepine can be decreased when it is combined with Orlistat.	Approved, Investigational
Perampanel	The serum concentration of Oxcarbazepine can be increased when it is combined with Perampanel.	Approved
Phenobarbital	The 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
Phenytoin	The 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
Polythiazide	The risk or severity of adverse effects can be increased when Polythiazide is combined with Oxcarbazepine.	Approved
Quinethazone	The risk or severity of adverse effects can be increased when Quinethazone is combined with Oxcarbazepine.	Approved
Rilpivirine	The serum concentration of Rilpivirine can be decreased when it is combined with Oxcarbazepine.	Approved
Saxagliptin	The serum concentration of Saxagliptin can be decreased when it is combined with Oxcarbazepine.	Approved
Selegiline	Oxcarbazepine may increase the serotonergic activities of Selegiline.	Approved, Investigational, Vet Approved
Sofosbuvir	The serum concentration of Sofosbuvir can be decreased when it is combined with Oxcarbazepine.	Approved
Synthetic Conjugated Estrogens, A	The serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Oxcarbazepine.	Approved
Trichlormethiazide	The risk or severity of adverse effects can be increased when Trichlormethiazide is combined with Oxcarbazepine.	Approved, Vet Approved
Ulipristal	The serum concentration of Ulipristal can be decreased when it is combined with Oxcarbazepine.	Approved
Valproic Acid	The 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

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

Resource	Link
Human Metabolome Database (HMDB)	HMDB14914
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
Drug Product Database	11984
RxList	http://www.rxlist.com/cgi/generic3/oxcarbazepine.htm
Drugs.com	http://www.drugs.com/cdi/oxcarbazepine.html
PDRhealth	http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/tri1563.shtml
Wikipedia	Oxcarbazepine

ATC Codes

N03AF02 — Oxcarbazepine

AHFS Codes

28:12.92

PDB Entries

Not Available

FDA label

Download (195 KB)

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Healthy Volunteers	2
1	Completed	Treatment	Epilepsies	2
1	Completed	Treatment	Epilepsies / Epilepsy, Localization Related	1
1	Completed	Treatment	Epilepsy, Localization Related	1
1	Completed	Treatment	Seizures	2
1	Terminated	Supportive Care	Cancers	1
2	Recruiting	Treatment	Disseminated Sclerosis	1
2, 3	Active Not Recruiting	Treatment	Partial onset seizure Epilepsy	1
2, 3	Completed	Treatment	Schizophrenic Disorders	1
3	Active Not Recruiting	Treatment	Adverse Effects / Epilepsy, Localization Related	1
3	Completed	Treatment	Agitation Aggression in Dementia	1
3	Completed	Treatment	Epilepsies	2
3	Completed	Treatment	Epilepsies / Epilepsy, Localization Related	1
3	Completed	Treatment	Epilepsy, Localization Related	2
3	Recruiting	Treatment	Anxiety Disorder / Dementias / Depressive State / Psychosomatic Disorders / Schizophrenic Disorders	1
3	Terminated	Treatment	Epilepsy, Localization Related	1
4	Completed	Treatment	Bipolar Disorder (BD)	2
4	Completed	Treatment	Bronchial Asthma	1
4	Completed	Treatment	Epilepsies	1
4	Completed	Treatment	Epilepsy, Partial Seizures	2
4	Completed	Treatment	Oppositional Defiant Disorder	1
4	Completed	Treatment	Peripheral Nerve Injury (PNI) / Polyneuropathies / Postherpetic Neuralgia	1
4	Completed	Treatment	Seizures, Focal	1
4	Completed	Treatment	Neurocostal neuralgia / Spinal Cord Injuries (SCI)	1
4	Recruiting	Treatment	Bipolar Disorder (BD)	1
Not Available	Completed	Not Available	Healthy Volunteers	2
Not Available	Completed	Treatment	Autism, Early Infantile	1
Not Available	Completed	Treatment	Epilepsies / Seizures	3
Not Available	Not Yet Recruiting	Not Available	Bipolar Disorder (BD)	1
Not Available	Recruiting	Not Available	Epilepsies	1
Not Available	Unknown Status	Treatment	Pediatric Chronic Neuropathic Pain	1

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
Suspension	Oral	300 mg/5mL
Suspension	Oral	60 mg/mL
Tablet, film coated	Oral	150 mg/1
Tablet, film coated	Oral	300 mg/1
Tablet, film coated	Oral	600 mg/1
Tablet	Oral	150 mg/1
Tablet	Oral	300 mg/1
Tablet	Oral	600 mg/1
Tablet	Oral	150 mg
Tablet	Oral	300 mg
Tablet	Oral	600 mg
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)
CA2277791	No	2008-11-18	2018-02-12	Canada
US7037525	Yes	1998-08-12	2018-08-12	US
US7722898	No	2007-04-13	2027-04-13	US
US7910131	No	2007-04-13	2027-04-13	US
US8119148	Yes	2001-06-19	2021-06-19	US
US8617600	No	2007-04-13	2027-04-13	US
US8821930	No	2007-04-13	2027-04-13	US
US9119791	No	2007-04-13	2027-04-13	US

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	215.5 °C	PhysProp
water solubility	308 mg/L at 25 °C (SRC PhysProp estimated -- MEYLAN,WM et al. (1996))	Not Available
logP	1.5	Not Available

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)	12.92	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f8i-1790000000-cd62672e7fa7c39f0be1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0kar-0690000000-cbc95a31913165d691a7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-2910000000-d1242af6b8148ffac3a9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities 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

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Benzazepines

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

Details

1. Sodium channel protein type 5 subunit alpha

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

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 ]
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 ]
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

Details

1. Cytochrome P450 2C19

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

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 ]
Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Details

2. Cytochrome P450 3A4

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

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 ]

Details

3. Cytochrome P450 3A5

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

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

Details

1. Serum albumin

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

Drug created on June 13, 2005 07:24 / Updated on July 21, 2017 17:46

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Structure for DB00776 (Oxcarbazepine)

Targets

References

Enzymes

References

References

References

Carriers