Oxcarbazepine

Identification

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Oxcarbazepine (DB00776)

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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

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Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Oxcarbazepine	Tablet	600 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable
Oxcarbazepine	Tablet	300 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable
Oxcarbazepine	Tablet	150 mg	Oral	Jubilant Generics Limited	Not applicable	Not applicable
Oxtellar XR	Tablet	600 mg/1	Oral	Supernus Pharmaceuticals, Inc.	2013-01-17	Not applicable
Oxtellar XR	Tablet	300 mg/1	Oral	Supernus Pharmaceuticals, Inc.	2013-01-17	Not applicable
Oxtellar XR	Tablet	150 mg/1	Oral	Supernus Pharmaceuticals, Inc.	2013-01-17	Not applicable
Trileptal	Tablet, film coated	150 mg/1	Oral	Novartis Pharmaceuticals Corporation	2006-05-10	2006-05-10
Trileptal	Tablet, film coated	300 mg/1	Oral	Physicians Total Care, Inc.	2003-07-02	Not applicable
Trileptal	Tablet, film coated	150 mg/1	Oral	Physicians Total Care, Inc.	2003-07-07	Not applicable
Trileptal	Tablet, film coated	300 mg/1	Oral	REMEDYREPACK INC.	2018-08-07	Not applicable

Additional Data Available

Application Number
Application Number
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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Apo-oxcarbazepine	Tablet		Oral	Apotex Corporation	2006-08-01	Not applicable
Apo-oxcarbazepine	Tablet		Oral	Apotex Corporation	2006-08-01	Not applicable
Apo-oxcarbazepine	Tablet		Oral	Apotex Corporation	2006-08-01	Not applicable
Jamp-oxcarbazepine	Tablet		Oral	Jamp Pharma Corporation	2015-06-08	Not applicable
Jamp-oxcarbazepine	Tablet		Oral	Jamp Pharma Corporation	2015-06-08	Not applicable
Jamp-oxcarbazepine	Tablet		Oral	Jamp Pharma Corporation	2015-06-08	Not applicable
Novo-oxcarbazepine	Tablet		Oral	Novopharm Limited	Not applicable	Not applicable
Novo-oxcarbazepine	Tablet		Oral	Novopharm Limited	Not applicable	Not applicable
Novo-oxcarbazepine	Tablet		Oral	Novopharm Limited	Not applicable	Not applicable
Oxcarbazepine	Tablet	150 mg/1	Oral	West-Ward Pharmaceticals Corp.	2007-10-09	Not applicable

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
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International/Other Brands

Actinium / Barzepin / Carbox / Deprectal / Lonazet / Oxalepsy / Oxetol / Oxpin / Oxrate / Oxypine / Pharozepine / Prolepsi / Timox / Trexapin / Trileptin

Categories

• Anti-epileptic Agent
• Anticonvulsants
• Carboxamide Derivatives
• Central Nervous System Agents
• Central Nervous System Depressants
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
• Cytochrome P-450 CYP3A Inducers
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A4 Inducers
• Cytochrome P-450 CYP3A4 Inducers (strength unknown)
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A5 Inducers
• Cytochrome P-450 CYP3A5 Inducers (strength unknown)
• Cytochrome P-450 CYP3A5 Inhibitors
• Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Decreased Central Nervous System Disorganized Electrical Activity
• Dibenzazepines
• Enzyme Inducing Antiepileptic Drugs
• Heterocyclic Compounds, Fused-Ring
• Membrane Transport Modulators
• Miscellaneous Anticonvulsants
• Nervous System
• P-glycoprotein inducers
• P-glycoprotein substrates
• Sodium Channel Blockers
• Voltage-Gated Sodium Channel Blockers

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

• Partial-Onset Seizures

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

Target	Actions	Organism
USodium channel protein	inhibitor	Humans

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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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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Blackbox Warnings

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Absorption

Oxcarbazepine is completely absorbed following oral administration. A single 600mg dose of oxcarbazepine resulted in an MHD C_max of 34 μmol/L and a median T_max 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

• Oxcarbazepine
  (R)-MHD
  • (R)-MHD
    trans-10,11-dihydro-10,11-dihydroxycarbamazepine
  • (R)-MHD
    cis-10,11-dihydro-10,11-dihydroxycarbamazepine
  • (R)-MHD
    (R)-MHD glucuronide metabolite
• Oxcarbazepine
  (S)-MHD
  • (S)-MHD
    trans-10,11-dihydro-10,11-dihydroxycarbamazepine
  • (S)-MHD
    cis-10,11-dihydro-10,11-dihydroxycarbamazepine
  • (S)-MHD
    (S)-MHD glucuronide metabolite
• Oxcarbazepine
  Oxcarbazepine sulfate metabolite
• Oxcarbazepine
  Oxcarbazepine glucuronide metabolite

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

Pathway	Category
Carbamazepine Metabolism Pathway	Drug metabolism

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	ADR Directly Studied	Patients who carry this allele may be at an increased risk of Stevens-Johnson Syndrome and toxic epidermal necrolysis when treated with oxcarbazepine.	Details

Interactions

Drug Interactions

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.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be increased when combined with Oxcarbazepine.
(S)-Warfarin	The metabolism of (S)-Warfarin can be increased when combined with Oxcarbazepine.
2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Oxcarbazepine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthine	Oxcarbazepine 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-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Oxcarbazepine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be increased when combined with Oxcarbazepine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Oxcarbazepine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Oxcarbazepine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanine	Oxcarbazepine may increase the excretion rate of 6-O-benzylguanine which could result in a lower serum level and potentially a reduction in efficacy.
7-Deazaguanine	Oxcarbazepine may increase the excretion rate of 7-Deazaguanine which could result in a lower serum level and potentially a reduction in efficacy.

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Extended Description
Extended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
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Severity
Severity
A severity rating for each drug interaction, from minor to major.
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Evidence Level
Evidence Level
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Action
Action
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Food Interactions

• Avoid alcohol. Oxcarbazepine has CNS depressant properties that may be potentiated by co-administration with alcohol.
• Take with or without food. Co-administration with food does not significantly affect absorption.

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

RxNav

32624

ChEBI

7824

ChEMBL

CHEMBL1068

ZINC

ZINC000000004724

Therapeutic Targets Database

DAP000528

PharmGKB

PA450732

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Oxcarbazepine

ATC Codes

N03AF02 — Oxcarbazepine

• N03AF — Carboxamide derivatives
• N03A — ANTIEPILEPTICS
• N03 — ANTIEPILEPTICS
• N — NERVOUS SYSTEM

AHFS Codes

• 28:12.92 — Miscellaneous Anticonvulsants

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Healthy Volunteers	2
1	Completed	Basic Science	Epilepsies	1
1	Completed	Treatment	Epilepsies	3
1	Completed	Treatment	Epilepsies / Epilepsy, Localization Related	1
1	Completed	Treatment	Epilepsy, Localization Related	1
1	Completed	Treatment	Seizures	2
1	Terminated	Supportive Care	Malignancies	1
2	Completed	Treatment	Disseminated Sclerosis	1
2, 3	Completed	Treatment	Partial-Onset Seizures	1
2, 3	Completed	Treatment	Schizophrenia	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	Not Yet Recruiting	Treatment	Pediatric Chronic Neuropathic Pain	1
3	Terminated	Treatment	Anxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenia	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	Metabolic Clearance Rate	1
4	Completed	Treatment	Neuralgia / Spinal Cord Injuries (SCI)	1
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	Enrolling by Invitation	Treatment	Depression, Bipolar / Measure-based Guidance / Treatment Effectiveness	1
4	Not Yet Recruiting	Treatment	Benign Childhood Epilepsy With Centrotemporal Spikes	1
4	Not Yet Recruiting	Treatment	Epilepsy, Localization Related	1
4	Recruiting	Treatment	Bipolar Disorder (BD)	1
4	Withdrawn	Treatment	Trigeminal Neuralgia (TN)	1
Not Available	Completed	Not Available	Epilepsies	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	Enrolling by Invitation	Not Available	Bipolar Disorder (BD)	1
Not Available	Recruiting	Not Available	Epilepsies	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/1mL
Tablet	Oral	150 mg
Tablet	Oral	150 mg/1
Tablet	Oral	300 mg
Tablet	Oral	600 mg/1
Tablet	Oral	600 mg
Tablet, film coated	Oral	150 mg/1
Tablet, film coated	Oral	300 mg/1
Tablet, film coated	Oral	600 mg/1
Tablet	Oral	300 mg/1
Tablet	Oral
Suspension	Oral

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)
Unlock Additional Data
CA2277791	No	2008-11-18	2018-02-12
US7037525	Yes	2006-05-02	2018-08-12
US8119148	Yes	2012-02-21	2021-06-19
US7910131	No	2011-03-22	2027-04-13
US9119791	No	2015-09-01	2027-04-13
US8821930	No	2014-09-02	2027-04-13
US8617600	No	2013-12-31	2027-04-13
US7722898	No	2010-05-25	2027-04-13
US9370525	No	2016-06-21	2027-04-13
US9351975	No	2016-05-31	2027-04-13
US9855278	No	2018-01-02	2027-04-13
US10220042	No	2019-03-05	2027-04-13

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

Property	Value	Source
logP	1.5	Not Available
pKa	13.73	Canadian label

Predicted Properties

Property	Value	Source
Water Solubility	0.16 mg/mL	ALOGPS
logP	1.76	ALOGPS
logP	1.82	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.18	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.4 Å2	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.56 m3·mol-1	ChemAxon
Polarizability	25.72 Å3	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9894
Blood Brain Barrier	+	0.9975
Caco-2 permeable	+	0.6299
P-glycoprotein substrate	Non-substrate	0.7157
P-glycoprotein inhibitor I	Non-inhibitor	0.7193
P-glycoprotein inhibitor II	Non-inhibitor	0.9348
Renal organic cation transporter	Non-inhibitor	0.8176
CYP450 2C9 substrate	Non-substrate	0.773
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.6022
CYP450 1A2 substrate	Non-inhibitor	0.7266
CYP450 2C9 inhibitor	Non-inhibitor	0.7371
CYP450 2D6 inhibitor	Non-inhibitor	0.9329
CYP450 2C19 inhibitor	Non-inhibitor	0.7428
CYP450 3A4 inhibitor	Non-inhibitor	0.8819
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8034
Ames test	Non AMES toxic	0.5078
Carcinogenicity	Non-carcinogens	0.9118
Biodegradation	Not ready biodegradable	0.8977
Rat acute toxicity	1.9871 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9327
hERG inhibition (predictor II)	Non-inhibitor	0.869

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

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0pb9-0090000000-46d01e1171f998679d03
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0f8i-1790000000-cd62672e7fa7c39f0be1
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0kar-0690000000-cbc95a31913165d691a7
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001i-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)

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Drug created on June 13, 2005 07:24 / Updated on April 02, 2020 01:50