Drug/Small Molecule:
oxcarbazepine

2D structure

Overview

Generic Names: Oxcarbamazepine
Trade Names: Trileptal
PharmGKB Accession Id: PA450732

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. (source: Drug Bank)

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. (source: Drug Bank)

ATC Therapeutic Category

  • N03AF:Carboxamide derivatives

Pharmacology, Interactions, and Contraindications

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. (source: Drug Bank)

Pharmacology

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 the same conditions. (source: Drug Bank)

Food Interactions

Take without regard to meals. Avoid alcohol. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Oxcarbazepine is completely absorbed and extensively metabolized to its pharmacologically active 10-monohydroxy metabolite (MHD). MHD is metabolized further by conjugation with glucuronic acid. (source: Drug Bank)

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 blycoprotein. (source: Drug Bank)

Absorption

Completely absorbed following oral administration. Food has no effect on the rate and extent of absorption of oxcarbazepine. (source: Drug Bank)

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. (source: Drug Bank)

Isomeric SMILES Code:

c1ccc2c(c1)CC(=O)c3ccccc3N2C(=O)N (source: Drug Bank)

Curated Annotations (Curated Annotation)

  1. rs2304016 at chr2:165876749 in SCN2A, SCN2A2
    The A allele of this SNP was associated with resistance to sodium channel-blocking anti-epileptic drugs in a Chinese patient population.
    Variant Name:
    SCN2A:IVS7-32A>G
    Related Drugs:
    carbamazepine, lamotrigine, oxcarbazepine, phenytoin, topiramate
    Related Diseases:
    Epilepsy
    Evidence:
    PMID:18784617
Variant names are different names that have been used in the literature and other resources to refer to the same variant.

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
  •   
  •   
  • PK
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
HLA-B
  • CO
  •   
  •   
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
NR1I2
  •   
  •   
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
SCN2A
  •   
  •   
  •   
  •   
  •   
Variants
No phenotype data No genotype data No literature annotations Not annotated
SCN2A2
  •   
  •   
  •   
  •   
  •   
Variants

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
SCN5A Uncurated Annotation (source: Drug Bank)

The following drugs are in curated knowledge about this drug.

  Drug Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
donepezil
  •   
  •   
  • PK
  •   
  •   
Publications

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
cyclosporine Uncurated Annotation Oxcarbazepine decreases the effect of cyclosporine (source: Drug Bank)
ethinyl estradiol Uncurated Annotation Oxcarbazepine decreases the effect of the contraceptive (source: Drug Bank)
felodipine Uncurated Annotation Oxcarbazepine decreases the levels of felodipine (source: Drug Bank)
mephenytoin Uncurated Annotation Oxcarbazepine increases the effect of hydantoin (source: Drug Bank)
mestranol Uncurated Annotation Oxcarbazepine decreases the effect of the contraceptive (source: Drug Bank)
phenytoin Uncurated Annotation Oxcarbazepine increases the effect of hydantoin (source: Drug Bank)

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Drug Toxicity
  • CO
  •   
  •   
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Epidermal Necrolysis, Toxic
  • CO
  •   
  •   
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Epilepsy
  •   
  • PD
  •   
  •   
  • GN
Publications, Variants
No phenotype data No genotype data Literature annotations available Not annotated
Stevens-Johnson Syndrome
  • CO
  •   
  •   
  •   
  • GN
Publications

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00776
KEGG Compound ID:
C07492
KEGG Drug ID:
D00533
PubChem Compound ID:
34312
PubChem Substance ID:
9695

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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