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 (
)
-
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
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
|---|---|---|---|
|
|
CYP3A4 |
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Publications |
|
|
HLA-B |
|
Publications |
|
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NR1I2 |
|
Publications |
|
|
SCN2A |
|
Variants |
|
|
SCN2A2 |
|
Variants |
A list of non-curated publications that mention this drug along with other genes is available.
Drug Targets
| Gene | Description | |
|---|---|---|
| SCN5A |
|
(source: Drug Bank) |
The following drugs are in curated knowledge about this drug.
| Drug | Relationship | Evidence | |
|---|---|---|---|
|
|
donepezil |
|
Publications |
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| Drug | Description | |
|---|---|---|
| cyclosporine |
|
Oxcarbazepine decreases the effect of cyclosporine (source: Drug Bank) |
| ethinyl estradiol |
|
Oxcarbazepine decreases the effect of the contraceptive (source: Drug Bank) |
| felodipine |
|
Oxcarbazepine decreases the levels of felodipine (source: Drug Bank) |
| mephenytoin |
|
Oxcarbazepine increases the effect of hydantoin (source: Drug Bank) |
| mestranol |
|
Oxcarbazepine decreases the effect of the contraceptive (source: Drug Bank) |
| phenytoin |
|
Oxcarbazepine increases the effect of hydantoin (source: Drug Bank) |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
|---|---|---|---|
|
|
Drug Toxicity |
|
Publications |
|
|
Epidermal Necrolysis, Toxic |
|
Publications |
|
|
Epilepsy |
|
Publications, Variants |
|
|
Stevens-Johnson Syndrome |
|
Publications |
LinkOuts
Common Searches
Search PubMed
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.
