Oxcarbazepine
Overview
Description
Oxcarbazepine is a medication primarily used to treat epilepsy. It is a structural derivative of carbamazepine and is known for its anticonvulsant properties. This compound is marketed under various brand names, including Trileptal and Oxtellar XR. It is used to manage partial-onset seizures in both adults and children .
Preparation Methods
Synthetic Routes and Reaction Conditions: Oxcarbazepine is synthesized from carbamazepine through a chemical reaction that involves the oxidation of the carbamazepine molecule. The process typically involves the use of oxidizing agents such as hydrogen peroxide or peracids. The reaction conditions include controlled temperature and pH to ensure the selective oxidation of the carbamazepine to this compound .
Industrial Production Methods: In industrial settings, the production of this compound involves large-scale oxidation reactions using similar oxidizing agents. The process is optimized for high yield and purity, often involving multiple purification steps such as recrystallization and chromatography to remove impurities and by-products .
Chemical Reactions Analysis
Types of Reactions: Oxcarbazepine undergoes various chemical reactions, including:
Oxidation: Conversion of this compound to its active metabolite, 10,11-dihydro-10-hydroxycarbamazepine (MHD).
Reduction: Reduction reactions can revert this compound to its precursor forms.
Substitution: Substitution reactions can occur at the amide or aromatic positions
Common Reagents and Conditions:
Oxidizing Agents: Hydrogen peroxide, peracids.
Reducing Agents: Sodium borohydride, lithium aluminum hydride.
Substitution Reagents: Halogens, alkylating agents
Major Products:
10,11-Dihydro-10-hydroxycarbamazepine (MHD): The primary active metabolite.
Various substituted derivatives: Depending on the reagents used in substitution reactions
Scientific Research Applications
Antiepileptic Use
Oxcarbazepine is effective in treating partial-onset seizures and primary generalized tonic-clonic seizures . It functions by blocking voltage-dependent sodium channels, which reduces abnormal electrical activity in the brain. The drug is indicated for use as both monotherapy and adjunctive therapy in adults and children aged four years and older .
Efficacy Studies
- Clinical Trials : Numerous studies have demonstrated that this compound has comparable efficacy to other antiepileptic drugs such as carbamazepine, valproate, and phenytoin, with advantages in terms of side effects and pharmacokinetics .
- Meta-Analysis : A meta-analysis indicated that this compound could effectively decrease seizure frequency in patients with drug-resistant epilepsy when used as an add-on therapy .
Psychiatric Applications
This compound has been explored as a mood stabilizer for conditions such as bipolar disorder . Although not FDA-approved for this indication, it is used off-label with some success.
Case Studies
- A case report documented a 53-year-old male with schizoaffective disorder who developed hyponatremia during treatment with this compound, highlighting both its psychiatric application and potential side effects .
- Another study observed significant improvements in symptoms of bipolar disorder when this compound was administered, suggesting its utility in managing mood disorders .
Neuropathic Pain Management
While evidence supporting this compound's effectiveness in treating neuropathic pain is limited, some studies have suggested it may provide relief for conditions such as trigeminal neuralgia.
Research Findings
- A review indicated that this compound could be beneficial for neuropathic pain management; however, the overall evidence remains inconclusive due to low patient numbers and event rates in studies .
Oncological Applications
Recent research has identified this compound as a potential pro-apoptotic agent in certain cancer cell lines, particularly those with IDH mutations.
Experimental Findings
- In vitro studies showed that this compound could inhibit the growth of glioma stem cells, suggesting a dual role as an antiepileptic and an antineoplastic agent . The treated cells exhibited significant reductions in size and increased apoptosis rates.
Adverse Effects and Considerations
Despite its therapeutic benefits, this compound is associated with several adverse effects:
Mechanism of Action
Oxcarbazepine and its active metabolite, MHD, exert their effects by blocking voltage-sensitive sodium channels. This action stabilizes hyperexcited neural membranes, inhibits repetitive neuronal firing, and reduces the propagation of synaptic impulses. These mechanisms are crucial in preventing the spread of seizures .
Comparison with Similar Compounds
Carbamazepine: The parent compound from which oxcarbazepine is derived.
Eslicarbazepine: Another derivative with similar anticonvulsant properties.
Lamotrigine: An anticonvulsant with a different chemical structure but similar therapeutic uses .
Comparison:
This compound vs. Carbamazepine: this compound has a better side effect profile and fewer drug interactions compared to carbamazepine.
This compound vs. Eslicarbazepine: Both have similar mechanisms of action, but eslicarbazepine is marketed as a prodrug with potentially improved pharmacokinetics.
This compound vs. Lamotrigine: While both are used to treat epilepsy, lamotrigine is also used for bipolar disorder and has a different mechanism of action involving the inhibition of glutamate release.
This compound stands out due to its reduced propensity for drug-drug interactions and its effectiveness in managing partial-onset seizures with a relatively favorable side effect profile .
Biological Activity
Oxcarbazepine (OXC) is an anticonvulsant medication primarily used for the treatment of epilepsy. It is a derivative of carbamazepine and functions by stabilizing neuronal membranes and inhibiting repetitive neuronal firing. This article explores the biological activity of this compound, focusing on its mechanisms of action, therapeutic efficacy, and emerging research findings.
This compound acts through several mechanisms:
- Sodium Channel Blockade : OXC inhibits voltage-gated sodium channels, which reduces the excitability of neurons. This action is crucial in preventing seizures by decreasing abnormal electrical activity in the brain .
- Potassium Conductance : The drug enhances potassium conductance, contributing to its anticonvulsant properties .
- Calcium Channel Modulation : OXC modulates voltage-activated calcium channels, which may play a secondary role in its efficacy against seizures .
- Neurotransmitter Effects : Although initially thought to inhibit glutamatergic activity, this effect has not been consistently replicated in vivo .
Efficacy in Epilepsy Treatment
Numerous studies have evaluated the effectiveness of this compound in treating various seizure types:
- Clinical Trials : A double-blind trial comparing this compound with phenytoin (PHT) found no significant differences in seizure frequency between the two drugs. However, OXC demonstrated better tolerability with fewer severe side effects .
- Monotherapy vs. Add-on Therapy : In a study involving children and adolescents, OXC was shown to be effective as both a first-line monotherapy and an add-on therapy for partial seizures (PS) and generalized tonic-clonic seizures (GTCS) with comparable efficacy to carbamazepine .
- Long-Term Outcomes : A six-month follow-up study indicated that patients on OXC had significant improvements in mood and anxiety scales (SAS and SDS), suggesting additional psychological benefits beyond seizure control .
Proapoptotic Effects in Cancer Research
Recent research has identified this compound's potential role beyond epilepsy treatment. A study published in 2023 highlighted its proapoptotic effects on IDH-mutant glioma cells, showing that OXC significantly reduced cell viability and induced apoptosis in tumor spheroids. The treated spheroids were found to be 82% smaller than controls after 72 hours, indicating substantial growth inhibition .
Table 1: Summary of Biological Activities of this compound
Case Studies and Emerging Research
- Efficacy in Bipolar Disorder : A pilot study suggested that this compound may help prevent impulsivity and depressive episodes in bipolar patients when used as an adjunctive therapy to lithium. The results indicated a lower relapse rate among those treated with OXC compared to placebo .
- Retinoprotective Properties : Preliminary findings suggest that this compound may have retinoprotective effects, showing no cytotoxicity in retinal cells while promoting cell proliferation under certain conditions .
Q & A
Basic Research Questions
Q. How should researchers design pharmacokinetic studies to compare immediate-release (OXC-IR) and extended-release (OXC-XR) formulations of oxcarbazepine?
- Methodological Answer : Utilize crossover study designs to minimize inter-individual variability, and employ population pharmacokinetic models to account for covariates like age, weight, and renal/hepatic function. Parameters such as AUC, Cmax, and t1/2 should be analyzed under both fed and fasted conditions. Reference adult and pediatric population data from clinical trials (e.g., studies 804P103, 804P301, and 804P107) to validate dose-response relationships .
Q. What are the key considerations for validating analytical methods to quantify this compound and its metabolites in plasma?
- Methodological Answer : Ensure validation parameters include specificity, linearity (e.g., 0.1–20 µg/mL), accuracy (recovery ≥95%), precision (CV <15%), and stability under long-term storage. Cross-validate assays using techniques like HPLC or LC-MS/MS, and reference established protocols for metabolite quantification (e.g., MDH) .
Q. How can researchers systematically review literature on this compound’s efficacy in refractory epilepsy?
- Methodological Answer : Follow PRISMA guidelines, search databases (MEDLINE, Cochrane Library, EMBASE) using Boolean operators (e.g., "this compound AND (epilepsy OR seizure)"), and include both published/unpublished trials. Assess heterogeneity using chi-squared tests and I² statistics, and prioritize studies with intention-to-treat (ITT) analysis to minimize attrition bias .
Q. What frameworks are recommended for formulating research questions on this compound’s mechanisms in bipolar disorder?
- Methodological Answer : Apply PICO (Population: bipolar patients; Intervention: OXC; Comparison: placebo/standard therapy; Outcome: manic/depressive episodes) and FINER criteria (Feasible, Interesting, Novel, Ethical, Relevant). Prioritize hypotheses that address gaps in double-blind RCTs versus case reports .
Advanced Research Questions
Q. How should conflicting efficacy data between this compound and carbamazepine in partial seizures be analyzed?
- Methodological Answer : Conduct meta-analyses using hazard ratios (HRs) for time-to-treatment withdrawal and odds ratios (ORs) for adverse events. Address heterogeneity via subgroup analysis (e.g., dosing regimens, study blinding) and sensitivity analysis to exclude high-risk-of-bias trials. Note that wide confidence intervals (e.g., HR 0.78–1.39 for withdrawal) may indicate underpowered studies .
Q. What methodologies resolve contradictions in this compound’s therapeutic drug monitoring (TDM) for pediatric populations?
- Methodological Answer : Develop population pharmacokinetic models incorporating covariates (e.g., age, CYP3A4 activity) and validate using bootstrap resampling. Compare TDM outcomes (efficacy/toxicity) against historical controls, and adjust for protein binding variations in free drug assays .
Q. Data Presentation and Reporting Guidelines
Properties
IUPAC Name |
5-oxo-6H-benzo[b][1]benzazepine-11-carboxamide |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
CTRLABGOLIVAIY-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C1C2=CC=CC=C2N(C3=CC=CC=C3C1=O)C(=O)N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C15H12N2O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID0045703 |
Source
|
| Record name | Oxcarbazepine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0045703 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
252.27 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Oxcarbazepine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014914 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
Slightly soluble in chloroform, dichloromethane, acetone, and methanol and practically insoluble in ethanol, ether, and water., 1.60e-01 g/L |
Source
|
| Record name | OXCARBAZEPINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7524 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Oxcarbazepine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014914 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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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. 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. 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. Increased potassium conductance and modulation of voltage-activated calcium channels is also thought to play a role in the anti-seizure activity of oxcarbazepine. Inhibition of glutamatergic activity was thought to contribute to oxcarbazepine's activity, but this effect could not be replicated _in vivo_., The pharmacological activity of Trileptal (oxcarbazepine) is primarily exerted through the 10-monohydroxy metabolite (MHD) of oxcarbazepine. The precise mechanism by which oxcarbazepine and MHD exert their antiseizure effect is unknown; however, in vitro electrophysiological studies indicate that they produce blockade of voltage-sensitive sodium channels, resulting in stabilization of hyperexcited neural membranes, inhibition of repetitive neuronal firing, and diminution of propagation of synaptic impulses. These actions are thought to be important in the prevention of seizure spread in the intact brain. In addition, increased potassium conductance and modulation of high-voltage activated calcium channels may contribute to the anticonvulsant effects of the drug. No significant interactions of oxcarbazepine or MHD with brain neurotransmitter or modulator receptor sites have been demonstrated. |
Source
|
| Record name | Oxcarbazepine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00776 | |
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| Record name | OXCARBAZEPINE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7524 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Crystals from ethanol, White to faintly orange crystalline powder | |
CAS No. |
28721-07-5 |
Source
|
| Record name | Oxcarbazepine | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=28721-07-5 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Oxcarbazepine [USAN:USP:INN:BAN] | |
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| Record name | Oxcarbazepine | |
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| URL | https://www.drugbank.ca/drugs/DB00776 | |
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| Record name | Oxcarbazepine | |
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| Record name | Oxcarbazepine | |
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| Record name | OXCARBAZEPINE | |
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| Record name | Oxcarbazepine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014914 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
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Melting Point |
215-216 °C, 215.5 °C |
Source
|
| Record name | OXCARBAZEPINE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/7524 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Oxcarbazepine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014914 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
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Retrosynthesis Analysis
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
