Oxcarbazepine

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Cat Number

API28721075

CAS Number

28721-07-5

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Product Detail Description Scientific Support Customer Q&A

CAS Number

28721-07-5

EINECS

249-188-8

Storage

Store at room temperature

Synonyms

10-Oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide; GP-47680; Oxtellar XR; KIN-493

Molecular Formula

C15H12N2O2

Molecular Weight

252.27

Smiles

C1C2=CC=CC=C2N(C3=CC=CC=C3C1=O)C(=O)N

Appearance

White to faintly orange crystalline powder

Melting Point

215-216℃

Boiling Point

457.2℃

Relative Density

1.329

General Description

Oxcarbazepine is an anticonvulsant agent structurally related to carbamazepine but with a distinct metabolic profile that offers improved tolerability. It is available in oral tablets and suspension, serving as a first-line or adjunctive therapy for certain seizure types. The drug is a 10-keto analogue of carbamazepine, and this modification eliminates the production of the toxic epoxide metabolite responsible for many adverse effects of the parent compound.

Mechanism of Action

Oxcarbazepine and its active monohydroxy derivative stabilize neuronal membranes by blocking voltage-gated sodium channels, particularly in their inactivated state. This blockade prevents sustained repetitive firing of neurons and limits the propagation of seizure activity. Additionally, it modulates potassium conductance and high-voltage-activated calcium channels, contributing to its anticonvulsant and mood-stabilizing effects. Unlike carbamazepine, it has minimal autoinduction of its own metabolism.

Application

It is indicated as monotherapy or adjunctive therapy for the treatment of partial-onset seizures in adults and children as young as two years of age. It is also approved for use in pediatric patients with refractory seizures. Due to its favorable drug interaction profile and lack of hepatic autoinduction, it is often preferred over carbamazepine when polytherapy with other medications is required. Hyponatremia is a well-recognized adverse effect requiring periodic serum sodium monitoring.

An updated Cochrane review (five trials, 862 participants) assessed oxcarbazepine for painful diabetic peripheral neuropathy, radiculopathy, and mixed neuropathies. For diabetic neuropathy, one trial reported that 34.8% of oxcarbazepine‑treated participants achieved >50% pain relief versus 18.2% with placebo (NNTB 6), but two other trials showed no benefit and could not be meta‑analyzed due to missing data.

Fig. 1 Study flow diagram. (Zhou M, et al., 2017)

References

Zhou M, et al. Oxcarbazepine for neuropathic pain. Cochrane Database Syst Rev. 2017; 12(12):CD007963.

Does Oxcarbazepine require protection from light during long-term storage?

Yes, it is photosensitive. Prolonged exposure to UV light can cause photodegradation and discoloration. Store in light-resistant, opaque containers.

What is the recommended storage temperature for Oxcarbazepine?

Store at controlled room temperature (15-25°C). It is thermally stable, but avoid excessive heat above 30°C to prevent potential polymorphic changes.

Is Oxcarbazepine hygroscopic, and how does this affect stability?

It exhibits low hygroscopicity. However, under high humidity (>75% RH), it may absorb moisture, leading to partial conversion to the dihydrate form, which can affect dissolution.

How is the impurity 10,11-dihydro-10,11-dihydroxy-5H-dibenzazepine-5-carboxamide monitored?

This degradation product is quantified using a validated HPLC method, ensuring it remains below pharmacopoeial limits for oral solid dosage forms.