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O3764

Sigma-Aldrich

Oxcarbazepine

≥98% (HPLC), solid

Synonym(s):

10,11-Dihydro-10-oxo-5h-dibenz[b,f]azepine-5-carboxamide, Oxacarbazepine

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About This Item

Empirical Formula (Hill Notation):
C15H12N2O2
CAS Number:
Molecular Weight:
252.27
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: ~9 mg/mL

originator

Novartis

SMILES string

O=C1CC2=C(C=CC=C2)N(C(N)=O)C3=CC=CC=C31

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)

InChI key

CTRLABGOLIVAIY-UHFFFAOYSA-N

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General description

Oxcarbazepine (OXC) is the keto-analog of carbamazepine. Unlike carbamazepine, oxcarbazepine has no side effects. It is an antiepileptic drug, with an antineuralgic property. It has a pharmacokinetic advantage over carbamazepine. It is prescribed for neuropathic pain and serves as an effective pain reliever in trigeminal neuralgia. The catabolism of OXC to its monohydroxy derivative has significant pharmacologic property. It modulates potassium channels and voltage-dependent sodium channels. OXC modulates V2 receptor-G protein complex in collecting tubules and is used for treating diabetes insipidus.

Application

Oxcarbazepine has been used in reversed-phase high-performance liquid chromatography of human epileptic brain endothelial cells.

Biochem/physiol Actions

Anticonvulsant, antineuralgic. Inhibits veratrine-induced transmitter release.

Features and Benefits

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oxcarbazepine Therapy for Complete Central Diabetes Insipidus.
Abdallah B, et al.
Case Reports in Neurological Medicine, 8(1), 20-24 (2018)
Joanna M Zakrzewska et al.
Pain, 95(3), 259-266 (2002-02-13)
Trigeminal neuralgia is a recurrent severe shooting neuropathic pain which can be managed both pharmacologically and surgically. However, there are no prospective data that compare these two therapeutic strategies. This study therefore aimed to assess long-term outcome in patients with
Oxcarbazepine: Drug of the Future in the Treatment of Trigeminal Neuralgia.
Chole R, et al.
Journal of Indian Academy of Oral Medicine and Radiology, 23(1), S340-S343 (2011)
E Perucca
Fundamental & clinical pharmacology, 15(6), 405-417 (2002-02-28)
Although older generation antiepileptic drugs (AEDs) such as carbamazepine, phenytoin and valproic acid continue to be widely used in the treatment of epilepsy, these drugs have important shortcomings such as a highly variable and nonlinear pharmacokinetics, a narrow therapeutic index
Modulation of glucocorticoid receptor in human epileptic endothelial cells impacts drug biotransformation in an in vitro blood-brain barrier model.
Ghosh C, et al.
Epilepsia, 59(11), 2049-2060 (2018)

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