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O3764

Sigma-Aldrich

Oxcarbazepine

≥98% (HPLC), solid

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Synonym(s):
10,11-Dihydro-10-oxo-5h-dibenz[b,f]azepine-5-carboxamide, Oxacarbazepine
Empirical Formula (Hill Notation):
C15H12N2O2
CAS Number:
28721-07-5
Molecular Weight:
252.27
EC Number:
249-188-8
MDL number:
MFCD00865307
PubChem Substance ID:
24724563
NACRES:
NA.77

Quality Level

100

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

Gene Information

human ... SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)
rat ... Scnn1g(24768)

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This Item
PHR163519532Y0001576
Oxcarbazepine ≥98% (HPLC), solid

Sigma-Aldrich

O3764

Oxcarbazepine

Oxcarbazepine Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1635

Oxcarbazepine

Oxcarbazepine analytical standard

Supelco

19532

Oxcarbazepine

Oxcarbazepine European Pharmacopoeia (EP) Reference Standard

Y0001576

Oxcarbazepine

form

solid

form

-

form

-

form

-

color

white

color

-

color

-

color

-

solubility

DMSO: ~9 mg/mL

solubility

-

solubility

-

solubility

-

originator

Novartis

originator

-

originator

-

originator

-

Quality Level

100

Quality Level

300

Quality Level

100

Quality Level

-

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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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)

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Clinical pharmacogenetics implementation consortium guideline for HLA genotype and use of carbamazepine and oxcarbazepine: 2017 update.
Phillips EJ, et al.
Clinical Pharmacology and Therapeutics, 103(4), 574-581 (2018)
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
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
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)
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