Rufinamide

Title: Rufinamide
CAS Registry Number: 106308-44-5
CAS Name: 1-[(2,6-Difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide
Additional Names: 1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide
Manufacturers' Codes: CGP-33101
Trademarks: Inovelon (Eisai)
Molecular Formula: C10H8F2N4O
Molecular Weight: 238.19
Percent Composition: C 50.42%, H 3.39%, F 15.95%, N 23.52%, O 6.72%
Literature References: Antiepileptic triazole derivative which decreases firing by neurons at sodium channels. Prepn: R. Meier, EP 199262; eidem, US 4789680 (1986, 1988 both to Ciba-Geigy). HPLC determn in human plasma: L. A. Brunner, M. L. Powell, Biomed. Chromatogr. 6, 278 (1992). Clinical pharmacokinetics: W. K. Cheung et al., Pharm. Res. 12, 1878 (1995); and tolerability: J.-M. Cardot et al., Biopharm. Drug Dispos. 19, 259 (1998). Clinical study in epilepsy: S. Palhagen et al., Epilepsy Res. 43, 115 (2001). Review of clinical experience: K. K. Jain et al., Exp. Opin. Invest. Drugs 9, 829-840 (2000).
Properties: Crystals from ethanol, mp 237-240°. Moderate soly in 0.1N HCl.
Melting point: mp 237-240°
Therap-Cat: Anticonvulsant.
Keywords: Anticonvulsant.
Rufloxacin Rugulovasines Rumex Rupatadine Rutecarpine

Rufinamide
Rufinamide.png
Systematic (IUPAC) name
1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide
Clinical data
AHFS/Drugs.com Consumer Drug Information
MedlinePlus a609001
Licence data EMA:Link, US FDA:link
Legal status Prescription only
Routes Oral
Identifiers
CAS number 106308-44-5 N
ATC code N03AF03
PubChem CID 129228
ChemSpider 114471 YesY
UNII WFW942PR79 YesY
ChEMBL CHEMBL1201754 N
Chemical data
Formula C10H8F2N4O 
Mol. mass 238.194
 N (what is this?)  (verify)

Rufinamide is an anticonvulsant medication. It is used in combination with other medication and therapy to treat Lennox–Gastaut syndrome[1] and various other seizure disorders. Rufinamide, a triazole derivative, was developed in 2004 by Novartis Pharma, AG, and is manufactured by Eisai.

Rufinamide was approved by the US Food and Drug Administration on November 14, 2008 as adjunctive treatment of seizures associated with Lennox-Gastaut syndrome in children 4 years and older and adults. Its official FDA-approved labeling does not mention use in the treatment of partial seizures inasmuch as clinical trials submitted to the FDA were marginal. However, several recent clinical trials suggest that the drug has efficacy for partial seizures [2] It is marketed under the brand name Banzel.[3] It is also marketed in the European Union under the brand name Inovelon.[4]

The mechanism of action of rufinamide is unknown. However, it is presumed to involve stabilization of the sodium channel inactive state, effectively keeping these ion channels closed. Although the direct mechanism of action may be different, several other antiepileptic agents also stabilize a sodium channel inactive state including phenytoin, carbamazepine, and lacosamide (stabilizes the slow inactive state).