8293. Rufinamide

Nomenclature

CAS number: 106308-44-5
1-[(2,6-Difluorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide; 1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide; CGP-33101; Banzel (Eisai); Inovelon (Eisai).
C10H8F2N4O; mol wt 238.19.
C 50.42%, H 3.39%, F 15.95%, N 23.52%, O 6.72%.

Description and 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) DOI PubMed. Clinical study in epilepsy: S. Palhagen et al., Epilepsy Res. 43, 115 (2001) DOI PubMed. Clinical evaluation in generalized seizures associated with Lennox-Gastaut syndrome: T. Glauser et al., Neurology 70, 1950 (2008) DOI PubMed. Review of clinical experience: K. K. Jain et al., Exp. Opin. Invest. Drugs 9, 829-840 (2000); of clinical pharmacokinetics: E. Perucca et al., Epilepsia 49, 1123-1141 (2008) DOI PubMed.

Chemical structure

Properties

Crystals from ethanol, mp 237-240°. Moderate soly in 0.1N HCl; slightly sol in tetrahydrofuran, methanol; very slightly sol in ethanol, acetonitrile. Practically insol in water.

Therapeutic Category

Anticonvulsant.

Keywords

Anticonvulsant