Rufinamide

Rufinamide
Clinical data
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a609001
License data	EU EMA: by INN; US FDA: Rufinamide;
Pregnancy; category	US: C (Risk not ruled out) ;
Routes of; administration	By mouth (tablets)
ATC code	N03AF03 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only) ; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	85% (under fed conditions); tmax = 4–6 hours
Protein binding	34%
Metabolism	Carboxylesterase-mediated hydrolysis (CYP not involved)
Metabolites	Inactive
Elimination half-life	6–10 hours
Excretion	Urine (85%)[1]
Identifiers
	IUPAC name 1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide;
CAS Number	106308-44-5 ;
PubChem CID	129228;
IUPHAR/BPS	7470;
ChemSpider	114471 ;
UNII	WFW942PR79;
ChEMBL	ChEMBL1201754 ;
CompTox Dashboard (EPA)	DTXSID1046506 ;
Chemical and physical data
Formula	C10H8F2N4O
Molar mass	238.194 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1nnn(c1)Cc2c(F)cccc2F)N;
	InChI InChI=1S/C10H8F2N4O/c11-7-2-1-3-8(12)6(7)4-16-5-9(10(13)17)14-15-16/h1-3,5H,4H2,(H2,13,17) ; Key:POGQSBRIGCQNEG-UHFFFAOYSA-N ;
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Rufinamide is an anticonvulsant medication. It is used in combination with other medication and therapy to treat Lennox–Gastaut syndrome[2] 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 [3] It is marketed under the brand name Banzel.[4] It is also marketed in the European Union under the brand name Inovelon.[5]

The mechanism of action of rufinamide is unknown. There is some evidence that rufinamide can modulate the gating of voltage-gated sodium channels,[6] a common target for antiepileptic drugs.[7] A recent study indicates subtle effects on the voltage-dependence of gating and the time course of inactivation in some sodium channel isoforms that could reduce neuronal excitability.[8] However, this action cannot explain the unique spectrum of activity of rufinamide.

References

"Banzel (rufinamide) Film-Coated Tablet, for Oral Use, Oral Suspension. Full Prescribing Information" (PDF). Eisai Inc. Retrieved 15 February 2017.
Hakimian S, Cheng-Hakimian A, Anderson GD, Miller JW (August 2007). "Rufinamide: a new anti-epileptic medication". Expert Opin Pharmacother. 8 (12): 1931–40. doi:10.1517/14656566.8.12.1931. PMID 17696794.
Brodie MJ, Rosenfeld WE, Vazquez B, Sachdeo R, Perdomo C, Mann A, Arroyo S (August 2009). "Rufinamide for the adjunctive treatment of partial seizures in adults and adolescents: a randomized placebo-controlled trial". Epilepsia. 50 (8): 1899–909. doi:10.1111/j.1528-1167.2009.02160.x. PMID 19490053.
FDA press release - FDA Approves New Drug to Treat Severe Form of Epilepsy
European Public Assessment Report for rufinamide (INOVELON)
Rogawski, M. A. (2006). "Diverse mechanisms of antiepileptic drugs in the development pipeline". Epilepsy Research. 69 (3): 273–94. doi:10.1016/j.eplepsyres.2006.02.004. PMC 1562526. PMID 16621450.
Rogawski, A.; Löscher, W. (Jul 2004). "The neurobiology of antiepileptic drugs" (PDF). Nature Reviews. Neuroscience. 5 (7): 553–564. doi:10.1038/nrn1430. ISSN 1471-003X. PMID 15208697.
Gilchrist, J; Dutton, S; Diaz-Bustamante, M; McPherson, A; Olivares, N; Kalia, J; Escayg, A; Bosmans, F (2014). "Nav1.1 modulation by a novel triazole compound attenuates epileptic seizures in rodents". ACS Chemical Biology. 9 (5): 1204–12. doi:10.1021/cb500108p. PMC 4027953. PMID 24635129.

External links

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[PI-1] "Banzel (rufinamide) Film-Coated Tablet, for Oral Use, Oral Suspension. Full Prescribing Information" (PDF). Eisai Inc. Retrieved 15 February 2017.

[pmid17696794-2] Hakimian S, Cheng-Hakimian A, Anderson GD, Miller JW (August 2007). "Rufinamide: a new anti-epileptic medication". Expert Opin Pharmacother. 8 (12): 1931–40. doi:10.1517/14656566.8.12.1931. PMID 17696794.

[pmid19490053-3] Brodie MJ, Rosenfeld WE, Vazquez B, Sachdeo R, Perdomo C, Mann A, Arroyo S (August 2009). "Rufinamide for the adjunctive treatment of partial seizures in adults and adolescents: a randomized placebo-controlled trial". Epilepsia. 50 (8): 1899–909. doi:10.1111/j.1528-1167.2009.02160.x. PMID 19490053.

[4] FDA press release - FDA Approves New Drug to Treat Severe Form of Epilepsy

[5] European Public Assessment Report for rufinamide (INOVELON)

[6] Rogawski, M. A. (2006). "Diverse mechanisms of antiepileptic drugs in the development pipeline". Epilepsy Research. 69 (3): 273–94. doi:10.1016/j.eplepsyres.2006.02.004. PMC 1562526. PMID 16621450.

[7] Rogawski, A.; Löscher, W. (Jul 2004). "The neurobiology of antiepileptic drugs" (PDF). Nature Reviews. Neuroscience. 5 (7): 553–564. doi:10.1038/nrn1430. ISSN 1471-003X. PMID 15208697.

[8] Gilchrist, J; Dutton, S; Diaz-Bustamante, M; McPherson, A; Olivares, N; Kalia, J; Escayg, A; Bosmans, F (2014). "Nav1.1 modulation by a novel triazole compound attenuates epileptic seizures in rodents". ACS Chemical Biology. 9 (5): 1204–12. doi:10.1021/cb500108p. PMC 4027953. PMID 24635129.