rufinamide

{{Short description|Chemical compound}}

{{Use dmy dates|date=November 2022}}

{{Distinguish|ralfinamide}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464384547

| IUPAC_name = 1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide

| image = Rufinamide.svg

| image_class = skin-invert-image

| tradename = Banzel, Inovelon

| Drugs.com = {{drugs.com|monograph|rufinamide}}

| MedlinePlus = a609001

| licence_EU = yes

| DailyMedID = Rufinamide

| licence_US = Rufinamide

| pregnancy_AU = B3

| routes_of_administration = By mouth

| ATC_prefix = N03

| ATC_suffix = AF03

| legal_AU =

| legal_BR = C1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA =

| legal_DE =

| legal_NZ =

| legal_UK = POM

| legal_US = Rx-only

| legal_US_comment =

| legal_status = Rx-only

| bioavailability = 85% (under fed conditions); t_max = 4–6 hours

| protein_bound = 34%

| metabolism = Carboxylesterase-mediated hydrolysis (CYP not involved)

| metabolites = Inactive

| elimination_half-life = 6–10 hours

| excretion = Urine (85%){{cite web | title=Banzel- rufinamide tablet, film coated Banzel- rufinamide suspension | website=DailyMed | date=15 April 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=0a3fa925-1abd-458a-bd57-4ae780a1ef2d | access-date=21 October 2020}}

| IUPHAR_ligand = 7470

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 106308-44-5

| PubChem = 129228

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 114471

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = WFW942PR79

| KEGG = D05775

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201754

| C=10 | H=8 | F=2 | N=4 | O=1

| smiles = O=C(c1nnn(c1)Cc2c(F)cccc2F)N

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = POGQSBRIGCQNEG-UHFFFAOYSA-N

}}

Rufinamide is an anticonvulsant medication. It is used in combination with other medication and therapy to treat Lennox–Gastaut syndrome{{cite journal | vauthors = Hakimian S, Cheng-Hakimian A, Anderson GD, Miller JW | title = Rufinamide: a new anti-epileptic medication | journal = Expert Opinion on Pharmacotherapy | volume = 8 | issue = 12 | pages = 1931–1940 | date = August 2007 | pmid = 17696794 | doi = 10.1517/14656566.8.12.1931 | s2cid = 19522242 }} 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 (FDA) in November 2008, as adjunctive treatment of seizures associated with Lennox-Gastaut syndrome in children four 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 {{cite journal | vauthors = Brodie MJ, Rosenfeld WE, Vazquez B, Sachdeo R, Perdomo C, Mann A, Arroyo S | title = Rufinamide for the adjunctive treatment of partial seizures in adults and adolescents: a randomized placebo-controlled trial | journal = Epilepsia | volume = 50 | issue = 8 | pages = 1899–1909 | date = August 2009 | pmid = 19490053 | doi = 10.1111/j.1528-1167.2009.02160.x | s2cid = 38485532 | doi-access = free }} It is marketed under the brand name Banzel.[https://web.archive.org/web/20090606191152/http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2008/ucm116980.htm FDA press release - FDA Approves New Drug to Treat Severe Form of Epilepsy] It is also marketed in the European Union under the brand name Inovelon.{{Cite web |url=http://www.emea.europa.eu/humandocs/Humans/EPAR/inovelon/inovelon.htm |title=European Public Assessment Report for rufinamide (INOVELON) |access-date=25 November 2008 |archive-date=14 March 2009 |archive-url=https://web.archive.org/web/20090314201206/http://www.emea.europa.eu/humandocs/Humans/EPAR/inovelon/inovelon.htm |url-status=dead }} It is available as a generic medication.{{cite web | title=2022 First Generic Drug Approvals | website=U.S. Food and Drug Administration (FDA) | date=3 March 2023 | url=https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/2022-first-generic-drug-approvals | archive-url=https://web.archive.org/web/20230630003602/https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/2022-first-generic-drug-approvals | archive-date=30 June 2023 | url-status=dead | access-date=30 June 2023}}

The mechanism of action of rufinamide is not fully understood. There is some evidence that rufinamide can modulate the gating of voltage-gated sodium channels,{{cite journal | vauthors = Rogawski MA | title = Diverse mechanisms of antiepileptic drugs in the development pipeline | journal = Epilepsy Research | volume = 69 | issue = 3 | pages = 273–294 | date = June 2006 | pmid = 16621450 | pmc = 1562526 | doi = 10.1016/j.eplepsyres.2006.02.004 }}{{cite journal | vauthors = Striano P, McMurray R, Santamarina E, Falip M | title = Rufinamide for the treatment of Lennox-Gastaut syndrome: evidence from clinical trials and clinical practice | journal = Epileptic Disorders | volume = 20 | issue = 1 | pages = 13–29 | date = February 2018 | pmid = 29313492 | doi = 10.1684/epd.2017.0950 | doi-access = free }} a common target for antiepileptic drugs.{{cite journal | vauthors = Rogawski MA, Löscher W | title = The neurobiology of antiepileptic drugs | journal = Nature Reviews. Neuroscience | volume = 5 | issue = 7 | pages = 553–564 | date = July 2004 | pmid = 15208697 | doi = 10.1038/nrn1430 | s2cid = 2201038 | url = https://zenodo.org/record/1233562 }} 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.{{cite journal | vauthors = Gilchrist J, Dutton S, Diaz-Bustamante M, McPherson A, Olivares N, Kalia J, Escayg A, Bosmans F | display-authors = 6 | title = Nav1.1 modulation by a novel triazole compound attenuates epileptic seizures in rodents | journal = ACS Chemical Biology | volume = 9 | issue = 5 | pages = 1204–1212 | date = May 2014 | pmid = 24635129 | pmc = 4027953 | doi = 10.1021/cb500108p }} However, this action cannot explain the unique spectrum of activity of rufinamide.