Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H8F2N4O |
Molecular Weight | 238.1935 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=CN(CC2=C(F)C=CC=C2F)N=N1
InChI
InChIKey=POGQSBRIGCQNEG-UHFFFAOYSA-N
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)
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.rxlist.com/banzel-drug.htm
https://www.drugs.com/mtm/rufinamide.html
Curator's Comment: description was created based on several sources, including:
http://www.rxlist.com/banzel-drug.htm
https://www.drugs.com/mtm/rufinamide.html
Rufinamide is an anti-epileptic drug that is FDA approved for the treatment of lennox-gastaut syndrome (LGS). The principal mechanism of action of rufinamide is modulation of the activity of sodium channels and, in particular, prolongation of the inactive state of the channel. Hormonal contraceptives may be less effective with rufinamide. Patients on valproate should begin at a rufinamide dose lower than 10 mg/kg per day (pediatric patients) or 400 mg per day (adults). Common adverse reactions include headache, dizziness, fatigue, somnolence, and nausea.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4296 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23221868 |
3.8 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | BANZEL Approved UseI NDICATIONS AND USAGE BANZEL is indicated for adjunctive treatment of seizures associated with Lennox-Gastaut Syndrome in pediatric patients 1 year of age and older and in adults. BANZEL is indicated for adjunctive treatment of seizures associated with Lennox-Gastaut Syndrome (LGS) in pediatric patients 1 year of age and older, and in adults (1) Launch Date1.2266208E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18503564/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
RUFINAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
70.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18503564/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
RUFINAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18503564/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
RUFINAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
10 h |
200 mg 2 times / day unknown, oral dose: 200 mg route of administration: Oral experiment type: UNKNOWN co-administered: |
RUFINAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
66% |
200 mg 2 times / day unknown, oral dose: 200 mg route of administration: Oral experiment type: UNKNOWN co-administered: |
RUFINAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
3600 mg 2 times / day multiple, oral MTD Dose: 3600 mg, 2 times / day Route: oral Route: multiple Dose: 3600 mg, 2 times / day Sources: Page: p.1125, p.1139 |
healthy n = 15 Health Status: healthy Population Size: 15 Sources: Page: p.1125, p.1139 |
|
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.1 |
Other AEs: Depression worsened, Suicidal behavior... Other AEs: Depression worsened Sources: Page: p.1Suicidal behavior (serious) Leukopenia (serious) Mood change Central nervous system disorder NOS Hypersensitivity reaction |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.4 |
Disc. AE: Fatigue... Other AEs: QT shortened... AEs leading to discontinuation/dose reduction: Fatigue (1-2) Other AEs:QT shortened (serious) Sources: Page: p.4 |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.7 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.7 |
Disc. AE: Convulsion, Rash... AEs leading to discontinuation/dose reduction: Convulsion (2%) Sources: Page: p.7Rash (2%) |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.8 |
Disc. AE: Vomiting, Dizziness... AEs leading to discontinuation/dose reduction: Vomiting (1%) Sources: Page: p.8Dizziness (3%) Headache (2%) Nausea (1%) Ataxia (1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Central nervous system disorder NOS | 22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.1 |
|
Depression worsened | 22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.1 |
|
Hypersensitivity reaction | 22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.1 |
|
Mood change | 22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.1 |
|
Leukopenia | serious | 22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.1 |
Suicidal behavior | serious | 22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.1 |
Fatigue | 1-2 Disc. AE |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.4 |
QT shortened | serious | 22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.4 |
Convulsion | 2% Disc. AE |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.7 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.7 |
Rash | 2% Disc. AE |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.7 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.7 |
Ataxia | 1% Disc. AE |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.8 |
Nausea | 1% Disc. AE |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.8 |
Vomiting | 1% Disc. AE |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.8 |
Headache | 2% Disc. AE |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.8 |
Dizziness | 3% Disc. AE |
22.5 mg/kg 2 times / day multiple, oral Studied dose Dose: 22.5 mg/kg, 2 times / day Route: oral Route: multiple Dose: 22.5 mg/kg, 2 times / day Sources: Page: p.8 |
unhealthy Health Status: unhealthy Condition: Lennox-Gastaut Syndrome Sources: Page: p.8 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021911Orig1s000ClinPharmR_P1.pdf Page: 21, 56 |
inconclusive | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021911Orig1s000ClinPharmR_P1.pdf Page: 56.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021911Orig1s000ClinPharmR_P1.pdf Page: 21.0 |
weak | yes (co-administration study) Comment: coadministration with triazolam resulted in a 37% decrease in AUC and 23% decrease in Cmax of triazolam Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021911Orig1s000ClinPharmR_P1.pdf Page: 21.0 |
||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021911Orig1s000ClinPharmR_P1.pdf Page: 21, 56 |
yes [Ki 450 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021911Orig1s000ClinPharmR_P1.pdf Page: 20.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/021911Orig1s000ClinPharmR_P1.pdf Page: 40, 56 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 39.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Rufinamide: Further evaluation is needed in Lennox-Gastaut syndrome. | 2008 Aug |
|
Update on the management of Lennox-Gastaut syndrome with a focus on rufinamide. | 2009 |
|
Onset of action and seizure control in Lennox-Gaustaut syndrome: focus on rufinamide. | 2009 Apr |
|
Rufinamide for the adjunctive treatment of partial seizures in adults and adolescents: a randomized placebo-controlled trial. | 2009 Aug |
|
Safety and tolerability of rufinamide in children with epilepsy: a pooled analysis of 7 clinical studies. | 2009 Dec |
|
Treatment of Lennox-Gastaut syndrome. | 2009 Jul 8 |
|
Minimizing AED adverse effects: improving quality of life in the interictal state in epilepsy care. | 2009 Jun |
|
Truly "rational" polytherapy: maximizing efficacy and minimizing drug interactions, drug load, and adverse effects. | 2009 Jun |
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Transitional polytherapy: tricks of the trade for monotherapy to monotherapy AED conversions. | 2009 Jun |
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Antiepileptic drug monotherapy: the initial approach in epilepsy management. | 2009 Jun |
|
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions. | 2009 Mar-Apr |
|
Adopting an orphan drug: rufinamide for Lennox-Gastaut syndrome. | 2009 May-Jun |
|
New drugs: Febuxostat, lacosamide, and rufinamide. | 2009 May-Jun |
|
Gateways to clinical trials. | 2009 Nov |
|
The possible antianxiety and mood-stabilizing effects of rufinamide. | 2010 |
|
The cost effectiveness of rufinamide in the treatment of Lennox-Gastaut syndrome in the UK. | 2010 |
|
Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs. | 2010 Apr |
|
Gateways to clinical trials. | 2010 Apr |
|
Rufinamide: a new antiepileptic medication for the treatment of seizures associated with lennox-gastaut syndrome. | 2010 Apr |
|
First European long-term experience with the orphan drug rufinamide in childhood-onset refractory epilepsy. | 2010 Apr |
|
"Epileptic encephalopathy" of infancy and childhood: electro-clinical pictures and recent understandings. | 2010 Dec |
|
New drugs for pediatric epilepsy. | 2010 Dec |
|
Post-treatment with voltage-gated Na(+) channel blocker attenuates kainic acid-induced apoptosis in rat primary hippocampal neurons. | 2010 Dec |
|
Ethyl 1-(2,6-difluoro-benz-yl)-1H-1,2,3-triazole-4-carboxyl-ate. | 2010 Dec 15 |
|
Selected pharmacokinetic issues of the use of antiepileptic drugs and parenteral nutrition in critically ill patients. | 2010 Dec 31 |
|
Supporting the recommended paediatric dosing regimen for rufinamide in Lennox-Gastaut syndrome using clinical trial simulation. | 2010 Feb |
|
New Drugs2010, PART 1. | 2010 Feb |
|
A 24-week multicenter, randomized, double-blind, parallel-group, dose-ranging study of rufinamide in adults and adolescents with inadequately controlled partial seizures. | 2010 Feb |
|
Simultaneous HPLC-UV analysis of rufinamide, zonisamide, lamotrigine, oxcarbazepine monohydroxy derivative and felbamate in deproteinized plasma of patients with epilepsy. | 2010 Feb 1 |
|
Lennox-Gastaut syndrome: An overview. | 2010 Jan |
|
Rufinamide: a novel broad-spectrum antiepileptic drug. | 2010 Jan |
|
Drug interactions involving the new second- and third-generation antiepileptic drugs. | 2010 Jan |
|
Cost-utility analysis of rufinamide versus topiramate and lamotrigine for the treatment of children with Lennox-Gastaut Syndrome in the United Kingdom. | 2010 Jan |
|
Drug-induced QT interval shortening: potential harbinger of proarrhythmia and regulatory perspectives. | 2010 Jan |
|
New antiepileptic drugs: lacosamide, rufinamide, and vigabatrin. | 2010 Jul |
|
Update on anticonvulsant drugs. | 2010 Jul |
|
Rufinamide: a new antiepileptic drug treatment for Lennox-Gastaut syndrome. | 2010 Jun |
|
Gateways to clinical trials. | 2010 Mar |
|
Stability of extemporaneously prepared rufinamide oral suspensions. | 2010 Mar |
|
Severe constipation associated with the use of rufinamide (Banzel) in an adolescent. | 2010 May |
|
[Antiepileptic drugs in North America]. | 2010 May |
|
Medical management of Lennox-Gastaut syndrome. | 2010 May |
|
Rufinamide in children and adults with Lennox-Gastaut syndrome: first Italian multicenter experience. | 2010 Nov |
|
Expression, regulation and function of phosphofructo-kinase/fructose-biphosphatases (PFKFBs) in glucocorticoid-induced apoptosis of acute lymphoblastic leukemia cells. | 2010 Nov 23 |
|
Treating Lennox-Gastaut syndrome in epileptic pediatric patients with third-generation rufinamide. | 2010 Oct 5 |
|
Antiepileptic drug interactions - principles and clinical implications. | 2010 Sep |
|
Experience with rufinamide in a pediatric population: a single center's experience. | 2010 Sep |
|
Emerging drugs for partial onset seizures. | 2010 Sep |
|
Adjunctive rufinamide in Lennox-Gastaut syndrome: a long-term, open-label extension study. | 2010 Sep |
|
Rufinamide for pediatric patients with Lennox-Gastaut syndrome: a comprehensive overview. | 2011 Apr 1 |
Patents
Sample Use Guides
Starting daily dose: 400-800 mg per day in two equally divided doses. Increase by 400-800 mg every other day until a maximum dose of 3200 mg per day, in two divided doses, is reached.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18503564
In vitro studies with human liver microsomes using con-centrations of rufinamide in the range of 10–300 µmol/L(2.4–72 µg/ml) found no significant inhibition of any ofeight major human CYP isozymes—CYP1A2, CYP2A6,CYP2C9, CYP2C19, CYP2D6, CYP2E1, CYP3A4/5, andCYP4A9/11.
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Classification Tree | Code System | Code | ||
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WHO-ATC |
N03AF03
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NCI_THESAURUS |
C264
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WHO-VATC |
QN03AF03
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LIVERTOX |
NBK548457
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EU-Orphan Drug |
EU/3/04/240
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EMA ASSESSMENT REPORTS |
INOVELON (AUTHORIZED: EPILEPSY)
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FDA ORPHAN DRUG |
193504
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C079703
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7387
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RUFINAMIDE
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106308-44-5
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WFW942PR79
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129228
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7470
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SUB10403MIG
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WFW942PR79
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CHEMBL1201754
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69036
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Rufinamide
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100000089186
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m9696
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1606401
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C75167
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SS-30
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DB06201
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DTXSID1046506
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3534
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ACTIVE MOIETY
METABOLITE (PARENT)