U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H8F2N4O
Molecular Weight 238.1939
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUFINAMIDE

SMILES

c1cc(c(Cn2cc(C(=N)O)nn2)c(c1)F)F

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)

HIDE SMILES / InChI

Description
Curator's Comment:: 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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BANZEL

Approved Use

I 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 Date

1226620800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.8 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
70.3 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
7.2 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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:
healthy
Health Status: healthy
Sources:
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:
unhealthy
Disc. AE: Vomiting, Dizziness...
AEs leading to
discontinuation/dose reduction:
Vomiting (1%)
Dizziness (3%)
Headache (2%)
Nausea (1%)
Ataxia (1%)
Sources:
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:
unhealthy
Disc. AE: Convulsion, Rash...
AEs leading to
discontinuation/dose reduction:
Convulsion (2%)
Rash (2%)
Sources:
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:
unhealthy
Other AEs: Depression worsened, Suicidal behavior...
Other AEs:
Depression worsened
Suicidal behavior (serious)
Leukopenia (serious)
Mood change
Central nervous system disorder NOS
Hypersensitivity reaction
Sources:
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:
unhealthy
Disc. AE: Fatigue...
Other AEs: QT shortened...
AEs leading to
discontinuation/dose reduction:
Fatigue (1-2)
Other AEs:
QT shortened (serious)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
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
Transitional polytherapy: tricks of the trade for monotherapy to monotherapy AED conversions.
2009 Jun
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 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.
Name Type Language
RUFINAMIDE
DASH   EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
1-(2,6-DIFLUOROBENZYL)-1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE
Systematic Name English
1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE, 1-((2,6-DIFLUOROPHENYL)METHYL)-
Systematic Name English
RUFINAMIDE [ORANGE BOOK]
Common Name English
RUFINAMIDE [WHO-DD]
Common Name English
RUFINAMIDE [JAN]
Common Name English
INOVELON
Brand Name English
RUFINAMIDE [MART.]
Common Name English
RUF 331
Code English
RUFINAMIDE [EMA EPAR]
Common Name English
CGP 33101
Code English
E-2080
Code English
CGP-33101
Code English
RUFINAMIDE [VANDF]
Common Name English
RUFINAMIDE [USP MONOGRAPH]
Common Name English
RUF-331
Code English
60231/4
Code English
RUFINAMIDE [MI]
Common Name English
E2080
Code English
RUFINAMIDE [USP-RS]
Common Name English
RUFINAMIDE [USAN]
Common Name English
RUFINAMIDE [INN]
Common Name English
BANZEL
Brand Name English
Classification Tree Code System Code
WHO-ATC N03AF03
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
NCI_THESAURUS C264
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
WHO-VATC QN03AF03
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
LIVERTOX 865
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
EU-Orphan Drug EU/3/04/240
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
EMA ASSESSMENT REPORTS INOVELON (AUTHORIZED: EPILEPSY)
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
FDA ORPHAN DRUG 193504
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
Code System Code Type Description
MESH
C079703
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
INN
7387
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
WIKIPEDIA
RUFINAMIDE
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
CAS
106308-44-5
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
FDA UNII
WFW942PR79
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
USP_CATALOG
1606401
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY USP-RS
PUBCHEM
129228
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
IUPHAR
7470
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
EVMPD
SUB10403MIG
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201754
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
RXCUI
69036
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY RxNorm
LACTMED
Rufinamide
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
MERCK INDEX
M9696
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C75167
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
DRUG BANK
DB06201
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
EPA CompTox
106308-44-5
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY
DRUG CENTRAL
3534
Created by admin on Sat Jun 26 05:39:44 UTC 2021 , Edited by admin on Sat Jun 26 05:39:44 UTC 2021
PRIMARY