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

Molecular Formula C10H8F2N4O
Molecular Weight 238.1939
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

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

1.2266208E12
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: Page: p.1125, p.1139
healthy
n = 15
Health Status: healthy
Population Size: 15
Sources: Page: p.1125, p.1139
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
Suicidal behavior (serious)
Leukopenia (serious)
Mood change
Central nervous system disorder NOS
Hypersensitivity reaction
Sources: Page: p.1
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%)
Rash (2%)
Sources: Page: p.7
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%)
Dizziness (3%)
Headache (2%)
Nausea (1%)
Ataxia (1%)
Sources: Page: p.8
AEs

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effects of antiepileptic drugs on cognition.
2001
Rufinamide: a double-blind, placebo-controlled proof of principle trial in patients with epilepsy.
2001 Feb
New antiepileptic drugs that are second generation to existing antiepileptic drugs.
2006 Jun
Rufinamide: Pharmacology, clinical trials, and role in clinical practice.
2006 Nov
Gateways to clinical trials.
2006 Oct
Gateways to clinical trials.
2006 Sep
Rufinamide.
2007 Jan
Progress report on new antiepileptic drugs: a summary of the Eigth Eilat Conference (EILAT VIII).
2007 Jan
Rufinamide.
2007 Jul
[Rufinamide. An orphan drug for treatment of Lennox-Gastaut syndrome].
2007 Oct
Pharmacological management of epilepsy: recent advances and future prospects.
2008
Use of second-generation antiepileptic drugs in the pediatric population.
2008
Pregabalin for the management of partial epilepsy.
2008 Dec
Rufinamide: clinical pharmacokinetics and concentration-response relationships in patients with epilepsy.
2008 Jul
The anticonvulsant profile of rufinamide (CGP 33101) in rodent seizure models.
2008 Jul
Rufinamide for generalized seizures associated with Lennox-Gastaut syndrome.
2008 May 20
American Epilepsy Society--62nd Annual Meeting. 5-9 December 2008, Seattle, USA.
2009 Feb
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
Effectiveness and tolerability of rufinamide in children and adults with refractory epilepsy: first European experience.
2009 Mar
Rufinamide (Banzel) for epilepsy.
2009 Mar 9
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
Gateways to clinical trials.
2009 Nov
Gateways to clinical trials.
2010 Apr
"Epileptic encephalopathy" of infancy and childhood: electro-clinical pictures and recent understandings.
2010 Dec
Ethyl 1-(2,6-difluoro-benz-yl)-1H-1,2,3-triazole-4-carboxyl-ate.
2010 Dec 15
Supporting the recommended paediatric dosing regimen for rufinamide in Lennox-Gastaut syndrome using clinical trial simulation.
2010 Feb
New Drugs2010, PART 1.
2010 Feb
Rufinamide: a novel broad-spectrum antiepileptic drug.
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
Severe constipation associated with the use of rufinamide (Banzel) in an adolescent.
2010 May
[Antiepileptic drugs in North America].
2010 May
Experience with rufinamide in a pediatric population: a single center's experience.
2010 Sep
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:39:43 UTC 2021
Edited
by admin
on Sat Jun 26 05:39:43 UTC 2021
Record UNII
WFW942PR79
Record Status Validated (UNII)
Record Version
  • Download
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
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