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Details

Stereochemistry RACEMIC
Molecular Formula C17H20F6N2O3
Molecular Weight 414.3434
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLECAINIDE

SMILES

C1CCNC(C1)CN=C(c2cc(ccc2OCC(F)(F)F)OCC(F)(F)F)O

InChI

InChIKey=DJBNUMBKLMJRSA-UHFFFAOYSA-N
InChI=1S/C17H20F6N2O3/c18-16(19,20)9-27-12-4-5-14(28-10-17(21,22)23)13(7-12)15(26)25-8-11-3-1-2-6-24-11/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26)

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/flecainide.html

Flecainide is a potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial arrhythmias and tachycardias. Flecainide has local anesthetic activity and belongs to the membrane stabilizing (Class 1) group of antiarrhythmic agents; it has electrophysiologic effects characteristic of the IC class of antiarrhythmics. Flecainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers. Flecainide is a sodium channel blocker, binding to voltage gated sodium channels. It stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole. Flecainide is sold under the trade name Tambocor (manufactured by 3M pharmaceuticals). Flecainide went off-patent on February 10, 2004. In addition to being marketed as Tambocor, it is also available in generic version and under the trade names Almarytm, Apocard, Ecrinal, and Flécaine.

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Flecainide

Approved Use

In patients without structural heart disease, Flecainide is indicated for the prevention of - paroxysmal supraventricular tachycardias (PSVT), including atrioventricular nodal reentrant tachycardia, atrioventricular reentrant tachycardia and other supraventricular tachycardias of unspecified mechanism associated with disabling symptoms - paroxysmal atrial fibrillation/flutter (PAF) associated with disabling symptoms Flecainide is also indicated for the prevention of - documented ventricular arrhythmias, such as sustained ventricular tachycardia (sustained VT), that in the judgment of the physician, are lifethreatening.

Launch Date

9.9645122E11
Preventing
Flecainide

Approved Use

In patients without structural heart disease, Flecainide is indicated for the prevention of - paroxysmal supraventricular tachycardias (PSVT), including atrioventricular nodal reentrant tachycardia, atrioventricular reentrant tachycardia and other supraventricular tachycardias of unspecified mechanism associated with disabling symptoms - paroxysmal atrial fibrillation/flutter (PAF) associated with disabling symptoms Flecainide is also indicated for the prevention of - documented ventricular arrhythmias, such as sustained ventricular tachycardia (sustained VT), that in the judgment of the physician, are lifethreatening.

Launch Date

9.9645122E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
355 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLECAINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1710 ng/mL
2 mg/kg single, intravenous
dose: 2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLECAINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5979 ng × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLECAINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6238 ng × h/mL
2 mg/kg single, intravenous
dose: 2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
FLECAINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.9 μg × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLECAINIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.5 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLECAINIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
60%
FLECAINIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources: Page: p.487
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.487
Disc. AE: Unconsciousness, Cyanosis...
AEs leading to
discontinuation/dose reduction:
Unconsciousness
Cyanosis
Bradycardia
Arrhythmia
Sources: Page: p.487
3800 mg single, oral
Overdose
Dose: 3800 mg
Route: oral
Route: single
Dose: 3800 mg
Co-administed with::
diazepam, p.o(50 mg)
loperamide, p.o(20 mg)
Sources:
healthy, 28
n = 1
Health Status: healthy
Age Group: 28
Sex: F
Population Size: 1
Sources:
Disc. AE: Polymorphic ventricular tachycardia...
AEs leading to
discontinuation/dose reduction:
Polymorphic ventricular tachycardia
Sources:
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.423
healthy, 36
n = 1
Health Status: healthy
Age Group: 36
Sex: M
Population Size: 1
Sources: Page: p.423
Disc. AE: Ventricular tachycardia, Hypotension...
AEs leading to
discontinuation/dose reduction:
Ventricular tachycardia
Hypotension
Cardiopulmonary arrest
Sources: Page: p.423
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Co-administed with::
lamotrigine, p.o
quetiapine, p.o
Sources: Page: p.1
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Atrial fibrillation
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.1
Disc. AE: Brugada syndrome, Mental status changes...
AEs leading to
discontinuation/dose reduction:
Brugada syndrome
Mental status changes
Fatigue
Sources: Page: p.1
200 mg 2 times / day multiple, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Paroxysmal supraventricular tachycardias|paroxysmal atrial fibrillation/flutter|Sustained ventricular tachycardia
Sources:
Disc. AE: Ventricular tachycardia, Cardiac arrest...
AEs leading to
discontinuation/dose reduction:
Ventricular tachycardia
Cardiac arrest
Sources:
AEs

AEs

AESignificanceDosePopulation
Arrhythmia Disc. AE
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources: Page: p.487
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.487
Bradycardia Disc. AE
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources: Page: p.487
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.487
Cyanosis Disc. AE
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources: Page: p.487
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.487
Unconsciousness Disc. AE
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources: Page: p.487
healthy, 18
n = 1
Health Status: healthy
Age Group: 18
Sex: F
Population Size: 1
Sources: Page: p.487
Polymorphic ventricular tachycardia Disc. AE
3800 mg single, oral
Overdose
Dose: 3800 mg
Route: oral
Route: single
Dose: 3800 mg
Co-administed with::
diazepam, p.o(50 mg)
loperamide, p.o(20 mg)
Sources:
healthy, 28
n = 1
Health Status: healthy
Age Group: 28
Sex: F
Population Size: 1
Sources:
Cardiopulmonary arrest Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.423
healthy, 36
n = 1
Health Status: healthy
Age Group: 36
Sex: M
Population Size: 1
Sources: Page: p.423
Hypotension Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.423
healthy, 36
n = 1
Health Status: healthy
Age Group: 36
Sex: M
Population Size: 1
Sources: Page: p.423
Ventricular tachycardia Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources: Page: p.423
healthy, 36
n = 1
Health Status: healthy
Age Group: 36
Sex: M
Population Size: 1
Sources: Page: p.423
Brugada syndrome Disc. AE
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Co-administed with::
lamotrigine, p.o
quetiapine, p.o
Sources: Page: p.1
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Atrial fibrillation
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.1
Fatigue Disc. AE
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Co-administed with::
lamotrigine, p.o
quetiapine, p.o
Sources: Page: p.1
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Atrial fibrillation
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.1
Mental status changes Disc. AE
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Co-administed with::
lamotrigine, p.o
quetiapine, p.o
Sources: Page: p.1
unhealthy, 62
n = 1
Health Status: unhealthy
Condition: Atrial fibrillation
Age Group: 62
Sex: M
Population Size: 1
Sources: Page: p.1
Cardiac arrest Disc. AE
200 mg 2 times / day multiple, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Paroxysmal supraventricular tachycardias|paroxysmal atrial fibrillation/flutter|Sustained ventricular tachycardia
Sources:
Ventricular tachycardia Disc. AE
200 mg 2 times / day multiple, oral
Recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: Paroxysmal supraventricular tachycardias|paroxysmal atrial fibrillation/flutter|Sustained ventricular tachycardia
Sources:
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 0.44 uM]
yes [IC50 0.49 uM]
yes [IC50 191 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes (co-administration study)
Comment: During the period in which the CYP2D6 inhibitor paroxetine was administered, the flecainide AUC in extensive and intermediate metabolizers was increased to 128.5% of basal values (90% CI, 122.2%– 135.2%) and 116.6% of basal values (90% CI, 107.3%–126.8%). However, poor metabolizers exhibited no alterations in AUC after administration of paroxetine (pharmacogenomic studies were also performed)
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Comparative haemodynamic effects of intravenous lignocaine, disopyramide and flecainide in uncomplicated acute myocardial infarction.
1986 Dec
Dysarthria and visual hallucinations due to flecainide toxicity.
1986 Jan
Rapid suppression of flecainide-induced incessant ventricular tachycardia with high-dose intravenous amiodarone.
1988 Apr
[Central nervous system side effects due to anti-arrhythmia therapy. Psychotic depression due to flecainide].
1988 Mar 11
Prevention of symptomatic recurrences of paroxysmal atrial fibrillation in patients initially tolerating antiarrhythmic therapy. A multicenter, double-blind, crossover study of flecainide and placebo with transtelephonic monitoring. Flecainide Supraventricular Tachycardia Study Group.
1989 Dec
Reversal of proarrhythmic effects of flecainide acetate and encainide hydrochloride by propranolol.
1989 Dec
Flecainide-induced ventricular tachycardia and fibrillation in patients treated for atrial fibrillation.
1989 Jul 15
[Arrhythmogenic effect of flecainide--treatment with i.v. magnesium].
1989 Sep
Possible atrial proarrhythmic effects of class 1C antiarrhythmic drugs.
1990 Aug 1
Acute urinary retention associated with flecainide.
1990 Jan-Feb
[Effects of oral flecainide treatment of refractory tachyarrhythmias].
1990 May
Proarrhythmia, cardiac arrest and death in young patients receiving encainide and flecainide. The Pediatric Electrophysiology Group.
1991 Aug
Increased risk of death and cardiac arrest from encainide and flecainide in patients after non-Q-wave acute myocardial infarction in the Cardiac Arrhythmia Suppression Trial. CAST Investigators.
1991 Dec 15
Mortality and morbidity in patients receiving encainide, flecainide, or placebo. The Cardiac Arrhythmia Suppression Trial.
1991 Mar 21
Proarrhythmic and antiarrhythmic effects of flecainide on nonsustained reentry around the canine atrial tricuspid ring in vitro.
1991 Nov
Flecainide in quinidine-resistant atrial fibrillation.
1992 Aug 20
Long-term safety and efficacy of flecainide in the treatment of supraventricular tachyarrhythmias: the United States experience. The Flecainide Supraventricular Tachyarrhythmia Investigators.
1992 Aug 20
Asystole and cardiogenic shock due to combined treatment with verapamil and flecainide.
1992 Aug 29
Pseudo infarction ECG pattern occurring during intravenous treatment with flecainide acetate.
1992 Jan
Effects of advancing age on the efficacy and side effects of antiarrhythmic drugs in post-myocardial infarction patients with ventricular arrhythmias. The CAST Investigators.
1992 Jul
Efficacy of flecainide, sotalol, and verapamil in the treatment of right ventricular tachycardia in patients without overt cardiac abnormality.
1992 Oct
Flecainide induced peripheral neuropathy.
1992 Oct 3
A randomized double-blind crossover study comparing the efficacy and tolerability of flecainide and quinidine in the control of patients with symptomatic paroxysmal atrial fibrillation.
1992 Sep
Symptomatic bradycardia secondary to interaction between topical timolol maleate, verapamil, and flecainide: a case report.
2002 Apr
Selection of drugs to test the specificity of the Tg.AC assay by screening for induction of the gadd153 promoter in vitro.
2003 Aug
Flecainide test in Brugada syndrome: a reproducible but risky tool.
2003 Jan
Safety and feasibility of a clinical pathway for the outpatient initiation of antiarrhythmic medications in patients with atrial fibrillation or atrial flutter.
2003 Jun 15
Flecainide induced ventricular fibrillation in a neonate.
2003 Oct
Flecainide induced ventricular tachycardia (torsades de pointes).
2003 Sep
Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels.
2004 Jul
Brugada pattern electrocardiographic changes associated with profound electrolyte disturbance.
2004 Jul
Different clinical courses and predictors of atrial fibrillation occurrence after transisthmic ablation in patients with preablation lone atrial flutter, coexistent atrial fibrillation, and drug induced atrial flutter.
2004 Nov
Electrocardiographical case. Asymptomatic patient with ST-segment elevation.
2004 Nov
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system.
2005 Feb
[Intravenous flecainide administration for conversion of paroxysmal atrial fibrillation in the emergency room].
2006 May
Management of atrial fibrillation.
2007
[Clinical case of the month. Atrial flutter with rapid ventricular response (1:1 atrioventricular conduction) caused by flecaïnide].
2007 Dec
Determination of phospholipidosis potential based on gene expression analysis in HepG2 cells.
2007 Mar
[Sinus caroticus syndrome diagnosed after 43 years].
2007 Nov 12
The use of bupropion SR in cigarette smoking cessation.
2008
Paranoid psychosis and myoclonus: flecainide toxicity in renal failure.
2008
Drug therapy considerations in arrhythmias in children.
2008 Aug 1
Lidocaine-induced Brugada syndrome phenotype linked to a novel double mutation in the cardiac sodium channel.
2008 Aug 15
Ventricular dysfunction: tachycardia induced cardiomyopathy.
2008 May 1
Role of cytochrome P450 in drug interactions.
2008 Oct 18
Is flecainide dangerous in long QT-3 patients?
2009 Jan
Iatrogenic Flecainide toxicity.
2010 Dec
Tpeak-Tend interval and Tpeak-Tend/QT ratio as markers of ventricular tachycardia inducibility in subjects with Brugada ECG phenotype.
2010 Feb
Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis.
2011 Oct
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.
2013 Dec
Patents

Sample Use Guides

Usual Adult Dose for Ventricular Tachycardia Initial dose: 100 mg orally every 12 hours. Maintenance dose: May be increased in increments of 50 mg bid every 4 days until efficacy is achieved. Most patients with SUSTAINED VT do not require more than 150 mg every 12 hours (300 mg/day), and the maximum dose recommended is 400 mg/day. Usual Adult Dose for Atrial Fibrillation Initial dose: 50 mg orally every 12 hours. Maintenance dose: May be increased in increments of 50 mg bid every 4 days until efficacy is achieved.
Route of Administration: Oral
Flecainide produced a dose-dependent prolongation of the cardiac action potential at 1 and 3uM in human pluripotent stem cell-derived cardiomyocytes.
Name Type Language
FLECAINIDE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
N-(2-PIPERIDYLMETHYL)-2,5-BIS(2,2,2-TRIFLUOROETHOXY)BENZAMIDE
Systematic Name English
FLECAINIDE [VANDF]
Common Name English
THN102 COMPONENT FLECAINIDE
Common Name English
THN-102 COMPONENT FLECAINIDE
Code English
FLECAINIDE [MI]
Common Name English
FLECAINIDE [WHO-DD]
Common Name English
NSC-719273
Code English
FLECAINIDE [INN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175426
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
WHO-VATC QC01BC04
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
LIVERTOX 416
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
WHO-ATC C01BC04
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
NCI_THESAURUS C47793
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
FDA ORPHAN DRUG 536716
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
NCI_THESAURUS C93038
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
Code System Code Type Description
MERCK INDEX
M5400
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY Merck Index
PUBCHEM
3356
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
NCI_THESAURUS
C62029
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PRIMARY
EVMPD
SUB07637MIG
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PRIMARY
MESH
D005424
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
RXCUI
4441
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY RxNorm
FDA UNII
K94FTS1806
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PRIMARY
DRUG CENTRAL
1176
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
WIKIPEDIA
FLECAINIDE
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
DRUG BANK
DB01195
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
CAS
54143-55-4
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
EPA CompTox
54143-55-4
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
LACTMED
Flecainide
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL652
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
IUPHAR
2560
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY
INN
4096
Created by admin on Fri Jun 25 21:51:44 UTC 2021 , Edited by admin on Fri Jun 25 21:51:44 UTC 2021
PRIMARY