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Details

Stereochemistry RACEMIC
Molecular Formula C17H20F6N2O3
Molecular Weight 414.3427
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLECAINIDE

SMILES

FC(F)(F)COC1=CC=C(OCC(F)(F)F)C(=C1)C(=O)NCC2CCCCN2

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

Molecular Formula C17H20F6N2O3
Molecular Weight 414.3427
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

2001
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

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
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:
healthy, 18
Health Status: healthy
Age Group: 18
Sex: F
Sources:
Disc. AE: Unconsciousness, Cyanosis...
AEs leading to
discontinuation/dose reduction:
Unconsciousness
Cyanosis
Bradycardia
Arrhythmia
Sources:
3800 mg single, oral
Overdose
Dose: 3800 mg
Route: oral
Route: single
Dose: 3800 mg
Sources:
healthy, 28
Health Status: healthy
Age Group: 28
Sex: F
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:
healthy, 36
Health Status: healthy
Age Group: 36
Sex: M
Sources:
Disc. AE: Ventricular tachycardia, Hypotension...
AEs leading to
discontinuation/dose reduction:
Ventricular tachycardia
Hypotension
Cardiopulmonary arrest
Sources:
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: M
Sources:
Disc. AE: Brugada syndrome, Mental status changes...
AEs leading to
discontinuation/dose reduction:
Brugada syndrome
Mental status changes
Fatigue
Sources:
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
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:
healthy, 18
Health Status: healthy
Age Group: 18
Sex: F
Sources:
Bradycardia Disc. AE
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
healthy, 18
Health Status: healthy
Age Group: 18
Sex: F
Sources:
Cyanosis Disc. AE
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
healthy, 18
Health Status: healthy
Age Group: 18
Sex: F
Sources:
Unconsciousness Disc. AE
1200 mg single, oral
Overdose
Dose: 1200 mg
Route: oral
Route: single
Dose: 1200 mg
Sources:
healthy, 18
Health Status: healthy
Age Group: 18
Sex: F
Sources:
Polymorphic ventricular tachycardia Disc. AE
3800 mg single, oral
Overdose
Dose: 3800 mg
Route: oral
Route: single
Dose: 3800 mg
Sources:
healthy, 28
Health Status: healthy
Age Group: 28
Sex: F
Sources:
Cardiopulmonary arrest Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
healthy, 36
Health Status: healthy
Age Group: 36
Sex: M
Sources:
Hypotension Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
healthy, 36
Health Status: healthy
Age Group: 36
Sex: M
Sources:
Ventricular tachycardia Disc. AE
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
healthy, 36
Health Status: healthy
Age Group: 36
Sex: M
Sources:
Brugada syndrome Disc. AE
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: M
Sources:
Fatigue Disc. AE
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: M
Sources:
Mental status changes Disc. AE
1 g single, oral
Overdose
Dose: 1 g
Route: oral
Route: single
Dose: 1 g
Sources:
unhealthy, 62
Health Status: unhealthy
Age Group: 62
Sex: M
Sources:
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
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
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
Refining the human iPSC-cardiomyocyte arrhythmic risk assessment model.
2013-12
The effects of jaspamide on human cardiomyocyte function and cardiac ion channel activity.
2013-03
Palmitate increases the susceptibility of cells to drug-induced toxicity: an in vitro method to identify drugs with potential contraindications in patients with metabolic disease.
2012-10
Comparison of a genomic and a multiplex cell imaging approach for the detection of phospholipidosis.
2011-10
Estimating the risk of drug-induced proarrhythmia using human induced pluripotent stem cell-derived cardiomyocytes.
2011-09
Carvedilol and its new analogs suppress arrhythmogenic store overload-induced Ca2+ release.
2011-07-10
Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy.
2011-06
Iatrogenic Flecainide toxicity.
2010-12
Tachycardia due to atrial flutter with rapid 1:1 conduction following treatment of atrial fibrillation with flecainide.
2010-03-10
Tpeak-Tend interval and Tpeak-Tend/QT ratio as markers of ventricular tachycardia inducibility in subjects with Brugada ECG phenotype.
2010-02
A case of flecainide-induced hyponatremia.
2009-10
Delirium in a patient with toxic flecainide plasma concentrations: the role of a pharmacokinetic drug interaction with paroxetine.
2009-07
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current.
2009-06
A preliminary assessment of the effects of ATI-2042 in subjects with paroxysmal atrial fibrillation using implanted pacemaker methodology.
2009-04
Is flecainide dangerous in long QT-3 patients?
2009-01
ECGs in the ED.
2008-11
Role of cytochrome P450 in drug interactions.
2008-10-18
Drug therapy considerations in arrhythmias in children.
2008-08-01
The Relationship Between HIV Infection and Cardiovascular Disease.
2008-08
Proarrhythmia, cardiac arrest and death in young patients receiving encainide and flecainide. The Pediatric Electrophysiology Group.
1991-08
Mortality and morbidity in patients receiving encainide, flecainide, or placebo. The Cardiac Arrhythmia Suppression Trial.
1991-03-21
Safety and efficacy of oral flecainide therapy in patients with atrioventricular re-entrant tachycardia.
1991-02-01
Flecainide acetate treatment of paroxysmal supraventricular tachycardia and paroxysmal atrial fibrillation: dose-response studies. The Flecainide Supraventricular Tachycardia Study Group.
1991-02
Reversion of recent-onset atrial fibrillation to sinus rhythm by intravenous flecainide.
1991-01-15
Flecainide acetate prevents recurrence of symptomatic paroxysmal supraventricular tachycardia. The Flecainide Supraventricular Tachycardia Study Group.
1991-01
Combined application of class I antiarrhythmic drugs causes "additive", "reductive", or "synergistic" sodium channel block in cardiac muscles.
1990-11
Relative efficacy and safety of intravenous drugs for termination of sustained ventricular tachycardia.
1990-09-15
Possible atrial proarrhythmic effects of class 1C antiarrhythmic drugs.
1990-08-01
Dangerous recurrence of arrhythmia following withdrawal of flecainide.
1990-08
Amiodarone toxicity: myopathy and neuropathy.
1990-05
[Effects of oral flecainide treatment of refractory tachyarrhythmias].
1990-05
Serious interactions of sotalol with amiodarone and flecainide.
1990-03-05
Profound exacerbation of neuromuscular weakness by flecainide.
1990-02
Acute urinary retention associated with flecainide.
1990-01-01
Torsades de pointe with flecainide-amiodarone therapy.
1990
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.
1989-12
Reversal of proarrhythmic effects of flecainide acetate and encainide hydrochloride by propranolol.
1989-12
[Bidirectional tachycardia during therapy with lorajmine].
1989-10
Generalized seizures as the presentation of flecainide toxicity.
1989-10
[Arrhythmogenic effect of flecainide--treatment with i.v. magnesium].
1989-09
Flecainide-induced ventricular tachycardia and fibrillation in patients treated for atrial fibrillation.
1989-07-15
Cardioprotective effects of various class I antiarrhythmic drugs in canine hearts.
1989-07
Rapid suppression of flecainide-induced incessant ventricular tachycardia with high-dose intravenous amiodarone.
1988-04
[Central nervous system side effects due to anti-arrhythmia therapy. Psychotic depression due to flecainide].
1988-03-11
Flecainide-induced sustained ventricular tachycardia successfully treated with lidocaine.
1987-09
Flecainide acetate in the treatment of tachycardias associated with Mahaim fibres.
1987-08
[Hemodynamic effects of the anti-arrhythmia agent flecainide (Tambocor) in coronary surgery patients].
1987-06
[Drug-induced intrahepatic cholestasis caused by flecainide acetate and enalapril].
1987-03
Comparative haemodynamic effects of intravenous lignocaine, disopyramide and flecainide in uncomplicated acute myocardial infarction.
1986-12
Dysarthria and visual hallucinations due to flecainide toxicity.
1986-01
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.
Substance Class Chemical
Created
by admin
on Wed Apr 02 09:30:17 GMT 2025
Edited
by admin
on Wed Apr 02 09:30:17 GMT 2025
Record UNII
K94FTS1806
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-719273
Preferred Name English
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 [WHO-DD]
Common Name English
FLECAINIDE [MI]
Common Name English
flecainide [INN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175426
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
WHO-VATC QC01BC04
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
LIVERTOX NBK548023
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
FDA ORPHAN DRUG 536716
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
WHO-ATC C01BC04
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
NCI_THESAURUS C47793
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
NCI_THESAURUS C93038
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
Code System Code Type Description
MERCK INDEX
m5400
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY Merck Index
PUBCHEM
3356
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
NCI_THESAURUS
C62029
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
EVMPD
SUB07637MIG
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
MESH
D005424
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
DAILYMED
K94FTS1806
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
NSC
719273
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
RXCUI
4441
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY RxNorm
CHEBI
75984
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
FDA UNII
K94FTS1806
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
DRUG CENTRAL
1176
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
WIKIPEDIA
FLECAINIDE
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
DRUG BANK
DB01195
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
CAS
54143-55-4
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID8023054
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
LACTMED
Flecainide
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
SMS_ID
100000080972
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
ChEMBL
CHEMBL652
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
IUPHAR
2560
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
INN
4096
Created by admin on Wed Apr 02 09:30:17 GMT 2025 , Edited by admin on Wed Apr 02 09:30:17 GMT 2025
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
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PARENT -> IMPURITY
Intermediate
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ACTIVE MOIETY