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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

Molecular Formula C17H20F6N2O3
Molecular Weight 414.3434
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: 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

TargetsConditions

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

996451200000
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

996451200000
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:
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
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
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
Flecainide-induced ventricular tachycardia and fibrillation in patients treated for atrial fibrillation.
1989 Jul 15
Profound exacerbation of neuromuscular weakness by flecainide.
1990 Feb
Acute urinary retention associated with flecainide.
1990 Jan-Feb
Combined application of class I antiarrhythmic drugs causes "additive", "reductive", or "synergistic" sodium channel block in cardiac muscles.
1990 Nov
Relative efficacy and safety of intravenous drugs for termination of sustained ventricular tachycardia.
1990 Sep 15
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
Flecainide acetate treatment of paroxysmal supraventricular tachycardia and paroxysmal atrial fibrillation: dose-response studies. The Flecainide Supraventricular Tachycardia Study Group.
1991 Feb
Safety and efficacy of oral flecainide therapy in patients with atrioventricular re-entrant tachycardia.
1991 Feb 1
Flecainide acetate prevents recurrence of symptomatic paroxysmal supraventricular tachycardia. The Flecainide Supraventricular Tachycardia Study Group.
1991 Jan
Reversion of recent-onset atrial fibrillation to sinus rhythm by intravenous flecainide.
1991 Jan 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
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
Flecainide overdose--support using an intra-aortic balloon pump.
2005 Dec 12
Long-term results of hybrid therapy in patients with atrial fibrillation who develop atrial flutter during flecainide infusion.
2005 Jan
Assessment of serum flecainide trough levels in patients with tachyarrhythmia.
2005 Jan
[Prevalence of Brugada syndrome among 35,309 inhabitants of Lorraine screened at a preventive medicine centre].
2005 Mar
Flecainide-induced neuropathy.
2005 Sep
Long-term protection of central axons with phenytoin in monophasic and chronic-relapsing EAE.
2006 Dec
[Intravenous flecainide administration for conversion of paroxysmal atrial fibrillation in the emergency room].
2006 May
[Life-threatening ventricular tachycardia during flecainide treatment for symptomatic atrial fibrillation in a patient with a structural cardiac disorder].
2006 May 6
[Clinical case of the month. Atrial flutter with rapid ventricular response (1:1 atrioventricular conduction) caused by flecaïnide].
2007 Dec
Torsade-de-pointes in a patient under flecainide treatment, an unusual case of proarrhythmicity.
2007 Jan 8
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
The Relationship Between HIV Infection and Cardiovascular Disease.
2008 Aug
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
Functional and pharmacological characterization of a Shal-related K+ channel subunit in Zebrafish.
2008 Feb 8
Criteria for arrhythmogenicity in genetically-modified Langendorff-perfused murine hearts modelling the congenital long QT syndrome type 3 and the Brugada syndrome.
2008 Jan
Ventricular dysfunction: tachycardia induced cardiomyopathy.
2008 May 1
ECGs in the ED.
2008 Nov
Role of cytochrome P450 in drug interactions.
2008 Oct 18
A preliminary assessment of the effects of ATI-2042 in subjects with paroxysmal atrial fibrillation using implanted pacemaker methodology.
2009 Apr
Is flecainide dangerous in long QT-3 patients?
2009 Jan
Delirium in a patient with toxic flecainide plasma concentrations: the role of a pharmacokinetic drug interaction with paroxetine.
2009 Jul
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current.
2009 Jun
A case of flecainide-induced hyponatremia.
2009 Oct
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
Tachycardia due to atrial flutter with rapid 1:1 conduction following treatment of atrial fibrillation with flecainide.
2010 Mar 10
Selective regulation of cardiac organic cation transporter novel type 2 (OCTN2) in dilated cardiomyopathy.
2011 Jun
The effects of jaspamide on human cardiomyocyte function and cardiac ion channel activity.
2013 Mar
Patents

Sample Use Guides

Usual Adult Dose for Ventricular Tachycardia
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 Fri Jun 25 21:51:44 UTC 2021
Edited
by admin
on Fri Jun 25 21:51:44 UTC 2021
Record UNII
K94FTS1806
Record Status Validated (UNII)
Record Version
  • Download
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
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
EVMPD
SUB07637MIG
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
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
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 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
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY