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
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)
DescriptionSources: http://www.drugbank.ca/drugs/DB01195Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/flecainide.html
Sources: http://www.drugbank.ca/drugs/DB01195
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1980 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21194571 |
67.2 µM [IC50] | ||
Target ID: CHEMBL2072 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20590641 |
18.0 µM [Ki] | ||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26159617 |
1.49 µM [IC50] | ||
Target ID: CHEMBL1964 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12875427 |
7.8 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Flecainide Approved UseIn 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 Date2001 |
|||
Preventing | Flecainide Approved UseIn 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 Date2001 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1710 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3094570 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3094570 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.9 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1782978 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3094570 |
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3094570 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
11.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1782978 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
60% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/6364769 |
FLECAINIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1200 mg single, oral Overdose |
healthy, 18 |
Disc. AE: Unconsciousness, Cyanosis... AEs leading to discontinuation/dose reduction: Unconsciousness Sources: Cyanosis Bradycardia Arrhythmia |
3800 mg single, oral Overdose |
healthy, 28 |
Disc. AE: Polymorphic ventricular tachycardia... AEs leading to discontinuation/dose reduction: Polymorphic ventricular tachycardia Sources: |
10 g single, oral Overdose |
healthy, 36 |
Disc. AE: Ventricular tachycardia, Hypotension... AEs leading to discontinuation/dose reduction: Ventricular tachycardia Sources: Hypotension Cardiopulmonary arrest |
1 g single, oral Overdose |
unhealthy, 62 |
Disc. AE: Brugada syndrome, Mental status changes... AEs leading to discontinuation/dose reduction: Brugada syndrome Sources: Mental status changes Fatigue |
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 Sources: |
Disc. AE: Ventricular tachycardia, Cardiac arrest... AEs leading to discontinuation/dose reduction: Ventricular tachycardia Sources: Cardiac arrest |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Arrhythmia | Disc. AE | 1200 mg single, oral Overdose |
healthy, 18 |
Bradycardia | Disc. AE | 1200 mg single, oral Overdose |
healthy, 18 |
Cyanosis | Disc. AE | 1200 mg single, oral Overdose |
healthy, 18 |
Unconsciousness | Disc. AE | 1200 mg single, oral Overdose |
healthy, 18 |
Polymorphic ventricular tachycardia | Disc. AE | 3800 mg single, oral Overdose |
healthy, 28 |
Cardiopulmonary arrest | Disc. AE | 10 g single, oral Overdose |
healthy, 36 |
Hypotension | Disc. AE | 10 g single, oral Overdose |
healthy, 36 |
Ventricular tachycardia | Disc. AE | 10 g single, oral Overdose |
healthy, 36 |
Brugada syndrome | Disc. AE | 1 g single, oral Overdose |
unhealthy, 62 |
Fatigue | Disc. AE | 1 g single, oral Overdose |
unhealthy, 62 |
Mental status changes | Disc. AE | 1 g single, oral Overdose |
unhealthy, 62 |
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 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 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 0.44 uM] | ||||
yes [IC50 0.49 uM] | ||||
yes [IC50 191 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Flecainide acetate in the treatment of tachycardias associated with Mahaim fibres. | 1987 Aug |
|
[Drug-induced intrahepatic cholestasis caused by flecainide acetate and enalapril]. | 1987 Mar |
|
Rapid suppression of flecainide-induced incessant ventricular tachycardia with high-dose intravenous amiodarone. | 1988 Apr |
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[Central nervous system side effects due to anti-arrhythmia therapy. Psychotic depression due to flecainide]. | 1988 Mar 11 |
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Torsades de pointe with flecainide-amiodarone therapy. | 1990 |
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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 |
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Safety and efficacy of oral flecainide therapy in patients with atrioventricular re-entrant tachycardia. | 1991 Feb 1 |
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Reversion of recent-onset atrial fibrillation to sinus rhythm by intravenous flecainide. | 1991 Jan 15 |
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Mortality and morbidity in patients receiving encainide, flecainide, or placebo. The Cardiac Arrhythmia Suppression Trial. | 1991 Mar 21 |
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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 |
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Pseudo infarction ECG pattern occurring during intravenous treatment with flecainide acetate. | 1992 Jan |
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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 |
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Efficacy of flecainide, sotalol, and verapamil in the treatment of right ventricular tachycardia in patients without overt cardiac abnormality. | 1992 Oct |
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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 |
|
Successful extracorporeal life support in a case of severe flecainide intoxication. | 2001 Apr |
|
[Protocols for the treatment of supraventricular tachycardias in the fetus]. | 2001 Jun 23 |
|
Supraventricular tachycardia with hydrops in a 27-week premature baby. | 2001 Oct |
|
Symptomatic bradycardia secondary to interaction between topical timolol maleate, verapamil, and flecainide: a case report. | 2002 Apr |
|
Characterisation of the human voltage-gated potassium channel gene, KCNA7, a candidate gene for inherited cardiac disorders, and its exclusion as cause of progressive familial heart block I (PFHBI). | 2002 Jan |
|
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 |
|
Use of ibutilide in cardioversion of patients with atrial fibrillation or atrial flutter treated with class IC agents. | 2004 Aug 18 |
|
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 |
|
Flecainide overdose--support using an intra-aortic balloon pump. | 2005 Dec 12 |
|
A toxicogenomic approach to drug-induced phospholipidosis: analysis of its induction mechanism and establishment of a novel in vitro screening system. | 2005 Feb |
|
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 |
|
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 |
|
Further evidence of inherited long QT syndrome gene mutations in antiarrhythmic drug-associated torsades de pointes. | 2007 May |
|
Flecainide cardiotoxicity precipitated by electrolyte imbalance. Caution with thiazide diuretics. | 2007 May |
|
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 |
|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/flecainide.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25219538
Flecainide produced a dose-dependent prolongation of the cardiac action potential at 1 and 3uM in human pluripotent stem cell-derived cardiomyocytes.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175426
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WHO-VATC |
QC01BC04
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LIVERTOX |
NBK548023
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FDA ORPHAN DRUG |
536716
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WHO-ATC |
C01BC04
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NCI_THESAURUS |
C47793
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NCI_THESAURUS |
C93038
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m5400
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3356
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K94FTS1806
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FLECAINIDE
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DB01195
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54143-55-4
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DTXSID8023054
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Flecainide
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100000080972
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CHEMBL652
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2560
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4096
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)