Flecainide

Identification

Summary

Flecainide is a class Ic antiarrhythmic agent used to manage atrial fibrillation and paroxysmal supraventricular tachycardias (PSVT).

Brand Names

Tambocor

Generic Name

Flecainide

DrugBank Accession Number

DB01195

Background

Flecainide is a Class I anti-arrhythmic agent like encainide and propafenone.⁷ Flecainide’s development began in 1966 and was first synthesized in 1972 as an attempt to generate new anesthetics.¹⁰ It is used to prevent supraventricular and ventricular arrhythmias, as well as paroxysmal atrial fibrillation and flutter.^12,13

Flecainide was granted FDA approval on 31 October 1985.¹¹

Type

Small Molecule

Groups

Approved, Withdrawn

Structure

Similar Structures

Weight: Average: 414.3427
Monoisotopic: 414.137811746
Chemical Formula: C₁₇H₂₀F₆N₂O₃

Synonyms

(±)-flecainide
Flecaine
Flecainida
Flécaïnide
Flecainide
Flecainidum
N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide

External IDs

CCRIS 313

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Pharmacology

Indication

In New Zealand and America, flecainide is indicated to prevent supraventricular arrhythmias and ventricular arrhythmias.¹² In the United States, it is also indicated to prevent paroxysmal atrial fibrillation and flutter.^9,13

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Associated Conditions

Indication Type	Indication	Approval Level
Treatment of	Atrial fibrillation	••• •••••
Prevention of	Ventricular tachycardia	••••••••••••
Prophylaxis of	Severe atrioventricular nodal reentrant tachycardia	••••••••••••
Prophylaxis of	Severe paroxysmal atrial fibrillation	••••••••••••
Prophylaxis of	Severe paroxysmal supraventricular tachycardia	••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Flecainide inhibits the action of sodium and potassium ion channels in the heart, raising the threshold for depolarization and correcting arrhythmias.¹⁰ Flecainide has a long duration of action, allowing for once daily dosing.¹² The therapeutic index is narrow.⁸ Patients should not take this medication if there is already structural heart disease or left ventricular systolic dysfunction.¹²

Mechanism of action

Flecainide blocks fast inward sodium channels and slowly unbinds during diastole, prolonging the refractory period of the heart.¹⁰ This blockade also shortens the duration of action potentials through the Purkinjie fibers.¹⁰ Flecainide also prevents delayed rectifier potassium channels from opening, lengthening the action potential through ventricular and atrial muscle fibers.¹⁰ Finally, flecainide also blocks ryanodine receptor opening, reducing calcium release from sarcoplasmic reticulum, which reduces depolarization of cells.¹⁰

Target	Actions	Organism
ASodium channel protein type 4 subunit alpha	inhibitor	Humans
ASodium channel protein type 5 subunit alpha	inhibitor	Humans
UPotassium voltage-gated channel subfamily H member 2	inhibitor	Humans
URyanodine receptor 2	inhibitor	Humans

Absorption

Oral flecainide has a T_max of 3-4h and a bioavialability of 90%.^6,10 Taking flecainide with food or aluminum hydroxide antacids do not significantly affect the absorption of flecainide.^6,12,13

Volume of distribution

The average volume of distribution in 8 male subjects is 5.0-13.4L/kg.⁶

Protein binding

Flecainide is 40% bound to protein in serum, mainly to alpha-1-acid glycoprotein and minorly to serum albumin.^6,13

Metabolism

Flecainide is mainly metabolized to meta-O-dealkylated flecainide or the meta-O-dealkylated lactam of flecainide.⁶ Meta-O-dealkylated flecainide has 20% the activity of flecainide.⁶ Both of these metabolites are generally detected as glucuronide or sulfate conjugates.⁶ Flecainide’s metabolism involves the action of CYP2D6 and CYP1A2.^13,10

Hover over products below to view reaction partners

Flecainide
- Meta-O-dealkylated flecainide
- Meta-o-dealkylated lactam

Route of elimination

Approximately 86% of a single oral dose is eliminated in the urine, with 42% as unchanged flecainide and 14% as meta-O-dealkylated flecainide, a similar amount of the meta-O-dealkylated lactam of flecainide, approximately 3% as an unidentified acid metabolite, and <1% as 2 other unknown metabolites.^6,12,13 5% is eliminated in the feces.^6,13

Half-life

In healthy subjects, intravenous flecainide has an average half life of 13 hours for a single dose and 16 hours for multiple oral doses.^6,12,13 In patients with a ventricular premature complex, flecainide has a half life of 20 hours.^6,13 The half life of meta-O-dealkylated flecainide, a major metabolite of flecainide, is 12.6h.⁶

Clearance

The average clearance of intravenous flecainide is 4.6-12.1mL/min/kg in 8 male subjects.⁶ For oral flecainide, the clearance was 4-20mL/min/kg.⁶

Adverse Effects

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Toxicity

The oral LD₅₀ in rats is 1346mg/kg and in mice is 170mg/kg.¹⁴ The subcutaneous LD₅₀ in rats is 215mg/kg and in mice is 188mg/kg.¹⁴ The oral TDLO in women is 20mg/kg and in men is 40mg/kg/2W.¹⁴

Patients experiencing an overdose may present with ECG abnormalities such as a lengthened PR interval, increased QRS duration, prolonged QT interval, increased amplitude of the T wave, reduced myocardial rate and contractility, hypotension, or death.^12,13 Treat patients with symptomatic and supportive treatment which may involve administration of inotropic agents, assisted respiration, circulatory assistance, and acidification of the urine.^12,13 Hemodialysis is not expected to be useful in the removal of flecainide from serum.^6,13

Pathways

Pathway	Category
Flecainide Action Pathway	Drug action

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abametapir	The serum concentration of Flecainide can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Flecainide can be increased when combined with Abatacept.
Abemaciclib	The excretion of Abemaciclib can be decreased when combined with Flecainide.
Abiraterone	The metabolism of Flecainide can be decreased when combined with Abiraterone.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Flecainide.

Food Interactions

Take with or without food. The absorption is unaffected by food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Flecainide acetate	M8U465Q1WQ	54143-56-5	RKXNZRPQSOPPRN-UHFFFAOYSA-N

Product Images

International/Other Brands

Almarytm / Apocard

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Flecainide	Tablet	50 mg	Oral	Sanis Health Inc	2023-10-24	Not applicable
Flecainide	Tablet	100 mg	Oral	Sanis Health Inc	2023-10-24	Not applicable
Flecainide Acetate	Tablet	150 mg/1	Oral	Mylan Pharmaceuticals	2011-08-02	2011-11-30
Flecainide acetate	Tablet	50 mg/1	Oral	County Line Pharmaceuticals, LLC	2016-11-04	2019-10-01
Flecainide Acetate	Tablet	100 mg/1	Oral	Mylan Pharmaceuticals	2011-08-02	2012-03-31

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ag-flecainide	Tablet	50 mg	Oral	Angita Pharma Inc.	2023-06-08	Not applicable
Ag-flecainide	Tablet	100 mg	Oral	Angita Pharma Inc.	2023-06-08	Not applicable
Apo-flecainide	Tablet	100 mg	Oral	Apotex Corporation	2006-05-08	Not applicable
Apo-flecainide	Tablet	50 mg	Oral	Apotex Corporation	2006-05-08	Not applicable
Auro-flecainide	Tablet	50 mg	Oral	Auro Pharma Inc	2017-02-27	Not applicable

Chemical Identifiers

UNII: K94FTS1806
CAS number: 54143-55-4
InChI Key: DJBNUMBKLMJRSA-UHFFFAOYSA-N
InChI: 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)
IUPAC Name: N-[(piperidin-2-yl)methyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide
SMILES: FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1

References

Synthesis Reference

Bmitt, E.H. and Brown, W.R.; U.S. Patent 3,900,481; August 19,1975; assigned to Riker Laboratories, Inc.

US3900481A

General References

Gill JS, Mehta D, Ward DE, Camm AJ: Efficacy of flecainide, sotalol, and verapamil in the treatment of right ventricular tachycardia in patients without overt cardiac abnormality. Br Heart J. 1992 Oct;68(4):392-7. [Article]
Sakurada H, Hiyoshi Y, Tejima T, Yanase O, Tokuyasu Y, Watanabe K, Motomiya T, Sugiura M, Hiraoka M: [Effects of oral flecainide treatment of refractory tachyarrhythmias]. Kokyu To Junkan. 1990 May;38(5):471-6. [Article]
Echt DS, Liebson PR, Mitchell LB, Peters RW, Obias-Manno D, Barker AH, Arensberg D, Baker A, Friedman L, Greene HL, et al.: Mortality and morbidity in patients receiving encainide, flecainide, or placebo. The Cardiac Arrhythmia Suppression Trial. N Engl J Med. 1991 Mar 21;324(12):781-8. [Article]
Greenberg HM, Dwyer EM Jr, Hochman JS, Steinberg JS, Echt DS, Peters RW: Interaction of ischaemia and encainide/flecainide treatment: a proposed mechanism for the increased mortality in CAST I. Br Heart J. 1995 Dec;74(6):631-5. [Article]
Gasparini M, Priori SG, Mantica M, Napolitano C, Galimberti P, Ceriotti C, Simonini S: Flecainide test in Brugada syndrome: a reproducible but risky tool. Pacing Clin Electrophysiol. 2003 Jan;26(1 Pt 2):338-41. [Article]
Conard GJ, Ober RE: Metabolism of flecainide. Am J Cardiol. 1984 Feb 27;53(5):41B-51B. doi: 10.1016/0002-9149(84)90501-0. [Article]
Abi Samra F: The clinical use of class IC antiarrhythmic drugs. J La State Med Soc. 1989 May;141(5):27-31. [Article]
Tamargo J, Le Heuzey JY, Mabo P: Narrow therapeutic index drugs: a clinical pharmacological consideration to flecainide. Eur J Clin Pharmacol. 2015 May;71(5):549-67. doi: 10.1007/s00228-015-1832-0. Epub 2015 Apr 15. [Article]
Aliot E, Capucci A, Crijns HJ, Goette A, Tamargo J: Twenty-five years in the making: flecainide is safe and effective for the management of atrial fibrillation. Europace. 2011 Feb;13(2):161-73. doi: 10.1093/europace/euq382. Epub 2010 Dec 7. [Article]
Andrikopoulos GK, Pastromas S, Tzeis S: Flecainide: Current status and perspectives in arrhythmia management. World J Cardiol. 2015 Feb 26;7(2):76-85. doi: 10.4330/wjc.v7.i2.76. [Article]
FDA Approved Drug Products: Tambocor Flecainide Acetate Oral Tablets [Link]
Medsafe New Zealand Approved Drug Products: Tambocor Oral Tablets and Capsules [Link]
Flecainide Acetate [Link]
Cayman Chemicals: Flecainide MSDS [Link]

External Links

Human Metabolome Database: HMDB0015326
KEGG Drug: D07962
KEGG Compound: C07001
PubChem Compound: 3356
PubChem Substance: 46508078
ChemSpider: 3239
BindingDB: 50131434
RxNav: 4441
ChEBI: 75984
ChEMBL: CHEMBL652
Therapeutic Targets Database: DAP000518
PharmGKB: PA449646
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Flecainide

MSDS

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Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Not Available	Paroxysmal Atrial Fibrillation (PAF)	1
4	Completed	Treatment	Atrial Fibrillation	3
4	Completed	Treatment	Atrial Fibrillation / Brugada Syndrome (BrS) / Ventricular Tachycardia (VT)	1
4	Completed	Treatment	Paroxysmal Atrial Fibrillation (PAF)	1
4	Not Yet Recruiting	Treatment	Atrial Fibrillation / Surgery	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

3M Health Care
Alphapharm Party Ltd.
Amneal Pharmaceuticals
AQ Pharmaceuticals Inc.
Barr Pharmaceuticals
Graceway Pharmaceuticals
Kaiser Foundation Hospital
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Ohm Laboratories Inc.
Par Pharmaceuticals
Pharmaceutical Utilization Management Program VA Inc.
Physicians Total Care Inc.
Ranbaxy Laboratories
Roxane Labs
Southwood Pharmaceuticals

Dosage Forms

Form	Route	Strength
Injection, solution	Intravenous; Parenteral	150 MG/15ML
Capsule, extended release	Oral
Injection, solution	Parenteral	10 mg/ml
Tablet	Oral	50 mg
Tablet	Oral	100 mg/1
Tablet	Oral	150 mg/1
Tablet	Oral	50 mg/1
Tablet	Oral
Capsule, extended release	Oral	100 MG
Capsule, extended release	Oral	150 MG
Capsule, extended release	Oral	200 MG
Capsule, extended release	Oral	50 MG
Tablet	Oral	100.000 mg
Tablet	Oral	100000 ug/1
Tablet	Oral	150000 ug/1
Tablet	Oral	50000 ug/1
Tablet	Oral	100 mg

Prices

Unit description	Cost	Unit
Tambocor 150 mg tablet	5.75USD	tablet
Tambocor 100 mg tablet	4.27USD	tablet
Flecainide acetate 150 mg tablet	3.83USD	tablet
Flecainide acetate 100 mg tablet	2.95USD	tablet
Tambocor 50 mg tablet	2.72USD	tablet
Flecainide acetate 50 mg tablet	1.95USD	tablet
Tambocor 100 mg Tablet	1.19USD	tablet
Apo-Flecainide 100 mg Tablet	0.83USD	tablet
Tambocor 50 mg Tablet	0.6USD	tablet
Apo-Flecainide 50 mg Tablet	0.41USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	228-229	Bmitt, E.H. and Brown, W.R.; U.S. Patent 3,900,481; August 19,1975; assigned to Riker Laboratories, Inc.
water solubility	48.4 mg/mL at 37 °C (acetate form)	FDA Label
logP	3.78	MANNHOLD,R ET AL. (1990)
pKa	9.3	FDA Label

Predicted Properties

Property	Value	Source
Water Solubility	0.0324 mg/mL	ALOGPS
logP	2.98	ALOGPS
logP	3.19	Chemaxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.68	Chemaxon
pKa (Strongest Basic)	9.62	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	59.59 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	88.4 m³·mol^-1	Chemaxon
Polarizability	35.92 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9856
Blood Brain Barrier	+	0.8605
Caco-2 permeable	+	0.8867
P-glycoprotein substrate	Substrate	0.7773
P-glycoprotein inhibitor I	Inhibitor	0.5307
P-glycoprotein inhibitor II	Non-inhibitor	0.7716
Renal organic cation transporter	Non-inhibitor	0.6687
CYP450 2C9 substrate	Non-substrate	0.8921
CYP450 2D6 substrate	Substrate	0.8918
CYP450 3A4 substrate	Non-substrate	0.5957
CYP450 1A2 substrate	Inhibitor	0.9106
CYP450 2C9 inhibitor	Non-inhibitor	0.6853
CYP450 2D6 inhibitor	Non-inhibitor	0.6556
CYP450 2C19 inhibitor	Inhibitor	0.5307
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5538
Ames test	Non AMES toxic	0.672
Carcinogenicity	Non-carcinogens	0.8821
Biodegradation	Not ready biodegradable	0.9968
Rat acute toxicity	2.5680 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9409
hERG inhibition (predictor II)	Inhibitor	0.8474

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0f89-5009000000-7b1564870deda7f2d21e
Mass Spectrum (Electron Ionization)	MS	splash10-001i-9000000000-b732167df77d39193144
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00dl-0095000000-644485d209c90776a32d
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00di-0190000000-201f2152d161a1ff83e5
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-00di-0790000000-928874c4b348381ad1b8
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0596-0940000000-ee7a94ba0d7bcfa2fe93
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-052g-1910000000-a32ac2f605f11fbbc5e0
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0297-1900000000-f1c49d25a6b161ff44d9
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-014i-0000900000-9820e909cb01d45fa815
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00kb-2009500000-68b872fada8afdd4e580
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0f6t-5019000000-8fa5e4257c88beda0ea1
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0uea-8069000000-149a79cf429446ec77c2
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0uei-6292000000-103ccdef98c4b6c9e408
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0pdi-8970000000-9258d139b203d6c98df0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014j-5000900000-56a8717658af3e5b9033
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0018900000-21c26bd002144277529a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-00kb-1009500000-946b8843e36d59291cba
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00o0-0091000000-a668b2729f1f01634bb2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-052b-9231100000-42e91f558d20f4edf1f7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-044j-0192000000-c8bee568d36c3fff1a92
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	187.6621135	predicted	DarkChem Lite v0.1.0
[M-H]-	186.56973	predicted	DeepCCS 1.0 (2019)
[M+H]+	187.9683135	predicted	DarkChem Lite v0.1.0
[M+H]+	188.92775	predicted	DeepCCS 1.0 (2019)
[M+Na]+	187.9401135	predicted	DarkChem Lite v0.1.0
[M+Na]+	196.076	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Sodium channel protein type 4 subunit alpha

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Voltage-gated sodium channel activity
Specific Function: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the pr...
Gene Name: SCN4A
Uniprot ID: P35499
Uniprot Name: Sodium channel protein type 4 subunit alpha
Molecular Weight: 208059.175 Da

References

Desaphy JF, De Luca A, Didonna MP, George AL Jr, Camerino Conte D: Different flecainide sensitivity of hNav1.4 channels and myotonic mutants explained by state-dependent block. J Physiol. 2004 Jan 15;554(Pt 2):321-34. Epub 2003 Nov 7. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	6500	N/A	N/A	A29539

Details2. Sodium channel protein type 5 subunit alpha

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the pr...
Gene Name: SCN5A
Uniprot ID: Q14524
Uniprot Name: Sodium channel protein type 5 subunit alpha
Molecular Weight: 226937.475 Da

References

Nagatomo T, January CT, Makielski JC: Preferential block of late sodium current in the LQT3 DeltaKPQ mutant by the class I(C) antiarrhythmic flecainide. Mol Pharmacol. 2000 Jan;57(1):101-7. [Article]
Benhorin J, Taub R, Goldmit M, Kerem B, Kass RS, Windman I, Medina A: Effects of flecainide in patients with new SCN5A mutation: mutation-specific therapy for long-QT syndrome? Circulation. 2000 Apr 11;101(14):1698-706. [Article]
Priori SG, Napolitano C, Schwartz PJ, Bloise R, Crotti L, Ronchetti E: The elusive link between LQT3 and Brugada syndrome: the role of flecainide challenge. Circulation. 2000 Aug 29;102(9):945-7. [Article]
Cerrone M, Crotti L, Faggiano G, De Michelis V, Napolitano C, Schwartz PJ, Priori SG: [Long QT syndrome and Brugada syndrome: 2 aspects of the same disease?]. Ital Heart J Suppl. 2001 Mar;2(3):253-7. [Article]
Viswanathan PC, Bezzina CR, George AL Jr, Roden DM, Wilde AA, Balser JR: Gating-dependent mechanisms for flecainide action in SCN5A-linked arrhythmia syndromes. Circulation. 2001 Sep 4;104(10):1200-5. [Article]
Ramos E, O'leary ME: State-dependent trapping of flecainide in the cardiac sodium channel. J Physiol. 2004 Oct 1;560(Pt 1):37-49. Epub 2004 Jul 22. [Article]
Shimizu W, Antzelevitch C, Suyama K, Kurita T, Taguchi A, Aihara N, Takaki H, Sunagawa K, Kamakura S: Effect of sodium channel blockers on ST segment, QRS duration, and corrected QT interval in patients with Brugada syndrome. J Cardiovasc Electrophysiol. 2000 Dec;11(12):1320-9. [Article]
Liu H, Atkins J, Kass RS: Common molecular determinants of flecainide and lidocaine block of heart Na+ channels: evidence from experiments with neutral and quaternary flecainide analogues. J Gen Physiol. 2003 Mar;121(3):199-214. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	3890	N/A	N/A	A18337
IC 50 (nM)	3890.45	N/A	N/A	A27428 / A27431 / A27558

Details3. Potassium voltage-gated channel subfamily H member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name: KCNH2
Uniprot ID: Q12809
Uniprot Name: Potassium voltage-gated channel subfamily H member 2
Molecular Weight: 126653.52 Da

References

Chiu PJ, Marcoe KF, Bounds SE, Lin CH, Feng JJ, Lin A, Cheng FC, Crumb WJ, Mitchell R: Validation of a [3H]astemizole binding assay in HEK293 cells expressing HERG K+ channels. J Pharmacol Sci. 2004 Jul;95(3):311-9. [Article]

Details4. Ryanodine receptor 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Suramin binding
Specific Function: Calcium channel that mediates the release of Ca(2+) from the sarcoplasmic reticulum into the cytoplasm and thereby plays a key role in triggering cardiac muscle contraction. Aberrant channel activa...
Gene Name: RYR2
Uniprot ID: Q92736
Uniprot Name: Ryanodine receptor 2
Molecular Weight: 564562.71 Da

References

Mehra D, Imtiaz MS, van Helden DF, Knollmann BC, Laver DR: Multiple modes of ryanodine receptor 2 inhibition by flecainide. Mol Pharmacol. 2014 Dec;86(6):696-706. doi: 10.1124/mol.114.094623. Epub 2014 Oct 1. [Article]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Doki K, Homma M, Kuga K, Aonuma K, Kohda Y: Effects of CYP2D6 genotypes on age-related change of flecainide metabolism: involvement of CYP1A2-mediated metabolism. Br J Clin Pharmacol. 2009 Jul;68(1):89-96. doi: 10.1111/j.1365-2125.2009.03435.x. [Article]
Lim KS, Jang IJ, Kim BH, Kim J, Jeon JY, Tae YM, Yi S, Eum S, Cho JY, Shin SG, Yu KS: Changes in the QTc interval after administration of flecainide acetate, with and without coadministered paroxetine, in relation to cytochrome P450 2D6 genotype: data from an open-label, two-period, single-sequence crossover study in healthy Korean male subjects. Clin Ther. 2010 Apr;32(4):659-66. doi: 10.1016/j.clinthera.2010.04.002. [Article]
Walker DK, Alabaster CT, Congrave GS, Hargreaves MB, Hyland R, Jones BC, Reed LJ, Smith DA: Significance of metabolism in the disposition and action of the antidysrhythmic drug, dofetilide. In vitro studies and correlation with in vivo data. Drug Metab Dispos. 1996 Apr;24(4):447-55. [Article]
Andrikopoulos GK, Pastromas S, Tzeis S: Flecainide: Current status and perspectives in arrhythmia management. World J Cardiol. 2015 Feb 26;7(2):76-85. doi: 10.4330/wjc.v7.i2.76. [Article]
Flockhart Table of Drug Interactions [Link]

Details2. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Andrikopoulos GK, Pastromas S, Tzeis S: Flecainide: Current status and perspectives in arrhythmia management. World J Cardiol. 2015 Feb 26;7(2):76-85. doi: 10.4330/wjc.v7.i2.76. [Article]

Details3. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: Enzyme inhibition data based on findings of 1 in vitro study.

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Walker DK, Alabaster CT, Congrave GS, Hargreaves MB, Hyland R, Jones BC, Reed LJ, Smith DA: Significance of metabolism in the disposition and action of the antidysrhythmic drug, dofetilide. In vitro studies and correlation with in vivo data. Drug Metab Dispos. 1996 Apr;24(4):447-55. [Article]

Carriers

Details1. alpha1-acid glycoprotein (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Not Available
Specific Function: Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:

Name	UniProt ID
Alpha-1-acid glycoprotein 1	P02763
Alpha-1-acid glycoprotein 2	P19652

References

Conard GJ, Ober RE: Metabolism of flecainide. Am J Cardiol. 1984 Feb 27;53(5):41B-51B. doi: 10.1016/0002-9149(84)90501-0. [Article]

Details2. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

Conard GJ, Ober RE: Metabolism of flecainide. Am J Cardiol. 1984 Feb 27;53(5):41B-51B. doi: 10.1016/0002-9149(84)90501-0. [Article]

Transporters

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Doki K, Apati S, Sakata T, Homma M: Involvement of Renal Efflux Transporter MATE1 in Renal Excretion of Flecainide. Biol Pharm Bull. 2019;42(7):1226-1229. doi: 10.1248/bpb.b19-00031. [Article]

Details2. Multidrug and toxin extrusion protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Monovalent cation:proton antiporter activity
Specific Function: Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name: SLC47A1
Uniprot ID: Q96FL8
Uniprot Name: Multidrug and toxin extrusion protein 1
Molecular Weight: 61921.585 Da

References

Doki K, Apati S, Sakata T, Homma M: Involvement of Renal Efflux Transporter MATE1 in Renal Excretion of Flecainide. Biol Pharm Bull. 2019;42(7):1226-1229. doi: 10.1248/bpb.b19-00031. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Flecainide

Identification

Structure for Flecainide (DB01195)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

Enzymes

References

References

References

Carriers

Components:

References

References

Transporters

References

References