Flecainide acetate

Antiarrhythmic drug CAS# 54143-56-5

Flecainide acetate

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Chemical structure

Flecainide acetate

3D structure

Chemical Properties of Flecainide acetate

Cas No. 54143-56-5 SDF Download SDF
PubChem ID 41022 Appearance Powder
Formula C19H24F6N2O5 M.Wt 474.39
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 50 mg/mL (105.40 mM; Need ultrasonic)
H2O : 20 mg/mL (42.16 mM; Need ultrasonic)
Chemical Name acetic acid;N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
SMILES CC(=O)O.C1CCNC(C1)CNC(=O)C2=C(C=CC(=C2)OCC(F)(F)F)OCC(F)(F)F
Standard InChIKey RKXNZRPQSOPPRN-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H20F6N2O3.C2H4O2/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;1-2(3)4/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26);1H3,(H,3,4)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Flecainide acetate

DescriptionOpen Na+ channel blocker that inhibits fast Na+ current in cardiac muscle in a use- and concentration-dependent manner. Orally-active class Ic antiarrhythmic agent.

Flecainide acetate Dilution Calculator

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Flecainide acetate Molarity Calculator

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Preparing Stock Solutions of Flecainide acetate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.108 mL 10.5399 mL 21.0797 mL 42.1594 mL 52.6993 mL
5 mM 0.4216 mL 2.108 mL 4.2159 mL 8.4319 mL 10.5399 mL
10 mM 0.2108 mL 1.054 mL 2.108 mL 4.2159 mL 5.2699 mL
50 mM 0.0422 mL 0.2108 mL 0.4216 mL 0.8432 mL 1.054 mL
100 mM 0.0211 mL 0.1054 mL 0.2108 mL 0.4216 mL 0.527 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Flecainide acetate

Flecainide, a nonselective Na (+) channel blocker, is a class 1C antiarrhythmic drug, especially used for the management of supraventricular arrhythmia. Flecainide has been used extensively in the effect on providing long-term sinus rhythm (SR) restoration as well as decreasing AF symptoms.
Flecainide revealed to suppress the Nav1.5 sodium channel in the heart, leading to prolongation of the cardiac action potential. Flecainide showed to reduce Ca+ spark, wave frequency and Ca+ wave velocity in the intact rat cardiomyocyte. Besides, flecainide has shown to reduce Ca(2+) wave when I(Na) is active. It has been demonstrated that flecainide could remarkably increase the Na(+)/Ca(2+)-exchanger (NCX)-mediated Ca(2+) efflux  [1].
Flecainide has been reported to prolong ventricular repolarization, with the stronger effect at the left ventricular epicardium related to the right ventricular epicardium. Flecainide was found to produce a greater effective refractory period (ERP) lengthening at endocardium than epicardium, leading to a significant increase of ERP dispersion across the ventricular wall [2].
Flecainide has shown to dose-dependently reduce systemic pressures (32% at 0.8 μg/mL) and peripheral vascular resistance (15% at 0.8 μg/mL). In addition, at therapeutic plasma concentrations, flecainide at 0.8 μg/mL remarkably reduced the heart rate (55 beats/min) and increased QRS intervals (9.9 msec) in a rat hindlimb perfusion model [3].
References:
1.Sikkel MB1, Collins TP, Rowlands C, Shah M, O'Gara P, Williams AJ, Harding SE, Lyon AR, MacLeod KT. Flecainide reduces Ca(2+) spark and wave frequency via inhibition of the sarcolemmal sodium current. Cardiovasc Res. 2013 May 1;98(2):286-96. doi: 10.1093/cvr/cvt012. Epub 2013 Jan 19.
2.Osadchii OE.Flecainide-induced proarrhythmia is attributed to abnormal changes in repolarization and refractoriness in perfused guinea-pig heart. J Cardiovasc Pharmacol. 2012 Nov;60(5):456-66. doi: 10.1097/FJC.0b013e31826b86cf.
3.Allison B1, Yang Y, Pourrier M, Gibson JK. Comparison of the in vivo hemodynamic effects of the antiarrhythmic agents vernakalant and flecainide in a rat hindlimb perfusion model. J Cardiovasc Pharmacol. 2011 Apr;57(4):463-8. doi: 10.1097/FJC.0b013e318210276b.

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References on Flecainide acetate

Flecainide acetate for the treatment of atrial and ventricular arrhythmias.[Pubmed:23294160]

Expert Opin Pharmacother. 2013 Feb;14(3):347-57.

INTRODUCTION: Flecainide is a class Ic antiarrhythmic agent available in Europe since 1982. The clinical development program of flecainide provided good data on its antiarrhythmic effect for the prevention of ventricular and supraventricular arrhythmias. The Cardiac Arrhythmia Suppression Trial (CAST), conducted to test whether the arrhythmia suppression translates into prevention of sudden death, assessed the impact of flecainide and encainide therapy in patients with frequent ventricular ectopics and reduced left ventricular function who had survived an infarction. In that population, flecainide and encainide increased mortality. Consequently, sodium channel blockers are now rarely used to prevent sudden death and are not recommended in patients with heart failure. Current European and North American guidelines recommend the use of flecainide in carefully selected patients with atrial fibrillation (AF) and no documented structural heart disease. AREAS COVERED: The aim of this review is to evaluate the available data on efficacy and safety of flecainide in all the spectrum of its indications including cardioversion of recent-onset AF, sinus rhythm maintenance in paroxysmal AF and management of ventricular tachyarrhythmias. EXPERT OPINION: In the setting of AF and in carefully selected patients without structural heart disease, flecainide has shown a good efficacy and safety for both cardioversion and sinus rhythm maintenance.

Stability-indicating chromatographic methods for determination of flecainide acetate in the presence of its degradation products; isolation and identification of two of its impurities.[Pubmed:26992079]

Biomed Chromatogr. 2016 Oct;30(10):1541-8.

In this work, two stability-indicating chromatographic methods have been developed and validated for determination of Flecainide acetate (an antiarrhythmic drug) in the presence of its degradation products (flecainide impurities; B and D). Flecainide acetate was subjected to a stress stability study including acid, alkali, oxidative, photolytic and thermal degradation. The suggested chromatographic methods included the use of thin layer chromatography (TLC-densitometry) and high-performance liquid chromatography (HPLC). The TLC method employed aluminum TLC plates precoated with silica gel G.F254 as the stationary phase and methanol-ethyl acetate-33% ammonia (3:7:0.3, by volume) as the mobile phase. The chromatograms were scanned at 290 nm and visualized in daylight by the aid of iodine vapor. The developed HPLC method used a RP-C18 column with isocratic elution. Separation was achieved using a mobile phase composed of phosphate buffer pH 3.3-acetonitrile-triethylamine (53:47:0.03, by volume) at a flow rate of 1.0 mL/min and UV detection at 292 nm. Factors affecting the efficiency of HPLC method have been studied carefully to reach the optimum conditions for separation. The developed methods were validated according to the International Conference on Harmonization guidelines and were applied for bulk powder and dosage form. Copyright (c) 2016 John Wiley & Sons, Ltd.

Flecainide acetate acetic acid solvates.[Pubmed:21249720]

J Pharm Sci. 2011 Feb;100(2):604-11.

Flecainide acetate forms acetic acid solvates with 0.5 and 2 acetic acid molecules. Powder X-ray diffraction, differential thermal analysis/thermogravimetric, infrared, and potentiometric titration were used to determine the composition of solvates. Flecainide acetate hemisolvate with acetic acid decomposes to form a new crystalline form of Flecainide acetate. This form is less stable than the already known polymorphic form at all temperatures, and it is formed due to kinetic reasons. Both Flecainide acetate nonsolvated and Flecainide acetate hemisolvate forms crystallize in monoclinic crystals, but flecainide triacetate forms triclinic crystals. Solvate formation was not observed when flecainide base was treated with formic acid, propanoic acid, and butanoic acid. Only nonsolvated flecainide salts were obtained in these experiments.

Sudden death of a horse with supraventricular tachycardia following oral administration of flecainide acetate.[Pubmed:25388866]

J Vet Emerg Crit Care (San Antonio). 2014 Nov-Dec;24(6):759-63.

OBJECTIVE: To describe a case of supraventricular tachycardia and sudden death in a horse following administration of Flecainide acetate. CASE SUMMARY: An 8-year-old Hanoverian warmblood gelding was treated for chronic, naturally occurring, supraventricular tachycardia with digoxin, procainamide hydrochloride, quinidine sulfate, and Flecainide acetate. After oral administration of flecainide, polymorphic ventricular tachycardia (torsades de pointes) and ventricular fibrillation developed, leading to cardiovascular collapse and death. NEW OR UNIQUE INFORMATION PROVIDED: Atrial fibrillation is the most commonly diagnosed dysrhythmia associated with poor performance in horses, while atrial tachycardia is rarely documented. Here, we describe a case of sudden death in a horse with atrial tachycardia following the oral administration of Flecainide acetate, after the lack of response to other antiarrhythmic drugs. Information provided in this case report is new and will make clinicians aware of the potential complications of flecainide alone or in combination with other drugs, in horses with cardiac dysrhythmias.

Use- and concentration-dependent effects of flecainide in guinea pig right ventricular muscle.[Pubmed:7526048]

J Cardiovasc Pharmacol. 1994 Aug;24(2):177-83.

In clinical studies, flecainide, a class IC antiarrhythmic drug, exhibited antiarrhythmic properties against supraventricular arrhythmias but also showed proarrhythmic effects in ventricular arrhythmias. We studied the effects of flecainide on action potential (AP) maximum rate of increase (Vmax) in guinea-pig right ventricular muscle. The effects of flecainide were studied at 3 concentrations (10(-5), 5 x 10(-6), 10(-6) M) and five frequencies (0.5, 1, 1.5, 2, and 3 Hz). At these three concentrations, flecainide caused little and not significant tonic block. In contrast, flecainide caused a frequency-and dose-dependent reduction in Vmax (at 3 Hz, the time constant of Vmax decrease was 3.6 +/- 0.2 s for 10(-5) M, 3.8 +/- 0.2 s for 5 x 10(-6) M, and 7.1 +/- 1.3 s for 10(-6) M). At 3 Hz, the time constants measured as number of APs were 11 +/- 2 for flecainide 10(-5) M, 12 +/- 2 for 5 x 10(-6) M, and 22 +/- 2 for 10(-6) M, respectively. At 10(-6) M, spontaneous arrhythmias occurred at all frequencies studied. Assuming that changes in Vmax reflect changes in Na+ fast current amplitude, our results suggest that flecainide is an open Na channel blocker showing frequency- and dose-dependent effects in the range of 0.5-3 Hz.

Antiarrhythmics. 2. Synthesis and antiarrhythmic activity of N-(piperidylalkyl)trifluoroethoxybenzamides.[Pubmed:874956]

J Med Chem. 1977 Jun;20(6):821-6.

Benzamides characterized by one or more 2,2,2-trifluoroethoxy ring substituents and a heterocyclic amide side chain have been prepared and evaluated for oral antiarrhythmic activity in mice. The most potent compounds are derived from 2,5-bis(2,2,2-trifluoroethoxy)benzamide, and, within this group, both tertiary as well as secondary benzamides are active. Considerable variation in the heterocyclic ring is permissible, but antiarrhythmic activity is strongly influenced by the basicity of the amine nitrogen and the nature of the link between heterocycle and amide nitrogen. One of these compounds, N-(2-piperidylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide acetate (Flecainide acetate, USAN), was studied extensively in animals and selected for clinical trial as an antiarrhythmic.

Description

Flecainide acetate (R-818) is a class 1C antiarrhythmic drug especially used for the management of supraventricular arrhythmia; works by blocking the Nav1.5 sodium channel in the heart, causing prolongation of the cardiac action potential.

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