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HomeProduct name listFLECAINIDE ACETATE

FLECAINIDE ACETATE

Synonym(s):N-(2-Piperidylmethyl)-2,5-bis-(2,2,2-trifluoroethoxy)benzamide acetate salt;Flecainide acetate salt

  • CAS NO.:54143-56-5
  • Empirical Formula: C19H24F6N2O5
  • Molecular Weight: 474.39
  • MDL number: MFCD00214290
  • EINECS: 258-997-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 23:02:33
FLECAINIDE ACETATE Structural

What is FLECAINIDE ACETATE?

Description

Flecainide acetate (54143-56-5) is an open Na+?channel blocker that inhibits fast Na+?current in cardiac muscle in a use- and concentration-dependent manner.1?Orally-active class Ic antiarrhythmic agent2,3. Inhibits hERG potassium channels at clinically relevant concentrations.4

Chemical properties

White or almost white, very hygroscopic, crystalline powder.

The Uses of FLECAINIDE ACETATE

Flecainide acetate is used as a sodium channel blocker and as an anti-arrhythmic. In general, it is used to regulate heartbeats of the upper heart and lower heart chambers. It can also be used to slow down an overactive heart. It is also useful in the treatment of ventricular tachycardias and ventricular arrhythmias.

The Uses of FLECAINIDE ACETATE

Class I antiarrhythmic.

What are the applications of Application

Flecainide acetate is a cadiac Na+ channel blocker

Definition

ChEBI: An acetate salt obtained by combining flecainide with one molar equivalent of acetic acid. An antiarrhythmic agent used to prevent and treat tachyarrhythmia (abnormal fast rhythm of the heart).

brand name

Tambocor (3M Pharmaceuticals).

General Description

Flecainide acetate, N-(2-piperidinylmethyl)-2,5-bis (2,2,2-trifluoroethoxy)benzamide monoacetate(Tambocor), is a class IC antiarrhythmic drug withlocal anesthetic activity; it is a chemical derivative of benzamide.The drug undergoes biotransformation, forming ameta-O-dealkylated compound, whose antiarrhythmic propertiesare half as potent as those of the parent drug, and ameta-O-dealkylated lactam of flecainide with little pharmacologicalactivity. Flecainide acetate is given orally to suppresschronic ventricular ectopy and ventricular tachycardia.It has some limitations because of CNS side effects.

Biological Activity

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

Biochem/physiol Actions

Class IC antiarrhythmic agent; sodium channel blocker

Drug interactions

Potentially hazardous interactions with other drugs
Anti-arrhythmics: concentration increased by amiodarone - halve dose of flecainide; increased myocardial depression with other anti-arrhythmics.
Antidepressants: concentration increased by fluoxetine; increased risk of ventricular arrhythmias with tricyclics.
Antihistamines: increased risk of ventricular arrhythmias with mizolastine - avoid.
Antihypertensives: increased myocardial depression and bradycardia with beta-blockers; increased myocardial depression and asystole with verapamil.
Antimalarials: concentration increased by quinine; avoid with artemether/lumefantrine.
Antimuscarinics: increased risk of ventricular arrhythmias with tolterodine.
Antipsychotics: increased risk of ventricular arrhythmias with antipsychotics that prolong the QT interval and phenothiazines; increased risk of arrhythmias with clozapine.
Antivirals: concentration possibly increased by fosamprenavir, indinavir, lopinavir, ritonavir and saquinavir, increased risk of ventricular arrhythmias - avoid; use telaprevir with caution.
Diuretics: increased cardiac toxicity if hypokalaemia occurs.

Metabolism

Flecainide is extensively metabolised (subject to genetic polymorphism), the 2 major metabolites being m-Odealkylated flecainide and m-O-dealkylated lactam of flecainide, both of which may have some activity. Its metabolism appears to involve the cytochrome P450 isoenzyme CYP2D6, which shows genetic polymorphism.
Flecainide is excreted mainly in the urine, approximately 30% as unchanged drug and the remainder as metabolites. About 5% is excreted in the faeces. Haemodialysis removes only about 1% of unchanged flecainide.

storage

Desiccate at +4°C

References

1) Rouet and Ducouret (1994), Use- and concentration-dependent effects of flecainide in guinea pig right ventricular muscle; J. Cardiovasc. Pharmacol.,?24?177 2) Singh?et al. (1984),?The electrophysiology and pharmacology of verapamil, flecainide, and amiodarone: correlations with clinical effects and antiarrhythmic actions; Ann. N.Y. Acad. Sci.,?432?210 3) Banitt?et al.?(1977),?Anti-arrhythmics. 2. Synthesis and antiarrhythmic activity of N-(piperidylalkyl)trifluoroethoxybenzamides; J. Med. Chem.,?20?821 4) Melgari?et al.?(2015),?Molecular basis of hERG potassium channel blockade by the class Ic antiarrhythmic flecainide; J. Mol. Cell. Cardiol.,?86?42

Properties of FLECAINIDE ACETATE

Melting point: 145-147℃
storage temp.  2-8°C
solubility  Soluble in water and in anhydrous ethanol. It is freely soluble in dilute acetic acid and practically insoluble in dilute hydrochloric acid.
form  neat
form  Solid
color  White
Water Solubility  Soluble in dilute acetic acid, dimethyl sulfoxide, ethanol, methanol and water.
Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 month.

Safety information for FLECAINIDE ACETATE

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P201:Obtain special instructions before use.
P202:Do not handle until all safety precautions have been read and understood.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for FLECAINIDE ACETATE

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