54143-56-5 Usage
Description
Flecainide acetate, also known by the brand name Tambocor, is an open Na+ channel blocker and an orally-active class Ic antiarrhythmic agent. It is a chemical derivative of benzamide and is used to regulate heartbeats of the upper and lower heart chambers. Flecainide acetate is a white or almost white, very hygroscopic, crystalline powder that undergoes biotransformation, forming metabolites with varying antiarrhythmic properties. It is used to suppress chronic ventricular ectopy and ventricular tachycardia, but has some limitations due to CNS side effects.
Uses
Used in Pharmaceutical Industry:
Flecainide acetate is used as a class I antiarrhythmic agent for regulating heartbeats of the upper and lower heart chambers. It acts as a sodium channel blocker and is effective in treating ventricular tachycardias and ventricular arrhythmias.
Flecainide acetate is used as an anti-arrhythmic agent for slowing down an overactive heart, helping to prevent and treat tachyarrhythmia (abnormal fast rhythm of the heart).
Additionally, Flecainide acetate is used to inhibit hERG potassium channels at clinically relevant concentrations, which contributes to its antiarrhythmic properties.
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
Clinical Use
#N/A
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 54143-56-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,1,4 and 3 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 54143-56:
(7*5)+(6*4)+(5*1)+(4*4)+(3*3)+(2*5)+(1*6)=105
105 % 10 = 5
So 54143-56-5 is a valid CAS Registry Number.
InChI:InChI=1/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)
54143-56-5Relevant articles and documents
Process for the preparation of 2,5-bis-(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide and salts thereof
-
Page/Page column 4; 8, (2008/12/04)
A process for the preparation of Flecainide acetate, its salts, in particular its pharmaceutically acceptable salts, and intermediates thereof is described wherein 2,5-dibromotoluene is used as a starting material. The method involves a technique for preparing the starting material 2,5-bis(2,2,2-trifluroethoxy)toluene in high yields by reacting 2,5-dibromotoluene with 2,2,2-trifluoroethanol in the presence of a base and a copper-containing catalyst.
Novel process for the preparation of flecainide, its pharmaceutically acceptable salts and important intermediates thereof
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Page/Page column 4, (2010/02/11)
Process for the preparation of Flecainide, its pharmaceutically acceptable salts and important intermediates thereof that involves the use of the 2-halobenzoic acid and its derivatives as a starting material. The use of this process also allows for the synthesis of a novel intermediate useful in the production of Flecainide. This new process is an inexpensive and efficient process for the manufacture of these compounds.
Process for the preparation of derivatives of pyrrolidine and piperidine
-
, (2008/06/13)
Processes and intermediates for the preparation of the antiarrhythmic agent 2,5-bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide.
