flecainide

Names

[ Name ]:
flecainide

[Synonym ]:
N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
FLECAINTDE BASE
N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
2,5-bis-(2,2,2-Trifluoroethoxy)-n-(2-piperidyl-methyl)-benzamid
EINECS 200-659-6
N-(2-piperidylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
Flecainide
Benzamide,N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)
Flecanide
Flecaine
MFCD00864713

Biological Activity

[Description]:

Flecainide is a potent and orally active antiarrhythmic agent. Flecainide blocks the cardiac fast inward Na+ current (INa) and the rapid component of the delayed rectifier K+ current. Flecainide prolongs the action potential duration (APD) in ventricular and atrial muscle fibres. Flecainide has the potential for the research of fetal tachycardias[1][2][3].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

[References]

[1]. Echt DS, 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.

[2]. Aliot E, et al. Twenty-five years in the making: flecainide is safe and effective for the management of atrial fibrillation. Europace. 2011 Feb;13(2):161-73.

[3]. Allan LD, et al. Flecainide in the treatment of fetal tachycardias. Br Heart J. 1991 Jan;65(1):46-8.

Chemical & Physical Properties

[ Density]:
1.286 g/cm3

[ Boiling Point ]:
434.9ºC at 760 mmHg

[ Melting Point ]:
105-1070C

[ Molecular Formula ]:
C₁₇H₂₀F₆N₂O₃

[ Molecular Weight ]:
414.34300

[ Flash Point ]:
216.8ºC

[ Exact Mass ]:
414.13800

[ PSA ]:
59.59000

[ LogP ]:
4.16040

[ Storage condition ]:
Refrigerator

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Hazard Codes ]:
F,T

[ Risk Phrases ]:
11-23/24/25-39/23/24/25

[ Safety Phrases ]:
7-16-36/37-45

[ RIDADR ]:
3249

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Multiple modes of ryanodine receptor 2 inhibition by flecainide.

Mol. Pharmacol. 86(6) , 696-706, (2014)

Catecholaminergic polymorphic ventricular tachycardia (CPVT) causes sudden cardiac death due to mutations in cardiac ryanodine receptors (RyR2), calsequestrin, or calmodulin. Flecainide, a class I ant...

A misguided 'pill in the pocket' approach with flecainide leading to cardiac arrest.

BMJ Case Rep. 2012 , doi:10.1136/bcr-2012-006868, (2012)

A case of near-fatal flecainide overdose in a neonate successfully treated with sodium bicarbonate.

J. Emerg. Med. 44(4) , 781-3, (2013)

Flecainide is a class IC antidysrhythmic primarily indicated for ventricular dysrhythmias and supraventricular tachycardia (SVT). Class IC antidysrhythmic overdose has a reported mortality of 22%, and...