Repositioning Candidate Details

Candidate ID: R0442
Source ID: DB01195
Source Type: approved; withdrawn
Compound Type: small molecule
Compound Name: Flecainide
Synonyms: (±)-flecainide; Flecaine; Flecainide; N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide
Molecular Formula: C17H20F6N2O3
SMILES: FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1
Structure:
DrugBank Description: Flecainide is a Class I anti-arrhythmic agent like and . Flecainide’s development began in 1966 and was first synthesized in 1972 as an attempt to generate new anesthetics. It is used to prevent supraventricular and ventricular arrhythmias, as well as paroxysmal atrial fibrillation and flutter. Flecainide was granted FDA approval on 31 October 1985.
CAS Number: 54143-55-4
Molecular Weight: 414.3427
DrugBank Indication: In New Zealand and America, flecainide is indicated to prevent supraventricular arrhythmias and ventricular arrhythmias. In the United States, it is also indicated to prevent paroxysmal atrial fibrillation and flutter.
DrugBank Pharmacology: Flecainide inhibits the action of sodium and potassium ion channels in the heart, raising the threshold for depolarization and correcting arrhythmias. Flecainide has a long duration of action, allowing for once daily dosing. The therapeutic index is narrow. Patients should not take this medication if there is already structural heart disease or left ventricular systolic dysfunction.
DrugBank MoA: Flecainide blocks fast inward sodium channels and slowly unbinds during diastole, prolonging the refractory period of the heart. This blockade also shortens the duration of action potentials through the Purkinjie fibers. Flecainide also prevents delayed rectifier potassium channels from opening, lengthening the action potential through ventricular and atrial muscle fibers. Finally, flecainide also blocks ryanodine receptor opening, reducing calcium release from sarcoplasmic reticulum, which reduces depolarization of cells.
Targets: Sodium channel protein type 5 subunit alpha inhibitor; Sodium channel protein type 4 subunit alpha inhibitor; Potassium voltage-gated channel subfamily H member 2 inhibitor; Ryanodine receptor 2 inhibitor
Inclusion Criteria: Indication associated