99495-90-6

Basic information

• Product Name: (R)-Flecainide
• Synonyms: (R)-(-)-Flecainide;(R)-Flecainide;Benzamide, N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-, (R)-;Benzamide, N-[(2R)-2-piperidinylmethyl]-2,5-bis(2,2,2-trifluoroethoxy)-;N-[(2R)-2-Piperidinylmethyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide;N-[(R)-2-Piperidinylmethyl]-2,5-bis(2,2,2-trifluoroethoxy)benzamide
• CAS NO: 99495-90-6
• Molecular Formula: C₁₇H₂₀F₆N₂O₃
• Molecular Weight: 414.344
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 99495-90-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 434.9°C at 760 mmHg
• Flash Point: 216.8°C
• Appearance: /
• Density: 1.286g/cm³
• Vapor Pressure: 9.11E-08mmHg at 25°C
• Refractive Index: 1.457
• PKA: 14.15±0.46(Predicted)
• CAS DataBase Reference: (R)-Flecainide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Flecainide(99495-90-6)
• EPA Substance Registry System: (R)-Flecainide(99495-90-6)

Safety Data

• Hazardous Substances Data: 99495-90-6(Hazardous Substances Data)

Usage

Description

R-(–)-Flecainide is the (R) enantiomer of the antiarrhythmic agent flecainide . R-(–)-Flecainide prevents chloroform-induced ventricular fibrillation in mice (ED50 = 14.5 mg/kg). It also prevents ouabain-induced ectopic ventricular tachycardia in anesthetized dogs.

Uses

Different sources of media describe the Uses of 99495-90-6 differently. You can refer to the following data:
1. R-Enantiomer of Flecainide. Antiarrhythmic (class IC)
2. R-Enantiomer of Flecainide. Antiarrhythmic (class IC).

InChI:InChI=1/C17H20F6N2O3/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/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26)/t11-/m1/s1

Upstream product

• 54143-55-4 flecainide 

Relevant articles and documents

Resolution of Flecainide Acetate, N-(2-Piperidylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide Acetate, and Antiarrhythmic Properties of the Enantiomers

The antiarrhythmic agent flecainide acetate was resolved by fractional crystallization of its diastereomeric α-bromocamphor-?-sulfonate salts.Optical purity of the two enantiomers was shown to be > 99percent by an NMR technique using the chiral shift reagent Eu(hfbc)3.Antiarrhythmic effects of flecainide and its enantiomers were assessed in two different animal models, chloroform-induced ventricular fibrillation in mice and ouabain-induced verticular tachycardia in dogs.The two enantiomers were highly effective in suppressing both of these experimental arrhythmias and appeared to be essentially equipotent.No significant differences were found either between the two enantiomers or between the enantiomers and racemic flecainide.

Preparation, Optical Purity and Configuration of the Enantiomers of Flecainide

The chiral antiarrhythmic drug flecainide (rac-1) was resolved by fractional crystallization of the diastereomeric salts with optically active mandelic acid.Derivatization with (+)-1-phenylethyl isocyanate and analytical separation of the diastereomers 3