Flecainide

Base Information

• Chemical Name: Flecainide
• CAS No.: 54143-55-4
• Deprecated CAS: 99495-87-1
• Molecular Formula: C17H20F6N2O3
• Molecular Weight: 414.348
• European Community (EC) Number: 923-247-4,685-650-9
• NSC Number: 719273
• UNII: K94FTS1806
• DSSTox Substance ID: DTXSID8023054
• Nikkaji Number: J12.413C,J399.064H,J399.065F
• Wikipedia: Flecainide
• Wikidata: Q421381
• NCI Thesaurus Code: C62029
• RXCUI: 4441
• Pharos Ligand ID: WH3Z9G1L6VMT
• Metabolomics Workbench ID: 43411
• ChEMBL ID: CHEMBL652
• Mol file: 54143-55-4.mol

Synonyms:Apocard;Fléca?ne;Flecadura;Flecainid Isis;Flecainid-Isis;Flecainide;Flecainide Acetate;Flecainide Monoacetate;Flecainide Monoacetate, (+-)-Isomer;Flecainide Monoacetate, (R)-Isomer;Flecainide Monoacetate, (S)-Isomer;Flecainide, (R)-Isomer;Flecainide, (S)-Isomer;Flecainide, 5-HO-N-(6-oxo)-Derivative;Flecainide, 5-HO-N-(6-oxo)-Derivative, (+-)-Isomer;Flecatab;R818;Tambocor

Chemical Property of Flecainide

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 105-107 °C
• Boiling Point: 434.9 °C at 760 mmHg
• PKA: pKa 9.3 (Uncertain)
• Flash Point: 216.8 °C
• PSA: 59.59000
• Density: 1.286 g/cm³
• LogP: 4.16040
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 414.13781148
• Heavy Atom Count: 28
• Complexity: 500

Purity/Quality:

99.9% ^*data from raw suppliers

Flecainide-d4 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiarrhythmic Agents
• Canonical SMILES: C1CCNC(C1)CNC(=O)C2=C(C=CC(=C2)OCC(F)(F)F)OCC(F)(F)F
• Recent ClinicalTrials: Predictive Factors to Effectively Terminate Paroxysmal Atrial Fibrillation by Blocking Atrial Selective Ionic Currents
• Recent EU Clinical Trials: First-line cryoablation for early treatment of Persistent Atrial Fibrillation – a randomized study comparing early trigger isolation using the Cryoballoon versus antiarrhythmic medication.
• Recent NIPH Clinical Trials: Clinical study of transplacental anti-arrythmic treatment for fetal tachyarrythmias
• Description: From the chemical point, flecainide is an analog of procainamide, to which a 2.2.2-trifluoroethoxyl group was added at C2 and C3 of the benzene ring, and a diaminoethyl side chain is ended in the piperidine ring.
• Uses: Antiarrhythmic (class IC) Flecainide, as with other local anesthetics, is used for naturally occurring ventricular arrhythmia. Flecainide is an antiarrhythmic (class IC).
• Therapeutic Function: Antiarrhythmic
• Clinical Use: Flecainide (Tambocor) is a fluorinated aromatic hydrocarbon examined initially for its local anesthetic action and subsequently found to have antiarrhythmic effects. Flecainide inhibits the sodium channel, leading to conduction slowing in all parts of the heart, but most notably in the His-Purkinje system and ventricular myocardium. It has relatively minor effects on repolarization. Flecainide also inhibits abnormal automaticity. Flecainide is effective in treating most types of atrial arrhythmias. It is also used for life-threatening ventricular arrhythmias. However, flecainide should be used with extreme caution in any patient with structural heart disease. Flecainide crosses the placenta, with fetal levels reaching approximately 70% of maternal levels. In many centers, it is the second-line drug after digoxin for therapy of fetal arrhythmias. Because of the high incidence of proarrhythmia, initiation of therapy or significant increases in dosing should be performed only on inpatients.
• Drug interactions: In patients whose condition has been stabilized by flecainide, the addition of cimetidine may reduce the rate of flecainide’s hepatic metabolism, increasing the potential for toxicity. Flecainide may increase digoxin concentrations on concurrent administration.

Technology Process of Flecainide

There total 3 articles about Flecainide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

C-piperidin-2-yl-methylamine (22990-77-8,111478-74-1,111478-77-4) + methyl 2,5-bis(2,2,2-trifluoroethoxy)benzoate (35480-31-0) → flecainide (54143-55-4)

Guidance literature:

In toluene; for 10h; Heating / reflux;

Reference yield:

C-piperidin-2-yl-methylamine (22990-77-8,111478-74-1,111478-77-4) + trifluoroethanol 2,5-bis-trifluoroethoxybenzoate → flecainide (54143-55-4)

Guidance literature:

In methanol; water; toluene;

Reference yield:

→ flecainide (54143-55-4)

Guidance literature:

/BRN= 502551/ (8), kat. Hydr. m. HOAc/PtO2/H2;

DOI:10.1021/jm00216a016

upstream raw materials:

C-piperidin-2-yl-methylamine

methyl 2,5-bis(2,2,2-trifluoroethoxy)benzoate

Downstream raw materials:

N-(3-carboxypropyl)-N-(2-piperidylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide

flecainide acetate

(+)-Flecainide

(-)-Flecainide

Refernces

• 1、 -. "Process for the preparation of 2,5-bis-(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)-benzamide (FLECAINIDE)". . . Retrieved 2008/06/13.
• 2、 -. "Antiarrhythmic method utilizing fluoroalkoxy-N-piperidyl and pyridyl benzamides". . . Retrieved 2008/06/13.