Flecainide acetate

Base Information

• Chemical Name: Flecainide acetate
• CAS No.: 54143-56-5
• Molecular Formula: C19H24F6N2O5
• Molecular Weight: 474.4
• Hs Code.: 2933399090
• European Community (EC) Number: 258-997-5
• UNII: M8U465Q1WQ
• DSSTox Substance ID: DTXSID8020626
• Wikidata: Q27089351
• NCI Thesaurus Code: C499
• RXCUI: 42686
• ChEMBL ID: CHEMBL1200822
• Mol file: 54143-56-5.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 acetate

Chemical Property:

• Vapor Pressure: 9.11E-08mmHg at 25°C
• Melting Point: 145-147℃
• Boiling Point: 434.9 °C at 760 mmHg
• Flash Point: 216.8 °C
• PSA: 96.89000
• Density: 1.286 g/cm³
• LogP: 4.25130
• Storage Temp.: 2-8°C
• Solubility.: Soluble in water and in anhydrous ethanol. It is freely soluble in dilute acetic acid and practically insoluble in dilute hydrochloric acid.
• Water Solubility.: Soluble in dilute acetic acid, dimethyl sulfoxide, ethanol, methanol and water.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 474.15894084
• Heavy Atom Count: 32
• Complexity: 531

Purity/Quality:

99.9% ^*data from raw suppliers

Flecainide acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-63
• Safety Statements: 22-26-36/37/39-45-46

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)O.C1CCNC(C1)CNC(=O)C2=C(C=CC(=C2)OCC(F)(F)F)OCC(F)(F)F
• Recent ClinicalTrials: INhalation of Flecainide to Convert Recent Onset SympTomatic Atrial Fibrillation to siNus rhyThm (INSTANT)
• Recent EU Clinical Trials: A Phase 3, Randomized, Double-Blind, Placebo-Controlled Trial of Flecainide Acetate Inhalation Solution for Cardioversion of Recent-Onset, Symptomatic Atrial Fibrillation to Sinus Rhythm
• Description: Flecainide acetate (54143-56-5) is an open Na+?channel blocker that inhibits fast Na+?current in cardiac muscle in a use- and concentration-dependent manner.1?Orally-active class Ic antiarrhythmic agent2,3. Inhibits hERG potassium channels at clinically relevant concentrations.4
• Uses: Class I antiarrhythmic. Flecainide acetate is used as a sodium channel blocker and as an anti-arrhythmic. In general, it is used to regulate heartbeats of the upper heart and lower heart chambers. It can also be used to slow down an overactive heart. It is also useful in the treatment of ventricular tachycardias and ventricular arrhythmias.
• 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.

Technology Process of Flecainide acetate

There total 4 articles about Flecainide acetate 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: 89.0%

2,5-bis(2,2,2-trifluoroethoxy)-N-(pyridin-2-ylmethyl)-benzamide (57415-36-8) → flecainide acetate (54143-56-5)

Guidance literature:

Pt-C; In acetic acid;

Reference yield: 89.0%

flecainide (54143-55-4) + acetic acid (64-19-7,77671-22-8) → flecainide acetate (54143-56-5)

Guidance literature:

In isopropyl alcohol; for 2h; Heating / reflux;

Reference yield: 86.0%

2,5-bis(2,2,2-trifluoroethoxy)-N-(pyridin-2-ylmethyl)-benzamide (57415-36-8) + acetic acid (64-19-7,77671-22-8) → flecainide acetate (54143-56-5)

Guidance literature:

2,5-bis(2,2,2-trifluoroethoxy)-N-(pyridin-2-ylmethyl)-benzamide; With hydrogen; acetic acid; palladium 10% on activated carbon; platinum on carbon; at 69 - 72 ℃; for 5h; under 2925.29 - 4425.44 Torr;

With sodium hydroxide; In water; pH=13 - 14;

acetic acid; In ethyl acetate; at 31 ℃;

upstream raw materials:

flecainide

acetic acid

2,5-bis(2,2,2-trifluoroethoxy)-N-(pyridin-2-ylmethyl)-benzamide

Refernces

• 1、 -. "Preparation of acid addition salts of amine bases by solid phase-gas phase reactions". Page/Page column 3. . Retrieved 2008/06/13.
• 2、 -. "α,α-dibromo-α-chloro-acetophenones as synthons". . . Retrieved 2008/06/13.