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Flecainide acetate

Flecainide acetate structure

CAS No:
54143-56-5
Formula:
C17H20F6N2O3.C2H4O2
Chemical Name:
Flecainide acetate
Synonyms:
Benzamide,N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-,acetate (1:1);Benzamide,N-(2-piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)-,monoacetate;R 818;Flecainide acetate;(±)-Flecainide acetate;Tambocor;2,5-Bis(2,2,2-trifluoroethoxy)-N-(2-piperidylmethyl)benzamide acetate;Apocard;Ecrinal;Almarytm;R 818 (pharmaceutical);99495-88-2
Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs

Description

Flecainide(Tambocor) is a class 1C antiarrhythmic drug especially used for the management of supraventricular arrhythmia; works by blocking the Nav1.5 sodium channel in the heart, causing prolongation of the cardiac action potential.IC50 Value:Target: Nav1.5 channelFlecainide is a class 1C antiarrhythmic drug especially used for the management of supraventricular arrhythmia. Flecainide works by blocking the Nav1.5 sodium channel in the heart, causing prolongation of the cardiac action po

Flecainide acetate is an acetate salt obtained by combining flecainide with one molar equivalent of acetic acid. An antiarrhythmic agent used to prevent and treat tachyarrhythmia (abnormal fast rhythm of the heart). It has a role as an anti-arrhythmia drug. It contains a flecainide(1+).|Flecainide is an oral antiarrhythmic agent that has been in use for several decades. Long term flecainide therapy is associated with a low rate of serum enzyme elevations and is a very rare cause of clinically apparent acute liver injury.|A potent anti-arrhythmia agent, effective in a wide range of ventricular and atrial ARRHYTHMIAS and TACHYCARDIAS.

Flecainide acetate Basic Attributes

Molecular Weight：

474.39

Exact Mass：

474.158936

EC Number：

258-997-5

DSSTox ID：

DTXSID8020626

HScode：

2933399090

Characteristics

PSA：

96.9

XLogP3：

4.25130

Density：

1.286g/cm3

Melting Point：

145-147 °C

Boiling Point：

434.9ºC at 760mmHg

Flash Point：

216.8ºC

Water Solubility：

soluble in dilute acetic acid, dimethyl sulfoxide, ethanol, methanol and water.

Storage Conditions：

2-8°C

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

3249

hazard class code：

22-36/37/38-63

safety instructions：

22-26-36/37/39-45-46

RTECS Number：

CV5792550

Marks：

Precautionary statement(s)：

P201-P280-P301 + P312 + P330-P305 + P351 + P338-P308 + P313

Hazard Statements：

H302-H315-H319-H335-H360

GHS Classification：

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Hepatotoxicity：

In clinical trials, flecainide was associated with a low rate of serum aminotransferase and alkaline phosphatase elevations. Despite wide scale use, flecainide has only rarely been linked to cases of clinically apparent liver injury. The typical presentation is with a cholestatic hepatitis arising within 1 to 6 weeks of starting flecainide. In addition, instances of acute hepatic injury arising within 1 to 3 days of starting flecainide with marked, but short lived elevations in serum aminotransferase levels and minimal increases in alkaline phosphatase have been published, but may actually represent acute worsening of congestive heart failure and ischemic hepatitis due to the proarrhythmic effects of flecainide. In all instances, the liver injury was self limited. Immunoallergic and autoimmune features were not present.

Drug Information

LiverTox Summary：

Flecainide is an oral antiarrhythmic agent that has been in use for several decades. Long term flecainide therapy is associated with a low rate of serum enzyme elevations and is a very rare cause of clinically apparent acute liver injury.

Drug Classes：

Antiarrhythmic Agents

MeSH：

A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)|Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

MeSH Entry Terms：

Apocard

Flecainide acetate Use and Manufacturing

Uses

Antiarrhythmic

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:474.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:7
Exact Mass:474.15894084
Monoisotopic Mass:474.15894084
Topological Polar Surface Area:96.9
Heavy Atom Count:32
Complexity:531
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes