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Encainide

Encainide structure

CAS No:
66778-36-7
Formula:
C22H28N2O2
Chemical Name:
Encainide
Synonyms:
Benzamide,4-methoxy-N-[2-[2-(1-methyl-2-piperidinyl)ethyl]phenyl]-;Benzamide,4-methoxy-N-[2-[2-(1-methyl-2-piperidinyl)ethyl]phenyl]-,(±)-;4-Methoxy-N-[2-[2-(1-methyl-2-piperidinyl)ethyl]phenyl]benzamide;MJ 9067;Encainide;37612-13-8
Categories:
Organic Chemistry > Amides

Description

ChEBI: 4-Methoxy-N-phenylbenzamide in which the hydrogen at the 2 position of the phenyl group is substituted by a 2-(1-methylpiperidin-2-yl)ethyl group. A class Ic antiarrhythmic, the hydrochloride was used for the treatment of severe or life- hreatening ventricular arrhythmias, but it was associated with increased death rates in patients who had asymptomatic heart rhythm abnormalities after a recent heart attack and was withdrawn from the market.

Solid

Encainide is 4-Methoxy-N-phenylbenzamide in which the hydrogen at the 2 position of the phenyl group is substituted by a 2-(1-methylpiperidin-2-yl)ethyl group. A class Ic antiarrhythmic, the hydrochloride was used for the treatment of severe or life-threatening ventricular arrhythmias, but it was associated with increased death rates in patients who had asymptomatic heart rhythm abnormalities after a recent heart attack and was withdrawn from the market. It has a role as an anti-arrhythmia drug and a sodium channel blocker. It is a member of piperidines and a member of benzamides.|All drug products containing encainide hydrochloride. Encainide hydrochloride, formerly marketed as Enkaid capsules, was associated with increased death rates in patients who had asymptomatic heart rhythm abnormalities after a recent heart attack. The manufacturer of Enkaid capsules voluntarily withdrew the product from the US market on December 16, 1991.|One of the ANTI-ARRHYTHMIA AGENTS, it blocks VOLTAGE-GATED SODIUM CHANNELS and slows conduction within the His-Purkinje system and MYOCARDIUM.

Encainide Basic Attributes

Molecular Weight：

352.47

Exact Mass：

352.47

DSSTox ID：

DTXSID0022983

ATC Code：

C - Cardiovascular system

Characteristics

PSA：

41.6

XLogP3：

Appearance：

Solid

Melting Point：

128 - 131 °C (acetonitrile)

Water Solubility：

4.01e-03 g/L

Drug Information

Drug Indication：

Encainide is a class Ic antiarrhythmic agent which was used for management of irregular heartbeats, such as atrial fibrillation, atrial flutter, ventricular tachycardia, and ventricular fibrillation.

Pharmacology：

Used to treat irregular heartbeats, encainide decreases excitability, conduction velocity, and automaticity as a result of slowed atrial, atrioventricular (AV) nodal, His-Purkinje, and intraventricular conduction. It causes a slight but significant prolongation of refractory periods in these tissues. The greatest effect is on the His-Purkinje system. Encainide decreases the rate of rise of the action potential without markedly affecting its duration.

MeSH：

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.)|A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS. (See all compounds classified as Voltage-Gated Sodium Channel Blockers.)

Absorption：

A radiolabeled dose of encainide is excreted in approximately equal amounts in the urine and feces.

Metabolism/Metabolites：

Encainide has known human metabolites that include N-demethylencainide and O-demethylencainide.

Biological Half-Life：

1-2 hours

Mechanism of Action：

Encainide is a sodium channel blocker, binding to voltage gated sodium channels. It stabilizes the neuronal membrane by inhibiting the ionic fluxes required for the initiation and conduction of impulses. Ventricular excitability is depressed and the stimulation threshold of the ventricle is increased during diastole.

MeSH Entry Terms：

Encainide

Encainide Use and Manufacturing

Methods of Manufacturing

2-methylpyridine and methyl iodide are dissolved in isopropanol and react at 60-65°C. Cool, filter, wash the filter cake with isopropanol, and recrystallize from ethanol to obtain N-alkylated product. Dissolve it and o-nitrobenzaldehyde in acetic anhydride and reflux. Cool, filter, wash with a small amount of acetone, and dry to obtain a solid product. The product is dissolved in ethanol and reacted by passing hydrogen at room temperature and pressure in the presence of platinum oxide. The catalyst was filtered off, the ethanol was evaporated, dissolved in water, adjusted to alkaline with sodium hydroxide solution, and extracted with ether. The ether solution was added dropwise with an excess of 10% p-methoxybenzoyl chloride under stirring, and stirred at room temperature. The ether was decanted, and an aqueous sodium oxychloride solution was added to the residue and extracted with ether. The extract is washed, dried, and evaporated to obtain a light yellow solid, which can be recrystallized with isopropanol, which is encarni.

Uses

It is a class I c antiarrhythmic drug and has a certain anesthetic effect. Used for ventricular tachycardia, ventricular fibrillation, ventricular premature beats, preexcitation syndrome, etc.

Computed Properties

Molecular Weight:352.5
XLogP3:4.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:352.215078140
Monoisotopic Mass:352.215078140
Topological Polar Surface Area:41.6
Heavy Atom Count:26
Complexity:434
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

2-Methylpyridine