Basic information
- CAS
66778-36-7- Standard SMILES
COc1ccc(C(=O)Nc2ccccc2CCC2CCCCN2C)cc1- InChIKey
PJWPNDMDCLXCOM-UHFFFAOYSA-N- Molecular formula
- C22H28N2O2
- Average molar mass
- 352.5 g/mol
- Monoisotopic mass
- 352.21507814
Overview
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increased death rates in patients who had asymptomatic heart rhythm abnormalities after a recent heart attack and was withdrawn from the market.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 benzamides and a member of piperidines.
Names & identifiers
- Preferred name
- Encainide
- IUPAC
- 4-methoxy-N-[2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl]benzamide
- English name
- Benzamide, 4-methoxy-N-[2-[2-(1-methyl-2-piperidinyl)ethyl]phenyl]-
- Molecular formula
- C22H28N2O2
- Molecular weight
- 352.47
Names & synonyms
Encainide66778-36-7EncainidaEncainidum4-Methoxy-N-(2-(2-(1-methylpiperidin-2-yl)ethyl)phenyl)benzamideMJ 90674-methoxy-N-{2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl}benzamideSY3J0147NB(+-)-4-Methoxy-N-(2-(2-(1-methyl-2-piperidinyl)ethyl)phenyl)benzamide4-methoxy-N-[2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl]benzamideBENZAMIDE, 4-METHOXY-N-(2-(2-(1-METHYL-2-PIPERIDINYL)ETHYL)PHENYL)-, (+-)-CHEBI:4788
Show more names
EnkaidEnkadeMJ-9067M-9067-1Brn 0497572MJ-9067[AS BASE]Encainide [french]Encainida [spanish]
DTXSID0022983(+-)-2'-[2-(1-methyl-2-piperidyl)ethyl]-p-anisanilide4-methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide4-Methoxy-N-{2-[2-(1-methyl-piperidin-2-yl)-ethyl]-phenyl}-benzamide(+-)-2'-(2-(1-Methyl-2-piperidyl)ethyl)-P-anisanilide4-Methoxy-2'-(2-(1-methyl-2-piperidyl)ethyl)benzanilide4-Methoxy-N-(2-(2-(1-methyl-piperidin-2-yl)-ethyl)-phenyl)-benzamideRefChem:136750
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 41.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 434
Experimental & physicochemical properties
LogP4
Solubility4.01e-03 g/L
Physical DescriptionSolid
Physicochemical properties
- storage temp.
- -20 °C · Store at -20°C
- form
- Solid
- color
- White to off-white
- FDA UNII
- 3 J0147NB · SY3J0147NB
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Toxicology
Toxicity Summary
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.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Pharmacodynamics
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.
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.
Biological Half-Life1-2 hours
Metabolism/Metabolites
Encainide has known human metabolites that include N-demethylencainide and O-demethylencainide.
Route of Elimination: A radiolabeled dose of encainide is excreted in approximately equal amounts in the urine and feces. Half Life: 1-2 hours
MeSH Pharmacological Classification
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.
A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS.
Absorption, Distribution and Excretion
Related reactions
4 records
Compound notes
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