ContaminantDB: Encainide

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Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:14:08 UTC

Update Date

2016-11-09 01:09:11 UTC

Accession Number

CHEM003695

Identification

Common Name

Encainide

Class

Small Molecule

Description

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.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amide
Amine
Anti-Arrhythmia Agent
Drug
Ester
Ether
Organic Compound
Sodium Channel Blocker
Synthetic Compound
Voltage-Gated Sodium Channel Blocker

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-2'-[2-(1-Methyl-2-piperidyl)ethyl]-p-anisanilide	ChEBI
(+-)-4-Methoxy-N-(2-(2-(1-methyl-2-piperidinyl)ethyl)phenyl)benzamide	ChEBI
4-Methoxy-2'-[2-(1-methyl-2-piperidyl)ethyl]benzanilide	ChEBI
4-Methoxy-N-{2-[2-(1-methyl-piperidin-2-yl)-ethyl]-phenyl}-benzamide	ChEBI
Encainida	ChEBI
Encainidum	ChEBI
Encainide, (+)-isomer	HMDB
Enkaid	HMDB
Encainide hydrochloride	HMDB
Encainide hydrochloride, (+-)-isomer	HMDB
Bristol myers squibb brand OF encainide hydrochloride	HMDB
Bristol-myers squibb brand OF encainide hydrochloride	HMDB
Encainide, (-)-isomer	HMDB

Chemical Formula

C₂₂H₂₈N₂O₂

Average Molecular Mass

352.470 g/mol

Monoisotopic Mass

352.215 g/mol

CAS Registry Number

66778-36-7

IUPAC Name

4-methoxy-N-{2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl}benzamide

Traditional Name

encainide

SMILES

COC1=CC=C(C=C1)C(=O)NC1=CC=CC=C1CCC1CCCCN1C

InChI Identifier

InChI=1S/C22H28N2O2/c1-24-16-6-5-8-19(24)13-10-17-7-3-4-9-21(17)23-22(25)18-11-14-20(26-2)15-12-18/h3-4,7,9,11-12,14-15,19H,5-6,8,10,13,16H2,1-2H3,(H,23,25)

InChI Key

PJWPNDMDCLXCOM-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Benzanilides

Alternative Parents

Substituents

Benzanilide
Benzamide
Benzoic acid or derivatives
Alkaloid or derivatives
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Methoxybenzene
Aralkylamine
Alkyl aryl ether
Piperidine
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Hydrocarbon derivative
Organic oxygen compound
Amine
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:4788 )
benzamides (CHEBI:4788 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.004 g/L	ALOGPS
logP	4.29	ALOGPS
logP	4.49	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	9.48	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	107.77 m³·mol⁻¹	ChemAxon
Polarizability	41.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052n-9311000000-985044a85c7ca1fc4601	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0019000000-c3aba8c66a81550a1bc5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-4489000000-fb4fa7dd76074a147422	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbc-9741000000-30c243030c2a40b68b44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-ace9a97974ab75eb724b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1219000000-8488789ae9ebc4c00e17	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9511000000-c16ae5ec1e6ea9df3fb7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0509000000-1dacce0088b2fb6df452	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2922000000-d0a2447f1a18ba018bdd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aov-9500000000-bcebe1c95f279236a417	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-af987e6024645b1a42dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0zfr-4449000000-97433c4f98db5b174197	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9231000000-7c8bacd1fef271451d2b	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

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.

Metabolism

Route of Elimination: A radiolabeled dose of encainide is excreted in approximately equal amounts in the urine and feces. Half Life: 1-2 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID