Encainide (CED0007656)

Record Information

Version

1.0

Creation Date

2014-09-11 05:14:08 UTC

Update Date

2026-08-21 22:40:05 UTC

Accession Number

CHEM003695

Identification

Common Name

Encainide

Class

Small Molecule

Description

Encainide is an exogenous organic compound with the formula C22H28N2O2 and an average molecular weight of 352.47 g/mol. It exists as a solid at room temperature. Encainide belongs to the anilides, a subclass of benzene and substituted derivatives within the organic compounds. The compound targets the sodium channel protein type 5 subunit alpha (SCN5A). Recorded sources for encainide include antennas in electrical and electronic equipment, as well as pharmaceuticals and veterinary products specifically within the class i and iii antiarrhythmics. The recorded route of exposure is oral. Encainide hydrochloride was formerly marketed as Enkaid capsules, which were voluntarily withdrawn from the US market on December 16, 1991, by the manufacturer. This withdrawal followed associations with increased death rates in patients who had asymptomatic heart rhythm abnormalities after a recent heart attack.

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

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	Yes	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-052n-9311000000-985044a85c7ca1fc4601	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0019000000-c3aba8c66a81550a1bc5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-4489000000-fb4fa7dd76074a147422	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pbc-9741000000-30c243030c2a40b68b44	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0009000000-ace9a97974ab75eb724b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1219000000-8488789ae9ebc4c00e17	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9511000000-c16ae5ec1e6ea9df3fb7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udr-0509000000-1dacce0088b2fb6df452	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-2922000000-d0a2447f1a18ba018bdd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0aov-9500000000-bcebe1c95f279236a417	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0009000000-af987e6024645b1a42dc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfr-4449000000-97433c4f98db5b174197	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9231000000-7c8bacd1fef271451d2b	Not Available	View Spectrum

Toxicity Profile

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.

Carcinogenicity (IARC Classification)

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

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
217.0	Log mg/kg	[120:390]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
285	Antiarrhythmics, class i and iii	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
650	Purses Luggage Hand Bags	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Encainide Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	613.296
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	111.947
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	94.4311
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	398.977
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	256.124
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	336.776
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	419.529
Click to view 3D structure	Luciferin 4-monooxygenase	P08659	Photinus pyralis	Predicted (SEA)	31.0618
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	379.359
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	328.212
Click to view 3D structure	Serine/threonine-protein kinase pim-1	P11309	Humans	Predicted (SEA)	471.922
Click to view 3D structure	Histone deacetylase 1	Q13547	Humans	Predicted (SEA)	297.54
Click to view 3D structure	Muscarinic acetylcholine receptor M3	P20309	Humans	Predicted (SEA)	84.5443
Click to view 3D structure	Stromelysin-1	P08254	Humans	Predicted (SEA)	131.721
Click to view 3D structure	Collagenase 3	P45452	Humans	Predicted (SEA)	133.434
Click to view 3D structure	Matrilysin	P09237	Humans	Predicted (SEA)	121.912
Click to view 3D structure	Protective antigen	P13423	Bacillus anthracis	Predicted (SEA)	11.0546
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	253.555
Click to view 3D structure	Low-density lipoprotein receptor	P01130	Humans	Predicted (SEA)	3.89246
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	301.432
Click to view 3D structure	Histamine H1 receptor	P35367	Humans	Predicted (SEA)	257.914
Click to view 3D structure	Interstitial collagenase	P03956	Humans	Predicted (SEA)	166.052
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	661.018
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	352.19
Click to view 3D structure	Aurora kinase B	Q96GD4	Humans	Predicted (SEA)	632.603
Click to view 3D structure	Sodium channel protein type 5 subunit alpha	Q14524	Humans	Known	Not Available