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Details

Stereochemistry ACHIRAL
Molecular Formula C15H23N3O2
Molecular Weight 277.362
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACECAINIDE

SMILES

CCN(CC)CCNC(=O)C1=CC=C(NC(C)=O)C=C1

InChI

InChIKey=KEECCEWTUVWFCV-UHFFFAOYSA-N
InChI=1S/C15H23N3O2/c1-4-18(5-2)11-10-16-15(20)13-6-8-14(9-7-13)17-12(3)19/h6-9H,4-5,10-11H2,1-3H3,(H,16,20)(H,17,19)

HIDE SMILES / InChI
Molecular Formula C15H23N3O2
Molecular Weight 277.362
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Acecainide (N-acetylprocainamide), the N-acetylated metabolite of procainamide, is a Class III antiarrhythmic agent. Acecainide exerts cardiac anticholinergic effect. It elicits smooth muscle relaxation mainly through the activation of plasma membrane K+ channels. Acecainide markedly reduced premature ventricular beats and prevented induction of ventricular tachycardia. Acecainide appears to offer advantages over procainamide, particularly with respect to the reduced formation of antinuclear antibodies. Acecainide development has been discontinued.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
PubMed

PubMed

TitleDatePubMed
Development of multifocal atrial tachycardia in a patient using aminophylline -A case report-.
2010-12
Overview of therapeutic drug monitoring.
2009-03
The prince and the pauper. A tale of anticancer targeted agents.
2008-10-23
Drug therapy considerations in arrhythmias in children.
2008-08-01
Procainamide, but not N-acetylprocainamide, induces protein free radical formation on myeloperoxidase: a potential mechanism of agranulocytosis.
2008-05
Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury.
2008
Effect of drugs on defibrillation capacity.
2008
Drug-herb interaction: effect of St John's wort on bioavailability and metabolism of procainamide in mice.
2007-07
Simultaneous determination of procaine and para-aminobenzoic acid by LC-MS/MS method.
2007-03-01
Therapeutic levels of intravenous procainamide in neonates: a retrospective assessment.
2006-12
Application of a generic physiologically based pharmacokinetic model to the estimation of xenobiotic levels in human plasma.
2006-01
St. John's wort does not interfere with therapeutic drug monitoring of 12 commonly monitored drugs using immunoassays.
2006
Class I antiarrhythmics inhibit Na+ absorption and Cl- secretion in rabbit descending colon epithelium.
2005-06
High-throughput solution-based medicinal library screening against human serum albumin.
2005-03-01
Massive cell vacuolization induced by organic amines such as procainamide.
2004-07
cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney.
2002-07
N-substituted benzamides inhibit nuclear factor-kappaB and nuclear factor of activated T cells activity while inducing activator protein 1 activity in T lymphocytes.
2001-08
Quantitative estimation of renal clearance of N-acetylprocainamide in rats with various experimental acute renal failure.
2001-06
Role of K+ channels in N-acetylprocainamide-induced relaxation of bovine tracheal smooth muscle.
2001-03-09
Study of procainamide hapten-specific antibodies in rabbits and humans.
1993-11
Torsades de pointes due to n-acetylprocainamide.
1985-07
Torsade de pointes associated with elevated N-acetylprocainamide levels.
1985-02
Polymorphic ventricular tachycardia and ventricular fibrillation due to N-acetyl procainamide.
1985-01-01
Cumulation of N-acetylprocainamide, an active metabolite of procainamide, in patients with impaired renal function.
1977-07
Pharmacologically active drug metabolites: therapeutic and toxic activities, plasma and urine data in man, accumulation in renal failure.
1976-11-01
Patents

Patents

JP2007525670A
150
JP2011513484A
29
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:43:24 GMT 2025
Edited
by admin
on Mon Mar 31 21:43:24 GMT 2025
Record UNII
910Q707V6F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACECAINIDE
INN   MI   WHO-DD  
INN  
Official Name English
ACECAINIDE [MI]
Preferred Name English
N-ACETYL-PROCAINAMIDE
Common Name English
BENZAMIDE, 4-(ACETYLAMINO)-N-(2-(DIETHYLAMINO)ETHYL)-
Systematic Name English
4'-((2-(DIETHYLAMINO)ETHYL)CARBAMOYL)ACETANILIDE
Systematic Name English
N-ACETYLNOVOCAINAMIDE
Common Name English
Acecainide [WHO-DD]
Common Name English
N-ACETYLPROCAINAMIDE
Common Name English
acecainide [INN]
Common Name English
ACETYLPROCAINAMIDE, N-
Common Name English
N-ACETYLPROCAINE AMIDE
Common Name English
ACETYLPROCAINAMIDE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 35989
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
NCI_THESAURUS C47793
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
FDA ORPHAN DRUG 99196
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
NCI_THESAURUS C93038
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
Code System Code Type Description
MERCK INDEX
m1291
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY Merck Index
SMS_ID
100000081770
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
MESH
D000120
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
CHEBI
60728
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
WIKIPEDIA
N-ACETYLPROCAINAMIDE
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
PUBCHEM
4342
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
INN
4409
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
FDA UNII
910Q707V6F
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
ChEMBL
CHEMBL1097
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
NCI_THESAURUS
C75125
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
EVMPD
SUB07372MIG
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
CAS
32795-44-1
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID6048414
Created by admin on Mon Mar 31 21:43:24 GMT 2025 , Edited by admin on Mon Mar 31 21:43:24 GMT 2025
PRIMARY
Related Record Type Details
Structure of ACECAINIDE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
Related Record Type Details
Structure of PROCAINAMIDE
PARENT -> METABOLITE ACTIVE
Structure of PROCAINAMIDE
PARENT -> METABOLITE
Related Record Type Details
Structure of ACECAINIDE
ACTIVE MOIETY
NIH
NCATS
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