ACECAINIDE

Possibly Marketed Outside US

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1693889 | https://www.ncbi.nlm.nih.gov/pubmed/9730262 | https://www.ncbi.nlm.nih.gov/pubmed/6188570 | https://adisinsight.springer.com/drugs/800000315 | https://www.ncbi.nlm.nih.gov/pubmed/11245854

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

Targets

Primary Target	Pharmacology	Condition	Potency
Target ID: Potassium channel Sources: https://adisinsight.springer.com/drugs/800000315 \| https://www.ncbi.nlm.nih.gov/pubmed/11245854	Antagonist 2760

PubMed

Title	Date	PubMed
Pharmacologically active drug metabolites: therapeutic and toxic activities, plasma and urine data in man, accumulation in renal failure.	1976 Nov-Dec	799549
Cumulation of N-acetylprocainamide, an active metabolite of procainamide, in patients with impaired renal function.	1977 Jul	872496
Torsade de pointes associated with elevated N-acetylprocainamide levels.	1985 Feb	2578241
Study of procainamide hapten-specific antibodies in rabbits and humans.	1993 Nov	8253539
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 Aug	11566320
Quantitative estimation of renal clearance of N-acetylprocainamide in rats with various experimental acute renal failure.	2001 Jun	11384853
cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney.	2002 Jul	12089365
High-throughput solution-based medicinal library screening against human serum albumin.	2005 Mar 1	15732917
Therapeutic levels of intravenous procainamide in neonates: a retrospective assessment.	2006 Dec	17125432
Drug-herb interaction: effect of St John's wort on bioavailability and metabolism of procainamide in mice.	2007 Jul	17616997
Development of multifocal atrial tachycardia in a patient using aminophylline -A case report-.	2010 Dec	21286467

Patents

Substance Class	Chemical Created by `admin` on `Thu Jul 06 13:10:23 UTC 2023` Edited by `admin` on `Thu Jul 06 13:10:23 UTC 2023`
Record UNII	910Q707V6F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACECAINIDE

Official 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 [MI]

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