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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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Pharmacologically active drug metabolites: therapeutic and toxic activities, plasma and urine data in man, accumulation in renal failure.
1976 Nov-Dec
Cumulation of N-acetylprocainamide, an active metabolite of procainamide, in patients with impaired renal function.
1977 Jul
Polymorphic ventricular tachycardia and ventricular fibrillation due to N-acetyl procainamide.
1985 Jan 1
Study of procainamide hapten-specific antibodies in rabbits and humans.
1993 Nov
Quantitative estimation of renal clearance of N-acetylprocainamide in rats with various experimental acute renal failure.
2001 Jun
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
Massive cell vacuolization induced by organic amines such as procainamide.
2004 Jul
Patents
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:44:01 GMT 2023
Edited
by admin
on Sat Dec 16 07:44:01 GMT 2023
Record UNII
910Q707V6F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACECAINIDE
INN   MI   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
NCI_THESAURUS C47793
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
FDA ORPHAN DRUG 99196
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
NCI_THESAURUS C93038
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
Code System Code Type Description
MERCK INDEX
m1291
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY Merck Index
SMS_ID
100000081770
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
MESH
D000120
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
CHEBI
60728
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
WIKIPEDIA
N-ACETYLPROCAINAMIDE
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
PUBCHEM
4342
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
INN
4409
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
FDA UNII
910Q707V6F
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
ChEMBL
CHEMBL1097
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
NCI_THESAURUS
C75125
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
EVMPD
SUB07372MIG
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
CAS
32795-44-1
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID6048414
Created by admin on Sat Dec 16 07:44:01 GMT 2023 , Edited by admin on Sat Dec 16 07:44:01 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
Related Record Type Details
PARENT -> METABOLITE ACTIVE
PARENT -> METABOLITE
Percent of dose excreted in urine as metabolite.
AMOUNT EXCRETED
URINE
Related Record Type Details
ACTIVE MOIETY