CHEBI:8428 - procainamide

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ChEBI Name procainamide
ChEBI ID CHEBI:8428
Definition A benzamide that is 4-aminobenzamide substituted on the amide N by a 2-(diethylamino)ethyl group. It is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C13H21N3O
Net Charge 0
Average Mass 235.32546
Monoisotopic Mass 235.168
InChI InChI=1S/C13H21N3O/c1-3-16(4-2)10-9-15-13(17)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3,(H,15,17)
InChIKey REQCZEXYDRLIBE-UHFFFAOYSA-N
SMILES CCN(CC)CCNC(=O)c1ccc(N)cc1
Roles Classification
Biological Role(s): sodium channel blocker
An agent that inhibits sodium influx through cell membranes.
Application(s): anti-arrhythmia drug
A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.
platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
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ChEBI Ontology
Outgoing procainamide (CHEBI:8428) has role anti-arrhythmia drug (CHEBI:38070)
procainamide (CHEBI:8428) has role platelet aggregation inhibitor (CHEBI:50427)
procainamide (CHEBI:8428) has role sodium channel blocker (CHEBI:38633)
procainamide (CHEBI:8428) is a benzamides (CHEBI:22702)
Incoming procainamide hydrochloride (CHEBI:8429) has part procainamide (CHEBI:8428)
IUPAC Name
4-amino-N-[2-(diethylamino)ethyl]benzamide
INNs Sources
procainamida ChemIDplus
procaïnamide ChEBI
procainamide ChemIDplus
procainamidum ChemIDplus
Synonyms Sources
p-Amino-N-(2-diethylaminoethyl)benzamide ChemIDplus
p-Aminobenzoic diethylaminoethylamide ChemIDplus
Procainamide KEGG COMPOUND
Brand Name Source
Biocoryl DrugBank
Manual Xrefs Databases
2270 DrugCentral
C07401 KEGG COMPOUND
D08421 KEGG DRUG
DB01035 DrugBank
LSM-3681 LINCS
Procainamide Wikipedia
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Registry Numbers Types Sources
2214285 Reaxys Registry Number Reaxys
2214285 Beilstein Registry Number Beilstein
51-06-9 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16230360 PubMed citation Europe PMC
2494958 PubMed citation Europe PMC
29276243 PubMed citation Europe PMC
29494946 PubMed citation Europe PMC
Last Modified
30 April 2018