Procainamide

Procainamide
Clinical data
Pronunciation	/proʊˈkeɪnəmaɪd/
Trade names	Pronestyl, Procan, Procanbid, others
AHFS/Drugs.com	Monograph
Routes of; administration	IV, IM, by mouth
ATC code	C01BA02 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	85% (by mouth)
Protein binding	15 to 20%
Metabolism	Liver (CYP2D6-mediated)
Elimination half-life	~2.5 to 4.5 hours
Excretion	Kidney
Identifiers
	IUPAC name 4-amino-N-(2-diethylaminoethyl) benzamide;
CAS Number	51-06-9 ;
PubChem CID	4913;
IUPHAR/BPS	4811;
DrugBank	DB01035 ;
ChemSpider	4744 ;
UNII	L39WTC366D;
KEGG	D08421 ;
ChEBI	CHEBI:8428 ;
ChEMBL	ChEMBL640 ;
CompTox Dashboard (EPA)	DTXSID7023512 ;
ECHA InfoCard	100.000.072
Chemical and physical data
Formula	C13H21N3O
Molar mass	235.331 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1ccc(N)cc1)NCCN(CC)CC;
	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) ; Key:REQCZEXYDRLIBE-UHFFFAOYSA-N ;
	(verify)

Procainamide (PCA) is a medication of the antiarrhythmic class used for the treatment of cardiac arrhythmias. It is a sodium channel blocker of cardiomyocytes; thus it is classified by the Vaughan Williams classification system as class Ia. In addition to blocking the I_Na current, it inhibits the I_Kr rectifier K+ current.^[1] Procainamide is also known to induce a voltage-dependent open channel block on the batrachotoxin (BTX)-activated sodium channels in cardiomyocytes.^[2]

^ Osadchii OE (August 2014). "Procainamide and lidocaine produce dissimilar changes in ventricular repolarization and arrhythmogenicity in guinea-pig". Fundamental & Clinical Pharmacology. 28 (4): 382–393. doi:10.1111/fcp.12046. PMID 23952942. S2CID 5086017.
^ Zamponi GW, Sui X, Codding PW, French RJ (December 1993). "Dual actions of procainamide on batrachotoxin-activated sodium channels: open channel block and prevention of inactivation". Biophysical Journal. 65 (6): 2324–2334. Bibcode:1993BpJ....65.2324Z. doi:10.1016/S0006-3495(93)81291-8. PMC 1225974. PMID 8312472.

[Osadchii-1] Osadchii OE (August 2014). "Procainamide and lidocaine produce dissimilar changes in ventricular repolarization and arrhythmogenicity in guinea-pig". Fundamental & Clinical Pharmacology. 28 (4): 382–393. doi:10.1111/fcp.12046. PMID 23952942. S2CID 5086017.

[Zamponi-2] Zamponi GW, Sui X, Codding PW, French RJ (December 1993). "Dual actions of procainamide on batrachotoxin-activated sodium channels: open channel block and prevention of inactivation". Biophysical Journal. 65 (6): 2324–2334. Bibcode:1993BpJ....65.2324Z. doi:10.1016/S0006-3495(93)81291-8. PMC 1225974. PMID 8312472.

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