Procainamide

Procainamide

Clinical data
Pronunciation	/proʊˈkeɪnəmaɪd/
Trade names	Pronestyl, Procan, Procanbid
AHFS/Drugs.com	Monograph
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	IV, IM, oral
ATC code	C01BA02 (WHO)
Pharmacokinetic data
Bioavailability	85% (oral)
Protein binding	15 to 20%
Metabolism	Hepatic (CYP2D6-mediated)
Biological half-life	~2.5 to 4.5 hours
Excretion	Renal
Legal status
Legal status	UK: POM (Prescription only)
ECHA InfoCard	100.000.072
Identifiers
IUPAC name 4-amino-N-(2-diethylaminoethyl) benzamide
CAS Number	51-06-9 Y
PubChem CID	4913
IUPHAR/BPS	4811
DrugBank	DB01035 Y
ChemSpider	4744 Y
UNII	L39WTC366D
KEGG	D08421 Y
ChEBI	CHEBI:8428 Y
ChEMBL	CHEMBL640 Y
Chemical and physical data
Formula	C13H21N3O
Molar mass	235.325 g/mol
3D model (Jmol)	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) Y Key:REQCZEXYDRLIBE-UHFFFAOYSA-N Y

Procainamide is a medication of the antiarrhythmic class used for the treatment of cardiac arrhythmias. It is classified by the Vaughan Williams classification system as class Ia.

This drug is used for both supraventricular and ventricular arrhythmias. For example, it can be used to convert new-onset atrial fibrillation, though it is suboptimal for this purpose.

To have a high efficacy, the antiarrhythmic drug procainamide has to be dosed frequently to maintain an adequate serum concentration. Because of its short half-life it must be dosed every 3 or 4 hours. Also procainamide-induced antinuclear antibodies are formed after a 6 months treatment. But further research showed, that after a long-term therapy of procainamide, some subjects did not produce any antinuclear antibodies. Also procainamide can be acetylated to acecainide and to other reactive and toxic metabolites, which would contradict the efficacy.

There are many side effects following the induction of procainamide. These adverse effects are ventricular dysrhythmia, bradycardia, hypotension and shock. The adverse effects occur even more often if the daily doses is increased. Procainamide may also lead to drug fever and other allergic responses. There is also a chance that systemic lupus erythematosus occurs, which at the same time leads to polyarthralgia, myalgia and pleurisy. Most of these side effects may occur due to the acetylation of procainamide.