Editing Procainamide (section)

{{Short description|Medication to treat cardiac arrhythmias}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
| verifiedrevid = 477172111
| IUPAC_name = 4-amino-''N''-(2-diethylaminoethyl) benzamide
| image = Procainamide.svg
| image_class = skin-invert-image
<!--Clinical data-->
| tradename =  Pronestyl, Procan, Procanbid, others
| synonyms =
| pronounce = {{IPAc-en|p|r|oʊ|ˈ|k|eɪ|n|əm|aɪ|d}}
| Drugs.com = {{drugs.com|monograph|procainamide-hydrochloride}}
| pregnancy_US = C
| legal_UK = POM
| routes_of_administration = [[Intravenous therapy|IV]], [[Intramuscular injection|IM]], by mouth
<!--Pharmacokinetic data-->
| bioavailability = 85% (by mouth)
| protein_bound = 15 to 20%
| metabolism = [[Liver]] ([[CYP2D6]]-mediated)
| elimination_half-life = ~2.5 to 4.5 hours
| excretion = [[Kidney]]
<!--Identifiers-->
| IUPHAR_ligand = 4811
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 51-06-9
| ATC_prefix = C01
| ATC_suffix = BA02
| ATC_supplemental = 
| PubChem = 4913
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01035
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4744
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = L39WTC366D
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08421
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8428
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 640
<!--Chemical data-->
| C=13 | H=21 | N=3 | O=1
| smiles = O=C(c1ccc(N)cc1)NCCN(CC)CC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = REQCZEXYDRLIBE-UHFFFAOYSA-N
}}

'''Procainamide''' ('''PCA''') is a medication of the [[antiarrhythmic agent|antiarrhythmic class]] used for the treatment of [[cardiac arrhythmia]]s. It is a [[sodium channel blocker]] of [[Cardiac muscle cell|cardiomyocytes]]; thus it is classified by the [[Vaughan Williams classification]] system as class Ia. In addition to blocking the ''I''<sub>Na</sub> current, it inhibits the ''I''<sub>Kr</sub> rectifier K+ current.<ref name=Osadchii>{{cite journal | vauthors = Osadchii OE | title = Procainamide and lidocaine produce dissimilar changes in ventricular repolarization and arrhythmogenicity in guinea-pig | journal = Fundamental & Clinical Pharmacology | volume = 28 | issue = 4 | pages = 382–393 | date = August 2014 | pmid = 23952942 | doi = 10.1111/fcp.12046 | s2cid = 5086017 }}</ref> Procainamide is also known to induce a voltage-dependent open channel block on the batrachotoxin (BTX)-activated sodium channels in cardiomyocytes.<ref name=Zamponi>{{cite journal | vauthors = Zamponi GW, Sui X, Codding PW, French RJ | title = Dual actions of procainamide on batrachotoxin-activated sodium channels: open channel block and prevention of inactivation | journal = Biophysical Journal | volume = 65 | issue = 6 | pages = 2324–2334 | date = December 1993 | pmid = 8312472 | pmc = 1225974 | doi = 10.1016/S0006-3495(93)81291-8 | bibcode = 1993BpJ....65.2324Z }}</ref>