Structure via PubChem · Public domain (PubChem)
Procainamide
Sign in to saveAlso known as Procan®, Pronestyl®, p-Aminobenzoic diethylaminoethylamide, p-Amino-N-(2-diethylaminoethyl)benzamide, Biocoryl, Procainamida, Procainamidum
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 INa current, it inhibits the IKr rectifier K+ current. Procainamide is also known to induce a voltage-dependent open channel block on the batrachotoxin (BTX)-activated sodium channels in cardiomyocytes.
Chemical data
- Formula
- C13H21N3O
- Molecular weight
- 235.33 g/mol
- IUPAC name
- 4-amino-N-[2-(diethylamino)ethyl]benzamide
- SMILES
- CCN(CC)CCNC(=O)C1=CC=C(C=C1)N
- InChIKey
- REQCZEXYDRLIBE-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 58.4 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1950
- Admin. routes
- oral, parenteral
- Indications
- atrial fibrillation, heart failure, cardiac arrhythmia, myocardial infarction
via ChEMBL · EBI
Research
4,566 papers- Randomized comparison of intravenous procainamide vs. intravenous amiodarone for the acute treatment of tolerated wide QRS tachycardia: the PROCAMIO study.European heart journal · 2017
- Procainamide and disopyramide.European heart journal · 1987
- Procainamide pharmacokinetics during extracorporeal membrane oxygenation.Perfusion · 2023
- [Procainamide].Nihon rinsho. Japanese journal of clinical medicine · 1995
- Procainamide-induced psychosis.Critical care nurse · 1993
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 235.168462
- Has use
- medication
Show 7 more facts
- significant drug interaction
- thioridazine
- chemical formula
- C₁₃H₂₁N₃O
- medical condition treated
- supraventricular tachycardia
- canonical SMILES
- CCN(CC)CCNC(=O)C1=CC=C(C=C1)N
- World Health Organisation international non-proprietary name
- procainamide
- Commons category
- Procainamide
- has characteristic
- bitterness
via Wikidata · CC0