Procainamide

Base Information

• Chemical Name: Procainamide
• CAS No.: 51-06-9
• Molecular Formula: C13H21 N3 O
• Molecular Weight: 235.329
• Hs Code.: 2924299090
• European Community (EC) Number: 200-078-8
• NSC Number: 27461
• UNII: L39WTC366D
• DSSTox Substance ID: DTXSID7023512
• Nikkaji Number: J4.110F
• Wikipedia: Procainamide
• Wikidata: Q417597
• NCI Thesaurus Code: C61905
• RXCUI: 8700
• Pharos Ligand ID: TM5XNVYPJM31
• Metabolomics Workbench ID: 43277
• ChEMBL ID: CHEMBL640
• Mol file: 51-06-9.mol

Synonyms:Amide, Procaine;Apo-Procainamide;Biocoryl;Hydrochloride, Procainamide;Novocainamide;Novocamid;Procainamide;Procainamide Hydrochloride;Procaine Amide;Procamide;Procan;Procan SR;Procanbid;Pronestyl;Rhythmin

Chemical Property of Procainamide

Chemical Property:

• Melting Point: 47°C
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 421.8°Cat760mmHg
• PKA: pKa 9.24±0.10 (Uncertain)
• Flash Point: 208.9°C
• PSA: 58.36000
• Density: 1.060
• LogP: 2.31250
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 235.168462302
• Heavy Atom Count: 17
• Complexity: 221

Purity/Quality:

98%, ^*data from raw suppliers

Procainamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiarrhythmic Agents
• Canonical SMILES: CCN(CC)CCNC(=O)C1=CC=C(C=C1)N
• Recent ClinicalTrials: RAFF4 Trial: Vernakalant vs. Procainamide for Acute Atrial Fibrillation in the Emergency Department
• Recent EU Clinical Trials: Utilidad de la ajmalina intravenosa en el diagnóstico y tratamiento de las arritmias cardíacas
• Description: Procainamide and its analogs were employed by Dr Claude Beck in a series of cardiac surgeries during the early 1930s. The compound was used to alleviate arrhythmias that present during the procedures, and was selected for its favorable tissue absorption properties. Procainamide’s central amide provides it protection from inactivating esterase action and allows oral administration of the compound. Procainamide was approved for use in the United States in 1950.
• Uses: Procainamide is used in the management of atrial and ventricular tachydysrhythmias. Procainamide is intended for treating paroxysmal atrial tachycardia, atrial fibrillation, premature ventricular contraction, and ventricular tachycardia. For quickly reaching therapeutic concentrations, parenternal introduction of procainamide is preferred over cynidine.
• Biological Functions: Procainamide (Pronestyl, Procan SR) is a derivative of the local anesthetic agent procaine. Procainamide has a longer half-life, does not cause CNS toxicity at therapeutic plasma concentrations, and is effective orally. Procainamide is a particularly useful antiarrhythmic drug, effective in the treatment of supraventricular, ventricular, and digitalis-induced arrhythmias.
• Clinical Use: Procainamide is an effective antiarrhythmic agent when given in sufficient doses at relatively short (3–4 hours) dosage intervals. Procainamide is useful in the treatment of premature atrial contractions, paroxysmal atrial tachycardia, and atrial fibrillation of recent onset. Procainamide is only moderately effective in converting atrial flutter or chronic atrial fibrillation to sinus rhythm, although it has value in preventing recurrences of these arrhythmias once they have been terminated by direct current (DC) cardioversion. Procainamide can decrease the occurrence of all types of active ventricular dysrhythmias in patients with acute myocardial infarction who are free from A-V dissociation, serious ventricular failure, and cardiogenic shock. About 90% of patients with ventricular premature contractions and 80% of patients with ventricular tachycardia respond to procainamide administration. Although the spectrum of action and electrophysiological effects of quinidine and procainamide are similar, the relatively short duration of action of procainamide has tended to restrict its use to patients who are intolerant of or unresponsive to quinidine.
• Drug interactions: The inherent anticholinergic properties of procainamide may interfere with the therapeutic effect of cholinergic agents. Patients receiving cimetidine and procainamide may exhibit signs of procainamide toxicity, as cimetidine inhibits the metabolism of procainamide. Simultaneous use of alcohol will increase the hepatic clearance of procainamide. Procainamide may enhance or prolong the neuromuscular blocking activity of the aminoglycosides with the potential of producing respiratory depression. The simultaneous administration of quinidine or amiodarone may increase the plasma concentration of procainamide.

Technology Process of Procainamide

There total 11 articles about Procainamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

N-(2-(diethylamino)ethyl)-4-nitrobenzamide (1664-52-4) → 4-amino-N-(2-diethylaminoethyl)benzamide (51-06-9)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; silica gel; In methanol; for 6h; Milling;

DOI:10.3390/molecules23123163

Reference yield: 71.0%

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) + N,N-diethylethylenediamine (100-36-7) → 4-amino-N-(2-diethylaminoethyl)benzamide (51-06-9)

Guidance literature:

With 6Zr⁽⁴⁺⁾*4O^(2-)*6C₁₄H₈N₂O₄^(2-)*4HO^(1-); In tetrahydrofuran; at 70 ℃; for 24h; Molecular sieve; Sealed tube; Inert atmosphere;

DOI:10.1039/c5cc05985b

Reference yield:

procainamide hydrochloride (614-39-1) → 4-amino-N-(2-diethylaminoethyl)benzamide (51-06-9)

Guidance literature:

With sodium hydroxide; In water;

DOI:10.1002/bscb.19840930610

upstream raw materials:

N-(2-(diethylamino)ethyl)-4-nitrobenzamide

N,N-diethylethylenediamine

p-aminoethylbenzoate

procainamide hydrochloride

Downstream raw materials:

((2-{carboxymethyl-[2-(carboxymethyl-{[4-(2-diethylamino-ethylcarbamoyl)-phenylcarbamoyl]-methyl}-amino)-ethyl]-amino}-ethyl)-{[4-(2-diethylamino-ethylcarbamoyl)-phenylcarbamoyl]-methyl}-amino)-acetic acid

N-glycyl procainamide hydrochloride

N-(4-amino butanoyl)procainamide hydrochloride

N-(6-aminohexanoyl)procainamide hydrochloride

Refernces

• 1、 Dalu, Francesca,Scorciapino, Mariano A.,Cara, Claudio,Luridiana, Alberto,Musinu, Anna,Casu, Mariano,Secci, Francesco,Cannas, Carla. "A catalyst-free, waste-less ethanol-based solvothermal synthesis of amides". supporting information. p. 375 - 381. Retrieved 2018/02/07.
• 2、 Ramesh, Perla,Fadnavis, Nitin W.. "Ammonium nitrate: A biodegradable and efficient catalyst for the direct amidation of esters under solvent-free conditions". . p. 138 - 140. Retrieved 2015/02/19.