Procainamide hydrochloride Chemical Properties

Melting point:

165-168 °C

Density 

1.2027 (rough estimate)

refractive index 

1.6330 (estimate)

storage temp. 

2-8°C

solubility 

H2O: soluble1g/10 mL, clear, greenish-yellow

form 

Powder

color 

White to slightly yellow

Water Solubility 

soluble

Sensitive 

Light Sensitive/Air Sensitive

Merck 

13,7845

BRN 

3729517

CAS DataBase Reference

614-39-1(CAS DataBase Reference)

EPA Substance Registry System

Benzamide, 4-amino-N-[2-(diethylamino)ethyl]-, monohydrochloride (614-39-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

CV2295000

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Procainamide hydrochloride Usage And Synthesis

Description

Procainamide (hydrochloride) (Item No. 24359) is an analytical reference standard categorized as a local anesthetic. This product is intended for research and forensic applications.

Chemical Properties

White to slightly yellow powder

Uses

Class I antiarrhythmic

Uses

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Uses

Procainamide hydrochloride (PAH) is suitable to investigate its binding behavior with human serum albumin and bovine serum albumin by fluorescence quenching study to understand the pharmacokinetic and pharmacodynamic mechanisms of PAH.

Definition

ChEBI: A hydrochloride which has procainamide as the amino component.

General Description

Procainamide hydrochloride,p-amino-N-[2-(diethylamino)ethyl]benzamidemonohydrochloride, procainamidium chloride (Pronestyl,Procan SR), has emerged as a major antiarrhythmic drug. Itwas developed in the course of research for compoundsstructurally similar to procaine, which had limited effectas an antiarrhythmic agent because of its central nervoussystem (CNS) side effects and short-lived action causedby rapid hydrolysis of its ester linkage by plasma esterases.Because of its amide structure, procainamide hydrochlorideis also more stable in water than is procaine. Aqueoussolutions of procainamide hydrochloride have a pH ofabout 5.5. A kinetic study of the acid-catalyzed hydrolysisof procainamide hydrochloride showed it to be unusuallystable to hydrolysis in the pH range 2 to 7, even at elevatedtemperatures.

Biochem/physiol Actions

Procainamide hydrochloride is a sodium channel blocker and Class IA anti-arrhythmic. It has also been shown to Inhibit DNA methyltransferase and modulate epigenetic regulation of gene expression.

Clinical Use

Procainamide hydrochloride is metabolized through theaction of N-acetyltransferase. The product of enzymaticmetabolism of procainamide hydrochloride is N-acetylprocainamide(NAPA), which possesses only 25% of the activityof the parent compound.26 A study of the disposition ofprocainamide hydrochloride showed that 50% of the drugwas excreted unchanged in the urine, with 7% to 24% recoveredas NAPA.28,29 Unlike quinidine, procainamide hydrochlorideis bound only minimally to plasma proteins.Between 75% and 95% of the drug is absorbed from the gastrointestinaltract. Plasma levels appear 20 to 30 minutesafter administration and peak in about 1 hour.30Procainamide hydrochloride appears to have all of theelectrophysiological effects of quinidine. It diminishesautomaticity, decreases conduction velocity, and increasesaction potential duration and, thereby, the refractory periodof myocardial tissue. Clinicians have favored the use of procainamidehydrochloride for ventricular tachycardias andquinidine for atrial arrhythmias, even though the two drugsare effective in either type of disorder.

Veterinary Drugs and Treatments

Procainamide potentially may be useful for the treatment of ventricular premature complexes (VPC’s), ventricular tachycardia, or supraventricular tachycardia associated with Wolff-Parkinson- White (WPW) syndrome with wide QRS complexes. Higher doses may be beneficial in the treatment of supraventricular tachycardias, although procainamide cannot be considered a first-line agent for this dysrhythmia.

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