Procainamide hydrochloride

Procainamide hydrochloride Basic information
Product Name:Procainamide hydrochloride
Synonyms:2-[[(4-aminophenyl)-oxomethyl]amino]ethyl-diethylammonium;4-AMINO-N-[2'-(DIETHYLAMINO)ETHYL]BENZAMIDE HCL;4-AMINO-N-(2-DIETHYLAMINOETHYL)BENZAMIDE HYDROCHLORIDE;4-AMINOBENZOIC ACID 2-DIETHYLAMINOETHYLAMIDE HYDROCHLORIDE;PROCAINE AMIDE HYDROCHLORIDE;PROCAINAMIDE HCL;PROCAINAMIDE HYDROCHLORIDE;N-(2-DIETHYLAMINOETHYL)-4-AMINOBENZAMIDE HYDROCHLORIDE
CAS:614-39-1
MF:C13H22ClN3O
MW:271.79
EINECS:210-381-7
Product Categories:API;C8 to C20+;Amides;Bioactive Small Molecules;Building Blocks;Carbonyl Compounds;Benzene derivatives;Sodium channel;Cell Biology;Chemical Synthesis;Organic Building Blocks;P;PROCAN
Mol File:614-39-1.mol
Procainamide hydrochloride Structure
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 Reference614-39-1(CAS DataBase Reference)
EPA Substance Registry SystemBenzamide, 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 Information
ProviderLanguage
SigmaAldrich English
ACROS English
Procainamide hydrochloride Usage And Synthesis
DescriptionProcainamide (hydrochloride) (Item No. 24359) is an analytical reference standard categorized as a local anesthetic. This product is intended for research and forensic applications.
Chemical PropertiesWhite to slightly yellow powder
UsesClass I antiarrhythmic
UsesThese 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.
UsesProcainamide 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.
DefinitionChEBI: A hydrochloride which has procainamide as the amino component.
General DescriptionProcainamide 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 ActionsProcainamide 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 UseProcainamide 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 TreatmentsProcainamide 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.
Procainamide hydrochloride Preparation Products And Raw materials
Raw materialsEthylbenzene-->4-Nitrobenzoyl chloride-->Benzamide-->4-AMINO-N-[2-(DIETHYLAMINO)ETHYL]BENZAMIDE
Procaine hydrochloride YM-09151-2, [N-METHYL-3H]- Metoclopramide hydrochloride Benoxinate Hydrochloride pancopride D-Glucosamine hydrochloride O-DESMETHYL METOCLOPRAMIDE, HYDROCHLORIDE batanopride Topotecan hydrochloride METOCLOPRAMIDE HCL N-(1-Naphthyl)ethylenediamine dihydrochloride Glycine N-ACETYLPROCAINAMIDE HYDROCHLORIDE Amiodarone hydrochloride Tris(hydroxymethyl)aminomethane AMINO ACIDS 3-Aminophenol Dopamine hydrochloride

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