| Identification | More | [Name]
Procainamide hydrochloride | [CAS]
614-39-1 | [Synonyms]
4-AMINOBENZOIC ACID 2-DIETHYLAMINOETHYLAMIDE HYDROCHLORIDE
4-AMINO-N-[2'-(DIETHYLAMINO)ETHYL]BENZAMIDE HCL
4-AMINO-N-(2-DIETHYLAMINOETHYL)BENZAMIDE HYDROCHLORIDE
N-(2-DIETHYLAMINOETHYL)-4-AMINOBENZAMIDE HYDROCHLORIDE
PROCAINAMIDE
PROCAINAMIDE HCL
PROCAINAMIDE HYDROCHLORIDE
PROCAINE AMIDE HYDROCHLORIDE
TIMTEC-BB SBB001067
4-amino-n-(2-(diethylamino)ethyl)benzamidemonohydrochloride
4-amino-n-[2-(diethylamino)ethyl]-benzamidmonohydrochloride
amidoprocain
novocamidhydrochloride
p-amino-n-(2-(diethylamino)ethyl)benzamidehydrochloride
p-amino-n-(2-(diethylamino)ethyl)-benzamidhydrochloride
procamidehydrochloride
procan-srhydrochloride
procapanhydrochloride
procardylhydrochloride
promidehydrochloride | [EINECS(EC#)]
210-381-7 | [Molecular Formula]
C13H22ClN3O | [MDL Number]
MFCD00012998 | [Molecular Weight]
271.79 | [MOL File]
614-39-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White to slightly yellow powder | [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 | [InChI]
InChI=1S/C13H21N3O.ClH/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);1H | [InChIKey]
ABTXGJFUQRCPNH-UHFFFAOYSA-N | [SMILES]
C1(=CC=C(N)C=C1)C(=O)NCCN(CC)CC.Cl | [CAS DataBase Reference]
614-39-1(CAS DataBase Reference) | [EPA Substance Registry System]
614-39-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
CV2295000
| [HS Code ]
29242990 |
| Hazard Information | Back Directory | [Chemical Properties]
Procainamide hydrochloride is a white or light yellow crystalline powder with a melting point of 165–169?°C. It is soluble in water and ethanol, slightly soluble in chloroform, and very slightly soluble in ether or benzene. It is odorless and hygroscopic. | [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. | [Uses]
Class I antiarrhythmic | [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. | [Pharmacokinetics]
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. A study of the disposition ofprocainamide hydrochloride showed that 50% of the drugwas excreted unchanged in the urine, with 7% to 24% recoveredas NAPA. 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. Procainamide 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. | [Mode of action]
Procainamide Hydrochloride is the hydrochloride salt form of procainamide, an amide derivative exhibiting class 1A antiarrhythmic property and analog of procaine. Procainamide hydrochloride reversibly binds to and blocks activated (open) voltage-gated sodium channels, thereby blocks the influx of sodium ions into the cell, which leads to an increase in threshold for excitation and inhibit depolarization during phase 0 of the action potential. In addition, the effective refractory period (ERP), action potential duration (APD), and ERP/APD ratios are increased, resulting in decreased impulse conduction velocity. The lasting action potential may also be due to blockage of outward K+ currents. The result is a decrease in automaticity, increase in refractory period and slowing of impulse conduction. | [References]
[1] KIRTHI BYADAGI. Investigation of binding behaviour of procainamide hydrochloride with human serum albumin using synchronous, 3D fluorescence and circular dichroism[J]. Journal of Pharmaceutical Analysis, 2017, 7 2: Pages 103-109. DOI:10.1016/j.jpha.2016.07.004.
[2] M. METI. Investigation of the interaction of the new antiarrhythmic drug procainamide hydrochloride with bovine serum albumin and the effect of some metal ions on the binding: a fluorescence quenching study[J]. Monatshefte für Chemie - Chemical Monthly, 2013, 163 1: 1253-1259. DOI:10.1007/s00706-013-0933-7. |
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