Procainamide Hydrochloride

HCID 66068CAS 614-39-1

Substructure search Find similar structures

Basic information

Standard SMILES: CCN(CC)CCNC(=O)c1ccc(N)cc1.Cl
InChIKey: ABTXGJFUQRCPNH-UHFFFAOYSA-N
Molecular formula: C13H22ClN3O
Average molar mass: 271.78 g/mol
Monoisotopic mass: 271.14514

Overview

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.

Names & identifiers

Preferred name: Procainamide Hydrochloride
IUPAC: 4-amino-N-[2-(diethylamino)ethyl]benzamide;hydrochloride

Names & synonyms

procainamide hydrochloride614-39-1Procainamide HclProcanbidProcapanProcan SRPronestyl-SrAmidoprocaineCardiorytminBenzamide, 4-amino-N-[2-(diethylamino)ethyl]-, monohydrochlorideNovocamid hydrochlorideDTXSID2049422

Show more names

NSC-757279SI4064O0LXProcainamidi hydrochloridumBenzamide, 4-amino-N-(2-(diethylamino)ethyl)-, monohydrochlorideCHEBI:8429DTXCID10293824-Amino-N-(2-(diethylamino)ethyl)benzamide monohydrochloride4-Amino-N-[2-(diethylamino)ethyl]benzamide monohydrochloride

Database identifiers

CAS: 614-39-1
PubChem CID: 66068
DTXSID: DTXSID2049422
ChEMBL: CHEMBL605
UNII: SI4064O0LX
EC Number: 210-381-7

Properties

Computed structural properties

Topological polar surface area: 58.4 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 6
Heavy atoms: 18
Formal charge: 0
Complexity: 221

Experimental & physicochemical properties

Solubility>40.8 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

Collision Cross Section155.8 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Other Safety InformationIMAP assessments - Benzamide, 4-amino-N-[2-(diethylamino)ethyl]-, monohydrochloride: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Procainamide hydrochloride

vLess-DILI-concern

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Chemistry & industry

Pharmacology

FDA Pharmacological Classification · 4 items

PROCAINAMIDE HCI

Antiarrhythmic [EPC]

PROCAINAMIDE HYDROCHLORIDE

Antiarrhythmic [EPC]

MeSH Pharmacological Classification · 2 items

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.

A class of drugs that inhibit the activation of VOLTAGE-GATED SODIUM CHANNELS.