APRINDINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H30N2
Molecular Weight	322.487
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCCN(C1CC2=C(C1)C=CC=C2)C3=CC=CC=C3

InChI

InChIKey=NZLBHDRPUJLHCE-UHFFFAOYSA-N

InChI=1S/C22H30N2/c1-3-23(4-2)15-10-16-24(21-13-6-5-7-14-21)22-17-19-11-8-9-12-20(19)18-22/h5-9,11-14,22H,3-4,10,15-18H2,1-2H3

HIDE SMILES / InChI

Description
Sources: http://www.ndrugs.com/?s=aprindine
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/6186851

Aprindine is a class Ib antiarrhythmic agent. It is not approved in USA, but is available in European countries, where it is used to treat supraventricular and ventricular arrhythmias. Aprindine acts by blocking sodium voltage channels and disrupting interactions between calmodulin and prosphodiesterase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 76 Target ID: CHEMBL2331043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1660104	Blocker 537
Calmodulin 17 Target ID: CHEMBL6093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6186851	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atrial fibrillation 131 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12074271	Preventing		Not Provided 504	Unknown Approved Use Unknown
Ventricular arrhythmia 50 Sources: http://flexikon.doccheck.com/de/Aprindin	Primary		Approved 8429	FIBORAN Approved Use Aprindine is indicated for treatment of therapy-resistant ventricular tachycardias and ventricular extrasystoles.

PubMed

Title	Date	PubMed
[Accident during local anesthesia in a patient with antiarrhythmic therapy].	1975 Jul	51544
New drugs for treating cardiac arrhythmias.	1981 Jan	6780988
Quantitative analysis of the antiarrhythmic effect of drugs on canine ventricular arrhythmias by the determination of minimum effective plasma concentrations.	1983 Jan	6827775
Combined application of class I antiarrhythmic drugs causes "additive", "reductive", or "synergistic" sodium channel block in cardiac muscles.	1990 Nov	2176934
Complex frequency-dependent interaction of class-I antiarrhythmic drugs as they affect intraventricular conduction.	1995 Jun	7588928
Effects of aprindine on ischemia/reperfusion-induced cardiac contractile dysfunction of perfused rat heart.	1996 Mar	8935716
Prediction of catalepsies induced by amiodarone, aprindine and procaine: similarity in conformation of diethylaminoethyl side chain.	1998 Nov	9808703
[Comparison of the efficacies of disopyramide, cibenzoline and aprindine for the termination of paroxysmal and persistent atrial fibrillation in elderly and non-elderly patients].	2003 Apr	12728540
Usefulness and safety of bepridil in converting persistent atrial fibrillation to sinus rhythm.	2003 Aug 15	12914884
Role of atrial fibrillation threshold evaluation on guiding treatment.	2003 Oct 1	16943922
Theoretical possibilities for the development of novel antiarrhythmic drugs.	2004 Jan	14754422
Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring.	2005 Feb	15658999
Proteasomal degradation of Kir6.2 channel protein and its inhibition by a Na+ channel blocker aprindine.	2005 Jun 17	15882977
Effect of antiarrhythmic agents on heart rate variability indices after myocardial infarction: comparative experimental study of aprindine and procainamide.	2005 Oct	16275488
Nonlinear mixed effects model analysis of the pharmacokinetics of routinely administered bepridil in Japanese patients with arrhythmias.	2006 Mar	16508157
Topics on the Na+/Ca2+ exchanger: pharmacological characterization of Na+/Ca2+ exchanger inhibitors.	2006 Sep	16990699
Pharmacological cardioversion of persistent atrial fibrillation with and without a history of drug-resistant paroxysmal atrial fibrillation.	2006 Sep	16936425
Pharmacological cardioversion of long-lasting atrial fibrillation.	2007	17587743
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current.	2009 Jun	19498275

Patents

Sample Use Guides

In Vivo Use Guide

150-200 mg daily in divided doses, up to 300 mg/day may be used under strict observation for the first 2-3 days if needed.

Route of Administration: Oral

In Vitro Use Guide

Effects of aprindine (3 umol/l) on the Na+ current using whole cell voltage clamp was studied in guinea-pig ventricular myocytesd. Aprindine revealed tonic block (Kdrest = 37.7 umol/l, Kdi = 0.74 umol/l) and shifted inactivation curve to hyperpolarizing direction by 11.4+3.5 mV (n = 4) without changes in slope factor.

Name

Type

Language

APRINDINE

Official Name

English

APRINDINE [MI]

Common Name

English

APRINDINE [USAN]

Common Name

English

COMPOUND 99170

Code

English

COMPOUND-99170

Code

English

Aprindine [WHO-DD]

Common Name

English

aprindine [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QC01BB04