U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C22H30N2
Molecular Weight 322.4878
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APRINDINE

SMILES

CCN(CC)CCCN(c1ccccc1)C2Cc3ccccc3C2

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
FIBORAN

Approved Use

Aprindine is indicated for treatment of therapy-resistant ventricular tachycardias and ventricular extrasystoles.
PubMed

PubMed

TitleDatePubMed
Antiarrhythmic and antifibrillatory properties of aprindine.
1975 Aug
[Accident during local anesthesia in a patient with antiarrhythmic therapy].
1975 Jul
New drugs for treating cardiac arrhythmias.
1981 Jan
Quantitative analysis of the antiarrhythmic effect of drugs on canine ventricular arrhythmias by the determination of minimum effective plasma concentrations.
1983 Jan
Effective plasma concentrations of aprindine in canine ventricular arrhythmias.
1984 Jan-Feb
Effect of sotalol, aprindine and their combination on maximum upstroke velocity of action potential in guinea-pig papillary muscle.
1986 Nov 19
Cardioprotective effects of various class I antiarrhythmic drugs in canine hearts.
1989 Jul
Broad sensitivity of rodent arrhythmia models to class I, II, III, and IV antiarrhythmic agents.
1989 Jun
Combined application of class I antiarrhythmic drugs causes "additive", "reductive", or "synergistic" sodium channel block in cardiac muscles.
1990 Nov
Hepatocellular peroxisomes in human alcoholic and drug-induced hepatitis: a quantitative study.
1991 Nov
Complex frequency-dependent interaction of class-I antiarrhythmic drugs as they affect intraventricular conduction.
1995 Jun
Effects of aprindine on ischemia/reperfusion-induced cardiac contractile dysfunction of perfused rat heart.
1996 Mar
Prediction of catalepsies induced by amiodarone, aprindine and procaine: similarity in conformation of diethylaminoethyl side chain.
1998 Nov
Inhibitory effects of aprindine on the delayed rectifier K+ current and the muscarinic acetylcholine receptor-operated K+ current in guinea-pig atrial cells.
1999 Feb
Nonlinear pharmacokinetics of aprindine in guinea pigs.
2002
Double-blind placebo-controlled trial of aprindine and digoxin for the prevention of symptomatic atrial fibrillation.
2002 Jun
Inhibitory effect of aprindine on Na+/Ca2+ exchange current in guinea-pig cardiac ventricular myocytes.
2002 Jun
Atrial fibrillation threshold predicted long-term efficacy of pharmacological treatment of patients without structural heart disease.
2002 Oct
[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
Usefulness and safety of bepridil in converting persistent atrial fibrillation to sinus rhythm.
2003 Aug 15
Role of atrial fibrillation threshold evaluation on guiding treatment.
2003 Oct 1
Theoretical possibilities for the development of novel antiarrhythmic drugs.
2004 Jan
Maintenance of sinus rhythm and recovery of atrial mechanical function after cardioversion with bepridil or in combination with aprindine in long-lasting persistent atrial fibrillation.
2004 Sep
Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring.
2005 Feb
Proteasomal degradation of Kir6.2 channel protein and its inhibition by a Na+ channel blocker aprindine.
2005 Jun 17
Effect of antiarrhythmic agents on heart rate variability indices after myocardial infarction: comparative experimental study of aprindine and procainamide.
2005 Oct
[Strategy for cardiac arrhythmias in acute coronary syndrome].
2006 Apr
Nonlinear mixed effects model analysis of the pharmacokinetics of routinely administered bepridil in Japanese patients with arrhythmias.
2006 Mar
Topics on the Na+/Ca2+ exchanger: pharmacological characterization of Na+/Ca2+ exchanger inhibitors.
2006 Sep
Pharmacological cardioversion of persistent atrial fibrillation with and without a history of drug-resistant paroxysmal atrial fibrillation.
2006 Sep
Pharmacological cardioversion of long-lasting atrial fibrillation.
2007
Na+/Ca2+ exchange inhibitors: a new class of calcium regulators.
2007 Sep
Relation of interleukin-6 and C-reactive protein levels to sinus maintenance after pharmacological cardioversion in persistent atrial fibrillation.
2007 Sep
Relationship between serum aprindine concentration and neurologic side effects in Japanese.
2009 Apr
Enantioselective plasma protein binding of propafenone: mechanism, drug interaction, and species difference.
2009 Jul
Effects of antiarrhythmic drugs on the hyperpolarization-activated cyclic nucleotide-gated channel current.
2009 Jun
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
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
APRINDINE [WHO-DD]
Common Name English
APRINDINE [MI]
Common Name English
APRINDINE [USAN]
Common Name English
COMPOUND 99170
Code English
COMPOUND-99170
Code English
APRINDINE [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QC01BB04
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
NCI_THESAURUS C47793
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
WHO-ATC C01BB04
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
Code System Code Type Description
MESH
D001073
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
DRUG CENTRAL
231
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
FDA UNII
5Y48085P9Q
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL1213033
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
NCI_THESAURUS
C77975
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
CAS
37640-71-4
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
RXCUI
1054
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
APRINDINE
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
EVMPD
SUB05542MIG
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
PUBCHEM
2218
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
INN
3179
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
EPA CompTox
37640-71-4
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY
MERCK INDEX
M2013
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB01429
Created by admin on Sat Jun 26 06:57:11 UTC 2021 , Edited by admin on Sat Jun 26 06:57:11 UTC 2021
PRIMARY