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Details

Stereochemistry ACHIRAL
Molecular Formula C22H30N2.ClH
Molecular Weight 358.948
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APRINDINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=KIPFVRHNAAZJOD-UHFFFAOYSA-N
InChI=1S/C22H30N2.ClH/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;1H

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.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
537
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Approved
8429
FIBORAN

Approved Use

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

PubMed

TitleDatePubMed
[Accident during local anesthesia in a patient with antiarrhythmic therapy].
1975 Jul
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
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
Drug-induced changes in fibrillation cycle length and organization index can predict chemical cardioversion of long-lasting atrial fibrillation with bepridil alone or in combination with aprindine.
2004 Dec
Additional gene variants reduce effectiveness of beta-blockers in the LQT1 form of long QT syndrome.
2004 Feb
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
Inflammatory cytokines and atrial fibrillation: current and prospective views.
2010
Patents

Patents

DE2346337A1
2
JP2011513484A
29

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 HYDROCHLORIDE
JAN   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
APRINDINE HYDROCHLORIDE [MI]
Common Name English
APRINDINE HYDROCHLORIDE [JAN]
Common Name English
COMPOUND 83846
Code English
COMPOUND-83846
Code English
NSC-284614
Code English
APRINDINE HCL
Common Name English
APRINIDINE CHLORIDE
Common Name English
APRINDINE HYDROCHLORIDE [MART.]
Common Name English
ASPENON
Brand Name English
APRINDINE HYDROCHLORIDE [USAN]
Common Name English
Aprindine hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47793
Created by admin on Fri Dec 15 15:30:59 GMT 2023 , Edited by admin on Fri Dec 15 15:30:59 GMT 2023
Code System Code Type Description
DRUG BANK
DBSALT000917
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PRIMARY
MERCK INDEX
m2013
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PRIMARY Merck Index
CAS
33237-74-0
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PRIMARY
EPA CompTox
DTXSID5046726
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PRIMARY
EVMPD
SUB00565MIG
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PRIMARY
PUBCHEM
71413
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PRIMARY
RXCUI
236158
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PRIMARY RxNorm
ECHA (EC/EINECS)
251-418-7
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PRIMARY
ChEMBL
CHEMBL1213033
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PRIMARY
FDA UNII
PB5EKT7Q2V
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PRIMARY
NSC
284614
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PRIMARY
NCI_THESAURUS
C77976
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PRIMARY
SMS_ID
100000085167
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PRIMARY
ACTIVE MOIETY
Structure of APRINDINE
NIH
NCATS
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