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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 of APRINDINE

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

Molecular Formula C22H30N2
Molecular Weight 322.487
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
[Accident during local anesthesia in a patient with antiarrhythmic therapy].
1975 Jul
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
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
Additional gene variants reduce effectiveness of beta-blockers in the LQT1 form of long QT syndrome.
2004 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
Relationship between serum aprindine concentration and neurologic side effects in Japanese.
2009 Apr
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:47:22 UTC 2023
Edited
by admin
on Sat Dec 16 16:47:22 UTC 2023
Record UNII
5Y48085P9Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APRINDINE
INN   MI   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
NCI_THESAURUS C47793
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
WHO-ATC C01BB04
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
Code System Code Type Description
MESH
D001073
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
DRUG CENTRAL
231
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
FDA UNII
5Y48085P9Q
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL1213033
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
NCI_THESAURUS
C77975
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
CAS
37640-71-4
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
RXCUI
1054
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
APRINDINE
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
EVMPD
SUB05542MIG
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
SMS_ID
100000087162
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
PUBCHEM
2218
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
INN
3179
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID3022615
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
MERCK INDEX
m2013
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB01429
Created by admin on Sat Dec 16 16:47:22 UTC 2023 , Edited by admin on Sat Dec 16 16:47:22 UTC 2023
PRIMARY
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