PILSICAINIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H24N2O
Molecular Weight	272.3853
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC(C)=C1NC(=O)CC23CCCN2CCC3

InChI

InChIKey=BCQTVJKBTWGHCX-UHFFFAOYSA-N

InChI=1S/C17H24N2O/c1-13-6-3-7-14(2)16(13)18-15(20)12-17-8-4-10-19(17)11-5-9-17/h3,6-7H,4-5,8-12H2,1-2H3,(H,18,20)

HIDE SMILES / InChI

Molecular Formula	C17H24N2O
Molecular Weight	272.3853
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/9711190
Curator's Comment: description was created based on several sources, including http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1112 http://www.ncbi.nlm.nih.gov/pubmed/1328732

Pilsicainide is marketed in Japan as (Sunrythm). Pilsicainide controls the cardiac conduction abnormalities and improves the symptoms of arrhythmia with the blocking action on Na channel. It is usually used to treat tachycardiac arrhythmia. Pilsicainide did not affect the resting membrane potential. Under the voltage-clamp condition, pilsicainide inhibited the transient outward current (Ito) that is more prominent in the atrium than in the ventricle in a concentration-dependent manner. However, in contrast to other class Ic agents, the inhibition to Ito by pilsicainide was observed only at much higher concentrations (IC50-300 uM) and did not affect the inactivation time-course of Ito. Moreover, the drug (10 uM) did not significantly affect the Ca2+, delayed rectifier K+, inward rectifying K+, acetylcholine-induced K+ or ATP-sensitive K+ currents. From these results pilsicainide could be differentiated as a pure Na+ channel blocker from other class Ic agents with diverse effects on membrane currents and should be recognized accordingly in clinical situations. A single oral dose of pilsicainide effectively restores normal sinus rhythm in patients with recent-onset atrial fibrillation and a healthy left ventricle. Long-term therapy with pilsicainide is successful in treating chronic atrial fibrillation

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel alpha subunit 72 Target ID: CHEMBL2331043 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1328732	Blocker 555

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tachyarrhythmia 17 Sources: http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1112	Primary		Approved 8583	SUNRYTHM Approved Use It is usually used to treat tachycardiac arrhythmia.

C_max

Value	Dose	Analyte	Population
0.34 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.25 mg/kg single, intravenous dose: 0.25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
0.54 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.5 mg/kg single, intravenous dose: 0.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1.05 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.75 mg/kg single, intravenous dose: 0.75 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
409 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
459 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
505 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
630 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
0.79 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.25 mg/kg single, intravenous dose: 0.25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
1.71 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.5 mg/kg single, intravenous dose: 0.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
2.72 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.75 mg/kg single, intravenous dose: 0.75 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3470 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
4760 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
7870 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
23800 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
5.19 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.25 mg/kg single, intravenous dose: 0.25 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
5.98 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.5 mg/kg single, intravenous dose: 0.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
5.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24480637/	0.75 mg/kg single, intravenous dose: 0.75 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED
3.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
5.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
9.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
23.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

F_unbound

Value	Dose	Analyte	Population
73.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
65.5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
63.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED
63% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2050177/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PILSICAINIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
150 mg single, oral Recommended Dose: 150 mg Route: oral Route: single Dose: 150 mg Sources: https://www.mims.com/hongkong/drug/info/pilsicainide%20hydrochloride?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.mims.com/hongkong/drug/info/pilsicainide%20hydrochloride?mtype=generic	Disc. AE: Myocardial infarct... AEs leading to discontinuation/dose reduction: Myocardial infarct Sources: https://www.mims.com/hongkong/drug/info/pilsicainide%20hydrochloride?mtype=generic
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10966544/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10966544/	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (2%) Sources: https://pubmed.ncbi.nlm.nih.gov/10966544/
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16723783/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/16723783/	Sources: https://pubmed.ncbi.nlm.nih.gov/16723783/

AEs

AE	Significance	Dose	Population
Myocardial infarct	Disc. AE	150 mg single, oral Recommended Dose: 150 mg Route: oral Route: single Dose: 150 mg Sources: https://www.mims.com/hongkong/drug/info/pilsicainide%20hydrochloride?mtype=generic	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.mims.com/hongkong/drug/info/pilsicainide%20hydrochloride?mtype=generic
Rash	2% Disc. AE	50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10966544/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/10966544/

PubMed

Title	Date	PubMed
A Case of Sudden Cardiac Death due to Pilsicainide-Induced Torsades de Pointes.	2014-03	24653743
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).	2013-12	24014644
Pilsicainide-induced ST segment elevation and ST segment depression in two patients with variant forms of Brugada-type electrocardiographic abnormalities.	2009-06	19545347
Menstruation-dependent idiopathic ventricular arrhythmia.	2008-06	18573486
The effects of losartan on signal-averaged P wave in patients with atrial fibrillation.	2008-05-07	17509704
Repolarization heterogeneity in the right ventricular outflow tract: correlation with ventricular arrhythmias in Brugada patients and in an in vitro canine Brugada model.	2008-05	18452878
Use of bepridil in combination with Ic antiarrhythmic agent in converting persistent atrial fibrillation to sinus rhythm.	2008-05	18441448
Neutral endopeptidase inhibitor suppresses the early phase of atrial electrical remodeling in a canine rapid atrial pacing model.	2008-04-01	18379655
Re: Clinical significance of macroscopic T-wave alternans after sodium channel blocker administration in patients with Brugada syndrome.	2008-04	18298519
Longer repolarization in the epicardium at the right ventricular outflow tract causes type 1 electrocardiogram in patients with Brugada syndrome.	2008-03-25	18355652
Clinical and electrophysiological characteristics of patients having atrial flutter with 1:1 atrioventricular conduction.	2008-03	18258806
Clinical significance of macroscopic T-wave alternans after sodium channel blocker administration in patients with Brugada syndrome.	2008-01	17916151
Sodium channel blockers enhance the temporal QT interval variability in the right precordial leads in Brugada syndrome.	2008-01	18234009
Pilsicainide-induced Brugada-type ECG and ventricular arrhythmias originating from the left posterior fascicle in a case with Brugada syndrome associated with idiopathic left ventricular tachycardia.	2008-01	18037690
[Brugada syndrome].	2007-12	18078085
Effects of cooling on histamine-induced contractions of human umbilical artery: the role of ion channels.	2007-11	18193113
Mechanisms of the preventive effect of pilsicainide on atrial fibrillation originating from the pulmonary vein.	2007-11	17965507
[Elderly Brugada syndrome with recurrent syncope, diagnosed by pilsicainide challenge test].	2007-06-10	17607996
Incidence and initial characteristics of pilsicainide-induced ventricular arrhythmias in patients with Brugada syndrome.	2007-05	17461877
Pilsicainide-induced ventricular tachycardia originating from right ventricular outflow tract.	2007-05	17456136
Mechanism of the conversion of a pulmonary vein tachycardia to atrial fibrillation in normal canine hearts: role of autonomic nerve stimulation.	2007-05	17313531
Novel SCN5A mutation (Q55X) associated with age-dependent expression of Brugada syndrome presenting as neurally mediated syncope.	2007-04	17399644
Discrimination of Brugada syndrome patients from individuals with the saddle-back type ST-segment elevation using a marker of the standard 12-lead electrocardiography.	2007-04	17384457
Two-dimensional tracking and TDI are consistent methods for evaluating myocardial longitudinal peak strain in left and right ventricle basal segments in athletes.	2007-02-07	17286850
How can a single mutation cause such arrhythmic havoc?	2007-02	17275756
Temperature modulation of ventricular arrhythmogenicity in a canine tissue model of Brugada syndrome.	2007-02	17275755
Different effect of the pure Na+ channel-blocker pilsicainide on the ST-segment response in the right precordial leads in patients with normal left ventricular function.	2007-01	17186979
A case of a concealed type of Brugada syndrome with a J wave and mild ST-segment elevation in the inferolateral leads.	2007-01	17067625
Transition from purkinje fiber-related rapid polymorphic ventricular tachycardia to sustained monomorphic ventricular tachycardia in a patient with a structurally normal heart: a case report.	2007-01	16968523
Multiple premature beats triggered ventricular arrhythmias during pilsicainide infusion in a patient with inferior ST-segment elevation.	2006-12	17201857
Comment on severe arrhythmia as a result of the interaction of cetirizine and pilsicainide in a patient with renal insufficiency.	2006-12	17178271
High-frequency potentials developed in wavelet-transformed electrocardiogram as a novel indicator for detecting Brugada syndrome.	2006-12	17161786
Spatial distribution of repolarization and depolarization abnormalities evaluated by body surface potential mapping in patients with Brugada syndrome.	2006-10	17038144
Spontaneous polymorphic ventricular tachycardia after administration of pilsicainide in a patient resuscitated from ventricular fibrillation.	2006-09	16981928
Effects of antiarrhythmic drugs on apoptotic pathways in H9c2 cardiac cells.	2006-08	16891766
The full stomach test as a novel diagnostic technique for identifying patients at risk of Brugada syndrome.	2006-06	16836706
Randomized crossover study of the long-term effects of pilsicainide and cibenzoline in preventing recurrence of symptomatic paroxysmal atrial fibrillation: influence of the duration of arrhythmia before therapy.	2006-06	16723785
Cellular basis for trigger and maintenance of ventricular fibrillation in the Brugada syndrome model: high-resolution optical mapping study.	2006-05-16	16697328
Pilsicainide-induced verapamil sensitive idiopathic left ventricular tachycardia.	2006-05	16689855
Pilsicainide for atrial fibrillation.	2006	17112301
Long-term efficacy of hybrid pharmacologic and ablation therapy in patients with pilsicainide-induced atrial flutter.	2005-07	16075827
Pilsicainide-induced coronary vasospasm in a patient with Brugada-type electrocardiogram.	2005-07	15988113
A case of the toxicity of pilsicainide hydrochloride with comparison of the serial serum pilsicainide levels and electrocardiographic findings.	2004-11	15655281
[Brugada syndrome associated with ventricular fibrillation induced by administration of pilsicainide: a case report].	2003-11	14658412
Brugada disease: chronology of discovery and paternity. Preliminary observations and historical aspects.	2003-10-01	16943925
Role of atrial fibrillation threshold evaluation on guiding treatment.	2003-10-01	16943922
Tachycardiomyopathy.	2002-10-01	16951726
Class I antiarrhythmic drug and coronary vasospasm-induced T wave alternans and ventricular tachyarrhythmia in a patient with Brugada syndrome and vasospastic angina.	2002-02	11900298
A case of sinus pause due to the proarrhythmia of pilsicainide.	2000-05	10987357
General pharmacological studies on N-(2,6-dimethylphenyl)-8-pyrrolizidineacetamide hydrochloride hemihydrate. 1st communication: effect on the central nervous system.	1988-10	3196380

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Using a whole cell clamp technique, the blockade of sodium currents (INa) by pilsicainide applied either intracellularly or extracellularly, was studied in single myocytes isolated from guinea pig right ventricle. Pilsicainide applied extracellularly inhibited the peak amplitude of INa in concentration- (from 10(-5) M to 10(-4) M) and rate- (from 0.5 Hz to 3.0 Hz) dependent manners. Pilsicainide applied intracellularly inhibited INa in a rate-dependent manner. The blocking potency of internally applied pilsicainide almost corresponded to that of external 10(-5) M pilsicainide.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:15:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:17 GMT 2025`
Record UNII	AV0X7V6CSE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PILSICAINIDE

Official Name

English

PILSICAINIDE [MI]

Preferred Name

English

Pilsicainide [WHO-DD]

Common Name

English

pilsicainide [INN]

Common Name

English

TETRAHYDRO-1H-PYRROLIZINE-7A(5H)-ACETO-2',6'-XYLIDIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47793