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Details

Stereochemistry RACEMIC
Molecular Formula C24H34N2O.ClH
Molecular Weight 403.0
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPRIDIL HYDROCHLORIDE ANHYDROUS

SMILES

Cl.CC(C)COCC(CN(CC1=CC=CC=C1)C2=CC=CC=C2)N3CCCC3

InChI

InChIKey=JXBBWYGMTNAYNM-UHFFFAOYSA-N
InChI=1S/C24H34N2O.ClH/c1-21(2)19-27-20-24(25-15-9-10-16-25)18-26(23-13-7-4-8-14-23)17-22-11-5-3-6-12-22;/h3-8,11-14,21,24H,9-10,15-20H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula C24H34N2O
Molecular Weight 366.5396
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
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.drugs.com/mtm/bepridil.html | http://www.rad-ar.or.jp/siori/english/kekka.cgi?n=1075 | https://www.ncbi.nlm.nih.gov/pubmed/1280569

Bepridil is a calcium channel blocker that has well characterized anti-anginal properties and known but poorly characterized type 1 anti-arrhythmic and anti-hypertensive properties. It has inhibitory effects on both the slow calcium and fast sodium inward currents in myocardial and vascular smooth muscle, interferes with calcium binding to calmodulin, and blocks both voltage and receptor operated calcium channels. It is used to treat hypertension (high blood pressure), angina (chest pain), sustained atrial fibrillation and tachyarrhythmia. The most common side effects were upper gastrointestinal complaints (nausea, dyspepsia or GI distress), diarrhea, dizziness, asthenia and nervousness. Certain drugs could increase the likelihood of potentially serious adverse effects with bepridil hydrochloride. In general, these are drugs that have one or more pharmacologic activities similar to bepridil hydrochloride, including anti-arrhythmic agents such as quinidine and procainamide, cardiac glycosides and tricyclic anti-depressants. Anti-arrhythmics and tricyclic anti-depressants could exaggerate the prolongation of the QT interval observed with bepridil hydrochloride. Cardiac glycosides could exaggerate the depression of AV nodal conduction observed with bepridil hydrochloride.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.0 µM [IC50]
1.0 µM [IC50]
Target ID: Voltage and receptor operated calcium channels
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BEPRICOR

Approved Use

Bepridil hydrochloride is indicated for the treatment of chronic stable angina (classic effort-associated angina).
Primary
BEPRICOR

Approved Use

Bepridil is used to treat hypertension (high blood pressure) and to treat angina (chest pain).
Primary
BEPRICOR

Approved Use

It is usually used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina.
Primary
BEPRICOR

Approved Use

It is usually used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
806 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BEPRIDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.87 ng × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BEPRIDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
38.2 h
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BEPRIDIL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.3%
BEPRIDIL plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
400 mg 1 times / day steady, oral
Studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 34-77 years
Health Status: unhealthy
Age Group: 34-77 years
Sex: M+F
Sources:
Disc. AE: Weakness, Lightheadedness...
AEs leading to
discontinuation/dose reduction:
Weakness (2 patients)
Lightheadedness (1 patient)
Syncopal attack (1 patient)
Sources:
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, 39-84 years
Health Status: unhealthy
Age Group: 39-84 years
Sex: M+F
Sources:
Disc. AE: Electrocardiogram QTc interval prolonged...
AEs leading to
discontinuation/dose reduction:
Electrocardiogram QTc interval prolonged (1 patient)
Sources:
300 mg 1 times / day steady, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 43-80 years
Health Status: unhealthy
Age Group: 43-80 years
Sex: M+F
Sources:
Disc. AE: Nausea, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Nausea (1 patient)
Diarrhea (1 patient)
Anorexia (1 patient)
Bigeminy (1 patient)
Sources:
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy, 63.5 years
Health Status: unhealthy
Age Group: 63.5 years
Sex: M+F
Sources:
Disc. AE: Ventricular tachycardia, Bradycardia...
AEs leading to
discontinuation/dose reduction:
Ventricular tachycardia (1 patient)
Bradycardia (1 patient)
Sources:
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, 64.6 years
Health Status: unhealthy
Age Group: 64.6 years
Sex: M+F
Sources:
Disc. AE: Ventricular tachycardia, Bradycardia...
AEs leading to
discontinuation/dose reduction:
Ventricular tachycardia (grade 5, 1 patient)
Bradycardia (1 patient)
Electrocardiogram QTc interval prolonged (4 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Lightheadedness 1 patient
Disc. AE
400 mg 1 times / day steady, oral
Studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 34-77 years
Health Status: unhealthy
Age Group: 34-77 years
Sex: M+F
Sources:
Syncopal attack 1 patient
Disc. AE
400 mg 1 times / day steady, oral
Studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 34-77 years
Health Status: unhealthy
Age Group: 34-77 years
Sex: M+F
Sources:
Weakness 2 patients
Disc. AE
400 mg 1 times / day steady, oral
Studied dose
Dose: 400 mg, 1 times / day
Route: oral
Route: steady
Dose: 400 mg, 1 times / day
Sources:
unhealthy, 34-77 years
Health Status: unhealthy
Age Group: 34-77 years
Sex: M+F
Sources:
Electrocardiogram QTc interval prolonged 1 patient
Disc. AE
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, 39-84 years
Health Status: unhealthy
Age Group: 39-84 years
Sex: M+F
Sources:
Anorexia 1 patient
Disc. AE
300 mg 1 times / day steady, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 43-80 years
Health Status: unhealthy
Age Group: 43-80 years
Sex: M+F
Sources:
Bigeminy 1 patient
Disc. AE
300 mg 1 times / day steady, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 43-80 years
Health Status: unhealthy
Age Group: 43-80 years
Sex: M+F
Sources:
Diarrhea 1 patient
Disc. AE
300 mg 1 times / day steady, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 43-80 years
Health Status: unhealthy
Age Group: 43-80 years
Sex: M+F
Sources:
Nausea 1 patient
Disc. AE
300 mg 1 times / day steady, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: steady
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 43-80 years
Health Status: unhealthy
Age Group: 43-80 years
Sex: M+F
Sources:
Bradycardia 1 patient
Disc. AE
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy, 63.5 years
Health Status: unhealthy
Age Group: 63.5 years
Sex: M+F
Sources:
Ventricular tachycardia 1 patient
Disc. AE
100 mg 1 times / day steady, oral
Recommended
Dose: 100 mg, 1 times / day
Route: oral
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy, 63.5 years
Health Status: unhealthy
Age Group: 63.5 years
Sex: M+F
Sources:
Bradycardia 1 patient
Disc. AE
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, 64.6 years
Health Status: unhealthy
Age Group: 64.6 years
Sex: M+F
Sources:
Electrocardiogram QTc interval prolonged 4 patients
Disc. AE
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, 64.6 years
Health Status: unhealthy
Age Group: 64.6 years
Sex: M+F
Sources:
Ventricular tachycardia grade 5, 1 patient
Disc. AE
200 mg 1 times / day steady, oral
Recommended
Dose: 200 mg, 1 times / day
Route: oral
Route: steady
Dose: 200 mg, 1 times / day
Sources:
unhealthy, 64.6 years
Health Status: unhealthy
Age Group: 64.6 years
Sex: M+F
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cancer chemopreventive activities of S-3-1, a synthetic derivative of danshinone.
2001
Effect of nilvadipine in weak acidic medium by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay.
2001
Blocking effect of bepridil on Na+/Ca2+ exchange current in guinea pig cardiac ventricular myocytes.
2001 Apr
A new antioxidant monoterpene glycoside, alpha-benzoyloxypaeoniflorin from Paeonia suffruticosa.
2001 Apr
Ionic mechanisms of aglycemic axon injury in mammalian central white matter.
2001 Apr
New bis-catechols 5-lipoxygenase inhibitors.
2001 Feb
In vitro evaluation of the antioxidant activity and biomembrane interaction of the lazaroid U-74389G.
2001 Feb 9
Antioxidant principles from Bauhinia tarapotensis.
2001 Jul
Electron spin resonance assessment of the antioxidant potential of medicinal plants. Part I. Contribution of anthocyanosides and flavonoids to the radical scavenging ability of fruit and herbal teas.
2001 Jul-Aug
Evaluation of the absorption, excretion, and metabolism of the antihypertensive agent RWJ-26899 in male and female CR Wistar rats and Beagle dogs.
2001 Jul-Sep
Cyclooxygenase-inhibitory and antioxidant constituents of the aerial parts of Antirhea acutata.
2001 Jun 18
Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method.
2001 Mar
The antioxidant activity of the essential oils of Artemisia afra, Artemisia abyssinica and Juniperus procera.
2001 Mar
Antioxidant activities of buckwheat hull extract toward various oxidative stress in vitro and in vivo.
2001 Mar
Relationship between effects of phenolic compounds on the generation of free radicals from lactoperoxidase-catalyzed oxidation of NAD(P)H or GSH and their DPPH scavenging ability.
2001 Mar
Traumatic axonal injury induces calcium influx modulated by tetrodotoxin-sensitive sodium channels.
2001 Mar 15
Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G.
2001 May
A novel series of thromboxane A2 synthetase inhibitors with free radical scavenging and anti-peroxidative activities.
2001 May
Effect of the antianginal drug bepridil on intracellular Ca2+ release and extracellular Ca2+ influx in human neutrophils.
2001 May
Screening of chemiluminescence constituents of cereals and DPPH radical scavenging activity of gamma-oryzanol.
2001 May-Jun
Scavenging of reactive oxygen species by chlorophyllin: an ESR study.
2001 Nov
Inhibitory effect of bepridil on hKv1.5 channel current: comparison with amiodarone and E-4031.
2001 Nov 2
Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities.
2001 Nov-Dec
Antioxidative components from the aerial parts of Lactuca scariola L.
2001 Oct
Effect of calcium antagonists, calcium channel blockers and calmodulin inhibitors on the growth and encystation of Entamoeba histolytica and E. invadens.
2001 Oct
DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity of flavonoids obtained from some medicinal plants.
2001 Oct
Scavenging of free radicals, antimicrobial, and cytotoxic activities of the Maillard reaction products of beta-lactoglobulin glycated with several sugars.
2001 Oct
Antioxidant activities of dioscorin, the storage protein of yam (Dioscorea batatas Decne) tuber.
2001 Oct
Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis).
2001 Oct
Interaction of bepridil with the cardiac troponin C/troponin I complex.
2001 Sep 28
Antioxidative activity and safety of the 50 ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1.
2002 Apr 10
Antioxidant capacities of ten edible North American plants.
2002 Feb
Interaction of digoxin with antihypertensive drugs via MDR1.
2002 Feb 15
Antioxidant enzymes and DPPH-radical scavenging activity in chilled and heat-shocked rice (Oryza sativa L.) seedlings radicles.
2002 Jan 30
Free radical scavenging activity of red ginseng aqueous extracts.
2002 Mar 20
Free radical studies of ellagic acid, a natural phenolic antioxidant.
2002 Mar 27
Antioxidant properties of ferulic acid and its related compounds.
2002 Mar 27
Beta-blocker decreases the increase in QT dispersion and transmural dispersion of repolarization induced by bepridil.
2002 Nov
Sodium-calcium exchange influences the response to endothelin-1 in lens epithelium.
2003 Sep
Bioequivalence study of two formulations of simvastatin tablets in healthy Thai volunteers.
2004
Differential effect of HERG blocking agents on cardiac electrical alternans in the guinea pig.
2004 Feb 20
Evidence for a protective role played by the Na+/Ca2+ exchanger in cerebral ischemia induced by middle cerebral artery occlusion in male rats.
2004 Mar
Patents

Sample Use Guides

In Vivo Use Guide
Initial dose: 200 mg once a day. Maintenance dose: 300-400 mg once a day.
Route of Administration: Oral
In APP-overexpressing HEK293 cells lower Ab38, Ab40 and Ab42 generation was detected after Bepridil treatment (30 uM) for 16 h.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:43:55 GMT 2025
Edited
by admin
on Mon Mar 31 21:43:55 GMT 2025
Record UNII
2TN7FF3W4M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-(2-(N-BENZYLANILINO)-1-(ISOBUTOXYMETHYL)ETHYL)-PYRROLIDINE MONOHYDROCHLORIDE
Preferred Name English
BEPRIDIL HYDROCHLORIDE ANHYDROUS
Common Name English
1-PYRROLIDINEETHANAMINE, .BETA.-((2-METHYLPROPOXY)METHYL)-N-PHENYL-N-(PHENYLMETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
SMS_ID
100000091249
Created by admin on Mon Mar 31 21:43:55 GMT 2025 , Edited by admin on Mon Mar 31 21:43:55 GMT 2025
PRIMARY
PUBCHEM
50088
Created by admin on Mon Mar 31 21:43:55 GMT 2025 , Edited by admin on Mon Mar 31 21:43:55 GMT 2025
PRIMARY
EVMPD
SUB26024
Created by admin on Mon Mar 31 21:43:55 GMT 2025 , Edited by admin on Mon Mar 31 21:43:55 GMT 2025
PRIMARY
CAS
68099-86-5
Created by admin on Mon Mar 31 21:43:55 GMT 2025 , Edited by admin on Mon Mar 31 21:43:55 GMT 2025
PRIMARY
FDA UNII
2TN7FF3W4M
Created by admin on Mon Mar 31 21:43:55 GMT 2025 , Edited by admin on Mon Mar 31 21:43:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID00964274
Created by admin on Mon Mar 31 21:43:55 GMT 2025 , Edited by admin on Mon Mar 31 21:43:55 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY