U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry RACEMIC
Molecular Formula C24H34N2O.ClH.H2O
Molecular Weight 421.016
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPRIDIL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=UEECHQPWQHYEDE-UHFFFAOYSA-N
InChI=1S/C24H34N2O.ClH.H2O/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;1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Biliary drug lithiasis: dipyridamole gallstones.
1992 Nov 28
Cancer chemopreventive activities of S-3-1, a synthetic derivative of danshinone.
2001
Blocking effect of bepridil on Na+/Ca2+ exchange current in guinea pig cardiac ventricular myocytes.
2001 Apr
A quinolone alkaloid with antioxidant activity from the aleurone layer of anthocyanin-pigmented rice.
2001 Dec
New bis-catechols 5-lipoxygenase inhibitors.
2001 Feb
Axonal L-type Ca2+ channels and anoxic injury in rat CNS white matter.
2001 Feb
Stimulation of nitric oxide-cGMP pathway excites striatal cholinergic interneurons via protein kinase G activation.
2001 Feb 15
In vitro evaluation of the antioxidant activity and biomembrane interaction of the lazaroid U-74389G.
2001 Feb 9
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
Synthesis and in vitro studies of pyrone derivatives as scavengers of active oxygen species.
2001 Nov
Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690.
2001 Oct
Superoxide- and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities of soyasaponin beta g related to gallic acid.
2001 Oct
Antagonistic effects of 24R,25-dihydroxyvitamin D3 and 25-hydroxyvitamin D3 on L-type Ca2+ channels and Na+/Ca2+ exchange in enterocytes from Atlantic cod (Gadus morhua).
2002 Feb
Antioxidant capacities of ten edible North American plants.
2002 Feb
Interaction of digoxin with antihypertensive drugs via MDR1.
2002 Feb 15
Antioxidant effects of 1,5-anhydro-D-fructose, a new natural sugar, in vitro.
2002 Jan
Free radical scavenging properties of wheat extracts.
2002 Mar 13
Na+/Ca2+ exchanger in Na+ efflux-Ca2+ influx mode of operation exerts a neuroprotective role in cellular models of in vitro anoxia and in vivo cerebral ischemia.
2002 Nov
Beta-blocker decreases the increase in QT dispersion and transmural dispersion of repolarization induced by bepridil.
2002 Nov
Na(+)/Ca(2+) exchanger in porcine oocytes.
2002 Oct
Transepithelial transport of bepridil in the human intestinal cell line, Caco-2, using a "dynamic model".
2003 Apr-Jun
Usefulness and safety of bepridil in converting persistent atrial fibrillation to sinus rhythm.
2003 Aug 15
Bepridil prevents paroxysmal atrial fibrillation by a class III antiarrhythmic drug effect.
2003 Jan
Sodium-calcium exchange influences the response to endothelin-1 in lens epithelium.
2003 Sep
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 17:53:44 GMT 2025
Edited
by admin
on Mon Mar 31 17:53:44 GMT 2025
Record UNII
4W2P15D93M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BEPRIDIL HYDROCHLORIDE MONOHYDRATE
MI   WHO-DD  
Preferred Name English
BEPRIDIL HYDROCHLORIDE
MART.   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
Bepridil hydrochloride monohydrate [WHO-DD]
Common Name English
1-PYRROLIDENEETHANAMINE, .BETA.-((2-METHYLPROPOXY)METHYL)-N-PHENYL-N-(PHENYLMETHYL)-, MONOHYDROCHLORIDE, MONOHYDRATE
Common Name English
BEPRIDIL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
CERM 1978
Code English
BEPADIN
Brand Name English
NSC-758390
Code English
UNICORDIUM
Brand Name English
1-[2-(N-Benzylanilino)-1-(isobutoxymethyl)ethyl]-pyrrolidine monohydrochloride monohydrate
Systematic Name English
BEPRIDIL HYDROCHLORIDE [MART.]
Common Name English
BEPRIDIL HYDROCHLORIDE [VANDF]
Common Name English
CORDIUM
Brand Name English
BEPRIDIL HYDROCHLORIDE HYDRATE
JAN  
Common Name English
BEPRIDIL HYDROCHLORIDE HYDRATE [JAN]
Common Name English
BEPRIDIL HYDROCHLORIDE MONOHYDRATE [MI]
Common Name English
CERM-1978
Code English
VASCOR
Brand Name English
BEPRIDIL HYDROCHLORIDE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C333
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
Code System Code Type Description
CHEBI
52715
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
SMS_ID
100000091268
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
CHEBI
3061
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
EVMPD
SUB13042MIG
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
FDA UNII
4W2P15D93M
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
PUBCHEM
91725
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
RXCUI
235752
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY RxNorm
NCI_THESAURUS
C47412
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
ChEMBL
CHEMBL1008
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID5040176
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
NSC
758390
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
EVMPD
SUB26026
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
DRUG BANK
DBSALT001436
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
CAS
74764-40-2
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
MERCK INDEX
m2422
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
Bepridil hydrochloride
Created by admin on Mon Mar 31 17:53:44 GMT 2025 , Edited by admin on Mon Mar 31 17:53:44 GMT 2025
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY