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Details

Stereochemistry RACEMIC
Molecular Formula C24H34N2O
Molecular Weight 366.5396
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEPRIDIL

SMILES

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

InChI

InChIKey=UIEATEWHFDRYRU-UHFFFAOYSA-N
InChI=1S/C24H34N2O/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

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 ( + / - )

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
Design, synthesis, and biological evaluation of novel T-Type calcium channel antagonists.
2004-07-16
Atrial fibrillatory frequency, atrial fibrillatory rate, or atrial cycle length--does it matter?
2004-07-01
Evidence for a protective role played by the Na+/Ca2+ exchanger in cerebral ischemia induced by middle cerebral artery occlusion in male rats.
2004-03
Differential effect of HERG blocking agents on cardiac electrical alternans in the guinea pig.
2004-02-20
Bepridil block of recombinant human cardiac IKs current shows a time-dependent unblock.
2004-02
Bioequivalence study of two formulations of simvastatin tablets in healthy Thai volunteers.
2004
Slick (Slo2.1), a rapidly-gating sodium-activated potassium channel inhibited by ATP.
2003-12-17
A case of bepridil induced interstitial pneumonitis.
2003-12
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.
2003-11-17
Role of Na(+)-Ca(2+) exchanger after traumatic or hypoxic/ischemic injury to spinal cord white matter.
2003-11-01
A case of sick sinus syndrome that developed torsades de pointes, pacing failure and sensing failure during administration of bepridil.
2003-09
Sodium-calcium exchange influences the response to endothelin-1 in lens epithelium.
2003-09
Usefulness and safety of bepridil in converting persistent atrial fibrillation to sinus rhythm.
2003-08-15
Transepithelial transport of bepridil in the human intestinal cell line, Caco-2, using a "dynamic model".
2003-07-25
Detection of proarrhythmia in the female rabbit heart: blinded validation.
2003-03
Blockers of sodium and calcium entry protect axons from nitric oxide-mediated degeneration.
2003-02
Bepridil prevents paroxysmal atrial fibrillation by a class III antiarrhythmic drug effect.
2003-01
Evaluation of the effect of bepridil on paroxysmal atrial fibrillation: relationship between efficacy and the f-f interval in surface ECG recordings.
2003-01
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.
2002-11
Beta-blocker decreases the increase in QT dispersion and transmural dispersion of repolarization induced by bepridil.
2002-11
Na(+)/Ca(2+) exchanger in porcine oocytes.
2002-10
[Successful hybrid therapy combined with oral bepridil and ICD in a patient with amiodarone refractory life-threatening ventricular tachyarrhythmia associated with ischemic cardiomyopathy].
2002-09-01
Possible role of calcium ions, calcium channels and calmodulin in excystation and metacystic development of Entamoeba invadens.
2002-09
Structure of the regulatory N-domain of human cardiac troponin C in complex with human cardiac troponin I147-163 and bepridil.
2002-08-23
Effects of 12 Ca2+ antagonists on multidrug resistance, MDR1-mediated transport and MDR1 mRNA expression.
2002-08
Identification of radical scavengers in sweet grass (Hierochloe odorata).
2002-05-08
Assessment of pro-oxidant activity of foods by kinetic analysis of crocin bleaching.
2002-05-08
Antioxidant functions of selected allium thiosulfinates and S-alk(en)yl-L-cysteine sulfoxides.
2002-04-24
On-line HPLC-DPPH screening method for evaluation of radical scavenging phenols extracted from apples (Malus domestica L.).
2002-04-24
Comparison of radical scavenging effect, inhibition of microsomal oxygen free radical generation, and serum lipoprotein oxidation of several natural antioxidants.
2002-04-10
Antioxidative activity and safety of the 50 ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1.
2002-04-10
Free radical studies of ellagic acid, a natural phenolic antioxidant.
2002-03-27
Antioxidant properties of ferulic acid and its related compounds.
2002-03-27
Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities.
2002-03-26
Free radical scavenging activity of red ginseng aqueous extracts.
2002-03-20
Free radical scavenging properties of wheat extracts.
2002-03-13
Antioxidants from the bark of Burkea africana, an African medicinal plant.
2002-03
Interaction of digoxin with antihypertensive drugs via MDR1.
2002-02-15
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).
2002-02
Antioxidant capacities of ten edible North American plants.
2002-02
Antioxidant enzymes and DPPH-radical scavenging activity in chilled and heat-shocked rice (Oryza sativa L.) seedlings radicles.
2002-01-30
Antioxidant effects of 1,5-anhydro-D-fructose, a new natural sugar, in vitro.
2002-01
Scavenging of reactive oxygen species by chlorophyllin: an ESR study.
2001-11
Synthesis and in vitro studies of pyrone derivatives as scavengers of active oxygen species.
2001-11
Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690.
2001-10
Superoxide- and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities of soyasaponin beta g related to gallic acid.
2001-10
[Bepridil inhibition on the delayed rectifier K+ currents in thyroxine induced hypertrophied guinea pig ventricular myocytes].
2001-07
Is cytotoxic cellular edema real? The effect of calcium ion on water homeostasis in the rat heart.
2001
Biliary drug lithiasis: dipyridamole gallstones.
1992-11-28
Evaluation of bepridil efficacy by electrophysiologic testing in patients with recurrent ventricular tachycardia: comparison of two regimens.
1992-04
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 Wed Apr 02 06:59:39 GMT 2025
Edited
by admin
on Wed Apr 02 06:59:39 GMT 2025
Record UNII
755BO701MA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
1-PYRROLIDENEETHANAMINE, .BETA.-((2-METHYLPROPOXY)METHYL)-N-PHENYL-N-(PHENYLMETHYL)-
Preferred Name English
BEPRIDIL
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
Bepridil [WHO-DD]
Common Name English
1-(2-(N-BENZYLANILINO)-1-(ISOBUTOXYMETHYL)ETHYL)-PYRROLIDINE
Systematic Name English
BEPRIDIL [VANDF]
Common Name English
BEPRIDIL [MI]
Common Name English
bepridil [INN]
Common Name English
Classification Tree Code System Code
WHO-VATC QC08EA02
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
NCI_THESAURUS C333
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
WHO-ATC C08EA02
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
Code System Code Type Description
CHEBI
3061
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
WIKIPEDIA
Bepridil
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
CAS
64706-54-3
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
INN
3465
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
DRUG CENTRAL
342
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
IUPHAR
2337
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
PUBCHEM
2351
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
MERCK INDEX
m2422
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY Merck Index
SMS_ID
100000077185
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
MESH
D015764
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
EVMPD
SUB13041MIG
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
EPA CompTox
DTXSID3022663
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
NCI_THESAURUS
C87448
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
FDA UNII
755BO701MA
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
DRUG BANK
DB01244
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
RXCUI
1436
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL1008
Created by admin on Wed Apr 02 06:59:39 GMT 2025 , Edited by admin on Wed Apr 02 06:59:39 GMT 2025
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
TARGET -> INHIBITOR
BINDER->LIGAND
BINDING
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC