U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
n = 44
Health Status: unhealthy
Condition: angina
Age Group: 34-77 years
Sex: M+F
Population Size: 44
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
n = 43
Health Status: unhealthy
Condition: angina
Age Group: 39-84 years
Sex: M+F
Population Size: 43
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
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
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
n = 33
Health Status: unhealthy
Condition: angina
Age Group: 63.5 years
Sex: M+F
Population Size: 33
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
n = 29
Health Status: unhealthy
Condition: angina
Age Group: 64.6 years
Sex: M+F
Population Size: 29
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
n = 44
Health Status: unhealthy
Condition: angina
Age Group: 34-77 years
Sex: M+F
Population Size: 44
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
n = 44
Health Status: unhealthy
Condition: angina
Age Group: 34-77 years
Sex: M+F
Population Size: 44
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
n = 44
Health Status: unhealthy
Condition: angina
Age Group: 34-77 years
Sex: M+F
Population Size: 44
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
n = 43
Health Status: unhealthy
Condition: angina
Age Group: 39-84 years
Sex: M+F
Population Size: 43
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
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
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
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
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
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
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
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
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
n = 33
Health Status: unhealthy
Condition: angina
Age Group: 63.5 years
Sex: M+F
Population Size: 33
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
n = 33
Health Status: unhealthy
Condition: angina
Age Group: 63.5 years
Sex: M+F
Population Size: 33
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
n = 29
Health Status: unhealthy
Condition: angina
Age Group: 64.6 years
Sex: M+F
Population Size: 29
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
n = 29
Health Status: unhealthy
Condition: angina
Age Group: 64.6 years
Sex: M+F
Population Size: 29
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
n = 29
Health Status: unhealthy
Condition: angina
Age Group: 64.6 years
Sex: M+F
Population Size: 29
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Biliary drug lithiasis: dipyridamole gallstones.
1992 Nov 28
[Bepridil: importance of serum level in treatment surveillance].
2000 Apr 1
Is cytotoxic cellular edema real? The effect of calcium ion on water homeostasis in the rat heart.
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
Ionic mechanisms of aglycemic axon injury in mammalian central white matter.
2001 Apr
Broussochalcone A, a potent antioxidant and effective suppressor of inducible nitric oxide synthase in lipopolysaccharide-activated macrophages.
2001 Apr 15
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
Antioxidant benzoylated flavan-3-ol glycoside from Celastrus orbiculatus.
2001 Jan
Anti-oxidative properties of fluvastatin, an HMG-CoA reductase inhibitor, contribute to prevention of atherosclerosis in cholesterol-fed rabbits.
2001 Jan
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
2,2-Diphenyl-1-picrylhydrazyl hydrate, a stable free radical, is an alpha-glucosidase inhibitor.
2001 Jun
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
Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G.
2001 May
Screening of chemiluminescence constituents of cereals and DPPH radical scavenging activity of gamma-oryzanol.
2001 May-Jun
Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities.
2001 Nov-Dec
Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690.
2001 Oct
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
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
Vasorelaxing and antioxidant constituents from Hernandia nymphaeifolia.
2001 Oct
Two new diterpenoids from Plectranthus nummularius Briq.
2001 Sep
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
Effects of 12 Ca2+ antagonists on multidrug resistance, MDR1-mediated transport and MDR1 mRNA expression.
2002 Aug
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
Antioxidant enzymes and DPPH-radical scavenging activity in chilled and heat-shocked rice (Oryza sativa L.) seedlings radicles.
2002 Jan 30
Free radical scavenging properties of wheat extracts.
2002 Mar 13
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
Assessment of pro-oxidant activity of foods by kinetic analysis of crocin bleaching.
2002 May 8
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
Detection of proarrhythmia in the female rabbit heart: blinded validation.
2003 Mar
A case of sick sinus syndrome that developed torsades de pointes, pacing failure and sensing failure during administration of bepridil.
2003 Sep
Bioequivalence study of two formulations of simvastatin tablets in healthy Thai volunteers.
2004
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 Sat Dec 16 15:59:38 GMT 2023
Edited
by admin
on Sat Dec 16 15:59:38 GMT 2023
Record UNII
755BO701MA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
1-PYRROLIDENEETHANAMINE, .BETA.-((2-METHYLPROPOXY)METHYL)-N-PHENYL-N-(PHENYLMETHYL)-
Common 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 Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
NCI_THESAURUS C333
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
WHO-ATC C08EA02
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
Code System Code Type Description
CHEBI
3061
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
WIKIPEDIA
Bepridil
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
CAS
64706-54-3
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
INN
3465
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
DRUG CENTRAL
342
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
IUPHAR
2337
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
PUBCHEM
2351
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
MERCK INDEX
m2422
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY Merck Index
SMS_ID
100000077185
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
MESH
D015764
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
EVMPD
SUB13041MIG
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID3022663
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
NCI_THESAURUS
C87448
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
FDA UNII
755BO701MA
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
DRUG BANK
DB01244
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY
RXCUI
1436
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1008
Created by admin on Sat Dec 16 15:59:39 GMT 2023 , Edited by admin on Sat Dec 16 15:59:39 GMT 2023
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