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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

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
[Bepridil: importance of serum level in treatment surveillance].
2000 Apr 1
Cancer chemopreventive activities of S-3-1, a synthetic derivative of danshinone.
2001
Broussochalcone A, a potent antioxidant and effective suppressor of inducible nitric oxide synthase in lipopolysaccharide-activated macrophages.
2001 Apr 15
Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia.
2001 Aug
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
Activation of Na(+), K(+), Cl(-)-cotransport mediates intracellular Ca(2+) increase and apoptosis induced by Pinacidil in HepG2 human hepatoblastoma cells.
2001 Feb 23
In vitro evaluation of the antioxidant activity and biomembrane interaction of the lazaroid U-74389G.
2001 Feb 9
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
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
A novel series of thromboxane A2 synthetase inhibitors with free radical scavenging and anti-peroxidative activities.
2001 May
Screening of chemiluminescence constituents of cereals and DPPH radical scavenging activity of gamma-oryzanol.
2001 May-Jun
Antioxidant properties of methanolic extracts from several ear mushrooms.
2001 Nov
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
Vasorelaxing and antioxidant constituents from Hernandia nymphaeifolia.
2001 Oct
Antiradical and antilipoperoxidative effects of some plant extracts used by Sri Lankan traditional medical practitioners for cardioprotection.
2001 Sep
Comparison of radical scavenging effect, inhibition of microsomal oxygen free radical generation, and serum lipoprotein oxidation of several natural antioxidants.
2002 Apr 10
On-line HPLC-DPPH screening method for evaluation of radical scavenging phenols extracted from apples (Malus domestica L.).
2002 Apr 24
Effects of 12 Ca2+ antagonists on multidrug resistance, MDR1-mediated transport and MDR1 mRNA expression.
2002 Aug
Antioxidant capacities of ten edible North American plants.
2002 Feb
Slick (Slo2.1), a rapidly-gating sodium-activated potassium channel inhibited by ATP.
2003 Dec 17
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.
2003 Nov 17
Bepridil block of recombinant human cardiac IKs current shows a time-dependent unblock.
2004 Feb
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.
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 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
NCI_THESAURUS C333
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
WHO-ATC C08EA02
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
Code System Code Type Description
CHEBI
3061
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
WIKIPEDIA
Bepridil
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
CAS
64706-54-3
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
INN
3465
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
DRUG CENTRAL
342
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
IUPHAR
2337
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
PUBCHEM
2351
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
MERCK INDEX
m2422
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY Merck Index
SMS_ID
100000077185
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
MESH
D015764
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
EVMPD
SUB13041MIG
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
EPA CompTox
DTXSID3022663
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
NCI_THESAURUS
C87448
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
FDA UNII
755BO701MA
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
DRUG BANK
DB01244
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY
RXCUI
1436
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1008
Created by admin on Sat Dec 16 15:59:39 UTC 2023 , Edited by admin on Sat Dec 16 15:59:39 UTC 2023
PRIMARY