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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 ClH
Molecular Weight 36.461
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 ( + / - )

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
Is cytotoxic cellular edema real? The effect of calcium ion on water homeostasis in the rat heart.
2001
Assessment of antioxidant activity of some antileprotic drugs.
2001
Antioxidant activity of 5-alkoxymethyl-6-chromanols.
2001
1,1-Diphenyl-2-picrylhydrazyl radical-scavenging active compounds from greater cardamom (Amomum subulatum Roxb.).
2001 Apr
Blocking effect of bepridil on Na+/Ca2+ exchange current in guinea pig cardiac ventricular myocytes.
2001 Apr
Broussochalcone A, a potent antioxidant and effective suppressor of inducible nitric oxide synthase in lipopolysaccharide-activated macrophages.
2001 Apr 15
[Bepridil inhibition on the delayed rectifier K+ currents in thyroxine induced hypertrophied guinea pig ventricular myocytes].
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
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
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
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
Antioxidative components from the aerial parts of Lactuca scariola L.
2001 Oct
Scavenging of free radicals, antimicrobial, and cytotoxic activities of the Maillard reaction products of beta-lactoglobulin glycated with several sugars.
2001 Oct
Vasorelaxing and antioxidant constituents from Hernandia nymphaeifolia.
2001 Oct
Two new diterpenoids from Plectranthus nummularius Briq.
2001 Sep
Antiradical and antilipoperoxidative effects of some plant extracts used by Sri Lankan traditional medical practitioners for cardioprotection.
2001 Sep
Antioxidative activity and safety of the 50 ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1.
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
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
Role of Na(+)-Ca(2+) exchanger after traumatic or hypoxic/ischemic injury to spinal cord white matter.
2002 Jan-Feb
Antioxidants from the bark of Burkea africana, an African medicinal plant.
2002 Mar
Free radical scavenging activity of red ginseng aqueous extracts.
2002 Mar 20
Identification of radical scavengers in sweet grass (Hierochloe odorata).
2002 May 8
Assessment of pro-oxidant activity of foods by kinetic analysis of crocin bleaching.
2002 May 8
Na(+)/Ca(2+) exchanger in porcine oocytes.
2002 Oct
[Successful hybrid therapy combined with oral bepridil and ICD in a patient with amiodarone refractory life-threatening ventricular tachyarrhythmia associated with ischemic cardiomyopathy].
2002 Sep 1
A case of bepridil induced interstitial pneumonitis.
2003 Dec
Slick (Slo2.1), a rapidly-gating sodium-activated potassium channel inhibited by ATP.
2003 Dec 17
Blockers of sodium and calcium entry protect axons from nitric oxide-mediated degeneration.
2003 Feb
Evaluation of the effect of bepridil on paroxysmal atrial fibrillation: relationship between efficacy and the f-f interval in surface ECG recordings.
2003 Jan
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
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
Atrial fibrillatory frequency, atrial fibrillatory rate, or atrial cycle length--does it matter?
2004 Jul 1
Design, synthesis, and biological evaluation of novel T-Type calcium channel antagonists.
2004 Jul 16
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 07:50:57 GMT 2023
Edited
by admin
on Sat Dec 16 07:50:57 GMT 2023
Record UNII
2TN7FF3W4M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BEPRIDIL HYDROCHLORIDE ANHYDROUS
Common Name English
1-PYRROLIDINEETHANAMINE, .BETA.-((2-METHYLPROPOXY)METHYL)-N-PHENYL-N-(PHENYLMETHYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
1-(2-(N-BENZYLANILINO)-1-(ISOBUTOXYMETHYL)ETHYL)-PYRROLIDINE MONOHYDROCHLORIDE
Systematic Name English
Code System Code Type Description
SMS_ID
100000091249
Created by admin on Sat Dec 16 07:50:58 GMT 2023 , Edited by admin on Sat Dec 16 07:50:58 GMT 2023
PRIMARY
PUBCHEM
50088
Created by admin on Sat Dec 16 07:50:58 GMT 2023 , Edited by admin on Sat Dec 16 07:50:58 GMT 2023
PRIMARY
EVMPD
SUB26024
Created by admin on Sat Dec 16 07:50:57 GMT 2023 , Edited by admin on Sat Dec 16 07:50:57 GMT 2023
PRIMARY
CAS
68099-86-5
Created by admin on Sat Dec 16 07:50:57 GMT 2023 , Edited by admin on Sat Dec 16 07:50:57 GMT 2023
PRIMARY
FDA UNII
2TN7FF3W4M
Created by admin on Sat Dec 16 07:50:57 GMT 2023 , Edited by admin on Sat Dec 16 07:50:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID00964274
Created by admin on Sat Dec 16 07:50:57 GMT 2023 , Edited by admin on Sat Dec 16 07:50:57 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY