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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

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
Evaluation of bepridil efficacy by electrophysiologic testing in patients with recurrent ventricular tachycardia: comparison of two regimens.
1992 Apr
Biliary drug lithiasis: dipyridamole gallstones.
1992 Nov 28
Antioxidant benzoylated flavan-3-ol glycoside from Celastrus orbiculatus.
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
DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity of flavonoids obtained from some medicinal plants.
2001 Oct
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
Interaction of bepridil with the cardiac troponin C/troponin I complex.
2001 Sep 28
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
Role of Na(+)-Ca(2+) exchanger after traumatic or hypoxic/ischemic injury to spinal cord white matter.
2002 Jan-Feb
Free radical scavenging activity of red ginseng aqueous extracts.
2002 Mar 20
Usefulness and safety of bepridil in converting persistent atrial fibrillation to sinus rhythm.
2003 Aug 15
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
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
A case of sick sinus syndrome that developed torsades de pointes, pacing failure and sensing failure during administration of bepridil.
2003 Sep
Bepridil block of recombinant human cardiac IKs current shows a time-dependent unblock.
2004 Feb
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
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 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
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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