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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

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.

Originator

Approval Year

1990
108
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 6.0 µM [IC50]
Modulator
828
Inhibitor
8297
 1.0 µM [IC50]
Voltage and receptor operated calcium channels
3
Target ID: Voltage and receptor operated calcium channels
Blocker
537
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
BEPRICOR

Approved Use

Bepridil hydrochloride is indicated for the treatment of chronic stable angina (classic effort-associated angina).
Primary
Approved
8429
BEPRICOR

Approved Use

Bepridil is used to treat hypertension (high blood pressure) and to treat angina (chest pain).
Primary
Approved
8429
BEPRICOR

Approved Use

It is usually used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina.
Primary
Approved
8429
BEPRICOR

Approved Use

It is usually used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
806 ng/mL
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/7650227
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/7650227
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/7650227
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%
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/3875635
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 34-77 years
n = 44
Health Status: unhealthy
Condition: angina
Age Group: 34-77 years
Sex: M+F
Population Size: 44
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
Disc. AE: Weakness, Lightheadedness...
AEs leading to
discontinuation/dose reduction:
Weakness (2 patients)
Lightheadedness (1 patient)
Syncopal attack (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 39-84 years
n = 43
Health Status: unhealthy
Condition: angina
Age Group: 39-84 years
Sex: M+F
Population Size: 43
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
Disc. AE: Electrocardiogram QTc interval prolonged...
AEs leading to
discontinuation/dose reduction:
Electrocardiogram QTc interval prolonged (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 43-80 years
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
Disc. AE: Nausea, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Nausea (1 patient)
Diarrhea (1 patient)
Anorexia (1 patient)
Bigeminy (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/19359813/
unhealthy, 63.5 years
n = 33
Health Status: unhealthy
Condition: angina
Age Group: 63.5 years
Sex: M+F
Population Size: 33
Sources:
https://pubmed.ncbi.nlm.nih.gov/19359813/
Disc. AE: Ventricular tachycardia, Bradycardia...
AEs leading to
discontinuation/dose reduction:
Ventricular tachycardia (1 patient)
Bradycardia (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/19359813/
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:
https://pubmed.ncbi.nlm.nih.gov/19359813/
unhealthy, 64.6 years
n = 29
Health Status: unhealthy
Condition: angina
Age Group: 64.6 years
Sex: M+F
Population Size: 29
Sources:
https://pubmed.ncbi.nlm.nih.gov/19359813/
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:
https://pubmed.ncbi.nlm.nih.gov/19359813/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 34-77 years
n = 44
Health Status: unhealthy
Condition: angina
Age Group: 34-77 years
Sex: M+F
Population Size: 44
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 34-77 years
n = 44
Health Status: unhealthy
Condition: angina
Age Group: 34-77 years
Sex: M+F
Population Size: 44
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 34-77 years
n = 44
Health Status: unhealthy
Condition: angina
Age Group: 34-77 years
Sex: M+F
Population Size: 44
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 39-84 years
n = 43
Health Status: unhealthy
Condition: angina
Age Group: 39-84 years
Sex: M+F
Population Size: 43
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 43-80 years
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 43-80 years
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 43-80 years
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/3919556/
unhealthy, 43-80 years
n = 46
Health Status: unhealthy
Condition: angina
Age Group: 43-80 years
Sex: M+F
Population Size: 46
Sources:
https://pubmed.ncbi.nlm.nih.gov/3919556/
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:
https://pubmed.ncbi.nlm.nih.gov/19359813/
unhealthy, 63.5 years
n = 33
Health Status: unhealthy
Condition: angina
Age Group: 63.5 years
Sex: M+F
Population Size: 33
Sources:
https://pubmed.ncbi.nlm.nih.gov/19359813/
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:
https://pubmed.ncbi.nlm.nih.gov/19359813/
unhealthy, 63.5 years
n = 33
Health Status: unhealthy
Condition: angina
Age Group: 63.5 years
Sex: M+F
Population Size: 33
Sources:
https://pubmed.ncbi.nlm.nih.gov/19359813/
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:
https://pubmed.ncbi.nlm.nih.gov/19359813/
unhealthy, 64.6 years
n = 29
Health Status: unhealthy
Condition: angina
Age Group: 64.6 years
Sex: M+F
Population Size: 29
Sources:
https://pubmed.ncbi.nlm.nih.gov/19359813/
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:
https://pubmed.ncbi.nlm.nih.gov/19359813/
unhealthy, 64.6 years
n = 29
Health Status: unhealthy
Condition: angina
Age Group: 64.6 years
Sex: M+F
Population Size: 29
Sources:
https://pubmed.ncbi.nlm.nih.gov/19359813/
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:
https://pubmed.ncbi.nlm.nih.gov/19359813/
unhealthy, 64.6 years
n = 29
Health Status: unhealthy
Condition: angina
Age Group: 64.6 years
Sex: M+F
Population Size: 29
Sources:
https://pubmed.ncbi.nlm.nih.gov/19359813/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737

inhibitor
1587
inhibitor
1767
inhibitor
1852

substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2A6
707

CYP2E1
882
CYP1A2
1054

P-gp
1537

BCRP
561
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2A6
739
 no
CYP2C9
1819
 no
CYP2E1
970
 no
CYP3A4
1925
 no
CYP1A2
1692
 yes
CYP2D6
1891
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
561
 no
CYP1A2
1054
 yes
CYP2D6
1217
 yes
CYP3A4
1737
 yes
P-gp
1537
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY565364
https://www.001chemical.com/chem/64706-54-3
3B Scientific (Wuhan) Corp
3B2-0571
http://www.3bsc.com/index/pro_info.php?id=19927
AHH Chemical co.,ltd
API-1541
http://www.ahhchemical.com/product/API-1541.html
AK Scientific, Inc. (AKSCI)
K042
http://www.aksci.com/item_detail.php?cat=K042
Achemo Scientific Limited
AC-11145
http://www.achemo.com/search/?Keyword=64706-54-3
Angel Pharmatech
AG121309
http://www.angelpharmatech.com/64706-54-3.html
BLD Pharm
BD116381
http://www.bldpharm.com/products/64706-54-3.html
CSNpharm
CSN10416
https://www.csnpharm.com/products/bepridil.html
ChemMol
30105085
http://www.chemmol.com/chemmol/30105085.html
ChemMol
99124623
http://www.chemmol.com/chemmol/99124623.html
Chemspace
CSSB00000047941
https://chem-space.com/CSSB00000047941
Debye Scientific
DB-054717
http://www.debyesci.com/cas_64706-54-3.html
Finetech
FT-0630749
http://www.finetechnology-ind.com/prod/detail/pub/64706-54-3.html
Glentham Life Sciences
GP4395
http://www.glentham.com/products/product/GP4395/
Lab Network
LN00330174
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00330174
Molcore
MC565364
https://www.molcore.com/product/64706-54-3
Smolecule
S520991
http://www.smolecule.com/products/s520991
Smolecule
S772535
https://www.smolecule.com/products/s772535
THE BioTek
bt-261730
https://www.thebiotek.com/product/inhibitors/bt-261730
THE BioTek
bt-311849
https://www.thebiotek.com/product/others/bt-311849
Vesino Industrial Co Ltd
VA10387
http://www.vsnchem.com/goto/product/23859/
abcr GmbH
AB542520
http://www.abcr.com/shop/en/AB542520
PubMed

PubMed

TitleDatePubMed
Antioxidant activity of 5-alkoxymethyl-6-chromanols.
2001
A new antioxidant monoterpene glycoside, alpha-benzoyloxypaeoniflorin from Paeonia suffruticosa.
2001 Apr
KCNQ4 channels expressed in mammalian cells: functional characteristics and pharmacology.
2001 Apr
Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia.
2001 Aug
Phenolic constituents and antioxidant activity of an extract of Anthuriumversicolor leaves.
2001 Aug
Axonal L-type Ca2+ channels and anoxic injury in rat CNS white matter.
2001 Feb
Activation of Na(+), K(+), Cl(-)-cotransport mediates intracellular Ca(2+) increase and apoptosis induced by Pinacidil in HepG2 human hepatoblastoma cells.
2001 Feb 23
Antioxidant benzoylated flavan-3-ol glycoside from Celastrus orbiculatus.
2001 Jan
[Bepridil inhibition on the delayed rectifier K+ currents in thyroxine induced hypertrophied guinea pig ventricular myocytes].
2001 Jul
Antioxidant activities of buckwheat hull extract toward various oxidative stress in vitro and in vivo.
2001 Mar
Inhibitory effect of bepridil on hKv1.5 channel current: comparison with amiodarone and E-4031.
2001 Nov 2
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
Antioxidant activities of dioscorin, the storage protein of yam (Dioscorea batatas Decne) tuber.
2001 Oct
Vasorelaxing and antioxidant constituents from Hernandia nymphaeifolia.
2001 Oct
Comparison of radical scavenging effect, inhibition of microsomal oxygen free radical generation, and serum lipoprotein oxidation of several natural antioxidants.
2002 Apr 10
Structure of the regulatory N-domain of human cardiac troponin C in complex with human cardiac troponin I147-163 and bepridil.
2002 Aug 23
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
Assessment of pro-oxidant activity of foods by kinetic analysis of crocin bleaching.
2002 May 8
Possible role of calcium ions, calcium channels and calmodulin in excystation and metacystic development of Entamoeba invadens.
2002 Sep
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
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
Patents

Patents

DE2310918
3
JP3352095B2
17
US3962238
3

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 Vitro Use Guide
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 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
ACTIVE MOIETY
Structure of BEPRIDIL
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
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