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
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
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
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 | ( + / - ) |
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 |
DescriptionSources: http://www.rxlist.com/vascor-drug.htmCurator'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
Sources: http://www.rxlist.com/vascor-drug.htm
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2111390 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20592218 |
6.0 µM [IC50] | ||
Target ID: CHEMBL2094135 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20592218 |
|||
Target ID: 57582.0 Gene Symbol: KCNT1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16876206 |
1.0 µM [IC50] | ||
Target ID: Voltage and receptor operated calcium channels Sources: http://www.rxlist.com/vascor-drug.htm |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BEPRICOR Approved UseBepridil hydrochloride is indicated for the treatment of chronic stable angina (classic effort-associated angina). |
|||
Primary | BEPRICOR Approved UseBepridil is used to treat hypertension (high blood pressure) and to treat angina (chest pain). |
|||
Primary | BEPRICOR Approved UseIt is usually used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina. |
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Primary | BEPRICOR Approved UseIt is usually used to treat sustained atrial fibrillation, tachyarrhythmia (ventricular) and angina. |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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) Sources: Lightheadedness (1 patient) Syncopal attack (1 patient) |
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) Sources: Diarrhea (1 patient) Anorexia (1 patient) Bigeminy (1 patient) |
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) Sources: Bradycardia (1 patient) |
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) Sources: Bradycardia (1 patient) Electrocardiogram QTc interval prolonged (4 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Biliary drug lithiasis: dipyridamole gallstones. | 1992 Nov 28 |
|
Cancer chemopreventive activities of S-3-1, a synthetic derivative of danshinone. | 2001 |
|
Blocking effect of bepridil on Na+/Ca2+ exchange current in guinea pig cardiac ventricular myocytes. | 2001 Apr |
|
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 |
|
In vitro evaluation of the antioxidant activity and biomembrane interaction of the lazaroid U-74389G. | 2001 Feb 9 |
|
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 |
|
Traumatic axonal injury induces calcium influx modulated by tetrodotoxin-sensitive sodium channels. | 2001 Mar 15 |
|
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 |
|
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 |
|
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 |
|
Free radical scavenging properties of wheat extracts. | 2002 Mar 13 |
|
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 |
|
Beta-blocker decreases the increase in QT dispersion and transmural dispersion of repolarization induced by bepridil. | 2002 Nov |
|
Na(+)/Ca(2+) exchanger in porcine oocytes. | 2002 Oct |
|
Transepithelial transport of bepridil in the human intestinal cell line, Caco-2, using a "dynamic model". | 2003 Apr-Jun |
|
Usefulness and safety of bepridil in converting persistent atrial fibrillation to sinus rhythm. | 2003 Aug 15 |
|
Bepridil prevents paroxysmal atrial fibrillation by a class III antiarrhythmic drug effect. | 2003 Jan |
|
Sodium-calcium exchange influences the response to endothelin-1 in lens epithelium. | 2003 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/mtm/bepridil.html
Initial dose: 200 mg once a day.
Maintenance dose: 300-400 mg once a day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24260442
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
Edited
Mon Mar 31 17:53:44 GMT 2025
by
admin
on
Mon Mar 31 17:53:44 GMT 2025
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Record UNII |
4W2P15D93M
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C333
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C47412
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CHEMBL1008
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m2422
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Bepridil hydrochloride
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Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |