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
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
| 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 | ( + / - ) |
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 |
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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). |
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| Primary | BEPRICOR Approved UseBepridil is used to treat hypertension (high blood pressure) and to treat angina (chest pain). |
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| 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 |
|---|---|---|
| Design, synthesis, and biological evaluation of novel T-Type calcium channel antagonists. | 2004-07-16 |
|
| Atrial fibrillatory frequency, atrial fibrillatory rate, or atrial cycle length--does it matter? | 2004-07-01 |
|
| Evidence for a protective role played by the Na+/Ca2+ exchanger in cerebral ischemia induced by middle cerebral artery occlusion in male rats. | 2004-03 |
|
| Differential effect of HERG blocking agents on cardiac electrical alternans in the guinea pig. | 2004-02-20 |
|
| Bepridil block of recombinant human cardiac IKs current shows a time-dependent unblock. | 2004-02 |
|
| Bioequivalence study of two formulations of simvastatin tablets in healthy Thai volunteers. | 2004 |
|
| Slick (Slo2.1), a rapidly-gating sodium-activated potassium channel inhibited by ATP. | 2003-12-17 |
|
| A case of bepridil induced interstitial pneumonitis. | 2003-12 |
|
| Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia. | 2003-11-17 |
|
| Role of Na(+)-Ca(2+) exchanger after traumatic or hypoxic/ischemic injury to spinal cord white matter. | 2003-11-01 |
|
| A case of sick sinus syndrome that developed torsades de pointes, pacing failure and sensing failure during administration of bepridil. | 2003-09 |
|
| Sodium-calcium exchange influences the response to endothelin-1 in lens epithelium. | 2003-09 |
|
| Usefulness and safety of bepridil in converting persistent atrial fibrillation to sinus rhythm. | 2003-08-15 |
|
| Transepithelial transport of bepridil in the human intestinal cell line, Caco-2, using a "dynamic model". | 2003-07-25 |
|
| Detection of proarrhythmia in the female rabbit heart: blinded validation. | 2003-03 |
|
| Blockers of sodium and calcium entry protect axons from nitric oxide-mediated degeneration. | 2003-02 |
|
| Bepridil prevents paroxysmal atrial fibrillation by a class III antiarrhythmic drug effect. | 2003-01 |
|
| Evaluation of the effect of bepridil on paroxysmal atrial fibrillation: relationship between efficacy and the f-f interval in surface ECG recordings. | 2003-01 |
|
| 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. | 2002-11 |
|
| Beta-blocker decreases the increase in QT dispersion and transmural dispersion of repolarization induced by bepridil. | 2002-11 |
|
| Na(+)/Ca(2+) exchanger in porcine oocytes. | 2002-10 |
|
| [Successful hybrid therapy combined with oral bepridil and ICD in a patient with amiodarone refractory life-threatening ventricular tachyarrhythmia associated with ischemic cardiomyopathy]. | 2002-09-01 |
|
| Possible role of calcium ions, calcium channels and calmodulin in excystation and metacystic development of Entamoeba invadens. | 2002-09 |
|
| Structure of the regulatory N-domain of human cardiac troponin C in complex with human cardiac troponin I147-163 and bepridil. | 2002-08-23 |
|
| Effects of 12 Ca2+ antagonists on multidrug resistance, MDR1-mediated transport and MDR1 mRNA expression. | 2002-08 |
|
| Identification of radical scavengers in sweet grass (Hierochloe odorata). | 2002-05-08 |
|
| Assessment of pro-oxidant activity of foods by kinetic analysis of crocin bleaching. | 2002-05-08 |
|
| Antioxidant functions of selected allium thiosulfinates and S-alk(en)yl-L-cysteine sulfoxides. | 2002-04-24 |
|
| On-line HPLC-DPPH screening method for evaluation of radical scavenging phenols extracted from apples (Malus domestica L.). | 2002-04-24 |
|
| Comparison of radical scavenging effect, inhibition of microsomal oxygen free radical generation, and serum lipoprotein oxidation of several natural antioxidants. | 2002-04-10 |
|
| Antioxidative activity and safety of the 50 ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1. | 2002-04-10 |
|
| Free radical studies of ellagic acid, a natural phenolic antioxidant. | 2002-03-27 |
|
| Antioxidant properties of ferulic acid and its related compounds. | 2002-03-27 |
|
| Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities. | 2002-03-26 |
|
| Free radical scavenging activity of red ginseng aqueous extracts. | 2002-03-20 |
|
| Free radical scavenging properties of wheat extracts. | 2002-03-13 |
|
| Antioxidants from the bark of Burkea africana, an African medicinal plant. | 2002-03 |
|
| Interaction of digoxin with antihypertensive drugs via MDR1. | 2002-02-15 |
|
| 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). | 2002-02 |
|
| Antioxidant capacities of ten edible North American plants. | 2002-02 |
|
| Antioxidant enzymes and DPPH-radical scavenging activity in chilled and heat-shocked rice (Oryza sativa L.) seedlings radicles. | 2002-01-30 |
|
| Antioxidant effects of 1,5-anhydro-D-fructose, a new natural sugar, in vitro. | 2002-01 |
|
| Scavenging of reactive oxygen species by chlorophyllin: an ESR study. | 2001-11 |
|
| Synthesis and in vitro studies of pyrone derivatives as scavengers of active oxygen species. | 2001-11 |
|
| Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690. | 2001-10 |
|
| Superoxide- and 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities of soyasaponin beta g related to gallic acid. | 2001-10 |
|
| [Bepridil inhibition on the delayed rectifier K+ currents in thyroxine induced hypertrophied guinea pig ventricular myocytes]. | 2001-07 |
|
| Is cytotoxic cellular edema real? The effect of calcium ion on water homeostasis in the rat heart. | 2001 |
|
| Biliary drug lithiasis: dipyridamole gallstones. | 1992-11-28 |
|
| Evaluation of bepridil efficacy by electrophysiologic testing in patients with recurrent ventricular tachycardia: comparison of two regimens. | 1992-04 |
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
Wed Apr 02 06:59:39 GMT 2025
by
admin
on
Wed Apr 02 06:59:39 GMT 2025
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| Record UNII |
755BO701MA
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| Record Status |
Validated (UNII)
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WHO-VATC |
QC08EA02
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NCI_THESAURUS |
C333
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WHO-ATC |
C08EA02
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3061
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Bepridil
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64706-54-3
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3465
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342
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m2422
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100000077185
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D015764
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SUB13041MIG
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DTXSID3022663
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C87448
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DB01244
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1436
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CHEMBL1008
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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TARGET -> INHIBITOR | |||
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BINDING
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ENANTIOMER -> RACEMATE |
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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