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
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 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) 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 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) 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 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) 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 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) 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 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: |
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 |
---|---|---|
[Bepridil: importance of serum level in treatment surveillance]. | 2000 Apr 1 |
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Cancer chemopreventive activities of S-3-1, a synthetic derivative of danshinone. | 2001 |
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Broussochalcone A, a potent antioxidant and effective suppressor of inducible nitric oxide synthase in lipopolysaccharide-activated macrophages. | 2001 Apr 15 |
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Samioside, a new phenylethanoid glycoside with free-radical scavenging and antimicrobial activities from Phlomis samia. | 2001 Aug |
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A quinolone alkaloid with antioxidant activity from the aleurone layer of anthocyanin-pigmented rice. | 2001 Dec |
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New bis-catechols 5-lipoxygenase inhibitors. | 2001 Feb |
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Axonal L-type Ca2+ channels and anoxic injury in rat CNS white matter. | 2001 Feb |
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Stimulation of nitric oxide-cGMP pathway excites striatal cholinergic interneurons via protein kinase G activation. | 2001 Feb 15 |
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Activation of Na(+), K(+), Cl(-)-cotransport mediates intracellular Ca(2+) increase and apoptosis induced by Pinacidil in HepG2 human hepatoblastoma cells. | 2001 Feb 23 |
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In vitro evaluation of the antioxidant activity and biomembrane interaction of the lazaroid U-74389G. | 2001 Feb 9 |
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2,2-Diphenyl-1-picrylhydrazyl hydrate, a stable free radical, is an alpha-glucosidase inhibitor. | 2001 Jun |
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Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method. | 2001 Mar |
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The antioxidant activity of the essential oils of Artemisia afra, Artemisia abyssinica and Juniperus procera. | 2001 Mar |
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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 |
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Radical scavenging activity against 1,1-diphenyl-2-picrylhydrazyl of ascorbic acid 2-glucoside (AA-2G) and 6-acyl-AA-2G. | 2001 May |
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A novel series of thromboxane A2 synthetase inhibitors with free radical scavenging and anti-peroxidative activities. | 2001 May |
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Screening of chemiluminescence constituents of cereals and DPPH radical scavenging activity of gamma-oryzanol. | 2001 May-Jun |
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Antioxidant properties of methanolic extracts from several ear mushrooms. | 2001 Nov |
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Scavenging of free radicals, antimicrobial, and cytotoxic activities of the Maillard reaction products of beta-lactoglobulin glycated with several sugars. | 2001 Oct |
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Antioxidant activities of dioscorin, the storage protein of yam (Dioscorea batatas Decne) tuber. | 2001 Oct |
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Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis). | 2001 Oct |
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Vasorelaxing and antioxidant constituents from Hernandia nymphaeifolia. | 2001 Oct |
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Antiradical and antilipoperoxidative effects of some plant extracts used by Sri Lankan traditional medical practitioners for cardioprotection. | 2001 Sep |
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Comparison of radical scavenging effect, inhibition of microsomal oxygen free radical generation, and serum lipoprotein oxidation of several natural antioxidants. | 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 |
|
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 |
|
Bepridil block of recombinant human cardiac IKs current shows a time-dependent unblock. | 2004 Feb |
|
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
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.
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Classification Tree | Code System | Code | ||
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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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Code System | Code | Type | Description | ||
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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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2337
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2351
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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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755BO701MA
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DB01244
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1436
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CHEMBL1008
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)