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 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 |
---|---|---|
Biliary drug lithiasis: dipyridamole gallstones. | 1992 Nov 28 |
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[Bepridil: importance of serum level in treatment surveillance]. | 2000 Apr 1 |
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Is cytotoxic cellular edema real? The effect of calcium ion on water homeostasis in the rat heart. | 2001 |
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Effect of nilvadipine in weak acidic medium by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. | 2001 |
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Blocking effect of bepridil on Na+/Ca2+ exchange current in guinea pig cardiac ventricular myocytes. | 2001 Apr |
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Ionic mechanisms of aglycemic axon injury in mammalian central white matter. | 2001 Apr |
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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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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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Antioxidant benzoylated flavan-3-ol glycoside from Celastrus orbiculatus. | 2001 Jan |
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Anti-oxidative properties of fluvastatin, an HMG-CoA reductase inhibitor, contribute to prevention of atherosclerosis in cholesterol-fed rabbits. | 2001 Jan |
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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 |
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Evaluation of the absorption, excretion, and metabolism of the antihypertensive agent RWJ-26899 in male and female CR Wistar rats and Beagle dogs. | 2001 Jul-Sep |
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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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Antioxidant activities of buckwheat hull extract toward various oxidative stress in vitro and in vivo. | 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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Screening of chemiluminescence constituents of cereals and DPPH radical scavenging activity of gamma-oryzanol. | 2001 May-Jun |
|
Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities. | 2001 Nov-Dec |
|
Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690. | 2001 Oct |
|
Antioxidative components from the aerial parts of Lactuca scariola L. | 2001 Oct |
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Effect of calcium antagonists, calcium channel blockers and calmodulin inhibitors on the growth and encystation of Entamoeba histolytica and E. invadens. | 2001 Oct |
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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 |
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Vasorelaxing and antioxidant constituents from Hernandia nymphaeifolia. | 2001 Oct |
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Two new diterpenoids from Plectranthus nummularius Briq. | 2001 Sep |
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Interaction of bepridil with the cardiac troponin C/troponin I complex. | 2001 Sep 28 |
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Antioxidative activity and safety of the 50 ethanolic extract from red bean fermented by Bacillus subtilis IMR-NK1. | 2002 Apr 10 |
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Effects of 12 Ca2+ antagonists on multidrug resistance, MDR1-mediated transport and MDR1 mRNA expression. | 2002 Aug |
|
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 |
|
Antioxidant enzymes and DPPH-radical scavenging activity in chilled and heat-shocked rice (Oryza sativa L.) seedlings radicles. | 2002 Jan 30 |
|
Free radical scavenging properties of wheat extracts. | 2002 Mar 13 |
|
Free radical scavenging activity of red ginseng aqueous extracts. | 2002 Mar 20 |
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Free radical studies of ellagic acid, a natural phenolic antioxidant. | 2002 Mar 27 |
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Antioxidant properties of ferulic acid and its related compounds. | 2002 Mar 27 |
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Assessment of pro-oxidant activity of foods by kinetic analysis of crocin bleaching. | 2002 May 8 |
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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 |
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Detection of proarrhythmia in the female rabbit heart: blinded validation. | 2003 Mar |
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A case of sick sinus syndrome that developed torsades de pointes, pacing failure and sensing failure during administration of bepridil. | 2003 Sep |
|
Bioequivalence study of two formulations of simvastatin tablets in healthy Thai volunteers. | 2004 |
|
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 15:59:38 GMT 2023
by
admin
on
Sat Dec 16 15:59:38 GMT 2023
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Record UNII |
755BO701MA
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Record Status |
Validated (UNII)
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Record Version |
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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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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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Related Record | Type | Details | ||
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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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BINDER->LIGAND |
BINDING
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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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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