| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
Bepridil is a potent calcium channel blocker/antagonist and class IV anti-arrhythmic agent once used to treat angina but is no longer on the market.
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Rapid and complete absorption after oral administration. Metabolism/Metabolites Hepatic metabolism. Biological Half-Life 24-50 hours. |
|---|---|
| Toxicity/Toxicokinetics |
Protein Binding
99% |
| References |
[1]. The relationship between the plasma concentration of bepridil and its efficacy in the treatment of atrial fibrillation in Japanese patients. Biol Pharm Bull. 2012;35(5):672-6.
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| Additional Infomation |
Bepodil is a tertiary amine with benzyl, phenyl, and 3-(2-methylpropoxy)-2-(pyrrolidine-1-yl)propyl substituents on its nitrogen atom. It has vasodilatory, antiarrhythmic, hypotensive, and calcium channel blocking effects. It is a tertiary amine belonging to the pyrrolidine class of compounds. Bepodil is a long-acting, non-selective calcium channel blocker with significant antianginal activity. It significantly dilates coronary arteries and produces mild peripheral effects. It has hypotensive and selective antiarrhythmic effects and acts as a calmodulin antagonist. This drug has been discontinued in the United States due to its association with ventricular arrhythmias, such as torsades de pointes. This is a long-acting calcium channel blocker with significant antianginal activity. It significantly dilates coronary arteries and produces mild peripheral effects. It has hypotensive and selective antiarrhythmic effects and acts as a calmodulin antagonist. Indications Bepredil is used to treat hypertension and chronic stable angina (classical exertional angina). Mechanism of Action Bepredil inhibits slow (L-type) calcium influx and fast sodium influx in myocardial and vascular smooth muscle, interferes with calcium binding to calmodulin, and blocks voltage-gated and receptor-gated calcium channels. Bepredil inhibits transmembrane influx of calcium ions into myocardial and vascular smooth muscle. In isolated myocardial and vascular smooth muscle preparations, bepredil has been shown to significantly reduce the slope of the calcium dose-response curve and the maximum calcium-induced positive inotropic response. In cultured cardiomyocytes, bepredil binds tightly to actin. Bepredil stably reduces heart rate and arterial blood pressure at rest and specific exercise levels by dilating peripheral arterioles and reducing the total peripheral resistance (afterload) overcome by cardiac work.
Pharmacodynamics Bepredil is a calcium channel blocker with well-established antianginal properties, as well as known but not fully elucidated type I antiarrhythmic and antihypertensive properties. Its chemical structure is independent of other calcium channel blockers such as diltiazem hydrochloride, nifedipine, and verapamil hydrochloride. |
| Molecular Formula |
C24H34N2O
|
|---|---|
| Molecular Weight |
366.53956
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| Exact Mass |
366.267
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| Elemental Analysis |
C, 78.64; H, 9.35; N, 7.64; O, 4.36
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| CAS # |
64706-54-3
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| Related CAS # |
Bepridil hydrochloride;68099-86-5;Bepridil hydrochloride hydrate;74764-40-2; Bepridil;64706-54-3; 64706-54-3; 99239-96-0 (S-isomer HCl); 110143-75-4 (S-isomer); 110143-74-3 (R-isomer)
|
| PubChem CID |
2351
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| Appearance |
White to light yellow solid
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| Density |
1.054 g/cm3
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| Boiling Point |
492.3ºC at 760 mmHg
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| Flash Point |
133.2ºC
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| Index of Refraction |
1.572
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| LogP |
4.768
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
10
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| Heavy Atom Count |
27
|
| Complexity |
382
|
| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)COCC(N1CCCC1)CN(CC2=CC=CC=C2)C3=CC=CC=C3
|
| InChi Key |
UIEATEWHFDRYRU-UHFFFAOYSA-N
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| InChi Code |
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
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| Chemical Name |
N-Benzyl-N-[3-(2-methylpropoxy)-2-pyrrolidin-1-ylpropyl]aniline
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| Synonyms |
CERM1978; CERM 1978; Angopril; bepridil; 64706-54-3; DTXSID3022663; N-benzyl-N-[3-(2-methylpropoxy)-2-(pyrrolidin-1-yl)propyl]aniline; 755BO701MA; CERM-1978; Bepadin.
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ~100 mg/mL (~272.8 mM; with ultrasonication)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.82 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (6.82 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Suspended solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (6.82 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (25.0 mg/mL) to 900 μL of corn oil and mix well.  (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7282 mL | 13.6411 mL | 27.2822 mL | |
| 5 mM | 0.5456 mL | 2.7282 mL | 5.4564 mL | |
| 10 mM | 0.2728 mL | 1.3641 mL | 2.7282 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration: mg/mL;
Method for preparing DMSO stock solution: mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation::Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.