| Size | Price | Stock | Qty |
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| 10mg |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg | |||
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| Targets |
Bupranolol targets β1- and β2-adrenergic receptors (ARs) as a competitive antagonist, with pA2 values of ≈9.0. It also antagonizes β3-AR with a pA2 value of 6.0. By blocking these receptors, bupranolol inhibits the effects of catecholamines such as adrenaline and noradrenaline, leading to reduced heart rate, myocardial contractility, and blood pressure. Bupranolol does not have intrinsic sympathomimetic activity (ISA).
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| ln Vitro |
In the presence of 30 μM propranolol, isoproterenol-induced relaxation is modified by buprolol (1~3 μM). Buprolol has a pA2 value of 5.90 and functions as a competitive antagonist of isoproterenol-induced relaxation in the presence of 300 nM propranolol. With a pA2 value of roughly 9.0, buprolol antagonizes β1- and β2-AR. It also antagonizes β3-AR, with a pA2 value of 6.0 [1].
In vitro, Bupranolol has been shown to antagonize isoprenaline-induced relaxation in various tissue preparations. It shifts isoprenaline-induced relaxation in the presence of propranolol. The compound exhibits β1- and β2-receptor blocking activity in a concentration-dependent manner. Bupranolol's membrane-stabilizing properties have also been demonstrated in vitro. The compound is used as a reference β-blocker in pharmacological studies. |
| ln Vivo |
In vivo, Bupranolol has been shown to be effective in reducing blood pressure and heart rate in hypertensive animal models and in humans. It is used clinically to manage hypertension, tachycardia, and glaucoma. Bupranolol has also been investigated for its antithrombotic effects. The compound's relatively short half-life makes it suitable for acute interventions.
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| Enzyme Assay |
In vitro receptor binding assays for Bupranolol typically involve measuring its affinity for β1, β2, and β3 adrenergic receptors using radioligand binding. The compound is incubated with membrane preparations from cells expressing the receptors and a radiolabeled ligand. The concentration of Bupranolol required to displace 50% of the radioligand (IC50) is determined, and the Ki or pA2 value is calculated. The selectivity of Bupranolol for different β-receptor subtypes can be assessed.
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| Cell Assay |
In vitro cell-based studies with Bupranolol typically involve cultured cells expressing β-adrenergic receptors, such as cardiomyocytes or smooth muscle cells. Cells are treated with Bupranolol at various concentrations and stimulated with isoprenaline or other β-agonists. The inhibition of cAMP accumulation or other downstream signaling events is measured. The IC50 value for inhibition of these responses is determined. The effect of Bupranolol on cell viability and receptor internalization can also be evaluated.
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| Animal Protocol |
In vivo animal studies with Bupranolol are typically conducted in rodent or canine models to evaluate its cardiovascular effects. The compound is administered orally or intravenously. Blood pressure, heart rate, and cardiac output are measured. The effect of Bupranolol on exercise-induced tachycardia and on isoprenaline-induced tachycardia is assessed. Pharmacokinetic studies are performed to evaluate the absorption, distribution, and elimination of the compound.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Rapidly and completely absorbed via the intestine; oral bioavailability is less than 10%. Metabolism/Metabolites Over 90% of the drug undergoes first-pass metabolism. The major metabolite is carboxybuprofenol, i.e., 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxypropoxy]benzoic acid, of which 88% is excreted by the kidneys within 24 hours. Biological Half-Life 2-4 hours Bupranolol is a well-characterized drug with established pharmacokinetic properties. Following oral administration, it is quickly and completely absorbed from the gut with less than 10% oral bioavailability. The drug is extensively metabolized in the liver. The elimination half-life is approximately 2-4 hours. Bupranolol is excreted in the urine primarily as metabolites. The compound's short half-life makes it suitable for acute interventions. |
| Toxicity/Toxicokinetics |
Protein Binding
76% Bupranolol has a well-established safety profile. The most common adverse effects are related to β-blockade and include bradycardia, hypotension, fatigue, and dizziness. Bronchospasm can occur in patients with asthma or COPD due to β2-receptor blockade. Bupranolol should be used with caution in patients with heart failure, diabetes, and peripheral vascular disease. The compound is for research use only and is not approved for human therapeutic use in some countries. |
| References |
[1]. Chino D, et al. Pharmacological identification of β-adrenoceptor subtypes mediating isoprenaline-induced relaxation of guinea pig colonic longitudinal smooth muscle. J Smooth Muscle Res. 2018;54(0):13-27.
[2]. Babu RJ, et al. Effect of cyclodextrins on the complexation and transdermal delivery of bupranolol through rat skin. Int J Pharm. 2004;271(1-2):155-165. |
| Additional Infomation |
Bupranolol is an aromatic ether. Bupranolol is a non-selective beta-blocker with potency similar to propranolol. It lacks intrinsic sympathomimetic activity (ISA) but possesses strong membrane-stabilizing activity. It is an adrenergic beta-2 receptor antagonist and has been used to treat arrhythmias, angina, hypertension, glaucoma, and as an antithrombotic drug. Drug Indications: Used to treat hypertension and tachycardia. Also used to treat glaucoma. Mechanism of Action: Bupranolol competitively binds to beta-1 adrenergic receptors in the heart with sympathomimetic neurotransmitters such as catecholamines, thereby inhibiting sympathetic nerve excitation. This leads to a decrease in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension. Pharmacodynamics: Bupranolol is a competitive, non-selective beta-blocker, similar to propranolol, but without intrinsic sympathomimetic activity.
Bupranolol is a non-selective β-adrenoceptor antagonist that has been used clinically for the management of hypertension, tachycardia, and glaucoma. It is available in various formulations for oral and ophthalmic administration. Bupranolol is structurally related to propranolol and shares a similar pharmacological profile. The compound is not widely approved as a drug and is not commercially available in many countries. |
| Molecular Formula |
C14H22NO2CL
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| Molecular Weight |
271.78298
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| Exact Mass |
271.134
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| CAS # |
14556-46-8
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| PubChem CID |
2475
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.098g/cm3
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| Boiling Point |
396.3ºC at 760mmHg
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| Flash Point |
193.5ºC
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| Vapour Pressure |
5.44E-07mmHg at 25°C
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| Index of Refraction |
1.522
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| LogP |
3.167
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
18
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| Complexity |
242
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| Defined Atom Stereocenter Count |
0
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| SMILES |
ClC1C=CC(C)=CC=1OCC(O)CNC(C)(C)C
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| InChi Key |
HQIRNZOQPUAHHV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3
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| Chemical Name |
1-(tert-butylamino)-3-(2-chloro-5-methylphenoxy)propan-2-ol
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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 : ~50 mg/mL (~183.97 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.20 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to 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 (9.20 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (9.20 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6794 mL | 18.3972 mL | 36.7945 mL | |
| 5 mM | 0.7359 mL | 3.6794 mL | 7.3589 mL | |
| 10 mM | 0.3679 mL | 1.8397 mL | 3.6794 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.
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