| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Beta-1 adrenergic receptors
(R)-(+)-Atenolol targets β1-adrenergic receptors. It is a cardioselective beta-1 adrenergic blocker. Its properties are similar to propranolol but without a negative inotropic effect. As the less active enantiomer of (R,S)-atenolol, it has lower potency at β1 receptors compared to the (S)-enantiomer. It is used to study the stereospecificity of beta-blocker binding and function. |
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| ln Vitro |
Atenolol, a β-adrenergic receptor antagonist, is a chiral compound used for the treatment of cardiovascular diseases and to treat hypertension, coronary heart disease, arrhythmias, sinus tachycardia and myocardial infarction, where it acts preferentially upon the β-adrenergic receptors in the heart. It is marketed as a racemate, but only the (S)-enantiomer of (RS)-atenolol is responsible for the β-adrenoceptor blocking activity. Different chromatographic methods have been applied for the separation and determination of enantiomers. In this article a review is presented on liquid chromatographic methods for enantioseparation of (RS)-atenolol by both direct and indirect approaches involving practical applications of several chiral stationary phases, chiral derivatization reagents and ligand exchange and impregnation methods. These include methods using both HPLC and TLC for separation, determination and bioassay of enantiomers of atenolol. In addition, some aspects of enantioseparation under achiral phases of liquid chromatography have been briefly mentioned as applicable to (RS)-atenolol. This review provides current available enantioseparation choices not only for (RS)-atenolol but also for other applicable racemic drugs [1].
In vitro, (R)-(+)-Atenolol acts as a β1-adrenergic receptor antagonist with lower potency than the (S)-enantiomer. Its activity is typically assessed by measuring its ability to inhibit agonist-induced cAMP accumulation in cells expressing β1 receptors. The compound's lower potency compared to the (S)-enantiomer makes it useful for studying the stereospecificity of beta-blocker pharmacology. Standard in vitro assays include receptor binding studies and functional assays measuring cAMP accumulation. |
| ln Vivo |
In a randomized, double-blind, cross-over study in 12 healthy volunteers, the effects of single oral doses of 100 mg rac-atenolol were compared during exercise to those of equal amounts of the optically pure enantiomers, i.e., 50 mg (R)- and 50 mg (S)-atenolol. The mean rate pressure product decreased with rac-atenolol (-37%; P < 0.01) and half-dosed (S)-atenolol (-35%; P < 0.01) to the same extent, whereas (R)-atenolol caused no effect. Radioligand binding studies in beta-adrenergic receptors of the guinea pig heart yielded a eudismic ratio of 46 for (S)- to (R)-atenolol. The mean AUCs, maximal plasma concentrations, and plasma half-lives of the enantiomers were similar regardless of whether they were administered as optically pure enantiomers or as racemic mixture. On the other hand, the AUC of (R)-atenolol was 1.08-fold greater (P < 0.01) than that of the (S)-enantiomer. The reason for this finding remains unclear. We conclude that only (S)-atenolol, but not (R)-atenolol, contributes to the beta-blocking effect of currently used rac-atenolol since the same effect can be elicited with the (S)-enantiomer alone[2].
In vivo, (R)-(+)-Atenolol is used as a research tool to study the stereospecificity of beta-blocker pharmacology. As a cardioselective beta-1 adrenergic blocker, it would be expected to reduce heart rate and cardiac contractility. However, as the less active enantiomer, its effects are less pronounced than those of the (S)-enantiomer. The compound is primarily used in research to study the pharmacological differences between enantiomers. |
| Enzyme Assay |
For non-cell-based receptor binding assays, (R)-(+)-Atenolol can be evaluated using membrane preparations from cells expressing human β1-adrenergic receptors. Radioligand binding displacement experiments are performed using a suitable radiolabeled ligand such as [3H]-CGP-12177. Membrane homogenates are incubated with increasing concentrations of the test compound and a fixed concentration of the radioligand at room temperature for 60-90 minutes. Bound radioligand is separated from free by rapid filtration through glass fiber filters. Non-specific binding is determined in the presence of excess unlabeled propranolol. Ki values are calculated from displacement curves using nonlinear regression analysis.
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| Cell Assay |
For in vitro cellular assays, cells expressing human β1-adrenergic receptors are cultured in appropriate media. For cAMP accumulation assays, cells are pre-incubated with forskolin to stimulate cAMP production, then treated with various concentrations of (R)-(+)-Atenolol in the presence of a β1-agonist. cAMP levels are measured using ELISA or HTRF-based detection. The compound's ability to inhibit agonist-induced cAMP accumulation is assessed, and IC50 values are calculated from dose-response curves.
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| Animal Protocol |
For in vivo animal studies, (R)-(+)-Atenolol can be administered to rodents via oral gavage or intraperitoneal injection. In cardiovascular studies, hemodynamic parameters including heart rate and blood pressure are monitored following compound administration. The compound's effects are compared to those of the (S)-enantiomer and the racemic mixture to assess stereospecificity. Dosing regimens vary depending on the specific model and desired exposure levels.
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| ADME/Pharmacokinetics |
(R)-(+)-Atenolol has a molecular weight of 266.34 and a molecular formula of C14H22N2O3. It is the less active enantiomer of (R,S)-atenolol. (R,S)-atenolol is a β-adrenergic receptor antagonist. The compound is for research use only and is not intended for human consumption.
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| Toxicity/Toxicokinetics |
The toxicity profile of (R)-(+)-Atenolol has not been extensively reported. As a β1-adrenergic receptor antagonist, potential adverse effects may include bradycardia, hypotension, and fatigue. However, as the less active enantiomer, its effects are less pronounced than those of the (S)-enantiomer. The compound is for research use only and is not intended for human consumption.
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| References |
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| Additional Infomation |
Esatenolol is the (S)-enantiomer of atenolol. It is a β-adrenergic antagonist. Exatenolol is a β-receptor blocker.
(R)-(+)-Atenolol (CAS 56715-13-0) is the less active enantiomer of (R,S)-atenolol. (R,S)-atenolol is a β-adrenergic receptor antagonist. (R)-(+)-Atenolol is a cardioselective beta-1 adrenergic blocker with properties similar to propranolol but without a negative inotropic effect. It is used in research to study the stereospecificity of beta-blocker pharmacology. It is available for research purposes only. |
| Molecular Formula |
C14H22N2O3
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|---|---|
| Molecular Weight |
266.34
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| Exact Mass |
266.163
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| Elemental Analysis |
C, 63.13; H, 8.33; N, 10.52; O, 18.02
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| CAS # |
56715-13-0
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| Related CAS # |
Atenolol-d7;1202864-50-3; 51706-40-2 (HCl); 29122-68-7;93379-54-5 (S isomer); 56715-13-0 (R isomer)
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| PubChem CID |
175540
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| Appearance |
White to off-white solid powder
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| Density |
1.125g/cm3
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| Boiling Point |
508ºC at 760mmHg
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| Melting Point |
148-152ºC(lit.)
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| Flash Point |
261.1ºC
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| Index of Refraction |
1.54
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| LogP |
1.543
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
19
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| Complexity |
263
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(C)NC[C@@H](COC1=CC=C(C=C1)CC(=O)N)O
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| InChi Key |
METKIMKYRPQLGS-LBPRGKRZSA-N
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| InChi Code |
InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)/t12-/m0/s1
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| Chemical Name |
2-[4-[(2S)-2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
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| Synonyms |
(R)-(+)-Atenolol; (R)-Atenolol; 56715-13-0; (+)-Atenolol; R(+)-Atenolol; (R)-2-(4-(2-Hydroxy-3-(isopropylamino)propoxy)phenyl)acetamide; Atenolol, (+)-; R-(+)-Atenolol;
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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 (375.46 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.39 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 (9.39 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 (9.39 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 | 3.7546 mL | 18.7730 mL | 37.5460 mL | |
| 5 mM | 0.7509 mL | 3.7546 mL | 7.5092 mL | |
| 10 mM | 0.3755 mL | 1.8773 mL | 3.7546 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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