CapadenosonAdenosine A1 receptor agonist CAS# 544417-40-5 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 544417-40-5 | SDF | Download SDF |
| PubChem ID | 9936489 | Appearance | Powder |
| Formula | C25H18ClN5O2S2 | M.Wt | 520.03 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | BAY 68-4986 | ||
| Solubility | DMSO : ≥ 50 mg/mL (96.15 mM) H2O : < 0.1 mg/mL (insoluble) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | 2-amino-6-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl]-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile | ||
| SMILES | C1=CC(=CC=C1C2=C(C(=NC(=C2C#N)SCC3=CSC(=N3)C4=CC=C(C=C4)Cl)N)C#N)OCCO | ||
| Standard InChIKey | CITWCLNVRIKQAF-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C25H18ClN5O2S2/c26-17-5-1-16(2-6-17)24-30-18(13-34-24)14-35-25-21(12-28)22(20(11-27)23(29)31-25)15-3-7-19(8-4-15)33-10-9-32/h1-8,13,32H,9-10,14H2,(H2,29,31) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Capadenoson is an agonist of adenosine A1 receptor . | |||||
| Targets | adenosine A1 receptor | |||||
Capadenoson Dilution Calculator
Capadenoson Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.923 mL | 9.6148 mL | 19.2297 mL | 38.4593 mL | 48.0741 mL |
| 5 mM | 0.3846 mL | 1.923 mL | 3.8459 mL | 7.6919 mL | 9.6148 mL |
| 10 mM | 0.1923 mL | 0.9615 mL | 1.923 mL | 3.8459 mL | 4.8074 mL |
| 50 mM | 0.0385 mL | 0.1923 mL | 0.3846 mL | 0.7692 mL | 0.9615 mL |
| 100 mM | 0.0192 mL | 0.0961 mL | 0.1923 mL | 0.3846 mL | 0.4807 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Capadenoson is a selective agonist of Adenosine A1 receptor [1].
Adenosine A1 receptor is a member of G-protein coupled receptor 1 family and plays an important role in the fertilization process, kidney function and ethanol intoxication. Many studies have shown that Adenosine A1 receptor is correlated with a variety of diseases, like angina, heart failure, and its agonist is becoming a promising target in clinic [1].
Capadenoson is a potent Adenosine A1 receptor agonist and belongs to the non-nucleosidic adenosine receptor family. When tested with perfused rat hearts isolated from Wista and SHR strains, capadenoson combined with CCPA treatment significantly decreased NE release in a dose-dependent manner [1].
In dog model with heart failure induced by microembolization, oral administration of capadenoson for 12 weeks improved left ventricular function and prevented progressive remodeling [2]. When pre-treated Wistar rats with capadenoson (0.15 mg/kg) for 5 days, physical restraint for 2 hours increased heart rate [1].
When tested with male patients with stable angina, oral administration of capadenoson lowered exercise heart failure at comparable maximum workload [3].
References:
[1].Bott-Flugel, L., et al., Selective attenuation of norepinephrine release and stress-induced heart rate increase by partial adenosine A1 agonism. PLoS One, 2011. 6(3): p. e18048.
[2].Sabbah, H.N., et al., Chronic therapy with a partial adenosine A1-receptor agonist improves left ventricular function and remodeling in dogs with advanced heart failure. Circ Heart Fail, 2013. 6(3): p. 563-71.
[3].Tendera, M., et al., The new oral adenosine A1 receptor agonist capadenoson in male patients with stable angina. Clin Res Cardiol, 2012. 101(7): p. 585-91.
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Capadenoson, a clinically trialed partial adenosine A1 receptor agonist, can stimulate adenosine A2B receptor biased agonism.[Pubmed:28344125]
Biochem Pharmacol. 2017 Jul 1;135:79-89.
The adenosine A2B receptor (A2BAR) has been identified as an important therapeutic target in cardiovascular disease, however in vitro and in vivo targeting has been limited by the paucity of pharmacological tools, particularly potent agonists. Interestingly, 2-((6-amino-3,5-dicyano-4-(4-(cyclopropylmethoxy)phenyl)-2-pyridinyl)thio)acetami de (BAY60-6583), a potent and subtype-selective A2BAR agonist, has the same core structure as 2-amino-6-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl]-4-[4-(2-hydroxyet hoxy)phenyl]pyridine-3,5-dicarbonitril (Capadenoson). Capadenoson, currently classified as an adenosine A1 receptor (A1AR) partial agonist, has undergone two Phase IIa clinical trials, initially in patients with atrial fibrillation and subsequently in patients with stable angina. Capadenoson has also been shown to decrease cardiac remodeling in an animal model of advanced heart failure and a Capadenoson derivative, neladenoson bialanate, recently entered clinical development for the treatment of chronic heart failure. The therapeutic effects of Capadenoson are currently thought to be mediated through the A1AR. However, the ability of Capadenoson to stimulate additional adenosine receptor subtypes, in particular the A2BAR, has not been rigorously assessed. In this study, we demonstrate that Capadenoson does indeed have significant A2BAR activity in physiologically relevant cells, cardiac fibroblasts and cardiomyocytes, which endogenously express the A2BAR. Relative to the non-selective adenosine receptor agonist NECA, Capadenoson was a biased A2BAR agonist with a preference for cAMP signal transduction over other downstream mediators in cells with recombinant and endogenous A2BAR expression. These findings suggest the reclassification of Capadenoson as a dual A1AR/A2BAR agonist. Furthermore, a potential A2BAR contribution should be an important consideration for the future clinical development of Capadenoson-like therapeutics, as the A2BAR can promote cardioprotection and modulate cardiac fibrosis in heart disease.
The new oral adenosine A1 receptor agonist capadenoson in male patients with stable angina.[Pubmed:22370739]
Clin Res Cardiol. 2012 Jul;101(7):585-91.
BACKGROUND: Anti-ischaemic effect of A1 adenosine receptor agonists was shown in animal and preclinical studies. The present proof-of-concept study aimed at evaluation of the efficacy and safety of a new adenosine A1 receptor agonist Capadenoson in patients with stable angina. METHODS: This was a randomized, double-blind, placebo-controlled, single dose-escalating, multicenter trial comparing the effect of Capadenoson at 1, 2.5, 5, 10, and 20 mg versus placebo. For each dose step patients were randomized to receive single doses of either Capadenoson or matching placebo in a 5:1 ratio. The primary efficacy variable was the absolute difference in heart rate (HR) at maximum comparable level of workload between baseline and post dose exercise tolerance test at maximum concentration of Capadenoson. Capadenoson effect on total exercise time and time to 1-mm ST-segment depression were also measured. RESULTS: Sixty-two male patients with stable angina were enrolled in the study. There was a consistent trend for HR reduction at comparable maximum work load in active treatment groups, with significant differences against placebo for 10 and 20 mg (HR reduction by 12.2 and 6.8 beats per min, p = 0.0002 and p = 0.032, respectively). A statistically significant trend (p = 0.0003) for a reduction in HR with increasing doses of Capadenoson was shown. Increases in total exercise time and time to 1-mm ST-segment depression were also observed. CONCLUSIONS: In patients with stable angina Capadenoson lowers exercise HR at comparable maximum workload, which is associated with improved total exercise time and prolongation of time to ischaemia.
Structure-kinetics relationships of Capadenoson derivatives as adenosine A1 receptor agonists.[Pubmed:26210506]
Eur J Med Chem. 2015 Aug 28;101:681-91.
We report the synthesis and biological evaluation of new derivatives of Capadenoson, a former drug candidate that was previously advanced to phase IIa clinical trials. 19 of the 20 ligands show an affinity below 100 nM at the human adenosine A1 receptor (hA1AR) and display a wide range of residence times at this target (from approx. 5 min (compound 10) up to 132 min (compound 5)). Structure-affinity and structure-kinetics relationships were established, and computational studies of a homology model of the hA1AR revealed crucial interactions for both the affinity and dissociation kinetics of this family of ligands. These results were also combined with global metrics (Ligand Efficiency, cLogP), showing the importance of binding kinetics as an additional way to better select a drug candidate amongst seemingly similar leads.
