MedKoo Cat#: 326718 | Name: Capadenoson
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Capadenoson, also known as BAY 68-4986, is an oral active, potent and selective adenosine A1 receptor agonist. Adenosine A1 receptor (A1AR) stimulation is a powerful protective mechanism in cerebral and cardiac ischemia-reperfusion injury.

Chemical Structure

Capadenoson
Capadenoson
CAS#544417-40-5

Theoretical Analysis

MedKoo Cat#: 326718

Name: Capadenoson

CAS#: 544417-40-5

Chemical Formula: C25H18ClN5O2S2

Exact Mass: 519.0590

Molecular Weight: 520.02

Elemental Analysis: C, 57.74; H, 3.49; Cl, 6.82; N, 13.47; O, 6.15; S, 12.33

Price and Availability

Size Price Availability Quantity
10mg USD 250.00 2 Weeks
25mg USD 500.00 2 Weeks
50mg USD 850.00 2 Weeks
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Synonym
BAY 68-4986; BAY-68-4986; BAY68-4986; Capadenoson
IUPAC/Chemical Name
2-amino-6-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl]-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitril
InChi Key
CITWCLNVRIKQAF-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
N#CC1=C(C2=CC=C(OCCO)C=C2)C(C#N)=C(SCC3=CSC(C4=CC=C(Cl)C=C4)=N3)N=C1N
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 520.02 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Baltos JA, Vecchio EA, Harris MA, Qin CX, Ritchie RH, Christopoulos A, White PJ, May LT. Capadenoson, a clinically trialed partial adenosine A1 receptor agonist, can stimulate adenosine A2B receptor biased agonism. Biochem Pharmacol. 2017 Jul 1;135:79-89. doi: 10.1016/j.bcp.2017.03.014. Epub 2017 Mar 23. PMID: 28344125. 2: Louvel J, Guo D, Soethoudt M, Mocking TA, Lenselink EB, Mulder-Krieger T, Heitman LH, IJzerman AP. Structure-kinetics relationships of Capadenoson derivatives as adenosine A1 receptor agonists. Eur J Med Chem. 2015 Aug 28;101:681-91. doi: 10.1016/j.ejmech.2015.07.023. Epub 2015 Jul 15. PMID: 26210506. 3: Tendera M, Gaszewska-Żurek E, Parma Z, Ponikowski P, Jankowska E, Kawecka- Jaszcz K, Czarnecka D, Krzemińska-Pakuła M, Bednarkiewicz Z, Sosnowski M, Ochan Kilama M, Agrawal R. The new oral adenosine A1 receptor agonist capadenoson in male patients with stable angina. Clin Res Cardiol. 2012 Jul;101(7):585-91. doi: 10.1007/s00392-012-0430-8. Epub 2012 Feb 28. PMID: 22370739. 4: Baltos JA, Gregory KJ, White PJ, Sexton PM, Christopoulos A, May LT. Quantification of adenosine A(1) receptor biased agonism: Implications for drug discovery. Biochem Pharmacol. 2016 Jan 1;99:101-12. doi: 10.1016/j.bcp.2015.11.013. Epub 2015 Nov 12. PMID: 26581123. 5: Bott-Flügel L, Bernshausen A, Schneider H, Luppa P, Zimmermann K, Albrecht- Küpper B, Kast R, Laugwitz KL, Ehmke H, Knorr A, Seyfarth M. Selective attenuation of norepinephrine release and stress-induced heart rate increase by partial adenosine A1 agonism. PLoS One. 2011 Mar 28;6(3):e18048. doi: 10.1371/journal.pone.0018048. PMID: 21464936; PMCID: PMC3065468. 6: Bhatt KN, Butler J. Myocardial Energetics and Heart Failure: a Review of Recent Therapeutic Trials. Curr Heart Fail Rep. 2018 Jun;15(3):191-197. doi: 10.1007/s11897-018-0386-8. PMID: 29707741. 7: Metzner K, Gross T, Balzulat A, Wack G, Lu R, Schmidtko A. Lack of efficacy of a partial adenosine A1 receptor agonist in neuropathic pain models in mice. Purinergic Signal. 2021 Sep;17(3):503-514. doi: 10.1007/s11302-021-09806-6. Epub 2021 Jul 27. PMID: 34313915; PMCID: PMC8410902. 8: Yang X, Dilweg MA, Osemwengie D, Burggraaff L, van der Es D, Heitman LH, IJzerman AP. Design and pharmacological profile of a novel covalent partial agonist for the adenosine A1 receptor. Biochem Pharmacol. 2020 Oct;180:114144. doi: 10.1016/j.bcp.2020.114144. Epub 2020 Jul 10. PMID: 32653590. 9: Kiesman WF, Elzein E, Zablocki J. A1 adenosine receptor antagonists, agonists, and allosteric enhancers. Handb Exp Pharmacol. 2009;(193):25-58. doi: 10.1007/978-3-540-89615-9_2. PMID: 19639278. 10: Müller CE, Jacobson KA. Recent developments in adenosine receptor ligands and their potential as novel drugs. Biochim Biophys Acta. 2011 May;1808(5):1290-308. doi: 10.1016/j.bbamem.2010.12.017. Epub 2010 Dec 23. PMID: 21185259; PMCID: PMC3437328. 11: Bailey IR, Laughlin B, Moore LA, Bogren LK, Barati Z, Drew KL. Optimization of Thermolytic Response to A1 Adenosine Receptor Agonists in Rats. J Pharmacol Exp Ther. 2017 Sep;362(3):424-430. doi: 10.1124/jpet.117.241315. Epub 2017 Jun 26. PMID: 28652388; PMCID: PMC5539588. 12: Dinh W, Albrecht-Küpper B, Gheorghiade M, Voors AA, van der Laan M, Sabbah HN. Partial Adenosine A1 Agonist in Heart Failure. Handb Exp Pharmacol. 2017;243:177-203. doi: 10.1007/164_2016_83. PMID: 27770217. 13: Elzein E, Zablocki J. A1 adenosine receptor agonists and their potential therapeutic applications. Expert Opin Investig Drugs. 2008 Dec;17(12):1901-10. doi: 10.1517/13543780802497284. PMID: 19012505. 14: Cooper SL, March J, Sabbatini AR, Hill SJ, Jörg M, Scammells PJ, Woolard J. The effect of two selective A1 -receptor agonists and the bitopic ligand VCP746 on heart rate and regional vascular conductance in conscious rats. Br J Pharmacol. 2020 Jan;177(2):346-359. doi: 10.1111/bph.14870. Epub 2020 Jan 1. PMID: 31596949; PMCID: PMC6989947. 15: Rueda P, Merlin J, Chimenti S, Feletou M, Paysant J, White PJ, Christopoulos A, Sexton PM, Summers RJ, Charman WN, May LT, Langmead CJ. Pharmacological Insights Into Safety and Efficacy Determinants for the Development of Adenosine Receptor Biased Agonists in the Treatment of Heart Failure. Front Pharmacol. 2021 Mar 11;12:628060. doi: 10.3389/fphar.2021.628060. PMID: 33776771; PMCID: PMC7991592. 16: Sabbah HN, Gupta RC, Kohli S, Wang M, Rastogi S, Zhang K, Zimmermann K, Diedrichs N, Albrecht-Küpper BE. 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 May;6(3):563-71. doi: 10.1161/CIRCHEARTFAILURE.112.000208. Epub 2013 Apr 5. PMID: 23564604; PMCID: PMC3790141. 17: Meibom D, Albrecht-Küpper B, Diedrichs N, Hübsch W, Kast R, Krämer T, Krenz U, Lerchen HG, Mittendorf J, Nell PG, Süssmeier F, Vakalopoulos A, Zimmermann K. Neladenoson Bialanate Hydrochloride: A Prodrug of a Partial Adenosine A1 Receptor Agonist for the Chronic Treatment of Heart Diseases. ChemMedChem. 2017 May 22;12(10):728-737. doi: 10.1002/cmdc.201700151. Epub 2017 May 10. PMID: 28488817. 18: Cooper SL, Soave M, Jörg M, Scammells PJ, Woolard J, Hill SJ. Probe dependence of allosteric enhancers on the binding affinity of adenosine A1 -receptor agonists at rat and human A1 -receptors measured using NanoBRET. Br J Pharmacol. 2019 Apr;176(7):864-878. doi: 10.1111/bph.14575. Epub 2019 Mar 6. PMID: 30644086; PMCID: PMC6433648. 19: Saecker L, Häberlein H, Franken S. Investigation of adenosine A1 receptor- mediated β-arrestin 2 recruitment using a split-luciferase assay. Front Pharmacol. 2023 May 30;14:1172551. doi: 10.3389/fphar.2023.1172551. PMID: 37324481; PMCID: PMC10268005.