Capadenoson
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MedKoo CAT#: 326718

CAS#: 544417-40-5

Description: 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

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Capadenoson
CAS# 544417-40-5
Instruction

Theoretical Analysis

MedKoo Cat#: 326718
Name: Capadenoson
CAS#: 544417-40-5
Chemical Formula: C25H18ClN5O2S2
Exact Mass: 519.06
Molecular Weight: 520.022
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
1mg USD 220
5mg USD 470
10mg USD 765
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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.