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

Theoretical Analysis

MedKoo Cat#: 326718
Name: Capadenoson
CAS#: 544417-40-5
Chemical Formula: C25H18ClN5O2S2
Exact Mass: 519.059
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
1.0mg USD 220.0 2 Weeks
5.0mg USD 470.0 2 Weeks
10.0mg USD 765.0 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

Preparing Stock Solutions

The following data is based on the product molecular weight 520.022 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

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1: 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. PubMed PMID: 26581123.

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. PubMed PMID: 26210506.

3: 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. PubMed PMID: 23564604; PubMed Central PMCID: PMC3790141.

4: 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. PubMed PMID: 22370739.

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. PubMed PMID: 21464936; PubMed Central PMCID: PMC3065468.

6: 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. Review. PubMed PMID: 21185259; PubMed Central PMCID: PMC3437328.

7: 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. Review. PubMed PMID: 19639278.

8: 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 . Review. PubMed PMID: 19012505.