Skip to Content
Merck
All Photos(1)

Documents

SML2852

Sigma-Aldrich

Capadenoson

≥98% (HPLC)

Synonym(s):

2-Amino-6-[[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl]sulfanyl]-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile, 2-Amino-6-[[[2-(4-chlorophenyl)-4-thiazolyl]methyl]thio]-4-[4-(2-hydroxyethoxy)phenyl]-3,5-pyridinedicarbonitrile, BAY 68-4986, BAY-68-4986, BAY68-4986

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C25H18ClN5O2S2
CAS Number:
544417-40-5
Molecular Weight:
520.03
MDL number:
MFCD09954113
UNSPSC Code:
12352200

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

N#CC1=C(C2=CC=C(OCCO)C=C2)C(C#N)=C(N)N=C1SCC3=CSC(C4=CC=C(Cl)C=C4)=N3

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)

InChI key

CITWCLNVRIKQAF-UHFFFAOYSA-N

Biochem/physiol Actions

Capadenoson (BAY 68-4986) is an adenosine receptor A1 (A1AR) partial agonist (GTPγS binding EC50/Emax = 0.1 nM/74% vs. 0.3 nM/100% with CCPA; human cortex membranes) that exerts additional biased A2BAR agonism toward cAMP signal transduction (pEC50 = 8.94/cAMP, 6.20/Ca+2, 6.12/pERK, 5.03/IP1), while exhibiting weak A2A & A3 potency. Capadenoson offers cardioprotection efficacy in an ischemia-reperfusion injury rat model in vivo (25/28% infarct size reduction with 0.1/0.3 mg/kg iv.) without the risk of a full atrioventricular (AV) block (isolated perfused rat heart rate = 100% up to 10 nM, 90% at ≥10 μM) seen with the full A1 agonist CCPA.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Daniel Meibom et al.
ChemMedChem, 12(10), 728-737 (2017-05-11)
Adenosine is known to be released under a variety of physiological and pathophysiological conditions to facilitate the protection and regeneration of injured ischemic tissues. The activation of myocardial adenosine A1 receptors (A1 Rs) has been shown to inhibit myocardial pathologies associated

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service