SML2852

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
• Empirical Formula (Hill Notation): C₂₅H₁₈ClN₅O₂S₂
• CAS Number: 544417-40-5
• Molecular Weight: 520.03
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD09954113
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Quality Segment: 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

Description

Biochem/physiol Actions

Capadenoson (BAY 68-4986) is an adenosine receptor A1 (A1AR) partial agonist (GTPγS binding EC₅₀/E_max = 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.

Partial adenosine receptor A1 and cAMP-biased A2B agonist with in vivo cardioprotection efficacy without the risk of a full atrioventricular block.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable