| Identification | Back Directory | [Name]
CAPADENOSON | [CAS]
544417-40-5 | [Synonyms]
CS-1666
BAY 68-4986
CAPADENOSON
Capadenoson, BAY 68-4986
2-Amino-6-[[[2-(4-chlorophenyl)-4-thiazolyl]methyl]thio]-4-[4-(2-hydroxyethoxy)phenyl]-3,5-pyridinedicarbonitrile
3,5-Pyridinedicarbonitrile, 2-amino-6-[[[2-(4-chlorophenyl)-4-thiazolyl]methyl]thio]-4-[4-(2-hydroxyethoxy)phenyl]-
2-amino-6-[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methylsulfanyl]-4-[4-(2-hydroxyethoxy)phenyl]pyridine-3,5-dicarbonitrile | [Molecular Formula]
C25H18ClN5O2S2 | [MDL Number]
MFCD09954113 | [MOL File]
544417-40-5.mol | [Molecular Weight]
520.035 |
| Chemical Properties | Back Directory | [Boiling point ]
787.9±70.0 °C(Predicted) | [density ]
1.51 | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
Powder | [pka]
13.98±0.10(Predicted) | [color ]
Light yellow to yellow | [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) | [InChIKey]
CITWCLNVRIKQAF-UHFFFAOYSA-N | [SMILES]
C1(N)=NC(SCC2=CSC(C3=CC=C(Cl)C=C3)=N2)=C(C#N)C(C2=CC=C(OCCO)C=C2)=C1C#N |
| Hazard Information | Back Directory | [Uses]
Capadenoson is a selective agonist of adenosine-A1 receptor. | [Biological Activity]
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) th at exerts additional biased A2BAR agonism toward cAMP signal transduction (pEC50 = 8.94/cAMP6.20/Ca+26.12/pERK5.03/IP1)while exhibiting weak A2A & A3 potency. Capadenoson offers cardioprotection efficacy in an ischemia-reperfusion injury r at 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 r at heart rate = 100% up to 10 nM90% at ≥10 μM) seen with the full A1 agonist CCPA. | [Synthesis]
5.334 kg (24.90 mol) of 2-[4-(2-hydroxyethoxy)benzylidene]malononitrile (XI) and 1.309 kg (13.07 mol) of 2-cyano thioacetamide (XII) were suspended in 27.4 kg (34.8 l) of methanol. The suspension was warmed to 40°C and 3.779 kg (37.35 mol) of triethylamin | [in vivo]
In the in vivo experiments, Wistar rats and SHR are pre-treated with Capadenoson at a concentration of 0.15 mg/kg for 5 days. On day 5, a stress test (physical restraint) is performed for 2 hours. The plasma concentration of Capadenoson measured 3 hours after drug intake remains constant in the 5 days prior to the restraint stress test and averaged 7.63 μg/L on day 4 and 5, respectively[1]. | [target]
adenosine A1 receptor | [References]
[1] Bott-Flügel L, et al. 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
[2] Bailey IR, et al. 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 |
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DKMbiochem.Co. Ltd Gold
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15901859516 |
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http://www.dkmbiochem.com/ |
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