CP-532,903

CP-532,903 is a selective adenosine A3 subtype receptor agonist. It has antiinflammatory effects and has been shown to reduce superoxide generation in damaged tissues,[1] and protects against tissue damage following myocardial ischemia,[2] mediated via an interaction with ATP-sensitive potassium channels.[3]

CP-532,903
Names
IUPAC name
6-{[(2,5-Dichlorophenyl)methyl]amino}-9H-purin-9-yl 3-amino-3-deoxy-N-methyl-β-D-ribofuranosiduronamide
Systematic IUPAC name
(2S,3S,4R,5R)-3-Amino-5-(6-{[(2,5-dichlorophenyl)methyl]amino}-9H-purin-9-yl)-4-hydroxy-N5-methyloxolane-2-carboxamide
Other names
CP-532,903
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C18H19Cl2N7O3/c1-22-17(29)14-11(21)13(28)18(30-14)27-7-26-12-15(24-6-25-16(12)27)23-5-8-4-9(19)2-3-10(8)20/h2-4,6-7,11,13-14,18,28H,5,21H2,1H3,(H,22,29)(H,23,24,25)/t11-,13+,14-,18+/m0/s1 checkY
    Key: WFRYPIJMCFQCGT-MHMFGPJMSA-N checkY
  • InChI=1/C18H19Cl2N7O3/c1-22-17(29)14-11(21)13(28)18(30-14)27-7-26-12-15(24-6-25-16(12)27)23-5-8-4-9(19)2-3-10(8)20/h2-4,6-7,11,13-14,18,28H,5,21H2,1H3,(H,22,29)(H,23,24,25)/t11-,13+,14-,18+/m0/s1
    Key: WFRYPIJMCFQCGT-MHMFGPJMBE
  • Clc3ccc(Cl)cc3CNc(c1nc4)ncnc1n4C(C(O)C2N)OC2C(=O)NC
  • Clc1cc(c(Cl)cc1)CNc4ncnc2c4ncn2[C@@H]3O[C@H](C(=O)NC)[C@@H](N)[C@H]3O
Properties
C18H19Cl2N7O3
Molar mass 452.294
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. van der Hoeven D, Wan TC, Auchampach JA. Activation of the A(3) adenosine receptor suppresses superoxide production and chemotaxis of mouse bone marrow neutrophils. Molecular Pharmacology. 2008 Sep;74(3):685-96. PMID 18583455
  2. Tracey WR, Magee WP, Oleynek JJ, Hill RJ, Smith AH, Flynn DM, Knight DR. Novel N6-substituted adenosine 5'-N-methyluronamides with high selectivity for human adenosine A3 receptors reduce ischemic myocardial injury. American Journal of Physiology. Heart and Circulatory Physiology. 2003 Dec;285(6):H2780-7. PMID 12919933
  3. Wan TC, Ge ZD, Tampo A, Mio Y, Bienengraeber MW, Tracey WR, Gross GJ, Kwok WM, Auchampach JA. The A3 adenosine receptor agonist CP-532,903 [N6-(2,5-dichlorobenzyl)-3'-aminoadenosine-5'-N-methylcarboxamide] protects against myocardial ischemia/reperfusion injury via the sarcolemmal ATP-sensitive potassium channel. Journal of Pharmacology and Experimental Therapeutics. 2008 Jan;324(1):234-43. doi:10.1124/jpet.107.127480 PMID 17906066


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