CP-532,903

CP-532,903

Names
IUPAC name (2S,3S,4R,5R)-3-amino-5-[6-(2,5-dichlorobenzylamino)purin-9-yl]-4-hydroxytetrahydrofuran-2-carboxylic acid methylamide
Other names CP-532,903
Identifiers
CAS Number	457612-59-8
3D model (Jmol)	Interactive image Interactive image
ChemSpider	8654410
PubChem	10479002
InChI 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 Key: WFRYPIJMCFQCGT-MHMFGPJMSA-N 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
SMILES 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
Chemical formula	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

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]

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