16. Acadesine

Nomenclature

CAS number: 2627-69-2
5-Amino-1-β-d-ribofuranosyl-1H-imidazole-4-carboxamide; 5-amino-4-imidazolecarboxamide ribonucleoside; AICA-riboside; Arasine (Gensia); Protara (Gensia).
C9H14N4O5; mol wt 258.23.
C 41.86%, H 5.46%, N 21.70%, O 30.98%.

Description and references

Purine nucleoside analog. Prototype adenosine regulating agent; enhances endogenous adenosine levels in ischemic tissue. Biosynthesis, isoln, and characterization: G. R. Greenberg, E. L. Spilman, J. Biol. Chem. 219, 411 (1956). Chemical synthesis: J. Baddiley et al., Proc. Chem. Soc. London 1957, 149; J. P. Ferris et al., J. Org. Chem. 50, 747 (1985); T. Saito et al., Chem. Pharm. Bull. 42, 2263 (1994). Pharmacology: Z.-Q. Zhao et al., Cardiovasc. Res. 29, 495 (1995). Antiplatelet activity: D. A. Bullough et al., J. Clin. Invest. 94, 1524 (1994). Disposition and metabolism: R. Dixon et al., J. Clin. Pharmacol. 33, 955 (1993). HPLC determn in plasma: L.-S. Chen et al., J. Liq. Chromatogr. 18, 1451 (1995). Review of pharmacology: K. Mullane, M. Young, Drug Dev. Res. 28, 336-343 (1993); of development: K. Mullane et al., Trends Cardiovasc. Med. 3, 227-234 (1993). Meta-analysis of clinical trials in coronary artery bypass graft surgery: D. T. Mangano et al., J. Am. Med. Assoc. 277, 325-332 (1997).

Chemical structure

Properties

Crystals from methanol or water, mp 213-214° (dec). Also reported as slightly brownish prisms from 90% aq ethanol, mp 206-208° (dec) (Saito). uv max (pH 7 and 1N NaOH): 265 nm (ε 12400). uv max (1N HCl): 245, 265 nm (ε 8670, 10320).

Therapeutic Category

Cardioprotective.

Keywords

Cardioprotective