Acadesine

Title: Acadesine
CAS Registry Number: 2627-69-2
CAS Name: 5-Amino-1-b-D-ribofuranosyl-1H-imidazole-4-carboxamide
Additional Names: 5-amino-4-imidazolecarboxamide ribonucleoside; AICA-riboside
Trademarks: Arasine (Gensia); Protara (Gensia)
Molecular Formula: C9H14N4O5
Molecular Weight: 258.23
Percent Composition: C 41.86%, H 5.46%, N 21.70%, O 30.98%
Literature 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).
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 (e 12400). uv max (1N HCl): 245, 265 nm (e 8670, 10320).
Melting point: mp 213-214° (dec); mp 206-208° (dec) (Saito)
Absorption maximum: uv max (pH 7 and 1N NaOH): 265 nm (e 12400); uv max (1N HCl): 245, 265 nm (e 8670, 10320)
Therap-Cat: Cardioprotective.
Keywords: Cardioprotective.
Acamprosate Calcium Acarbose Acebutolol Acecainide Acecarbromal

Acadesine
Acadesine structure.png
Systematic (IUPAC) name
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide
Clinical data
Legal status  ?
Identifiers
CAS number 2627-69-2 N
ATC code C01EB13
PubChem CID 17513
ChemSpider 16560 YesY
UNII 53IEF47846 YesY
KEGG D02742 YesY
Chemical data
Formula C9H14N4O5 
Mol. mass 258.231 g/mol
 N (what is this?)  (verify)

Acadesine (INN), also known as 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside, AICA-riboside, and AICAR, is an AMP-activated protein kinase activator[1] which is used for the treatment of acute lymphoblastic leukemia[2] and may have applications in treating other disorders such as diabetes.[3]

Acadesine is an adenosine regulating agent developed by PeriCor Therapeutics and licensed to Schering-Plough in 2007 for phase III studies. The drug is a potential first-in-class agent for prevention of reperfusion injury in CABG surgery. Schering began patient enrollment in phase III studies in May, 2009. The trial was terminated in late 2010 based on an interim futility analysis.[4][5]