Acadesine

Acadesine
Clinical data
Other names	5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranoside, AICA-riboside, AICAR
ATC code	C01EB13 (WHO) ;
Identifiers
	IUPAC name 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide;
CAS Number	2627-69-2 ;
PubChem CID	17513;
IUPHAR/BPS	5133;
ChemSpider	16560 ;
UNII	53IEF47846;
KEGG	D02742 ;
ChEBI	CHEBI:28498 ;
ChEMBL	ChEMBL1551724 ;
CompTox Dashboard (EPA)	DTXSID5046015 ;
ECHA InfoCard	100.018.271
Chemical and physical data
Formula	C9H14N4O5
Molar mass	258.234 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(c1ncn(c1N)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO)N;
	InChI InChI=1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1 ; Key:RTRQQBHATOEIAF-UUOKFMHZSA-N ;
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Acadesine (INN), also known as 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside, AICA-riboside, and AICAR, is an AMP-activated protein kinase activator which is used for the treatment of acute lymphoblastic leukemia and may have applications in treating other disorders such as diabetes. Acadesine has been used clinically to treat and protect against cardiac ischemic injury. The drug was first used in the 1980s as a method to preserve blood flow to the heart during surgery.

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.