Acadesine
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MedKoo CAT#: 200079

CAS#: 2627-69-2

Description: 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[2] and may have applications in treating other disorders such as diabetes. 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.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 250
1g
USD 950
Size
Price

25mg
USD 190
200mg
USD 350
2g
USD 1550
Size
Price

50mg
USD 210
500mg
USD 550

Acadesine (AIACR), purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200079
Name: Acadesine
CAS#: 2627-69-2
Chemical Formula: C9H14N4O5
Exact Mass: 258.09642
Molecular Weight: 258.231
Elemental Analysis: C, 41.86; H, 5.46; N, 21.70; O, 30.98


Synonym: GP 1 110; ARA100; ARA-100; ARA 100; SCH-900395; SCH 900395; SCH900395; AICA ribofuranoside; AICA ribonucleoside; AICA riboside; Z-riboside. Acadesinum; Acadesina; Protara.

IUPAC/Chemical Name: 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide

InChi Key: RTRQQBHATOEIAF-UUOKFMHZSA-N

InChi Code: 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

SMILES Code: O=C(C1=C(N)N([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C=N1)N


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

According to http://en.wikipedia.org/wiki/Acadesine, acadesine (INN) (5-aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside, AICA-riboside) is an AMP-activated protein kinase activator which is used for the treatment of acute lymphoblastic leukemia[2] and may have applications in treating other disorders such as diabetes. 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.
  
 
 


References

1: Montraveta A, Xargay-Torrent S, López-Guerra M, Rosich L, Pérez-Galán P, Salaverria I, Beà S, Kalko SG, de Frias M, Campàs C, Roué G, Colomer D. Synergistic anti-tumor activity of acadesine (AICAR) in combination with the anti-CD20 monoclonal antibody rituximab in in vivo and in vitro models of mantle cell lymphoma. Oncotarget. 2014 Feb 15;5(3):726-39. PubMed PMID: 24519895; PubMed Central PMCID: PMC3996675.

2: Glazunova VA, Lobanov KV, Shakulov RS, Mironov AS, Shtil AA. Acadesine Triggers Non-apoptotic Death in Tumor Cells. Acta Naturae. 2013 Jul;5(3):74-8. PubMed PMID: 24303202; PubMed Central PMCID: PMC3848068.

3: D'Errico S, Oliviero G, Borbone N, Amato J, Piccialli V, Varra M, Mayol L, Piccialli G. Synthesis of new acadesine (AICA-riboside) analogues having acyclic D-ribityl or 4-hydroxybutyl chains in place of the ribose. Molecules. 2013 Aug 6;18(8):9420-31. doi: 10.3390/molecules18089420. PubMed PMID: 23924994.

4: Van Den Neste E, Cazin B, Janssens A, González-Barca E, Terol MJ, Levy V, Pérez de Oteyza J, Zachee P, Saunders A, de Frias M, Campàs C. Acadesine for patients with relapsed/refractory chronic lymphocytic leukemia (CLL): a multicenter phase I/II study. Cancer Chemother Pharmacol. 2013 Mar;71(3):581-91. doi: 10.1007/s00280-012-2033-5. Epub 2012 Dec 11. PubMed PMID: 23228986; PubMed Central PMCID: PMC3579463.

5: Lim GB. Surgery: No benefit of acadesine in CABG. Nat Rev Cardiol. 2012 Sep;9(9):493. doi: 10.1038/nrcardio.2012.111. Epub 2012 Jul 31. PubMed PMID: 22847168.

6: Newman MF, Ferguson TB, White JA, Ambrosio G, Koglin J, Nussmeier NA, Pearl RG, Pitt B, Wechsler AS, Weisel RD, Reece TL, Lira A, Harrington RA; RED-CABG Steering Committee and Investigators. Effect of adenosine-regulating agent acadesine on morbidity and mortality associated with coronary artery bypass grafting: the RED-CABG randomized controlled trial. JAMA. 2012 Jul 11;308(2):157-64. doi: 10.1001/jama.2012.7633. PubMed PMID: 22782417.

7: Van Den Neste E, Van den Berghe G, Bontemps F. AICA-riboside (acadesine), an activator of AMP-activated protein kinase with potential for application in hematologic malignancies. Expert Opin Investig Drugs. 2010 Apr;19(4):571-8. doi: 10.1517/13543781003703694. Review. Erratum in: Expert Opin Investig Drugs. 2010 Jun;19(6):807. PubMed PMID: 20367195.

8: Zhang W, Wang J, Wang H, Tang R, Belcher JD, Viollet B, Geng JG, Zhang C, Wu C, Slungaard A, Zhu C, Huo Y. Acadesine inhibits tissue factor induction and thrombus formation by activating the phosphoinositide 3-kinase/Akt signaling pathway. Arterioscler Thromb Vasc Biol. 2010 May;30(5):1000-6. doi: 10.1161/ATVBAHA.110.203141. Epub 2010 Feb 25. PubMed PMID: 20185792; PubMed Central PMCID: PMC3626455.

9: Robert G, Ben Sahra I, Puissant A, Colosetti P, Belhacene N, Gounon P, Hofman P, Bost F, Cassuto JP, Auberger P. Acadesine kills chronic myelogenous leukemia (CML) cells through PKC-dependent induction of autophagic cell death. PLoS One. 2009 Nov 18;4(11):e7889. doi: 10.1371/journal.pone.0007889. PubMed PMID: 19924252; PubMed Central PMCID: PMC2775681.

10: Drew BG, Kingwell BA. Acadesine, an adenosine-regulating agent with the potential for widespread indications. Expert Opin Pharmacother. 2008 Aug;9(12):2137-44. doi: 10.1517/14656566.9.12.2137 . Review. PubMed PMID: 18671468.