Acadesine | AIACR | CAS#2627-69-2 | AMP-activated protein kinase activator

MedKoo Cat#: 200079 | Name: Acadesine

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Acadesine, also known as 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 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.

Chemical Structure

Acadesine

CAS#2627-69-2

Theoretical Analysis

MedKoo Cat#: 200079

Name: Acadesine

CAS#: 2627-69-2

Chemical Formula: C9H14N4O5

Exact Mass: 258.0964

Molecular Weight: 258.23

Elemental Analysis: C, 41.86; H, 5.46; N, 21.70; O, 30.98

Price and Availability

Size	Price	Availability
250mg	USD 250.00	2 Weeks
500mg	USD 400.00	2 Weeks
1g	USD 650.00	2 Weeks
2g	USD 950.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

ARA100; ARA-100; ARA 100; GP 1 110; SCH-900395; SCH 900395; SCH900395; AICA ribofuranoside; AICA ribonucleoside; AICA riboside; AICAR; NSC 105823; NSC105823; NSC-105823

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

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).

HS Tariff Code

2934.99.9001

More Info

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.

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 258.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

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.