Acadesine

Base Information

• Chemical Name: Acadesine
• CAS No.: 2627-69-2
• Molecular Formula: C9H14N4O5
• Molecular Weight: 258.234
• Hs Code.: 29349990
• European Community (EC) Number: 220-097-5
• UNII: 53IEF47846
• DSSTox Substance ID: DTXSID5046015
• Nikkaji Number: J14.878D
• Wikipedia: Acadesine
• Wikidata: Q4671562
• NCI Thesaurus Code: C71537
• Metabolomics Workbench ID: 149346
• ChEMBL ID: CHEMBL1551724
• Mol file: 2627-69-2.mol

Synonyms:1-ribosyl-4-carboxamido-5-aminoimidazole;5-aminoimidazole-4-carboxamide 1-ribofuranoside;5-aminoimidazole-4-carboxamide riboside;acadesine;AICA ribofuranoside;AICA ribonucleoside;AICA riboside;aminoimidazole carboxamide ribonucleoside;ARA 100;ARA-100;ARA100;arasine;GP 1 110;Z-riboside

Chemical Property of Acadesine

Chemical Property:

• Appearance/Colour: tan powder
• Vapor Pressure: 3.83E-22mmHg at 25°C
• Melting Point: 214-215 °C
• Refractive Index: 1.821
• Boiling Point: 726.3 °C at 760 mmHg
• PKA: 13.27±0.70(Predicted)
• Flash Point: 393.1 °C
• PSA: 156.85000
• Density: 2.06 g/cm³
• LogP: -1.54280
• Storage Temp.: −20°C
• Solubility.: H2O: >10 mg/mL
• Water Solubility.: Soluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 258.09641956
• Heavy Atom Count: 18
• Complexity: 330

Purity/Quality:

99% ^*data from raw suppliers

PRKAa1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-61
• Safety Statements: 26-36-45-53

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC(=C(N1C2C(C(C(O2)CO)O)O)N)C(=O)N
• Isomeric SMILES: C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N)C(=O)N
• Recent ClinicalTrials: GFM-Acadesine: A Phase I-II Trial of Acadesine
• Recent EU Clinical Trials: A phaseI-II trial of acadesine in ipss high and int 2 myelodysplastic syndromes, acute myeloid leukemia with 20-30% marrow blasts and chronic myelomonocytic leukemia type 2 not responding to azacitidine or decitabine for at least 6 courses or relapsing after a response
• Description: AICAR (2627-69-2) activates AMP-activated protein kinase (AMPK). Promotes ligand-independent activation of the insulin receptor.1 Promotes skeletal muscle autophagy via activation of FoxO3a.2 Controls smooth muscle cell hyperproliferation in vascular disease.3 ?Induces osteogenic differentiation in mesenchymal stem cells.4 Inhibits proinflammatory response in glial cells.5 Cell permeable.
• Uses: glucose uptake stimulant; AMPK activator AICAR is a nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) hav e been recognized for therapeutic potential in myocardial ischemia. Cardioprotective. 5-Aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside is used as a cell permeable activator of AMP-activated protein kinase (AMPK), a metabolic master regulator that is activated in times of reduced energy availability (high cellular AMP:ATP ratios) and serves to inhibit anabolic processes. In vivo, pharmacologic activation of AMPK with AICAR mimics exercise and triggers insulin-independent glucose uptake by skeletal muscle.
• Therapeutic Function: Cardiotonic, Platelet aggregation inhibitor

Technology Process of Acadesine

There total 34 articles about Acadesine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

5-amino-1-(5′-O-tert-butyldimethylsilyl-2′,3′-O-isopropylidene-β-D-ribofuranosyl)imidazole-4-carboxamide (197437-76-6) → AICA riboside (2627-69-2)

Guidance literature:

With trifluoroacetic acid; In acetonitrile; at 0 - 20 ℃; for 17h;

DOI:10.1016/j.bmc.2008.11.057

Reference yield: 74.0%

9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1-((2-methoxyethoxy)methyl)-1,9-dihydro-6H-purin-6-one (659746-61-9) → AICA riboside (2627-69-2)

Guidance literature:

With sodium hydroxide; for 1h; Reflux;

Reference yield: 72.0%

5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile (23192-64-5) → AICA riboside (2627-69-2)

Guidance literature:

With sodium hydroxide; at 100 ℃; for 2.5h;

DOI:10.1021/jo00206a004

upstream raw materials:

5-Amino-1-(β-D-ribofuranosyl)imidazole-4-carboxylic Acid Hydrazide

5-nitro-1-β-D-ribofuranosyl-1H-imidazole-4-carboxylic acid amide

5-amino-1-(β-D-ribofuranosyl)imidazole-4-(N-benzyl)carboxamide

2,3,5-tri-O-benzoyl-β-D-ribofuranosyl azide

Downstream raw materials:

5-aminoimidazole-4-carboxamide ribonucleotide

(5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-((phosphonooxy)methyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carbonyl)-L-aspartic acid

7-(2,3,5,-tri-O-acetyl-β-D-ribofuranosyl)imidazo[4,5-d][1,2,3]triazin-4-one

7-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,7-dihydro-4H-imidazo[4,5-d][1,2,3]triazin-4-one

Refernces

• 1、 Oliviero, Giorgia,Amato, Jussara,D'Errico, Stefano,Borbone, Nicola,Piccialli, Gennaro,Mayol, Luciano. "Solid phase synthesis of nucleobase and ribose modified inosine nucleoside analogues". . p. 1649 - 1652. Retrieved 2007.
• 2、 -. "SAICAR Synthesis method". Paragraph 0053; 0061-0062; 0076; 0083-0084; 0098; 0105-0106. . Retrieved 2021/11/06.