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2627-69-2

2627-69-2 Structure

2627-69-2 Structure
IdentificationMore
[Name]

AICAR
[CAS]

2627-69-2
[Synonyms]

5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-B-D-RIBOFURANOSIDE
5-AMINOIMIDAZOLE-4-CARBOXAMIDE 1-BETA-D-RIBOFURANOSIDE
5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-RIBOSIDE
ACADESINE
AICAR
AICA-RIBOSIDE
AMPK
N1-(BETA-D-RIBOFURANOSYL)-5-AMINOIMIDAZOLE-4-CARBOXAMIDE
Z-RIBOSIDE
5-amino-1-beta-d-ribofuranosyl-1h-imidazole-4-carboxamid
5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide
5-Amino-1-beta-ribofuranosyl-imidazole-4-carboxamide
5-Amino-4-imidazolecarboxamide ribofuranoside
5-Aminoimidazole-4-carboxamide ribonucleoside
5-Aminoimidazole-4-carboxamide riboside
AIC-Riboside
5-amino-1-beta-D-ribofuranosyl-1H-imidazole-4-carboxamide
Aminoimidazole-4-carboxamide-1-D-Ribofuranoside
5-AMINOIMIDAZOLE-4-BETA-D-RIBOFURANOSE
AMINOIMIDAZOLE-4-CARBOXAMIDE-1-SS-D-RIBOFURANOSIDE
[EINECS(EC#)]

220-097-5
[Molecular Formula]

C9H14N4O5
[MDL Number]

MFCD00869751
[Molecular Weight]

258.23
[MOL File]

2627-69-2.mol
Questions And AnswerBack Directory
[adenosine regulating agents]

Acadesine is the prototype of a new class of compounds termed adenosine regulating agents. Acadesine is a purine nucleosid analogue that enters the myocyte and is immediately phosphorylated to ZMP (AICA ribotide), which is further metabolised to Inosine mono-phosphate (an intermediate in the synthesis ofadenosine triphosphate (ATP) and guanosine triphos-phate).
Claims that acadesine may serve as a substrate for ATP synthesis and result in repletion of myocardial ATP were supported by some studies and refuted by others. Because acadesine may be a precursor in the synthesis of myocardial ATP it was proposed as a possible agent of myocardial protection during ischaemia, particularly because myocardial ATP depletion has been linked to cell death.
Chemical PropertiesBack Directory
[Appearance]

Solid
[Melting point ]

214-215 °C
[mp ]

214-215 °C
[Boiling point ]

726.3±60.0 °C(Predicted)
[density ]

2.06±0.1 g/cm3(Predicted)
[storage temp. ]

−20°C
[solubility ]

H2O: >10 mg/mL
[form ]

powder
[pka]

13.27±0.70(Predicted)
[color ]

tan
[Water Solubility ]

Soluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml
[Usage]

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) have been recognized for therapeutic potential in myocardial
[λmax]

265nm(NaOH)(lit.)
[Merck ]

14,16
[InChIKey]

RTRQQBHATOEIAF-UUOKFMHZSA-N
[CAS DataBase Reference]

2627-69-2(CAS DataBase Reference)
[EPA Substance Registry System]

2627-69-2(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[TSCA ]

Yes
[HS Code ]

29349990
Hazard InformationBack Directory
[Chemical Properties]

Solid
[Originator]

AICA,BIOMOL
[Uses]

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.
[Uses]

glucose uptake stimulant; AMPK activator
[Definition]

ChEBI: A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects.
[Manufacturing Process]

Adenosine 3', 5'-cyclic phosphate N'-oxide (76.0 g, 0.200 mole) as the dihydrate was dissolved in a solution of 400 ml DMSO and 31.0 g (0.204 mole) 1,5-diazabicyclo[5.4.0]undec-5-ene. The solution was cooled to 15°C and 40 ml methyl iodide was added with stirring at room temperature. After 30 min, the mixture had gelled; 1.5 L ethanol was added and the solid was thoroughly homogenized by vigorous stirring. The solid was filtered, and the resulting paste was resuspended in 2 L ethanol and homogenized. The product was again filtered, washed with ethanol and ether, and dried, giving 80.4 g of 1-methoxyadenosine 3',5'-cyclic phosphate suitable for further transformation (recrystallization from aqueous methanol with ether).
A solution of 30.0 g 1-methoxyadenosine 3',5'-cyclic phosphate (81.5 mmole), 20.0 g NaHCO3 (238 mmole), and 300 ml H2O was refluxed 45 mm. The pH of the solution was adjusted to 2.5 with Dowex 50x8 (H)+ while warm, and a water pump vacuum was applied to mixture to remove CO2. The pH was readjusted to 9-10 with NaOH, and the resin was removed by filtration. The solution was passed onto a column containing 400 ml Dowex 1x2 (formate, 100-200 mesh), and the column was washed well with water. The column was eluted with a gradient of 4 L water in the mixing chamber and 4 L 4 N formic acid in the reservoir. The first major product, coming after about 2 L eluate, was 5-amino-N-methoxy-1-β-D-ribofuranosylimidazole-4-carboxamidine 3',5'- cyclic phosphate, giving 5.4 g (19%) after evaporation of the solvent and trituration of the residue with ethanol (recrystallization from water). A solution of 5.0 g (14.3 mmoles) 5-amino-N-methoxy-1-β-Dribofuranosylimidazole- 4-carboxamidine 3',5'-cyclic phosphate in 200 ml H2 preheated to 60°C and containing approximately 5.0 g moist sponge nickel catalyst, was shaken with 2-3 atm. H2 at 60°C for 2 h. The filtered solution was evaporated to dryness to give 3.75 g of 5-amino-1-β-Dribofuranosylimidazole- 4-carboxamidine 3',5'-cyclic phosphate (82%), (recrystallization from water).
A mixture of 4.0 g (12.5 mmole) 5-amino-1-β-D-ribofuranosylimidazole-4- carboxamidine 3',5'-cyclic phosphate and 100 ml conc. NH4OH was heated in a bomb at 100°C for 16 h, then cooled and evaporated in vacuum. The residue was taken up in 100 ml H2O and applied to a 2.5x20 cm column of Dowex 1x2 (formate form, 100-200 mesh). After washing well with H2O the column was eluted with a gradient of 1 L H2O in the mixing chamber and 1 L 3 N formic acid in the reservoir. Fractions containing the product, appearing near the end of the elution, were evaporated. Trituration of the residue with EtOH gave 2.90 g (68%) of 5-amino-1-β-D-ribofuranosylimidazole-4- carboxamide 3',5'-cyclic phosphate.
The 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide may be produced by hydrolysis of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide 3',5'- cyclic phosphate with NaOH.
[Therapeutic Function]

Cardiotonic, Platelet aggregation inhibitor
[Biological Activity]

Cell-permeable, allosteric activator of AMP-activated protein kinase (AMPK). Augments proliferation, differentiation and mineralization of osteoblastic MC3T3-EI cells and attenuates psychosine-induced expression of proinflammatory cytokines and iNOS in astrocytes.
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

2627-69-2(sigmaaldrich)
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