| AICAR Basic information |
| adenosine regulating agents |
| Product Name: | AICAR |
| Synonyms: | ACADESINE;AICAR;AICA-RIBOSIDE;AMPK;5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-RIBOSIDE;5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-B-D-RIBOFURANOSIDE;5-AMINOIMIDAZOLE-4-CARBOXAMIDE 1-BETA-D-RIBOFURANOSIDE;Z-RIBOSIDE |
| CAS: | 2627-69-2 |
| MF: | C9H14N4O5 |
| MW: | 258.23 |
| EINECS: | 220-097-5 |
| Product Categories: | Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides;Protein Kinase;ARASINE;Cardiovascular APIs;PI3K/Akt/mTOR;Akt;mTOR;PI3K |
| Mol File: | |
| AICAR Chemical Properties |
| Melting point | 214-215 °C |
| storage temp. | −20°C |
| solubility | H2O: >10 mg/mL |
| form | powder |
| color | tan |
| Water Solubility | Soluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml |
| λmax | 265nm(NaOH)(lit.) |
| Merck | 14,16 |
| InChIKey | RTRQQBHATOEIAF-UUOKFMHZSA-N |
| CAS DataBase Reference | 2627-69-2(CAS DataBase Reference) |
| EPA Substance Registry System | 1H-Imidazole-4-carboxamide, .-D-ribofuranosyl- (2627-69-2) |
| Safety Information |
| Hazard Codes | Xi,T |
| Risk Statements | 36/37/38-61 |
| Safety Statements | 26-36-45-53 |
| WGK Germany | 3 |
| TSCA | Yes |
| AICAR Usage And Synthesis |
| 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 srylated to ZMP (AICA ribotide), which is further metabolised to Inosine mono-ste (an intermediate in the synthesis ofadenosine triste (ATP) and guanosine tris-te). 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 death. |
| Chemical Properties | Solid |
| Uses | glucose uptake stimulant; AMPK activator |
| 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. |
| 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 lymblastic leukemia and is reported to have cardioprotective effects. |
| Biological Activity | permeable, allosteric activator of AMP-activated protein kinase (AMPK). Augments proliferation, differentiation and mineralization of osteoblastic MC3T3-EI and attenuates psychosine-induced expression of proinflammatory cytokines and iNOS in astrocytes. |
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