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Product Name: | AICAR |
Synonyms: | ACADESINE;AICAR;AICA-RIBOSIDE;AMPK;1-Deoxy-1-[(4-carbamoyl-5-amino-1H-imidazole)-1-yl]-β-D-ribofuranose;1-β-D-Ribofuranosyl-5-amino-1H-imidazole-4-carboxamide;5-Amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide;AICA-β-D-Riboside |
CAS: | 2627-69-2 |
MF: | C9H14N4O5 |
MW: | 258.23 |
EINECS: | 220-097-5 |
Product Categories: | ARASINE;Cardiovascular APIs;PI3K/Akt/mTOR;PI3K;Bases & Related Reagents;Carbohydrates & Derivatives;Nucleotides;Protein Kinase;Akt;mTOR |
Mol File: | 2627-69-2.mol |
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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, 5-amino-1-.beta.-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 |
HS Code | 29349990 |
MSDS Information |
Provider | Language |
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SigmaAldrich | English |
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 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 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 lymphoblastic leukemia and is reported to have cardioprotective effects. |
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. |
Risk Statements:R36/37/38
Hazard Codes:Xi: Irritant;
CAS No.:2627-69-2
Synonyms:View MoreArasine; Acadesine,AICA; AICA-RIBOSIDE; GP 1-110; Acadesine; AMPK; AIC-Riboside; 5-amino-4-imidazole carboxamide ribonucleoside; ACADESINE; Z-RIBOSIDE;
Formula:C9H14N4O5
Exact Mass:258.09600
Molecular Weight:258.23100
PSA:156.85000
LogP:-1.54280
Aicar | |
CAS No.: | 2627-69-2 |
---|---|
Synonyms: | |
Formula: | C9H14N4O5 |
Exact Mass: | 258.09600 |
Molecular Weight: | 258.23100 |
PSA: | 156.85000 |
LogP: | -1.54280 |
Properties
|
|
Melting Point: | 214-215oC |
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Boiling Point: | 726.3oC at 760 mmHg |
Density: | 2.06 g/cm3 |
Storage Temp: | -20oC |
Flash Point: | 393.1oC |
Appearance: | Solid |
Vapor Pressure: | 3.83E-22mmHg at 25C |
Refractive Index: | 1.821 |
Safety Info
|
|
Safety Statements: | 26-36 |
---|---|
WGK Germany: | 3 |
Risk Statements: | R36/37/38 |
Hazard Codes: | Xi: Irritant; |
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