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AICAR

Item № 10010241
CAS № 2627-69-2
Purity ≥98%
product image
                (CAS 2627-69-2)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     50 mg $37.00 0.00
     100 mg $67.00 0.00
     250 mg $148.00 0.00
     500 mg $259.00 0.00

Pricing updated 2019-07-17. Prices are subject to change without notice.

Description
Synonyms
  • Acadesine
  • AICA riboside
  • NSC 105823

AMP-activated protein kinase (AMPK) functions as a metabolic sensor that regulates lipid and glucose metabolism to maintain cellular energy homeostasis and to protect against metabolic stress.1 AICAR is a selective activator of AMP-activated protein kinase (AMPK) in both hepatocytes and adipocytes.2 At 0.5 mM it inhibits the synthesis of fatty acids and sterols and inactivates HMG-CoA reductase in rat hepatocytes.2 AICAR (0.5 mM) inhibits insulin-stimulated glucose uptake to 62% of controls and reduces GLUT4 translocation 2.5-fold in 3T3-L1 adipocytes.3 It also blocks the expression of pro-inflammatory cytokines (TNF-α/IL-1β and IL-6), iNOS, COX-2, and MnSOD genes in glial cells and macrophages by inhibiting NF-κB and C/EBP pathways.4

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Technical Information
Formal Name
5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide
CAS Number
2627-69-2
Synonyms
  • Acadesine
  • AICA riboside
  • NSC 105823
Molecular Formula
C9H14N4O5
Formula Weight
258.2
Purity
≥98%
Formulation
A crystalline solid
λmax
268 nm
SMILES
OC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(N)=C(C(N)=O)N=C2)O1
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
InChI Key
RTRQQBHATOEIAF-UUOKFMHZSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
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Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

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References & Product Citations
Product Description References

1. Hardie, D.G., and Carling, D. The AMP-activated protein kinase. Fuel gauge of the mammalian cell? European Journal of Biochemistry 246, 259-273 (1997).

2. Corton, J.M., Gillespie, J.G., Hawley, S.A., et al. 5-aminoimidazole-4-carboxamide ribonucleoside. A specific method for activating AMP-activated protein kinase in intact cells? European Journal of Biochemistry 229, 558-565 (1995).

3. Salt, I.P., Connell, J.M.C., and Gould, G.W. 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR) inhibits insulin-stimulated glucose transport in 3T3-L1 adipocytes Diabetes 49, 1649-1656 (2000).

4. Ayasolla, K.R., Giri, S., Singh, A.K., et al. 5-aminoimidazole-4-carboxamide-Iβ4-ribofuranoside (AICAR) attenuates the expression of LPS- and Aβ peptide-induced inflammatory mediators in astroglia J. Neuroinflammation 2, 1-21 (2005).

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