AICAR

Cayman Chemical Item Number 10010241

AICA Riboside; Acadesine; NSC 105823 (CAS 2627-69-2)

AICAR (CAS 2627-69-2)

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Description

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 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 NFκB and C/EBP pathways.4

1 Hardie, D.G., and Carling, D. The AMP-activated protein kinase. Fuel gauge of the mammalian cell? Eur J Biochem 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? Eur J Biochem 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-I-beta-4-ribofuranoside (AICAR) attenuates the expression of LPS- and Aβ peptide-induced inflammatory mediators in astroglia. J Neuroinflammation 2 1-21 (2005).

Synonyms
  • AICA Riboside
  • Acadesine
  • NSC 105823
Formal Name 5-​amino-​1-​β-​D-​ribofuranosyl-​1H-​imidazole-​4-​carboxamide
CAS Number 2627-69-2
Molecular Formula C9H14N4O5
Formula Weight 258.2
Formulation A crystalline solid
Purity ≥98%
λmax 268 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OC[C@@H]​1[C@@H]​(O)​[C@@H]​(O)​[C@H]​(N2C(N)​=C(C(N)​=O)​N=C2)​O1
InCHI Code
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​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
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RTRQQBHATOEIAF-UUOKFMHZSA-N

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Size Price Quantity Subtotal
5 mg $8.00 $0.00
10 mg $15.00 $0.00
50 mg $64.00 $0.00
100 mg $112.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-23. Prices are subject to change without notice.

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