Potent AMPK activator. AICAR activates AMPK due to increased phosphorylation, causes phosphorylation and inactivation of HMG-CoA reductase, and almost total cessation of fatty acid and sterol synthesis. AICAR causes ZMP (a cellular mimetic of AMP) to accumulate inside the cell but does not perturb the cellular contents of ATP, ADP or AMP, and induces differentiation of acute myeloid leukemia cells, and astroglial differentiation of neural stem cells via activating the JAK/STAT3 pathway independently of AMP-activated protein kinase. AICAR can also significantly up-regulate pluripotency-associated genes and down-regulate differentiation-associated transcription factors.
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AICAR (AR50)
CAS number
2627-69-2
Purity
>98%
Molecular weight
258.23 Da
Molecular formula
C9H14N4O5
PubChem
17513
Nature
Synthetic
Biochemical name
Acadesine
Biological description
Cell-permeable activator of AMP-activated protein kinase. Is taken up into cells by adenosine transporters and phosphorylated by adenosine kinase to the active nucleotide ZMP (5-aminoimidazole-4-carboxamide ribonucleoside), which mimics effects of AMP on the AMPK system. Active in vivo and in vitro.
Canonical smiles
C1=NC(=C(N1C2C(C(C(O2)CO)O)O)N)C(=O)N
Isomeric smiles
C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N)C(=O)N
IUPAC Name
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
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