AICAR,5-amino-1-[(3R,4S,5R)-3,CAS:2627-69-2

Synonyms:

5-amino-1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)-2-oxolanyl]-4-imidazolecarboxamide;5-amino-1-[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide;SPECTRUM1505167;SCHEMBL2394079;CHEBI:93920;HMS3264I05;Pharmakon1600-01505167;NSC759596;CCG-214008;NSC-759596;NCGC00264064-02;5-amino-1-ribosyl-4-imidazolecarboxamide;AB01563376_01;SR-01000872728;SR-01000872728-1;BRD-A95696820-001-01-4;Q27165673

Canonical SMILES:

C1=NC(=C(N1C2C(C(C(O2)CO)O)O)N)C(=O)N

Isomeric SMILES:

C1=NC(=C(N1C2[C@@H]([C@@H]([C@H](O2)CO)O)O)N)C(=O)N

Description

AICAR (2627-69-2) activates AMP-activated protein kinase (AMPK). Promotes ligand-independent activation of the insulin receptor.1 Promotes skeletal muscle autophagy via activation of FoxO3a.2 Controls smooth muscle cell hyperproliferation in vascular disease.3 ?Induces osteogenic differentiation in mesenchymal stem cells.4 Inhibits proinflammatory response in glial cells.5 Cell permeable.

Uses

glucose uptake stimulant; AMPK activator 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. 5-Aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside is used as a cell permeable activator of AMP-activated protein kinase (AMPK), a metabolic master regulator that is activated in times of reduced energy availability (high cellular AMP:ATP ratios) and serves to inhibit anabolic processes. In vivo, pharmacologic activation of AMPK with AICAR mimics exercise and triggers insulin-independent glucose uptake by skeletal muscle.

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