AICA ribonucleotide
Identifiers
CAS number	3031-94-5
PubChem	65110
MeSH	AICA+ribonucleotide
SMILES	O=P(O)(O)OC[C@H]2O[C@@H](n1cnc(C(=O)N)c1N)[C@H](O)[C@@H]2O
InChI	1/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
InChI key	NOTGFIUVDGNKRI-UUOKFMHZBG
ChemSpider ID	58620
Properties
Molecular formula	C9H15N4O8P
Molar mass	338.211 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

AICA ribonucleotide or AICAR (aminoimidazole carboxamide ribonucleotide) is an intermediate in the generation of inosine monophosphate, which acts as an AMP-activated protein kinase agonist.^[1] It stimulates glucose uptake and increases the activity of p38 mitogen-activated protein kinases α and β in skeletal muscle tissue,^[2] as well as suppressing apoptosis by reducing production of reactive oxygen compounds inside the cell.^[3]

In 2008, researchers at the Salk Institute discovered that AICAR given to experimental mice significantly improves their performance in endurance-type exercise, apparently by converting fast-twitch muscle fibers to the more energy-efficient, fat-burning, slow-twitch type. They also looked at the administration of GW 501516 (also called GW1516) in combination with AICAR. Given to mice that did not exercise, this combination activated 40% of the genes that were turned on when mice were given GW1516 and made to exercise. This suggests it may be possible to obtain some of the benefits of exercising without actually exercising.^[4] Because of the enhanced endurance effects, this could potentially be used by athletes to enhance their performance. One of the lead researchers from this study has developed a urine test to detect it and has made the test available to the International Olympic Committee, and the World Anti-Doping Agency has added AICAR to the prohibited list from 2009 onwards.^[5]

[edit] See also

• GW 501516
• Inosine monophosphate synthase

[edit] References

v • d • e Nucleotide metabolic intermediates Purine metabolism Anabolism R5P→IMP: R5P · PRPP · PRA · GAR · FGAR · FGAM · AIR · CAIR · SAICAR · AICAR · FAICAR IMP→AMP: Adenylosuccinate IMP→GMP: Xanthosine monophosphate Catabolism Hypoxanthine · Xanthine · Uric acid · 5-Hydroxyisourate Pyrimidine metabolism Anabolism Carbamoyl phosphate · Carbamoyl aspartic acid · 4,5-Dihydroorotic acid · Orotic acid · Orotidine 5'-monophosphate · Uridine monophosphate Catabolism uracil: Dihydrouracil · 3-Ureidopropionic acid · β-Alanine thymine: Dihydrothymine · β-Ureidoisobutyric acid · 3-Aminoisobutyric acid see also enzymes, disorders

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