AICAR

SIGMA/A9978 - ≥98% (HPLC), powder

Synonym: 5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside; Acadesine; N¹-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide

CAS Number: 2627-69-2
Empirical Formula (Hill Notation): C₉H₁₄N₄O₅
Molecular Weight: 258.23
EC Number: 220-097-5
MDL Number: MFCD00869751
Linear Formula: C₉H₁₄N₄O₅
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-A9978-5MG	5 mg	$89.00 1/EA	Add To Favorites
45-A9978-25MG	25 mg	$308.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: A9978-25MG

Properties
Descriptions
Safety Info.
Basic Data

assay	≥98% (HPLC)
color	tan
form	powder
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
mp	214-215 °C
Quality Level	100
shipped in	dry ice
SMILES string	NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N
solubility	H₂O: >7 mg/mL
storage temp.	−20°C

Application:	AICAR has been used to provide protection against cisplatin-induced acute kidney injury through the JAK (tyrosine-protein kinase )/STAT (signal transducer and activator of transcription )/SOCS (suppressor of cytokine signaling) pathway. It also has been used in the assay of FapR (malonyl-CoA responsive bacterial transcriptional factor )-NLuc (nanoLuciferase) biosensor activity.
Biochem/physiol Actions:	AICAR is 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.
Biochem/physiol Actions:	AICAR is a cell permeable activator of AMP-activated protein kinase (AMPK).
Features and Benefits:	This compound is a featured product for Kinase Phosphatase Biology research. Click here to discover more featured Kinase Phosphatase Biology products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm .
General description:	Adenosine monophosphate protein kinase (AMPK) activator 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR) modulates cellular energy. It regulates lipid and glucose metabolism, pro-inflammatory responses, cytokine production, cell proliferation and apoptosis. AICAR improves ischemia or reperfusion injury and kidney fibrosis in rats. It provides protection against acute tubular necrosis.
Packaging:	5, 25 mg in glass bottle

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3

Purity	≥98% (HPLC)
mp	214-215 °C
Storage Temp.	−20°C
UNSPSC	12352200

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