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Merck

A9978

AICAR

≥98% (HPLC), powder, AMPK activator

Synonyme(s) :

5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside, Acadesine, N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide

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About This Item

Formule empirique (notation de Hill) :
C9H14N4O5
Numéro CAS:
2627-69-2
Poids moléculaire :
258.23
NACRES:
NA.77
PubChem Substance ID:
24724407
UNSPSC Code:
12352200
EC Number:
220-097-5
MDL number:
MFCD00869751

Nom du produit

AICAR, ≥98% (HPLC), 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

SMILES string

NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N

assay

≥98% (HPLC)

form

powder

color

tan

mp

214-215 °C

solubility

H2O: >7 mg/mL

shipped in

dry ice

storage temp.

−20°C

Quality Level

100

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Catégories apparentées

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.
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.

Classe de stockage

11 - Combustible Solids

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WGK 3

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Certificats d'analyse (COA)

Lot/Batch Number
0000488567
0000488562
0000488562
0000488567
0000452339

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  4. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

  5. How can I store a solution of AICAR, Product A9978?

    We do not test solution stability for this product. In general, drug solutions are best prepared immediately before use.  We recommend storing at -20°C in single use aliquots.

  6. What can I use to solubilize AICAR, Product A9978?

    We list the solubility in water on the lot specific Certificate of Analysis.  We typically test the solubility of AICAR in water (7 mg/mL).

  7. What is the appearance of Product A9978, AICAR?

    Product No. A9978, AICAR, is a powder.  The color of the powder will be described on the lot specific Certificate of Analysis.

  8. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Hiroaki Sunaga et al.
Scientific reports, 9(1), 11841-11841 (2019-08-16)
Fibroblast growth factor 21 (FGF21) is a metabolic hormone having anti-oxidative and anti-hypertrophic effects. However, the regulation of FGF21 expression during acute myocardial infarction (AMI) remains unclear. We tested blood samples from 50 patients with AMI and 43 patients with
Ai Ushiyama et al.
Biology of reproduction, 100(6), 1482-1491 (2019-02-06)
Despite knowledge that glucose metabolism is essential for the regulation of signaling cascades in the sperm that are pre-assembled into specific areas and function at multistage for fertilization, the physiological roles of glucose in avian sperm are poorly understood. Accumulated
AICAR, an AMPK activator, protects against cisplatin-induced acute kidney injury through the JAK/STAT/SOCS pathway
Tsogbadrakh B, et al.
Biochemical and Biophysical Research Communications (2019)
Genetically-encoded FapR-NLuc as a biosensor to determine malonyl-CoA in situ at subcellular scales
Du Y, et al.
Bioconjugate Chemistry (2019)
Sofija Mijic et al.
Nature communications, 8(1), 859-859 (2017-10-19)
Besides its role in homologous recombination, the tumor suppressor BRCA2 protects stalled replication forks from nucleolytic degradation. Defective fork stability contributes to chemotherapeutic sensitivity of BRCA2-defective tumors by yet-elusive mechanisms. Using DNA fiber spreading and direct visualization of replication intermediates
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