Merck
CN
All Photos(3)

Documents

A9978

Sigma-Aldrich

AICAR

≥98% (HPLC), powder

Sign Into View Organizational & Contract Pricing
All Photos(3)
Synonym(s):
5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside, Acadesine, N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide
Empirical Formula (Hill Notation):
C9H14N4O5
CAS Number:
2627-69-2
Molecular Weight:
258.23
EC Number:
220-097-5
MDL number:
MFCD00869751
PubChem Substance ID:
24724407

Assay

≥98% (HPLC)

form

powder

color

tan

mp

214-215 °C

solubility

H2O: >7 mg/mL

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

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

Looking for similar products? Visit Product Comparison Guide

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.

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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

  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
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)
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
Hongshun Wang et al.
Cell death & disease, 10(9), 627-627 (2019-08-21)
Oxysterol-binding protein like 2 (OSBPL2) was identified as a novel causal gene for autosomal dominant nonsyndromic hearing loss. However, the pathogenesis of OSBPL2 deficits in ADNSHL was still unclear. The function of OSBPL2 as a lipid-sensing regulator in multiple cellular
View All Related Papers

Related Content

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Discover Bioactive Small Molecules for Kinase Phosphatase Biology

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service