adenosine regulating agents
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AICAR

adenosine regulating agents
Product Name
AICAR
CAS No.
2627-69-2
Chemical Name
AICAR
Synonyms
AAKG;AMPK;ACADESINE;AMPK1;PRKAB1;Acadesine, AICA;5-Aminoimidazole-4-carboxamide riboside;5-Aminoimidazole-4-carboxamide ribonucleoside;5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-B-D-RIBOFURANOSIDE;{[(2S,3R,4R,5R)-5-(5-aMino-4-carbaMoyl-1H-iMidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]Methoxy}phosphonic acid
CBNumber
CB1675294
Molecular Formula
C9H14N4O5
Formula Weight
258.23
MOL File
2627-69-2.mol
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AICAR Property

Melting point:
214-215 °C
Boiling point:
726.3±60.0 °C(Predicted)
Density 
2.06±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
H2O: >10 mg/mL
form 
powder
pka
13.27±0.70(Predicted)
color 
tan
Water Solubility 
Soluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml
λmax
265nm(NaOH)(lit.)
Merck 
14,16
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months.
InChIKey
RTRQQBHATOEIAF-UUOKFMHZSA-N
CAS DataBase Reference
2627-69-2(CAS DataBase Reference)
EPA Substance Registry System
1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- (2627-69-2)
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Safety

Hazard Codes 
Xi,T
Risk Statements 
36/37/38-61
Safety Statements 
26-36-45-53
WGK Germany 
3
TSCA 
Yes
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SRP5003
Product name
AMPK (α2/β2/γ1), active, His tagged human
Purity
PRECISIO? Kinase, recombinant, expressed in baculovirus infected Sf9 cells, ≥70% (SDS-PAGE), buffered aqueous glycerol solution
Packaging
5μG
Price
$887
Updated
2024/03/01
Sigma-Aldrich
Product number
SAB1306034
Product name
ANTI-AMPK ALPHA2(C-TERMINAL) antibody produced in rabbit
Purity
IgG fraction of antiserum, buffered aqueous solution
Packaging
400μL
Price
$481
Updated
2024/03/01
Sigma-Aldrich
Product number
A9978
Product name
AICAR
Purity
≥98% (HPLC), powder
Packaging
5mg
Price
$80.7
Updated
2024/03/01
Sigma-Aldrich
Product number
SAB1306032
Product name
ANTI-AMPK ALPHA 1(C-TERMINAL) antibody produced in rabbit
Purity
IgG fraction of antiserum, buffered aqueous solution
Packaging
400μl
Price
$481
Updated
2024/03/01
Sigma-Aldrich
Product number
A9978
Product name
AICAR
Purity
≥98% (HPLC), powder
Packaging
25mg
Price
$279
Updated
2024/03/01
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AICAR Chemical Properties,Usage,Production

adenosine regulating agents

Acadesine is the prototype of a new class of compounds termed adenosine regulating agents. Acadesine is a purine nucleosid analogue that enters the myocyte and is immediately phosphorylated to ZMP (AICA ribotide), which is further metabolised to Inosine mono-phosphate (an intermediate in the synthesis ofadenosine triphosphate (ATP) and guanosine triphos-phate).
Claims that acadesine may serve as a substrate for ATP synthesis and result in repletion of myocardial ATP were supported by some studies and refuted by others. Because acadesine may be a precursor in the synthesis of myocardial ATP it was proposed as a possible agent of myocardial protection during ischaemia, particularly because myocardial ATP depletion has been linked to cell death.

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.

Chemical Properties

Solid

Originator

AICA,BIOMOL

Uses

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.

Uses

glucose uptake stimulant; AMPK activator

Uses

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.

Definition

ChEBI: A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects.

Manufacturing Process

Adenosine 3', 5'-cyclic phosphate N'-oxide (76.0 g, 0.200 mole) as the dihydrate was dissolved in a solution of 400 ml DMSO and 31.0 g (0.204 mole) 1,5-diazabicyclo[5.4.0]undec-5-ene. The solution was cooled to 15°C and 40 ml methyl iodide was added with stirring at room temperature. After 30 min, the mixture had gelled; 1.5 L ethanol was added and the solid was thoroughly homogenized by vigorous stirring. The solid was filtered, and the resulting paste was resuspended in 2 L ethanol and homogenized. The product was again filtered, washed with ethanol and ether, and dried, giving 80.4 g of 1-methoxyadenosine 3',5'-cyclic phosphate suitable for further transformation (recrystallization from aqueous methanol with ether).
A solution of 30.0 g 1-methoxyadenosine 3',5'-cyclic phosphate (81.5 mmole), 20.0 g NaHCO3 (238 mmole), and 300 ml H2O was refluxed 45 mm. The pH of the solution was adjusted to 2.5 with Dowex 50x8 (H)+ while warm, and a water pump vacuum was applied to mixture to remove CO2. The pH was readjusted to 9-10 with NaOH, and the resin was removed by filtration. The solution was passed onto a column containing 400 ml Dowex 1x2 (formate, 100-200 mesh), and the column was washed well with water. The column was eluted with a gradient of 4 L water in the mixing chamber and 4 L 4 N formic acid in the reservoir. The first major product, coming after about 2 L eluate, was 5-amino-N-methoxy-1-β-D-ribofuranosylimidazole-4-carboxamidine 3',5'- cyclic phosphate, giving 5.4 g (19%) after evaporation of the solvent and trituration of the residue with ethanol (recrystallization from water). A solution of 5.0 g (14.3 mmoles) 5-amino-N-methoxy-1-β-Dribofuranosylimidazole- 4-carboxamidine 3',5'-cyclic phosphate in 200 ml H2 preheated to 60°C and containing approximately 5.0 g moist sponge nickel catalyst, was shaken with 2-3 atm. H2 at 60°C for 2 h. The filtered solution was evaporated to dryness to give 3.75 g of 5-amino-1-β-Dribofuranosylimidazole- 4-carboxamidine 3',5'-cyclic phosphate (82%), (recrystallization from water).
A mixture of 4.0 g (12.5 mmole) 5-amino-1-β-D-ribofuranosylimidazole-4- carboxamidine 3',5'-cyclic phosphate and 100 ml conc. NH4OH was heated in a bomb at 100°C for 16 h, then cooled and evaporated in vacuum. The residue was taken up in 100 ml H2O and applied to a 2.5x20 cm column of Dowex 1x2 (formate form, 100-200 mesh). After washing well with H2O the column was eluted with a gradient of 1 L H2O in the mixing chamber and 1 L 3 N formic acid in the reservoir. Fractions containing the product, appearing near the end of the elution, were evaporated. Trituration of the residue with EtOH gave 2.90 g (68%) of 5-amino-1-β-D-ribofuranosylimidazole-4- carboxamide 3',5'-cyclic phosphate.
The 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide may be produced by hydrolysis of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide 3',5'- cyclic phosphate with NaOH.

Therapeutic Function

Cardiotonic, Platelet aggregation inhibitor

Biological Functions

The first direct AMPK activator, 5-aminoimidazole-4-carboxamide riboside (AICAR), is an adenosine analog taken up into cells by adenosine transporters and phosphorylated by adenosine kinase, thus generating the AMP-mimetic, AICAR monophosphate (ZMP). Similarly to cellular AMP, ZMP binds to site 3 on the AMPKγ subunit. Although ZMP is a much less potent AMPK activator than AMP in cell-free systems, AICAR directly activates AMPK in most cells because ZMP can accumulate to millimolar concentrations in cells. AICAR is able to activate many other AMP-dependent enzymes, such as fructose-1,6-bisphosphatase.

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.

Biological Activity

Cell-permeable, allosteric activator of AMP-activated protein kinase (AMPK). Augments proliferation, differentiation and mineralization of osteoblastic MC3T3-EI cells and attenuates psychosine-induced expression of proinflammatory cytokines and iNOS in astrocytes.

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.

storage

-20°C

Clinical claims and research

AICAR has proved in vivo anti-tumor effects in xenograft models. It is currently under clinical trial phase I/II to treat patients with chronic lymphocytic leukemia and has shown good safety and tolerability properties, although some side effects have been reported.

References

1) Chopra et al. (2012), Phosphorylation of the insulin receptor by AMP-activated protein kinase (AMPK) promotes ligand-independent activation of the insulin signalling pathway in rodent muscle; Diabetologia, 55 783 2) Sanchez et al. (2012), AMPK promotes skeletal muscle autophagy through activation of forkhead FoxO3a and interaction with Ulk1; J. Cell Biochem., 113 695 3) Ferri et al. (2012), AMP-activated protein kinase and the control of smooth muscle cell hyperproliferation in vascular disease; Vascul. Pharmacol., 56 9 4) Wu et al. (2011) AICAR, a small chemical molecule, primes osteogenic differentiation of adult mesenchymal stem cells; Int. J. Artif. Organs, 34 1128 5) Giri et al. (2004) 5-aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside inhibits proinflammatory response in glial cells: a possible role of AMP-activated protein kinase; J. Neurosci., 24 479

AICAR Preparation Products And Raw materials

Raw materials

Preparation Products

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AICAR Suppliers

NOTA Chemical (Shanghai) Co.,Ltd
Tel
021-50189163
Fax
021-51687927
Email
sales@notachem.com
Country
China
ProdList
200
Advantage
64
Hubei Lingyan Biotechnology Co., Ltd
Tel
13297019205
Email
2413323910@QQ.COM
Country
China
ProdList
354
Advantage
58
Jinan Junnuo Trading Co., LTD
Tel
13345898948
Email
1301260554@qq.com
Country
China
ProdList
116
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
ZHIWE CHEMTECH CO LTD
Tel
021-20221225 13917446399
Fax
QQ:115820162
Email
sales@zhiwe.net
Country
China
ProdList
604
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61
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6005
Advantage
61
Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12438
Advantage
60
JinYan Chemicals(ShangHai) Co.,Ltd.
Tel
13817811078
Fax
86-021-50426522,50426273
Email
sales@jingyan-chemical.com
Country
China
ProdList
9976
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60
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View Lastest Price from AICAR manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
AICAR 2627-69-2
Price
US $60.00/mg
Min. Order
50mg
Purity
99%
Supply Ability
20kg
Release date
2024-05-11
hebei hongtan Biotechnology Co., Ltd
Product
AICAR 2627-69-2
Price
US $40.00/g
Min. Order
10g
Purity
99%
Supply Ability
1000kg
Release date
2024-05-11
hebei hongtan Biotechnology Co., Ltd
Product
AICAR 2627-69-2
Price
US $60.00-45.00/box
Min. Order
1box
Purity
99.99%
Supply Ability
1000
Release date
2024-03-14

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