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AICAR

AICAR Structure
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
Molecular Weight:
258.23
MOL File:
2627-69-2.mol
MSDS File:
SDS
Modify Date:
2024/7/25 20:04:51
Request For Quotation

AICAR Properties

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)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Danger
Hazard statements  H315-H319-H360D
Precautionary statements  P202-P264-P280-P302+P352-P305+P351+P338-P308+P313
Hazard Codes  Xi,T
Risk Statements  36/37/38-61
Safety Statements  26-36-45-53
WGK Germany  3
TSCA  Yes
HS Code  29349990

AICAR price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) SRP5004 AMPK (α2/β2/γ2), active, His tagged human PRECISIO? Kinase, recombinant, expressed in baculovirus infected Sf9 cells, ≥70% (SDS-PAGE), buffered aqueous glycerol solution 2627-69-2 5μG ₹84415.5 2022-06-14 Buy
Sigma-Aldrich(India) SRP5003 AMPK (α2/β2/γ1), active, His tagged human PRECISIO? Kinase, recombinant, expressed in baculovirus infected Sf9 cells, ≥70% (SDS-PAGE), buffered aqueous glycerol solution 2627-69-2 5μG ₹84415.5 2022-06-14 Buy
Sigma-Aldrich(India) SAB4502332 Anti-AMPK β1 antibody produced in rabbit affinity isolated antibody 2627-69-2 100μG ₹50560.5 2022-06-14 Buy
Sigma-Aldrich(India) SAB1406293 Anti-PRKAA1 antibody produced in mouse purified immunoglobulin, buffered aqueous solution 2627-69-2 50μG ₹50671.5 2022-06-14 Buy
Sigma-Aldrich(India) SAB1306034 ANTI-AMPK ALPHA2(C-TERMINAL) antibody produced in rabbit IgG fraction of antiserum, buffered aqueous solution 2627-69-2 400μL ₹47796.6 2022-06-14 Buy
Product number Packaging Price Buy
SRP5004 5μG ₹84415.5 Buy
SRP5003 5μG ₹84415.5 Buy
SAB4502332 100μG ₹50560.5 Buy
SAB1406293 50μG ₹50671.5 Buy
SAB1306034 400μL ₹47796.6 Buy

AICAR Chemical Properties,Uses,Production

Chemical Properties

Solid

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.

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.

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.

AICAR Preparation Products And Raw materials

Raw materials

Iodomethane Cyclic AMP Sodium hydroxide Hydrogen Sodium bicarbonate
Nickel Formic acid Ammonium hydroxide
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Preparation Products

5-AMino-1-[2,3-O-(1-Methylethylidene)-β-D-ribofuranosyl]-1H-iMidazole-4-carboxaMide

AICAR Suppliers

Global( 345)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
TCI Chemicals (India) Pvt. Ltd. 1800 425 7889 New Delhi, India 6778 58 Inquiry
Gagri Global IT Services Pvt. Ltd. +91-40-27170174, Telangana, India 1321 58 Inquiry
CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6351 58 Inquiry
Alfa Aesar 1 800 209 7001 Maharashtra, India 6913 58 Inquiry
Pharmaffiliates Analytics and Synthetics P. Ltd +91-172-5066494 Haryana, India 6773 58 Inquiry
Navil Laboratories Private Limited 08069033805Ext 172 Ahmedabad, India 4 58 Inquiry
Vora Drugs And Chemicals Pvt Ltd 08069033728Ext 936 Delhi, India 4 58 Inquiry
Sigma-Aldrich Chemicals Private Limited 1-800-309-6000 Bangalore, India 6820 58 Inquiry
Hebei Anlijie Biotechnology Co., Ltd +8619031013551 China 145 58 Inquiry
Changzhou Xuanming Pharmaceutical Technology Co., Ltd. +8618068519287 China 833 58 Inquiry
Supplier Advantage
TCI Chemicals (India) Pvt. Ltd. 58
Gagri Global IT Services Pvt. Ltd. 58
CLEARSYNTH LABS LTD. 58
Alfa Aesar 58
Pharmaffiliates Analytics and Synthetics P. Ltd 58
Navil Laboratories Private Limited 58
Vora Drugs And Chemicals Pvt Ltd 58
Sigma-Aldrich Chemicals Private Limited 58
Hebei Anlijie Biotechnology Co., Ltd 58
Changzhou Xuanming Pharmaceutical Technology Co., Ltd. 58

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Related Qustion

AICAR Spectrum

AICAR(2627-69-2)1HNMR

2627-69-2(AICAR)Related Search:

AICAR (phosphate) Inosine Impurity 1 L-Inosine Inosine 2-CHLOROINOSINE
XANTHOSINE 2',3',5'-TRI-O-ACETYLINOSINE IDP 2'-Deoxyguanosine-5'-diphosphate trisodium salt 2',3'-O-Isopropylideneinosine
XANTHOSINE 5'-MONOPHOSPHATE DISODIUM SALT Disodium 5'-Inosinate 3'-GMP DISODIUM SALT Guanosine GUANOSINE 3':5'-CYCLIC MONOPHOSPHATE SODIUM SALT
Succino-AICAR 5-Amino-4-imidazolecarboxamide INOSINE-3',5'-CYCLIC PHOSPHATE
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5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside,98% 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosideAICAR 5-Aminomidazole-4-carboxamide-1-β-D-ribofuranoside AICAR AICA-RIBOSIDE 1-Deoxy-1-[(4-carbamoyl-5-amino-1H-imidazole)-1-yl]-β-D-ribofuranose 1-β-D-Ribofuranosyl-5-amino-1H-imidazole-4-carboxamide 5-Amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide AICA-β-D-Riboside 5-AMino-4-iMidazole carboxaMide Riboside Arasine GP 1-110 NSC 105823 AICAR, Free Base 5-aMino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)-1H-iMidazole-4-carboxaMide N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide AICAR,5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside, Acadesine, N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranose ,98% Acadesine(Aicar,NSC 105823) 5-Amino-4-carbamoyl-1-(beta-D-ribofuranosyl)-1H-imidazole, AICAR Acadesine/AICAR AICA, Acadesine, AICA-ribaoside 1H-IMidazole-4-carboxaMide,5-aMino-1-b-D-ribofuranosyl- 5′-AMP-activated protein kinase catalytic subunit alpha-1 ANTI-AMPK ALPHA 1(C-TERMINAL) antibody produced in rabbit Z-RIBOSIDE 5-amino-1-beta-d-ribofuranosyl-1h-imidazole-4-carboxamid N1-(BETA-D-RIBOFURANOSYL)-5-AMINOIMIDAZOLE-4-CARBOXAMIDE 5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide 5-Amino-1-beta-ribofuranosyl-imidazole-4-carboxamide 5-Amino-4-imidazolecarboxamide ribofuranoside AIC-Riboside Aminoimidazole-4-carboxamide-1-D-Ribofuranoside 5-AMINOIMIDAZOLE-4-BETA-D-RIBOFURANOSE AMINOIMIDAZOLE-4-CARBOXAMIDE-1-SS-D-RIBOFURANOSIDE AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSIDE AICAR, Acadesine 5-Aminoimidazole-4-carboxamide-1-b-D-ribofuranose 5-Aminoimidazole-4-carboxamide-1-β-riboside 5-amino-1-beta-D-ribofuranosyl-1H-imidazole-4-carboxamide Acadesine, N1-(β-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide, 5-Aminoimidazole-4-carboxamide 1-β-D-ribofuranoside Anti-PRKAB1 (Protein kinase, AMP-activated, beta 1 non-catalytic subunit) Hydroxymethylglutaryl-CoA reductase kinase 5′-AMP-activated protein kinase catalytic subunit alpha-2 AMPK2 ANTI-AMPK ALPHA2(C-TERMINAL) antibody produced in rabbit PRKAA2 5′-AMP-activated protein kinase subunit β-1 AMPK subunit β-1 AMPKb AMPK (α2/β2/γ1), active, His tagged human MGC61468 MGC8666 PRKAA PRKAB2 PRKAG1 Anti-AMPK β1 antibody produced in rabbit AMPKa1