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Aicar

CAS No.:
2627-69-2
Catalog Number:
AG0034FR
Molecular Formula:
C9H14N4O5
Molecular Weight:
258.2313
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
250mg
97%
In Stock USA
United States
$85
- +
1g
97%
In Stock USA
United States
$191
- +
5g
97%
In Stock USA
United States
$536
- +
10g
97%
In Stock USA
United States
$794
- +
Product Description
Catalog Number:
AG0034FR
Chemical Name:
Aicar
CAS Number:
2627-69-2
Molecular Formula:
C9H14N4O5
Molecular Weight:
258.2313
MDL Number:
MFCD00869751
IUPAC Name:
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
InChI:
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:
OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc(c1N)C(=O)N
EC Number:
220-097-5
UNII:
53IEF47846
Properties
Complexity:
330  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
258.096g/mol
Formal Charge:
0
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
258.234g/mol
Monoisotopic Mass:
258.096g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
157A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.2  
Literature
Title Journal
Identification of potent Yes1 kinase inhibitors using a library screening approach. Bioorganic & medicinal chemistry letters 20130801
Impact of glucagon-like peptide-1 (7-36) amide, isosteviol and 5-aminoimidazole-4-carboxamide 1-β-d-ribofuranoside on leucine-mediated α-cell dysfunction. Diabetes, obesity & metabolism 20121101
Surgery: No benefit of acadesine in CABG. Nature reviews. Cardiology 20120901
Effect of adenosine-regulating agent acadesine on morbidity and mortality associated with coronary artery bypass grafting: the RED-CABG randomized controlled trial. JAMA 20120711
Suppression of adipose lipolysis by long-chain fatty acid analogs. Journal of lipid research 20120501
Inhibition of AMP-activated protein kinase α (AMPKα) by doxorubicin accentuates genotoxic stress and cell death in mouse embryonic fibroblasts and cardiomyocytes: role of p53 and SIRT1. The Journal of biological chemistry 20120309
5-Aminoimidazole-4-carboxyamide ribonucleoside induces G(1)/S arrest and Nanog downregulation via p53 and enhances erythroid differentiation. Stem cells (Dayton, Ohio) 20120201
Novel approach to meta-analysis of microarray datasets reveals muscle remodeling-related drug targets and biomarkers in Duchenne muscular dystrophy. PLoS computational biology 20120201
Post-treatment with the combination of 5-aminoimidazole-4-carboxyamide ribonucleoside and carnitine improves renal function after ischemia/reperfusion injury. Shock (Augusta, Ga.) 20120101
Metabolomics of the effect of AMPK activation by AICAR on human umbilical vein endothelial cells. International journal of molecular medicine 20120101
5-aminoimidazole-4-carboxamide riboside enhances effect of ionizing radiation in PC3 prostate cancer cells. International journal of radiation oncology, biology, physics 20111201
Activated AMPK inhibits PPAR-{alpha} and PPAR-{gamma} transcriptional activity in hepatoma cells. American journal of physiology. Gastrointestinal and liver physiology 20111001
Deficiency of insulin-like growth factor 1 reduces vulnerability to chronic alcohol intake-induced cardiomyocyte mechanical dysfunction: role of AMPK. Journal of cellular and molecular medicine 20110801
Acute therapeutic use of 5-aminoimidazole-4-carboxamide ribonucleoside extends survival interval in response to severe hemorrhagic shock. Shock (Augusta, Ga.) 20110801
Activation of AMP-activated protein kinase may not be involved in AICAR- and metformin-mediated meiotic arrest in bovine denuded and cumulus-enclosed oocytes in vitro. Zygote (Cambridge, England) 20110501
Glucosensing by GnRH neurons: inhibition by androgens and involvement of AMP-activated protein kinase. Molecular endocrinology (Baltimore, Md.) 20110501
Genistein, resveratrol, and 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside induce cytochrome P450 4F2 expression through an AMP-activated protein kinase-dependent pathway. The Journal of pharmacology and experimental therapeutics 20110401
Contraction-induced skeletal muscle FAT/CD36 trafficking and FA uptake is AMPK independent. Journal of lipid research 20110401
Enhancement of extracellular purine nucleoside accumulation by Bacillus strains through genetic modifications of genes involved in nucleoside export. Journal of industrial microbiology & biotechnology 20110101
Potential role of adenosine monophosphate-activated protein kinase in regulation of energy metabolism in dairy goat mammary epithelial cells. Journal of dairy science 20110101
Novel trends in the treatment of cardiovascular disorders: site- and event- selective adenosinergic drugs. Current medicinal chemistry 20110101
AICAR induces apoptosis independently of AMPK and p53 through up-regulation of the BH3-only proteins BIM and NOXA in chronic lymphocytic leukemia cells. Blood 20101021
Studies on ligand binding to histidine triad nucleotide binding protein 1. Bioorganic & medicinal chemistry 20100915
Peroxisome proliferator-activated receptor gamma coactivator 1alpha or 1beta overexpression inhibits muscle protein degradation, induction of ubiquitin ligases, and disuse atrophy. The Journal of biological chemistry 20100618
Avoiding stroke during cardiac surgery. Seminars in cardiothoracic and vascular anesthesia 20100601
Acadesine inhibits tissue factor induction and thrombus formation by activating the phosphoinositide 3-kinase/Akt signaling pathway. Arteriosclerosis, thrombosis, and vascular biology 20100501
AICA-riboside (acadesine), an activator of AMP-activated protein kinase with potential for application in hematologic malignancies. Expert opinion on investigational drugs 20100401
AICAR and metformin, but not exercise, increase muscle glucose transport through AMPK-, ERK-, and PDK1-dependent activation of atypical PKC. American journal of physiology. Endocrinology and metabolism 20100201
Germline deletion of AMP-activated protein kinase beta subunits reduces bone mass without altering osteoclast differentiation or function. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20100101
AICAR (5-aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside) increases the production of toxic molecules and affects the profile of cytokines release in LPS-stimulated rat primary microglial cultures. Neurotoxicology 20100101
Whole blood transcriptomics in cardiac surgery identifies a gene regulatory network connecting ischemia reperfusion with systemic inflammation. PloS one 20100101
AMP-activated protein kinase enhances the expression of muscle-specific ubiquitin ligases despite its activation of IGF-1/Akt signaling in C2C12 myotubes. Journal of cellular biochemistry 20091001
Intra-arterial AICA-riboside administration induces NO-dependent vasodilation in vivo in human skeletal muscle. American journal of physiology. Endocrinology and metabolism 20090901
Adenosine and adenosine receptors: Newer therapeutic perspective. Indian journal of pharmacology 20090601
Blunting of AICAR-induced human skeletal muscle glucose uptake in type 2 diabetes is dependent on age rather than diabetic status. American journal of physiology. Endocrinology and metabolism 20090501
The regulation of p53 by phosphorylation: a model for how distinct signals integrate into the p53 pathway. Aging 20090501
AMP-activated protein kinase pathway: a potential therapeutic target in cardiometabolic disease. Clinical science (London, England : 1979) 20090401
Gateways to clinical trials. Methods and findings in experimental and clinical pharmacology 20090301
Kinase activity-independent suppression of p73alpha by AMP-activated kinase alpha (AMPKalpha). Oncogene 20090219
Beyond AICA riboside: in search of new specific AMP-activated protein kinase activators. IUBMB life 20090101
AICAR activates the pluripotency transcriptional network in embryonic stem cells and induces KLF4 and KLF2 expression in fibroblasts. BMC pharmacology 20090101
Acadesine kills chronic myelogenous leukemia (CML) cells through PKC-dependent induction of autophagic cell death. PloS one 20090101
Is ZMP the toxic metabolite in Lesch-Nyhan disease? Medical hypotheses 20081101
The need for a multi-level biochemical approach to defeat cancer that will also support the host. Medical hypotheses 20081001
Crosstalk between the AMP-activated kinase and insulin signaling pathways rescues murine blastocyst cells from insulin resistance. Reproduction (Cambridge, England) 20080901
Acadesine, an adenosine-regulating agent with the potential for widespread indications. Expert opinion on pharmacotherapy 20080801
Role of AMP-activated protein kinase in autophagy and proteasome function. Biochemical and biophysical research communications 20080509
Inhibition of lipopolysaccharide-induced inducible nitric oxide synthase and cyclooxygenase-2 gene expression by 5-aminoimidazole-4-carboxamide riboside is independent of AMP-activated protein kinase. Journal of cellular biochemistry 20080215
Acadesine: AICA riboside, ARA 100, arasine, GP 1 110. Drugs in R&D 20080101
Macropinocytosis is decreased in diabetic mouse macrophages and is regulated by AMPK. BMC immunology 20080101
5-aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside (AICA-riboside) as a targeting agent for therapy of patients with acute lymphoblastic leukemia: are we there and are there pitfalls? Journal of pediatric hematology/oncology 20071201
The AMP-activated protein kinase activator, 5-aminoimidazole-4-carboxamide-1-b-D-ribonucleoside, regulates lactate production in rat Sertoli cells. Journal of molecular endocrinology 20071001
Ischemic preconditioning: protection against myocardial necrosis and apoptosis. Vascular health and risk management 20071001
A pharmacological activator of AMP-activated protein kinase (AMPK) induces astrocyte stellation. Brain research 20070907
5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside acutely stimulates skeletal muscle 2-deoxyglucose uptake in healthy men. Diabetes 20070801
5-Aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside stimulates tyrosine hydroxylase activity and catecholamine secretion by activation of AMP-activated protein kinase in PC12 cells. Journal of neuroendocrinology 20070801
Covariate heterogeneity in meta-analysis: criteria for deciding between meta-regression and individual patient data. Statistics in medicine 20070710
AMP-activated protein kinase-independent inhibition of hepatic mitochondrial oxidative phosphorylation by AICA riboside. The Biochemical journal 20070615
Methotrexate and erythro-9-(2-hydroxynon-3-yl) adenine therapy for rat adjuvant arthritis and the effect of methotrexate on in vivo purine metabolism. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20070601
Interference with energy metabolism by 5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside induces HPV suppression in cervical carcinoma cells and apoptosis in the absence of LKB1. The Biochemical journal 20070501
5-Aminoimidazole-4-carboxamide riboside sensitizes TRAIL- and TNF{alpha}-induced cytotoxicity in colon cancer cells through AMP-activated protein kinase signaling. Molecular cancer therapeutics 20070501
Effect of acute activation of 5'-AMP-activated protein kinase on glycogen regulation in isolated rat skeletal muscle. Journal of applied physiology (Bethesda, Md. : 1985) 20070301
A role for AMP-activated protein kinase in diabetes-induced renal hypertrophy. American journal of physiology. Renal physiology 20070201
Metabolic signature of breast cancer cell line MCF-7: profiling of modified nucleosides via LC-IT MS coupling. BMC biochemistry 20070101
Diagnosing AICA-ribosiduria by capillary electrophoresis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20061020
Methotrexate enhances the antianabolic and antiproliferative effects of 5-aminoimidazole-4-carboxamide riboside. Molecular cancer therapeutics 20060901
Post-reperfusion myocardial infarction: long-term survival improvement using adenosine regulation with acadesine. Journal of the American College of Cardiology 20060704
Moving preconditioning from bench to bedside. Journal of the American College of Cardiology 20060704
Activation of AMP-activated protein kinase within the ventromedial hypothalamus amplifies counterregulatory hormone responses in rats with defective counterregulation. Diabetes 20060601
Adiponectin suppression of high-glucose-induced reactive oxygen species in vascular endothelial cells: evidence for involvement of a cAMP signaling pathway. Diabetes 20060601
MDM2 antagonists activate p53 and synergize with genotoxic drugs in B-cell chronic lymphocytic leukemia cells. Blood 20060515
Relationship between 5-aminoimidazole-4-carboxamide-ribotide and AMP-activated protein kinase activity in the perfused mouse heart. American journal of physiology. Heart and circulatory physiology 20060301
α2 isoform-specific activation of 5'adenosine monophosphate-activated protein kinase by 5-aminoimidazole-4-carboxamide-1-β-D-ribonucleoside at a physiological level activates glucose transport and increases glucose transporter 4 in mouse skeletal muscle. Metabolism: clinical and experimental 20060301
A3 adenosine receptors and mitogen-activated protein kinases in lung injury following in vivo reperfusion. Critical care (London, England) 20060101
AMPK or ZMPK? Medical hypotheses 20060101
Analysis of intracellular nucleotides by capillary electrophoresis-mass spectrometry. Nucleosides, nucleotides & nucleic acids 20060101
Synthesis and mass spectrometric fragmentation characteristics of imidazole ribosides-analogs of intermediates of purine de novo synthetic pathway. Nucleosides, nucleotides & nucleic acids 20060101
5 '-Amino-4-imidazolecarboxamide riboside induces apoptosis in human neuroblastoma cells via the mitochondrial pathway. Nucleosides, nucleotides & nucleic acids 20060101
Anti-lipolytic action of AMP-activated protein kinase in rodent adipocytes. The Journal of biological chemistry 20050701
Combination of 5-fluorouracil and genistein induces apoptosis synergistically in chemo-resistant cancer cells through the modulation of AMPK and COX-2 signaling pathways. Biochemical and biophysical research communications 20050701
AICAR suppresses IL-2 expression through inhibition of GSK-3 phosphorylation and NF-AT activation in Jurkat T cells. Biochemical and biophysical research communications 20050701
Enhanced insulin-stimulated glycogen synthesis in response to insulin, metformin or rosiglitazone is associated with increased mRNA expression of GLUT4 and peroxisomal proliferator activator receptor gamma co-activator 1. Diabetologia 20050601
5-amino-imidazole carboxamide riboside acutely potentiates glucose-stimulated insulin secretion from mouse pancreatic islets by KATP channel-dependent and -independent pathways. Biochemical and biophysical research communications 20050520
Mimicry of a cellular low energy status blocks tumor cell anabolism and suppresses the malignant phenotype. Cancer research 20050315
AMP-activated protein kinase mediates phenobarbital induction of CYP2B gene expression in hepatocytes and a newly derived human hepatoma cell line. The Journal of biological chemistry 20050211
Acadesine induces apoptosis in B cells from mantle cell lymphoma and splenic marginal zone lymphoma. Leukemia 20050201
Mechanism of action of Escherichia coli phosphoribosylaminoimidazolesuccinocarboxamide synthetase. Biochemistry 20050118
5-aminoimidazole-4-carboxamide riboside (AICAR) enhances GLUT2-dependent jejunal glucose transport: a possible role for AMPK. The Biochemical journal 20050115
Synthesis of 3-aminoimidazo[4,5-c]pyrazole nucleoside via the N-N bond formation strategy as a [5:5] fused analog of adenosine. Nucleosides, nucleotides & nucleic acids 20050101
Intracerebroventricular infusion of glucose, insulin, and the adenosine monophosphate-activated kinase activator, 5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside, controls muscle glycogen synthesis. Endocrinology 20040901
AMP-activated protein kinase: the guardian of cardiac energy status. The Journal of clinical investigation 20040816
AMP-activated protein kinase plays a role in the control of food intake. The Journal of biological chemistry 20040326
AICA riboside both activates AMP-activated protein kinase and competes with adenosine for the nucleoside transporter in the CA1 region of the rat hippocampus. Journal of neurochemistry 20040301
Okadaic acid-induced, naringin-sensitive phosphorylation of glycine N-methyltransferase in isolated rat hepatocytes. The Biochemical journal 20030715
Acadesine activates AMPK and induces apoptosis in B-cell chronic lymphocytic leukemia cells but not in T lymphocytes. Blood 20030501
AMP-activated protein kinase can induce apoptosis of insulin-producing MIN6 cells through stimulation of c-Jun-N-terminal kinase. Journal of molecular endocrinology 20030401
5-Aminoimidazole-4-carboxamide riboside induces apoptosis in Jurkat cells, but the AMP-activated protein kinase is not involved. The Biochemical journal 20030315
AICA-riboside induces apoptosis of pancreatic beta cells through stimulation of AMP-activated protein kinase. Diabetologia 20030201
5'-aminoimidazole-4-carboxamide riboside induces apoptosis in human neuroblastoma cells. Neuroscience 20030101
Protein kinase inhibitors block the stimulation of the AMP-activated protein kinase by 5-amino-4-imidazolecarboxamide riboside. FEBS letters 20021106
Activation of AMP-activated protein kinase leads to the phosphorylation of elongation factor 2 and an inhibition of protein synthesis. Current biology : CB 20020820
Effects of low-intensity prolonged exercise on PGC-1 mRNA expression in rat epitrochlearis muscle. Biochemical and biophysical research communications 20020816
Targeting the AMP-activated protein kinase for the treatment of type 2 diabetes. Current drug targets. Immune, endocrine and metabolic disorders 20020701
Characterization of the role of the AMP-activated protein kinase in the stimulation of glucose transport in skeletal muscle cells. The Biochemical journal 20020401
Glycogen-dependent effects of 5-aminoimidazole-4-carboxamide (AICA)-riboside on AMP-activated protein kinase and glycogen synthase activities in rat skeletal muscle. Diabetes 20020201
5'-AMP-activated protein kinase phosphorylates IRS-1 on Ser-789 in mouse C2C12 myotubes in response to 5-aminoimidazole-4-carboxamide riboside. The Journal of biological chemistry 20011214
Activation of acetyl-CoA carboxylase by a glutamate- and magnesium-sensitive protein phosphatase in the islet beta-cell. Diabetes 20010701
The protective effect of acadesine on lung ischemia-reperfusion injury. Anesthesia and analgesia 20010301
Effect of 5-aminoimidazole-4-carboxamide riboside (AICA-r) on isolated thoracic aorta responses in streptozotocin-diabetic rats. Journal of basic and clinical physiology and pharmacology 20010101
AMP-activated protein kinase, a metabolic master switch: possible roles in type 2 diabetes. The American journal of physiology 19990701
Acadesine: a unique cardioprotective agent for myocardial ischemia. Heart disease (Hagerstown, Md.) 19990101
AICA riboside increases AMP-activated protein kinase, fatty acid oxidation, and glucose uptake in rat muscle. The American journal of physiology 19971201
Acadesine: a new drug that may improve myocardial protection in coronary artery bypass grafting. Results of the first international multicenter study. Multinational Acadesine Study Group. The Journal of thoracic and cardiovascular surgery 19951001
5-aminoimidazole-4-carboxamide ribonucleoside. A specific method for activating AMP-activated protein kinase in intact cells? European journal of biochemistry 19950415
Acadesine (AICA-riboside): disposition and metabolism of an adenosine-regulating agent. Journal of clinical pharmacology 19931001
Detection of 5'-phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole in urine by use of the Bratton-Marshall reaction: identification of patients deficient in adenylosuccinate lyase activity. Analytical biochemistry 19860701
Properties