2627-69-2 | Aicar

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$35.00	$24.00
250mg	95%	in stock	$46.00	$32.00
1g	95%	in stock	$155.00	$108.00
5g	95%	in stock	$449.00	$315.00
10g	95%	in stock	$858.00	$600.00

Description

• Catalog Number: AB45519
• Chemical Name: Aicar
• CAS Number: 2627-69-2
• Molecular Formula: C9H14N4O5
• Molecular Weight: 258.2313
• MDL Number: MFCD00869751
• SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1cnc(c1N)C(=O)N

Computed Properties

• Complexity: 330
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 4
• Heavy Atom Count: 18
• Hydrogen Bond Acceptor Count: 7
• Hydrogen Bond Donor Count: 5
• Rotatable Bond Count: 3
• XLogP3: -2.2

Literature

• 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