Details
Stereochemistry | ACHIRAL |
Molecular Formula | C4H6N4O |
Molecular Weight | 126.1166 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(=O)C1=C(N)N=CN1
InChI
InChIKey=DVNYTAVYBRSTGK-UHFFFAOYSA-N
InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
Molecular Formula | C4H6N4O |
Molecular Weight | 126.1166 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Approval Year
PubMed
Title | Date | PubMed |
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Aryl and heterocyclic diazo compounds as potential environmental electrophiles. | 1977 May |
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Regulation of fatty acid oxidation and glucose metabolism in rat soleus muscle: effects of AICAR. | 2001 Aug |
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The AMP-activated protein kinase prevents ceramide synthesis de novo and apoptosis in astrocytes. | 2001 Feb 2 |
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Penetration of dacarbazine and its active metabolite 5-aminoimidazole-4-carboxamide into cutaneous metastases of human malignant melanoma. | 2001 Oct 15 |
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The effects of AICAR on adipocyte differentiation of 3T3-L1 cells. | 2001 Sep 7 |
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Effects of low-intensity prolonged exercise on PGC-1 mRNA expression in rat epitrochlearis muscle. | 2002 Aug 16 |
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Activation of GLUT1 by metabolic and osmotic stress: potential involvement of AMP-activated protein kinase (AMPK). | 2002 Jun 1 |
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Acute and chronic treatment of ob/ob and db/db mice with AICAR decreases blood glucose concentrations. | 2002 Jun 21 |
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Cloning and characterization of methenyltetrahydrofolate synthetase from Saccharomyces cerevisiae. | 2002 Jun 7 |
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Down-regulation of Lsm1 is involved in human prostate cancer progression. | 2002 Mar 18 |
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Regulation of GLUT4 biogenesis in muscle: evidence for involvement of AMPK and Ca(2+). | 2002 May |
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Regulation of glycogen synthase by glucose and glycogen: a possible role for AMP-activated protein kinase. | 2003 Jan |
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5-amino-imidazole carboxamide riboside increases glucose transport and cell-surface GLUT4 content in skeletal muscle from subjects with type 2 diabetes. | 2003 May |
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Glucose regulates EF-2 phosphorylation and protein translation by a protein phosphatase-2A-dependent mechanism in INS-1-derived 832/13 cells. | 2003 May 16 |
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Mapping of the bovine genes of the de novo AMP synthesis pathway. | 2004 Dec |
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Activation of glycogen phosphorylase with 5-aminoimidazole-4-carboxamide riboside (AICAR). Assessment of glycogen as a precursor of mannosyl residues in glycoconjugates. | 2004 Mar 26 |
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Adenosine induces apoptosis in the human gastric cancer cells via an intrinsic pathway relevant to activation of AMP-activated protein kinase. | 2004 May 15 |
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Prior serum- and AICAR-induced AMPK activation in primary human myocytes does not lead to subsequent increase in insulin-stimulated glucose uptake. | 2004 Sep |
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AICAR suppresses IL-2 expression through inhibition of GSK-3 phosphorylation and NF-AT activation in Jurkat T cells. | 2005 Jul 1 |
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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. | 2005 Jun |
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The glucose dependence of Akt-transformed cells can be reversed by pharmacologic activation of fatty acid beta-oxidation. | 2005 Jun 16 |
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Increased potency and efficacy of combined phosphorylase inactivation and glucokinase activation in control of hepatocyte glycogen metabolism. | 2005 Mar |
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Suppression of inflammation by low-dose methotrexate is mediated by adenosine A2A receptor but not A3 receptor activation in thioglycollate-induced peritonitis. | 2006 |
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Activation of the AMP-activated kinase by antidiabetes drug metformin stimulates nitric oxide synthesis in vivo by promoting the association of heat shock protein 90 and endothelial nitric oxide synthase. | 2006 Feb |
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Activation of AMP-activated protein kinase within the ventromedial hypothalamus amplifies counterregulatory hormone responses in rats with defective counterregulation. | 2006 Jun |
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Inhibition of lipid synthesis through activation of AMP kinase: an additional mechanism for the hypolipidemic effects of berberine. | 2006 Jun |
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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. | 2006 Mar |
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Pharmacogenomic and metabolic biomarkers in the folate pathway and their association with methotrexate effects during dosage escalation in rheumatoid arthritis. | 2006 Oct |
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Increased ATP-sensitive K+ channel expression during acute glucose deprivation. | 2006 Sep 29 |
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5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside acutely stimulates skeletal muscle 2-deoxyglucose uptake in healthy men. | 2007 Aug |
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Formamide as the main building block in the origin of nucleic acids. | 2007 Aug 16 |
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5'-AMP-activated protein kinase activation prevents postischemic leukocyte-endothelial cell adhesive interactions. | 2007 Jan |
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Cytotoxic effect of 5-aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside (AICAR) on childhood acute lymphoblastic leukemia (ALL) cells: implication for targeted therapy. | 2007 Jul 10 |
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Identification of new reference genes for the normalisation of canine osteoarthritic joint tissue transcripts from microarray data. | 2007 Jul 25 |
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Role of hypothalamic adenosine 5'-monophosphate-activated protein kinase in the impaired counterregulatory response induced by repetitive neuroglucopenia. | 2007 Mar |
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Role of glycogen content in insulin resistance in human muscle cells. | 2007 May |
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Ceramide and adenosine 5'-monophosphate-activated protein kinase are two novel regulators of 11beta-hydroxysteroid dehydrogenase type 1 expression and activity in cultured preadipocytes. | 2007 Nov |
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AMP kinase activation increases glucose uptake, decreases apoptosis, and improves pregnancy outcome in embryos exposed to high IGF-I concentrations. | 2007 Sep |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 19:49:16 UTC 2022
by
admin
on
Fri Dec 16 19:49:16 UTC 2022
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Record UNII |
3V0Y2PDE6K
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Record Status |
Validated (UNII)
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Record Version |
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LOINC |
79679-7
Created by
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LOINC |
79652-4
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admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
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79672-2
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admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
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9679
Created by
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2030
Created by
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3V0Y2PDE6K
Created by
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7784
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360-97-4
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DTXSID8059891
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206-641-4
Created by
admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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PARENT -> METABOLITE INACTIVE |
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PARENT -> IMPURITY | |||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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