Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H6N4O.ClH |
| Molecular Weight | 162.578 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC(=O)C1=C(N)NC=N1
InChI
InChIKey=MXCUYSMIELHIQL-UHFFFAOYSA-N
InChI=1S/C4H6N4O.ClH/c5-3-2(4(6)9)7-1-8-3;/h1H,5H2,(H2,6,9)(H,7,8);1H
| 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 |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| 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 |
|---|---|---|
| Regulation of fatty acid oxidation and glucose metabolism in rat soleus muscle: effects of AICAR. | 2001 Aug |
|
| Evaluation of the catalytic mechanism of AICAR transformylase by pH-dependent kinetics, mutagenesis, and quantum chemical calculations. | 2001 May 23 |
|
| Stimulation of glucose transport by AMP-activated protein kinase via activation of p38 mitogen-activated protein kinase. | 2001 Nov 2 |
|
| Penetration of dacarbazine and its active metabolite 5-aminoimidazole-4-carboxamide into cutaneous metastases of human malignant melanoma. | 2001 Oct 15 |
|
| Regulation of muscle GLUT-4 transcription by AMP-activated protein kinase. | 2001 Sep |
|
| The effects of AICAR on adipocyte differentiation of 3T3-L1 cells. | 2001 Sep 7 |
|
| Regulation of phosphatidylcholine and phosphatidylethanolamine synthesis in rat hepatocytes by 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR). | 2002 Feb 15 |
|
| 5-Aminoimidazole-4-carboxamide ribonucleoside treatment improves glucose homeostasis in insulin-resistant diabetic (ob/ob) mice. | 2002 Jan |
|
| Targeting the AMP-activated protein kinase for the treatment of type 2 diabetes. | 2002 Jul |
|
| AMP-activated protein kinase suppresses protein synthesis in rat skeletal muscle through down-regulated mammalian target of rapamycin (mTOR) signaling. | 2002 Jul 5 |
|
| Effect of fiber type and nutritional state on AICAR- and contraction-stimulated glucose transport in rat muscle. | 2002 Jun |
|
| Activation of GLUT1 by metabolic and osmotic stress: potential involvement of AMP-activated protein kinase (AMPK). | 2002 Jun 1 |
|
| Acute and chronic treatment of ob/ob and db/db mice with AICAR decreases blood glucose concentrations. | 2002 Jun 21 |
|
| Cloning and characterization of methenyltetrahydrofolate synthetase from Saccharomyces cerevisiae. | 2002 Jun 7 |
|
| Effect of AICAR treatment on glycogen metabolism in skeletal muscle. | 2002 Mar |
|
| Down-regulation of Lsm1 is involved in human prostate cancer progression. | 2002 Mar 18 |
|
| Regulation of GLUT4 biogenesis in muscle: evidence for involvement of AMPK and Ca(2+). | 2002 May |
|
| A potential role for AMP-activated protein kinase in meiotic induction in mouse oocytes. | 2002 May 1 |
|
| AMP-activated protein kinase kinase: detection with recombinant AMPK alpha1 subunit. | 2002 May 10 |
|
| AICAR and phlorizin reverse the hypoglycemia-specific defect in glucagon secretion in the diabetic BB rat. | 2002 Nov |
|
| 5-Aminoimidazole-4-carboxamide 1-beta -D-ribofuranoside (AICAR) stimulates myocardial glycogenolysis by allosteric mechanisms. | 2003 Apr |
|
| A possible linkage between AMP-activated protein kinase (AMPK) and mammalian target of rapamycin (mTOR) signalling pathway. | 2003 Jan |
|
| Regulation of glycogen synthase by glucose and glycogen: a possible role for AMP-activated protein kinase. | 2003 Jan |
|
| Increased AMP:ATP ratio and AMP-activated protein kinase activity during cellular senescence linked to reduced HuR function. | 2003 Jul 18 |
|
| 5-amino-imidazole carboxamide riboside increases glucose transport and cell-surface GLUT4 content in skeletal muscle from subjects with type 2 diabetes. | 2003 May |
|
| 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 |
|
| Requirement for 3-phosphoinositide-kependent dinase-1 (PDK-1) in insulin-induced glucose uptake in immortalized brown adipocytes. | 2003 Oct 3 |
|
| Mapping of the bovine genes of the de novo AMP synthesis pathway. | 2004 Dec |
|
| Ca2+ and AMPK both mediate stimulation of glucose transport by muscle contractions. | 2004 Feb |
|
| Multiple independent kinase cascades are targeted by hyperosmotic stress but only one activates stress kinase p38. | 2004 Jan 15 |
|
| Over-expression of sterol-regulatory-element-binding protein-1c (SREBP1c) in rat pancreatic islets induces lipogenesis and decreases glucose-stimulated insulin release: modulation by 5-aminoimidazole-4-carboxamide ribonucleoside (AICAR). | 2004 Mar 15 |
|
| 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 |
|
| Adenosine induces apoptosis in the human gastric cancer cells via an intrinsic pathway relevant to activation of AMP-activated protein kinase. | 2004 May 15 |
|
| MEK inhibitors block AICAR-induced maturation in mouse oocytes by a MAPK-independent mechanism. | 2005 Feb |
|
| Exercise-induced increase in muscle insulin sensitivity. | 2005 Jul |
|
| 5-aminoimidazole-4-carboxamide ribonucleoside: a novel immunomodulator with therapeutic efficacy in experimental autoimmune encephalomyelitis. | 2005 Jul 1 |
|
| AICAR suppresses IL-2 expression through inhibition of GSK-3 phosphorylation and NF-AT activation in Jurkat T cells. | 2005 Jul 1 |
|
| 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 |
|
| The glucose dependence of Akt-transformed cells can be reversed by pharmacologic activation of fatty acid beta-oxidation. | 2005 Jun 16 |
|
| Adenosine monophosphate-activated protein kinase suppresses vascular smooth muscle cell proliferation through the inhibition of cell cycle progression. | 2005 Oct 14 |
|
| AMP-activated protein kinase and type 2 diabetes. | 2006 |
|
| 5-aminoimidazole-4-carboxamide-1-beta-4-ribofuranoside attenuates experimental autoimmune encephalomyelitis via modulation of endothelial-monocyte interaction. | 2006 Aug 15 |
|
| AMPK-mediated AS160 phosphorylation in skeletal muscle is dependent on AMPK catalytic and regulatory subunits. | 2006 Jul |
|
| Activation of AMP-activated protein kinase within the ventromedial hypothalamus amplifies counterregulatory hormone responses in rats with defective counterregulation. | 2006 Jun |
|
| Fluid shear stress and NO decrease the activity of the hydroxy-methylglutaryl coenzyme A reductase in endothelial cells via the AMP-activated protein kinase and FoxO1. | 2007 Feb 2 |
|
| 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 |
|
| Role of hypothalamic adenosine 5'-monophosphate-activated protein kinase in the impaired counterregulatory response induced by repetitive neuroglucopenia. | 2007 Mar |
|
| Role of glycogen content in insulin resistance in human muscle cells. | 2007 May |
|
| 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
Mon Mar 31 19:29:22 GMT 2025
by
admin
on
Mon Mar 31 19:29:22 GMT 2025
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| Record UNII |
220691X0M3
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID00883234
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72-40-2
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66146
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PARENT -> SALT/SOLVATE |
