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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
Structure of 4-AMINO-5-IMIDAZOLE CARBOXAMIDE

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)

HIDE SMILES / InChI

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

PubMed

TitleDatePubMed
Effects of low-intensity prolonged exercise on PGC-1 mRNA expression in rat epitrochlearis muscle.
2002 Aug 16
The cryptic adenine deaminase gene of Escherichia coli. Silencing by the nucleoid-associated DNA-binding protein, H-NS, and activation by insertion elements.
2002 Aug 30
Targeting the AMP-activated protein kinase for the treatment of type 2 diabetes.
2002 Jul
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
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
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
Effects of acute bouts of running and swimming exercise on PGC-1alpha protein expression in rat epitrochlearis and soleus muscle.
2004 Feb
Sending the signal: molecular mechanisms regulating glucose uptake.
2004 Jul
Adenosine induces apoptosis in the human gastric cancer cells via an intrinsic pathway relevant to activation of AMP-activated protein kinase.
2004 May 15
A glucose response element from the S. cerevisiae hexose transporter HXT1 gene is sensitive to glucose in human fibroblasts.
2004 May 7
The effect of folic acid and folinic acid supplements on purine metabolism in methotrexate-treated rheumatoid arthritis.
2004 Oct
Prior serum- and AICAR-induced AMPK activation in primary human myocytes does not lead to subsequent increase in insulin-stimulated glucose uptake.
2004 Sep
MEK inhibitors block AICAR-induced maturation in mouse oocytes by a MAPK-independent mechanism.
2005 Feb
Increased potency and efficacy of combined phosphorylase inactivation and glucokinase activation in control of hepatocyte glycogen metabolism.
2005 Mar
AMP-activated protein kinase and type 2 diabetes.
2006
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
Activation of AMP-activated protein kinase reduces hyperglycemia-induced mitochondrial reactive oxygen species production and promotes mitochondrial biogenesis in human umbilical vein endothelial cells.
2006 Jan
AMPK-mediated AS160 phosphorylation in skeletal muscle is dependent on AMPK catalytic and regulatory subunits.
2006 Jul
Inhibition of lipid synthesis through activation of AMP kinase: an additional mechanism for the hypolipidemic effects of berberine.
2006 Jun
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
Increased ATP-sensitive K+ channel expression during acute glucose deprivation.
2006 Sep 29
5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside-induced AMP-activated protein kinase phosphorylation inhibits basal and insulin-stimulated glucose uptake, lipid synthesis, and fatty acid oxidation in isolated rat adipocytes.
2006 Sep 8
[Pemetrexed: from preclinic to clinic].
2007
Associations of common polymorphisms in the thymidylate synthase, reduced folate carrier and 5-aminoimidazole-4-carboxamide ribonucleotide transformylase/inosine monophosphate cyclohydrolase genes with folate and homocysteine levels and venous thrombosis risk.
2007
5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside acutely stimulates skeletal muscle 2-deoxyglucose uptake in healthy men.
2007 Aug
Polymorphisms in folate, pyrimidine, and purine metabolism are associated with efficacy and toxicity of methotrexate in psoriasis.
2007 Aug
Determination of 5-aminoimidazole-4-carboxamide in human plasma by ion-pair extraction and LC-MS/MS.
2007 Aug 15
Formamide as the main building block in the origin of nucleic acids.
2007 Aug 16
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
Identification of new reference genes for the normalisation of canine osteoarthritic joint tissue transcripts from microarray data.
2007 Jul 25
The role of AMP kinase in diabetes.
2007 Mar
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
A novel function for the N-terminal nucleophile hydrolase fold demonstrated by the structure of an archaeal inosine monophosphate cyclohydrolase.
2007 May 1
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
Structural insight into AMPK regulation: ADP comes into play.
2007 Oct
Proteomics analysis of hypothalamic response to energy restriction in dairy cows.
2007 Oct
AMP kinase activation increases glucose uptake, decreases apoptosis, and improves pregnancy outcome in embryos exposed to high IGF-I concentrations.
2007 Sep
Adiponectin antagonizes stimulatory effect of tumor necrosis factor-alpha on vascular smooth muscle cell calcification: regulation of growth arrest-specific gene 6-mediated survival pathway by adenosine 5'-monophosphate-activated protein kinase.
2008 Apr
Ethanol consumption impairs regulation of fatty acid metabolism by decreasing the activity of AMP-activated protein kinase in rat liver.
2008 Mar
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:24:24 GMT 2025
Edited
by admin
on Mon Mar 31 18:24:24 GMT 2025
Record UNII
3V0Y2PDE6K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DACARBAZINE RELATED COMPOUND A (FREE BASE)
USP  
Preferred Name English
4-AMINO-5-IMIDAZOLE CARBOXAMIDE
Systematic Name English
BA-2756
Code English
TEMOZOLOMIDE IMPURITY, AMINOIMIDAZOLECARBOXAMIDE [USP IMPURITY]
Common Name English
AIC
Common Name English
5-AMINO-1H-IMIDAZOLE-4-CARBOXAMIDE
Systematic Name English
TEMOZOLOMIDE IMPURITY A [EP IMPURITY]
Common Name English
5-AMINO-4-IMIDAZOLECARBOXAMIDE
Systematic Name English
DACARBAZINE IMPURITY B [EP IMPURITY]
Common Name English
IMIDAZOLE-4-CARBOXAMIDE, 5-AMINO-
Systematic Name English
NSC-7784
Code English
AICA
Common Name English
DACARBAZINE RELATED COMPOUND A (FREE BASE) [USP IMPURITY]
Common Name English
5-AMINOIMIDAZOLE-4-CARBOXAMIDE
Systematic Name English
Classification Tree Code System Code
LOINC 79679-7
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
LOINC 79652-4
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
LOINC 79672-2
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
Code System Code Type Description
PUBCHEM
9679
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
PRIMARY
CHEBI
2030
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
PRIMARY
FDA UNII
3V0Y2PDE6K
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
PRIMARY
NSC
7784
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
PRIMARY
CAS
360-97-4
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
PRIMARY
EPA CompTox
DTXSID8059891
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-641-4
Created by admin on Mon Mar 31 18:24:24 GMT 2025 , Edited by admin on Mon Mar 31 18:24:24 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
PARENT -> METABOLITE INACTIVE
Related Record Type Details
PARENT -> IMPURITY
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP