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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
Structure of 5-AMINOIMIDAZOLE-4-CARBOXAMIDE HYDROCHLORIDE

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

HIDE SMILES / InChI

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

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
The role of AMP-activated protein kinase in the action of ethanol in the liver.
2004 Dec
Mapping of the bovine genes of the de novo AMP synthesis pathway.
2004 Dec
Virtual screening of human 5-aminoimidazole-4-carboxamide ribonucleotide transformylase against the NCI diversity set by use of AutoDock to identify novel nonfolate inhibitors.
2004 Dec 30
Ca2+ and AMPK both mediate stimulation of glucose transport by muscle contractions.
2004 Feb
Sending the signal: molecular mechanisms regulating glucose uptake.
2004 Jul
Activation of AMP-activated protein kinase inhibits protein synthesis associated with hypertrophy in the cardiac myocyte.
2004 Jul 30
Preliminary study on pharmacokinetics of dacarbazine and fotemustine in glioblastoma multiforme patients does not indicate gender-specific differences.
2004 Jun
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
The effect of folic acid and folinic acid supplements on purine metabolism in methotrexate-treated rheumatoid arthritis.
2004 Oct
Polyglutamation of methotrexate with common polymorphisms in reduced folate carrier, aminoimidazole carboxamide ribonucleotide transformylase, and thymidylate synthase are associated with methotrexate effects in rheumatoid arthritis.
2004 Sep
Prior serum- and AICAR-induced AMPK activation in primary human myocytes does not lead to subsequent increase in insulin-stimulated glucose uptake.
2004 Sep
A role for hypothalamic malonyl-CoA in the control of food intake.
2005 Dec 2
MEK inhibitors block AICAR-induced maturation in mouse oocytes by a MAPK-independent mechanism.
2005 Feb
Role of neuronal energy status in the regulation of adenosine 5'-monophosphate-activated protein kinase, orexigenic neuropeptides expression, and feeding behavior.
2005 Jan
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
Increased potency and efficacy of combined phosphorylase inactivation and glucokinase activation in control of hepatocyte glycogen metabolism.
2005 Mar
Pharmacological inhibition of AMP-activated protein kinase provides neuroprotection in stroke.
2005 May 27
Adenosine monophosphate-activated protein kinase suppresses vascular smooth muscle cell proliferation through the inhibition of cell cycle progression.
2005 Oct 14
Suppression of inflammation by low-dose methotrexate is mediated by adenosine A2A receptor but not A3 receptor activation in thioglycollate-induced peritonitis.
2006
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
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
AMPK activation increases fatty acid oxidation in skeletal muscle by activating PPARalpha and PGC-1.
2006 Feb 3
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
Activation of AMP-activated protein kinase within the ventromedial hypothalamus amplifies counterregulatory hormone responses in rats with defective counterregulation.
2006 Jun
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
Pharmacogenomic and metabolic biomarkers in the folate pathway and their association with methotrexate effects during dosage escalation in rheumatoid arthritis.
2006 Oct
Diagnosing AICA-ribosiduria by capillary electrophoresis.
2006 Oct 20
[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
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
Structural insight into AMPK regulation: ADP comes into play.
2007 Oct
Proteomics analysis of hypothalamic response to energy restriction in dairy cows.
2007 Oct
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 Fri Dec 15 18:59:54 GMT 2023
Edited
by admin
on Fri Dec 15 18:59:54 GMT 2023
Record UNII
220691X0M3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
5-AMINOIMIDAZOLE-4-CARBOXAMIDE HYDROCHLORIDE
Systematic Name English
1H-IMIDAZOLE-4-CARBOXAMIDE, 5-AMINO-, HYDROCHLORIDE (1:1)
Systematic Name English
AICA HCI
Common Name English
5-AMINOIMIDAZOLE-4-CARBOXAMIDE HCL
Common Name English
5-AMINO-IMIDAZOLE-4-CARBOXAMIDE HYDROCHLORIDE SALT
Common Name English
1H-IMIDAZOLE-4-CARBOXAMIDE, 5-AMINO-, MONOHYDROCHLORIDE
Common Name English
IMIDAZOLE-4-CARBOXAMIDE, 5-AMINO-, MONOHYDROCHLORIDE
Common Name English
AICA HYDROCHLORIDE
Common Name English
DACARBAZINE RELATED COMPOUND A
USP   USP-RS  
Common Name English
5-AMINO-1H-IMIDAZOLE-4-CARBOXAMIDE HYDROCHLORIDE
Systematic Name English
DACARBAZINE RELATED COMPOUND A [USP-RS]
Common Name English
DACARBAZINE RELATED COMPOUND A [USP IMPURITY]
Common Name English
4-AMINO-5-IMIDAZOLE CARBOXAMIDE HYDROCHLORIDE
Systematic Name English
NSC-113496
Code English
Code System Code Type Description
ECHA (EC/EINECS)
200-778-3
Created by admin on Fri Dec 15 18:59:54 GMT 2023 , Edited by admin on Fri Dec 15 18:59:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID00883234
Created by admin on Fri Dec 15 18:59:54 GMT 2023 , Edited by admin on Fri Dec 15 18:59:54 GMT 2023
PRIMARY
CAS
72-40-2
Created by admin on Fri Dec 15 18:59:54 GMT 2023 , Edited by admin on Fri Dec 15 18:59:54 GMT 2023
PRIMARY
FDA UNII
220691X0M3
Created by admin on Fri Dec 15 18:59:54 GMT 2023 , Edited by admin on Fri Dec 15 18:59:54 GMT 2023
PRIMARY
RS_ITEM_NUM
1162320
Created by admin on Fri Dec 15 18:59:54 GMT 2023 , Edited by admin on Fri Dec 15 18:59:54 GMT 2023
PRIMARY
NSC
113496
Created by admin on Fri Dec 15 18:59:54 GMT 2023 , Edited by admin on Fri Dec 15 18:59:54 GMT 2023
PRIMARY
PUBCHEM
66146
Created by admin on Fri Dec 15 18:59:54 GMT 2023 , Edited by admin on Fri Dec 15 18:59:54 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE