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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
Aryl and heterocyclic diazo compounds as potential environmental electrophiles.
1977 May
Regulation of fatty acid oxidation and glucose metabolism in rat soleus muscle: effects of AICAR.
2001 Aug
The AMP-activated protein kinase prevents ceramide synthesis de novo and apoptosis in astrocytes.
2001 Feb 2
Penetration of dacarbazine and its active metabolite 5-aminoimidazole-4-carboxamide into cutaneous metastases of human malignant melanoma.
2001 Oct 15
The effects of AICAR on adipocyte differentiation of 3T3-L1 cells.
2001 Sep 7
Effects of low-intensity prolonged exercise on PGC-1 mRNA expression in rat epitrochlearis muscle.
2002 Aug 16
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
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
Regulation of glycogen synthase by glucose and glycogen: a possible role for AMP-activated protein kinase.
2003 Jan
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
Mapping of the bovine genes of the de novo AMP synthesis pathway.
2004 Dec
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
Prior serum- and AICAR-induced AMPK activation in primary human myocytes does not lead to subsequent increase in insulin-stimulated glucose uptake.
2004 Sep
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
Suppression of inflammation by low-dose methotrexate is mediated by adenosine A2A receptor but not A3 receptor activation in thioglycollate-induced peritonitis.
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 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
Increased ATP-sensitive K+ channel expression during acute glucose deprivation.
2006 Sep 29
5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside acutely stimulates skeletal muscle 2-deoxyglucose uptake in healthy men.
2007 Aug
Formamide as the main building block in the origin of nucleic acids.
2007 Aug 16
5'-AMP-activated protein kinase activation prevents postischemic leukocyte-endothelial cell adhesive interactions.
2007 Jan
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
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
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
AMP kinase activation increases glucose uptake, decreases apoptosis, and improves pregnancy outcome in embryos exposed to high IGF-I concentrations.
2007 Sep
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 16 19:49:16 UTC 2022
Edited
by admin
on Fri Dec 16 19:49:16 UTC 2022
Record UNII
3V0Y2PDE6K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
4-AMINO-5-IMIDAZOLE CARBOXAMIDE
Systematic Name English
BA-2756
Code English
DACARBAZINE RELATED COMPOUND A (FREE BASE)
USP  
Common Name 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 Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
LOINC 79652-4
Created by admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
LOINC 79672-2
Created by admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
Code System Code Type Description
PUBCHEM
9679
Created by admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
PRIMARY
CHEBI
2030
Created by admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
PRIMARY
FDA UNII
3V0Y2PDE6K
Created by admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
PRIMARY
NSC
7784
Created by admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
PRIMARY
CAS
360-97-4
Created by admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
PRIMARY
EPA CompTox
DTXSID8059891
Created by admin on Fri Dec 16 19:49:17 UTC 2022 , Edited by admin on Fri Dec 16 19:49:17 UTC 2022
PRIMARY
ECHA (EC/EINECS)
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
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