U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Penetration of dacarbazine and its active metabolite 5-aminoimidazole-4-carboxamide into cutaneous metastases of human malignant melanoma.
2001 Oct 15
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
Aberrant p38 mitogen-activated protein kinase signalling in skeletal muscle from Type 2 diabetic patients.
2003 Oct
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
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
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
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
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
Diagnosing AICA-ribosiduria by capillary electrophoresis.
2006 Oct 20
Induction of meiotic maturation in mouse oocytes by adenosine analogs.
2006 Sep
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
Determination of 5-aminoimidazole-4-carboxamide in human plasma by ion-pair extraction and LC-MS/MS.
2007 Aug 15
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
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 Fri Dec 15 16:18:03 UTC 2023
Edited
by admin
on Fri Dec 15 16:18:03 UTC 2023
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 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
LOINC 79652-4
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
LOINC 79672-2
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
Code System Code Type Description
PUBCHEM
9679
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
CHEBI
2030
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
FDA UNII
3V0Y2PDE6K
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
NSC
7784
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
CAS
360-97-4
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
EPA CompTox
DTXSID8059891
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-641-4
Created by admin on Fri Dec 15 16:18:03 UTC 2023 , Edited by admin on Fri Dec 15 16:18:03 UTC 2023
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