4-AMINO-5-IMIDAZOLE CARBOXAMIDE

Investigational

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

Structure Search

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

Title	Date	PubMed
Aryl and heterocyclic diazo compounds as potential environmental electrophiles.	1977 May	17015
Regulation of fatty acid oxidation and glucose metabolism in rat soleus muscle: effects of AICAR.	2001 Aug	11440910
The AMP-activated protein kinase prevents ceramide synthesis de novo and apoptosis in astrocytes.	2001 Feb 2	11165240
Penetration of dacarbazine and its active metabolite 5-aminoimidazole-4-carboxamide into cutaneous metastases of human malignant melanoma.	2001 Oct 15	11596037
The effects of AICAR on adipocyte differentiation of 3T3-L1 cells.	2001 Sep 7	11527376
Effects of low-intensity prolonged exercise on PGC-1 mRNA expression in rat epitrochlearis muscle.	2002 Aug 16	12163024
Activation of GLUT1 by metabolic and osmotic stress: potential involvement of AMP-activated protein kinase (AMPK).	2002 Jun 1	12006627
Acute and chronic treatment of ob/ob and db/db mice with AICAR decreases blood glucose concentrations.	2002 Jun 21	12061777
Cloning and characterization of methenyltetrahydrofolate synthetase from Saccharomyces cerevisiae.	2002 Jun 7	11923304
Down-regulation of Lsm1 is involved in human prostate cancer progression.	2002 Mar 18	11953827
Regulation of GLUT4 biogenesis in muscle: evidence for involvement of AMPK and Ca(2+).	2002 May	11934664
Regulation of glycogen synthase by glucose and glycogen: a possible role for AMP-activated protein kinase.	2003 Jan	12502487
5-amino-imidazole carboxamide riboside increases glucose transport and cell-surface GLUT4 content in skeletal muscle from subjects with type 2 diabetes.	2003 May	12716734
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	12644453
Mapping of the bovine genes of the de novo AMP synthesis pathway.	2004 Dec	15566465
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	14729664
Adenosine induces apoptosis in the human gastric cancer cells via an intrinsic pathway relevant to activation of AMP-activated protein kinase.	2004 May 15	15130776
Prior serum- and AICAR-induced AMPK activation in primary human myocytes does not lead to subsequent increase in insulin-stimulated glucose uptake.	2004 Sep	15149951
AICAR suppresses IL-2 expression through inhibition of GSK-3 phosphorylation and NF-AT activation in Jurkat T cells.	2005 Jul 1	15910743
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	15864539
The glucose dependence of Akt-transformed cells can be reversed by pharmacologic activation of fatty acid beta-oxidation.	2005 Jun 16	15806154
Increased potency and efficacy of combined phosphorylase inactivation and glucokinase activation in control of hepatocyte glycogen metabolism.	2005 Mar	15734835
Suppression of inflammation by low-dose methotrexate is mediated by adenosine A2A receptor but not A3 receptor activation in thioglycollate-induced peritonitis.	2006	16519795
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	16443786
Activation of AMP-activated protein kinase within the ventromedial hypothalamus amplifies counterregulatory hormone responses in rats with defective counterregulation.	2006 Jun	16731839
Inhibition of lipid synthesis through activation of AMP kinase: an additional mechanism for the hypolipidemic effects of berberine.	2006 Jun	16508037
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	16483872
Pharmacogenomic and metabolic biomarkers in the folate pathway and their association with methotrexate effects during dosage escalation in rheumatoid arthritis.	2006 Oct	17009228
Increased ATP-sensitive K+ channel expression during acute glucose deprivation.	2006 Sep 29	16904639
5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside acutely stimulates skeletal muscle 2-deoxyglucose uptake in healthy men.	2007 Aug	17513706
Formamide as the main building block in the origin of nucleic acids.	2007 Aug 16	17767725
5'-AMP-activated protein kinase activation prevents postischemic leukocyte-endothelial cell adhesive interactions.	2007 Jan	16935999
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	17623090
Identification of new reference genes for the normalisation of canine osteoarthritic joint tissue transcripts from microarray data.	2007 Jul 25	17651481
Role of hypothalamic adenosine 5'-monophosphate-activated protein kinase in the impaired counterregulatory response induced by repetitive neuroglucopenia.	2007 Mar	17185376
Role of glycogen content in insulin resistance in human muscle cells.	2007 May	17167773
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	17702848
AMP kinase activation increases glucose uptake, decreases apoptosis, and improves pregnancy outcome in embryos exposed to high IGF-I concentrations.	2007 Sep	17575082

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)

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