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
Effects of low-intensity prolonged exercise on PGC-1 mRNA expression in rat epitrochlearis muscle.	2002 Aug 16	12163024
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	12077137
Targeting the AMP-activated protein kinase for the treatment of type 2 diabetes.	2002 Jul	12476786
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
AMP-activated protein kinase kinase: detection with recombinant AMPK alpha1 subunit.	2002 May 10	12051742
AICAR and phlorizin reverse the hypoglycemia-specific defect in glucagon secretion in the diabetic BB rat.	2002 Nov	12376337
5-Aminoimidazole-4-carboxamide 1-beta -D-ribofuranoside (AICAR) stimulates myocardial glycogenolysis by allosteric mechanisms.	2003 Apr	12626360
A possible linkage between AMP-activated protein kinase (AMPK) and mammalian target of rapamycin (mTOR) signalling pathway.	2003 Jan	12558800
Regulation of glycogen synthase by glucose and glycogen: a possible role for AMP-activated protein kinase.	2003 Jan	12502487
Increased AMP:ATP ratio and AMP-activated protein kinase activity during cellular senescence linked to reduced HuR function.	2003 Jul 18	12730239
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
Requirement for 3-phosphoinositide-kependent dinase-1 (PDK-1) in insulin-induced glucose uptake in immortalized brown adipocytes.	2003 Oct 3	12855688
Mapping of the bovine genes of the de novo AMP synthesis pathway.	2004 Dec	15566465
Ca2+ and AMPK both mediate stimulation of glucose transport by muscle contractions.	2004 Feb	14747282
Effects of acute bouts of running and swimming exercise on PGC-1alpha protein expression in rat epitrochlearis and soleus muscle.	2004 Feb	14570700
Sending the signal: molecular mechanisms regulating glucose uptake.	2004 Jul	15235328
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
A glucose response element from the S. cerevisiae hexose transporter HXT1 gene is sensitive to glucose in human fibroblasts.	2004 May 7	15099735
The effect of folic acid and folinic acid supplements on purine metabolism in methotrexate-treated rheumatoid arthritis.	2004 Oct	15476202
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
MEK inhibitors block AICAR-induced maturation in mouse oocytes by a MAPK-independent mechanism.	2005 Feb	15570612
Increased potency and efficacy of combined phosphorylase inactivation and glucokinase activation in control of hepatocyte glycogen metabolism.	2005 Mar	15734835
AMP-activated protein kinase and type 2 diabetes.	2006	16515522
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 reduces hyperglycemia-induced mitochondrial reactive oxygen species production and promotes mitochondrial biogenesis in human umbilical vein endothelial cells.	2006 Jan	16380484
AMPK-mediated AS160 phosphorylation in skeletal muscle is dependent on AMPK catalytic and regulatory subunits.	2006 Jul	16804075
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
Increased ATP-sensitive K+ channel expression during acute glucose deprivation.	2006 Sep 29	16904639
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	16816404
[Pemetrexed: from preclinic to clinic].	2007	17845983
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	17439323
5-aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside acutely stimulates skeletal muscle 2-deoxyglucose uptake in healthy men.	2007 Aug	17513706
Polymorphisms in folate, pyrimidine, and purine metabolism are associated with efficacy and toxicity of methotrexate in psoriasis.	2007 Aug	17410198
Determination of 5-aminoimidazole-4-carboxamide in human plasma by ion-pair extraction and LC-MS/MS.	2007 Aug 15	17561451
Formamide as the main building block in the origin of nucleic acids.	2007 Aug 16	17767725
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	17218607
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
The role of AMP kinase in diabetes.	2007 Mar	17496363
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
A novel function for the N-terminal nucleophile hydrolase fold demonstrated by the structure of an archaeal inosine monophosphate cyclohydrolase.	2007 May 1	17407260
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
Structural insight into AMPK regulation: ADP comes into play.	2007 Oct	17937917
Proteomics analysis of hypothalamic response to energy restriction in dairy cows.	2007 Oct	17907270
AMP kinase activation increases glucose uptake, decreases apoptosis, and improves pregnancy outcome in embryos exposed to high IGF-I concentrations.	2007 Sep	17575082
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	18174285
Ethanol consumption impairs regulation of fatty acid metabolism by decreasing the activity of AMP-activated protein kinase in rat liver.	2008 Mar	17997005

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)

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