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

Details

Stereochemistry ACHIRAL
Molecular Formula C2H6N2O
Molecular Weight 74.0818
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AZOXYMETHANE

SMILES

C\N=[N+](\C)[O-]

InChI

InChIKey=DGAKHGXRMXWHBX-ARJAWSKDSA-N
InChI=1S/C2H6N2O/c1-3-4(2)5/h1-2H3/b4-3-

HIDE SMILES / InChI

Molecular Formula C2H6N2O
Molecular Weight 74.0818
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Chemopreventive effects of standardized ethanol extract from the aerial parts of Artemisia princeps Pampanini cv. Sajabal via NF-κB inactivation on colitis-associated colon tumorigenesis in mice.
2015-01
Isoliquiritigenin, a flavonoid from licorice, blocks M2 macrophage polarization in colitis-associated tumorigenesis through downregulating PGE2 and IL-6.
2014-09-15
Pomegranate polyphenolics suppressed azoxymethane-induced colorectal aberrant crypt foci and inflammation: possible role of miR-126/VCAM-1 and miR-126/PI3K/AKT/mTOR.
2013-12
Targeted deletion of the metastasis-associated phosphatase Ptp4a3 (PRL-3) suppresses murine colon cancer.
2013
Advanced glycation end products (AGE) induce the receptor for AGE in the colonic mucosa of azoxymethane-injected Fischer 344 rats fed with a high-linoleic acid and high-glucose diet.
2012-10
Arsenic and chromium in drinking water promote tumorigenesis in a mouse colitis-associated colorectal cancer model and the potential mechanism is ROS-mediated Wnt/β-catenin signaling pathway.
2012-07-01
Glucagon-like peptide-2 increases dysplasia in rodent models of colon cancer.
2012-04-15
Study of 5-hydroxymethylfurfural and its metabolite 5-sulfooxymethylfurfural on induction of colonic aberrant crypt foci in wild-type mice and transgenic mice expressing human sulfotransferases 1A1 and 1A2.
2012-04
Implementation of a high-throughput screen for identifying small molecules to activate the Keap1-Nrf2-ARE pathway.
2012
Dietary astaxanthin inhibits colitis and colitis-associated colon carcinogenesis in mice via modulation of the inflammatory cytokines.
2011-08-15
Accumulation of K-Ras codon 12 mutations in the F344 rat distal colon following azoxymethane exposure.
2011-06
Pterostilbene is more potent than resveratrol in preventing azoxymethane (AOM)-induced colon tumorigenesis via activation of the NF-E2-related factor 2 (Nrf2)-mediated antioxidant signaling pathway.
2011-03-23
Aspirin promotes apoptosis in a murine model of colorectal cancer by mechanisms involving downregulation of IL-6-STAT3 signaling pathway.
2011-01
Inhibition of experimental colorectal cancer and reduction in renal and gastrointestinal toxicities by copper-indomethacin in rats.
2010-09
Pterostilbene inhibits colorectal aberrant crypt foci (ACF) and colon carcinogenesis via suppression of multiple signal transduction pathways in azoxymethane-treated mice.
2010-08-11
N-acetylcysteine attenuates cerebral complications of non-acetaminophen-induced acute liver failure in mice: antioxidant and anti-inflammatory mechanisms.
2010-06
Scopolamine treatment and muscarinic receptor subtype-3 gene ablation augment azoxymethane-induced murine liver injury.
2010-06
Antioxidant and anti-inflammatory effects of mild hypothermia in the attenuation of liver injury due to azoxymethane toxicity in the mouse.
2010-03
Long-term administration of aspirin inhibits tumour formation and triggers anti-neoplastic molecular changes in a pre-clinical model of colon carcinogenesis.
2010-02
Increased visceral fat mass and insulin signaling in colitis-related colon carcinogenesis model mice.
2010-01-27
Dietary flavonoids suppress azoxymethane-induced colonic preneoplastic lesions in male C57BL/KsJ-db/db mice.
2010-01-27
Rimonabant inhibits human colon cancer cell growth and reduces the formation of precancerous lesions in the mouse colon.
2009-09-01
Effect of berberine on the antioxidant status, ultrastructural modifications and protein bound carbohydrates in azoxymethane-induced colon cancer in rats.
2009-02-12
Melatonin suppresses AOM/DSS-induced large bowel oncogenesis in rats.
2009-01-27
Quercetin may suppress rat aberrant crypt foci formation by suppressing inflammatory mediators that influence proliferation and apoptosis.
2009-01
Simvastatin induces apoptosis in human colon cancer cells and in tumor xenografts, and attenuates colitis-associated colon cancer in mice.
2008-08-15
Antiproliferative effect of sulindac in colonic neoplasia prevention: role of COOH-terminal Src kinase.
2008-07
Dietary soy protein inhibits DNA damage and cell survival of colon epithelial cells through attenuated expression of fatty acid synthase.
2008-04
Peroxisome proliferator-activated receptor-beta/delta protects against chemically induced liver toxicity in mice.
2008-01
Ligand activation of peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta) and inhibition of cyclooxygenase 2 (COX2) attenuate colon carcinogenesis through independent signaling mechanisms.
2008-01
Ursodeoxycholic acid suppresses Cox-2 expression in colon cancer: roles of Ras, p38, and CCAAT/enhancer-binding protein.
2008
Chemopreventive effect of a vitamin D(3) analog, alfacalcidol, on colorectal carcinogenesis in mice with ulcerative colitis.
2007-11
Ursodeoxycholic acid versus sulfasalazine in colitis-related colon carcinogenesis in mice.
2007-04-15
Effect of azoxymethane and curcumin on transcriptional levels of cyclooxygenase-1 and -2 during initiation of colon carcinogenesis.
2007-01
Altered gene expression in rat colonic adenocarcinomas induced in an azoxymethane plus 2-amino-1-methyl-6-phenylimidazo[4,5-b]- pyridine initiation-promotion model.
2007
Development of normal human colon cell cultures to identify priority unregulated disinfection by-products with a carcinogenic potential.
2007
Nitric oxide-releasing aspirin and indomethacin are potent inhibitors against colon cancer in azoxymethane-treated rats: effects on molecular targets.
2006-06
Red wine polyphenols influence carcinogenesis, intestinal microflora, oxidative damage and gene expression profiles of colonic mucosa in F344 rats.
2005-12-11
Suppression of colitis-related mouse colon carcinogenesis by a COX-2 inhibitor and PPAR ligands.
2005-05-16
Chemoprevention: mouse colon and lung tumor bioassay and modulation of DNA methylation as a biomarker.
2005-03
Folate transport gene inactivation in mice increases sensitivity to colon carcinogenesis.
2005-02-01
Vehicle and mode of administration effects on the induction of aberrant crypt foci in the colons of male F344/N rats exposed to bromodichloromethane.
2004-01-09
Unexpected antagonistic action of 3,2'-dimethyl-4-aminobiphenyl on aberrant crypt induction by 1,2-dimethylhydrazine or azoxymethane in rat colon.
1995-12
Metabolic alterations of zinc and prostaglandins in both human and animal colonic tumor cells.
1995-10
Modifying effects of naturally occurring products on the development of colonic aberrant crypt foci induced by azoxymethane in F344 rats.
1995-03-15
Chemoprevention of colon carcinogenesis by organosulfur compounds.
1993-08-01
Specificity study to evaluate induction of aberrant crypts in murine colons.
1988-11-01
Carcinogenesis by nitrosodialkylamines and azoxyalkanes given by gavage to rats and hamsters.
1987-08-01
Effect of different levels of dietary corn oil and lard during the initiation phase of colon carcinogenesis in F344 rats.
1986-09
Organ-specific carcinogenesis in rats by methyl- and ethylazoxyalkanes.
1985-01
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 18:45:41 GMT 2025
Edited
by admin
on Mon Mar 31 18:45:41 GMT 2025
Record UNII
MO0N1J0SEN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZOXYMETHANE
Systematic Name English
NSC-171779
Preferred Name English
Classification Tree Code System Code
NCI_THESAURUS C1916
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
Code System Code Type Description
MESH
D001397
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
PRIMARY
SMS_ID
300000053072
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
PRIMARY
FDA UNII
MO0N1J0SEN
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
PRIMARY
NCI_THESAURUS
C294
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
PRIMARY
WIKIPEDIA
AZOXYMETHANE
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
PRIMARY
NSC
171779
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID3020124
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
PRIMARY
CAS
25843-45-2
Created by admin on Mon Mar 31 18:45:41 GMT 2025 , Edited by admin on Mon Mar 31 18:45:41 GMT 2025
PRIMARY