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Details

Stereochemistry ACHIRAL
Molecular Formula C3H5NO2
Molecular Weight 87.0774
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VINYL CARBAMATE

SMILES

C=COC(=N)O

InChI

InChIKey=LVLANIHJQRZTPY-UHFFFAOYSA-N
InChI=1S/C3H5NO2/c1-2-6-3(4)5/h2H,1H2,(H2,4,5)

HIDE SMILES / InChI

Molecular Formula C3H5NO2
Molecular Weight 87.0774
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects.
1991 Mar-Apr
Vinyl carbamate epoxide, a major strong electrophilic, mutagenic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate (urethane).
1993 Mar
Chemopreventive effects of 2-(allylthio)pyrazine on hepatic lesion, mutagenesis and tumorigenesis induced by vinyl carbamate or vinyl carbamate epoxide.
1998 Jul
Prevention of mouse lung tumors by budesonide and its modulation of biomarkers.
2002 Jul
Effect of budesonide on the methylation and mRNA expression of the insulin-like growth factor 2 and c-myc genes in mouse lung tumors.
2002 Oct
Comparative prevalence, multiplicity, and progression of spontaneous and vinyl carbamate-induced liver lesions in five strains of male mice.
2002 Sep-Oct
Mutation analysis of vinyl carbamate or urethane induced lung tumors in rasH2 transgenic mice.
2003 Apr 30
Increased formation and persistence of 1,N(6)-ethenoadenine in DNA is not associated with higher susceptibility to carcinogenesis in alkylpurine-DNA-N-glycosylase knockout mice treated with vinyl carbamate.
2003 Nov 15
Carcinogen exposure differentially modulates RAR-beta promoter hypermethylation, an early and frequent event in mouse lung carcinogenesis.
2004 Apr
Carcinogen-specific targeting of chromosome 12 for loss of heterozygosity in mouse lung adenocarcinomas: implications for chromosome instability and tumor progression.
2004 Apr 15
Interactions in the tumor-promoting activity of carbon tetrachloride, trichloroacetate, and dichloroacetate in the liver of male B6C3F1 mice.
2004 Jul 1
Aberrant promoter hypermethylation of the death-associated protein kinase gene is early and frequent in murine lung tumors induced by cigarette smoke and tobacco carcinogens.
2004 Jun 1
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands.
2004 Oct 6
Chemoprevention: mouse colon and lung tumor bioassay and modulation of DNA methylation as a biomarker.
2005 Mar
Prevention of mouse lung tumors and modulation of DNA methylation by combined treatment with budesonide and R115777 (ZarnestraMT).
2006 Dec
A mouse model for tumor progression of lung cancer in ras and p53 transgenic mice.
2006 Feb 23
Prevention of mouse lung tumors by targretin.
2006 May 1
In vivo mutagenicity of vinyl carbamate and ethyl carbamate in lung and small intestine of F1 (Big Blue x A/J) transgenic mice.
2007 Apr 1
Inhibition of urethane-induced carcinogenicity in cyp2e1-/- in comparison to cyp2e1+/+ mice.
2007 Feb
Prevention of mouse lung tumors and modulation of DNA methylation by combined treatment with budesonide and R115777 (Zarnestra MT).
2007 Jan
Modulation by budesonide of DNA methylation and mRNA expression in mouse lung tumors.
2007 Mar 1
The synthetic triterpenoids CDDO-methyl ester and CDDO-ethyl amide prevent lung cancer induced by vinyl carbamate in A/J mice.
2007 Mar 15
Oxidation of vinyl carbamate and formation of 1,N6-ethenodeoxyadenosine in murine lung.
2007 May
A new rexinoid, NRX194204, prevents carcinogenesis in both the lung and mammary gland.
2007 Oct 15
Role of peroxisome proliferator-activated receptor gamma and its ligands in the treatment of hematological malignancies.
2008
Evidence of complete cellular repair of 1,N6-ethenoadenine, a mutagenic and potential damage for human cancer, revealed by a novel method.
2008 Jun
Modulation by bexarotene of mRNA expression of genes in mouse lung tumors.
2008 Mar
The rexinoid LG100268 and the synthetic triterpenoid CDDO-methyl amide are more potent than erlotinib for prevention of mouse lung carcinogenesis.
2008 May
Structure of the 1,N2-ethenodeoxyguanosine adduct opposite cytosine in duplex DNA: Hoogsteen base pairing at pH 5.2.
2008 Sep
Cancer is a preventable disease that requires major lifestyle changes.
2008 Sep
Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction.
2009 Apr 8
Triterpenoids CDDO-methyl ester or CDDO-ethyl amide and rexinoids LG100268 or NRX194204 for prevention and treatment of lung cancer in mice.
2009 Dec
Inhibition of vinyl carbamate-induced lung tumors and Kras2 mutations by the garlic derivative diallyl sulfone.
2009 Mar 9
FoxO3a gene is a target of deletion in mouse lung adenocarcinoma.
2009 Oct
Formation and repair of tobacco carcinogen-derived bulky DNA adducts.
2010 Dec 20
Alteration of microRNA expression in vinyl carbamate-induced mouse lung tumors and modulation by the chemopreventive agent indole-3-carbinol.
2010 Feb
Inhibition of vinyl carbamate-induced pulmonary adenocarcinoma by indole-3-carbinol and myo-inositol in A/J mice.
2010 Feb
Capsaicin: a novel chemopreventive molecule and its underlying molecular mechanisms of action.
2010 Jan-Mar
NADPH oxidase limits innate immune responses in the lungs in mice.
2010 Mar 16
Structure of the 1,N(2)-etheno-2'-deoxyguanosine lesion in the 3'-G(epsilon dG)T-5' sequence opposite a one-base deletion.
2010 Mar 30
Mechanisms of lung tumorigenesis by ethyl carbamate and vinyl carbamate.
2010 May
Chemopreventive effects of pioglitazone on chemically induced lung carcinogenesis in mice.
2010 Nov
Cigarette smoke induces C/EBP-β-mediated activation of miR-31 in normal human respiratory epithelia and lung cancer cells.
2010 Oct 29
Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.
2011 Mar 24
Substance Class Chemical
Created
by admin
on Sat Jun 26 08:34:52 UTC 2021
Edited
by admin
on Sat Jun 26 08:34:52 UTC 2021
Record UNII
7Y2431GOM5
Record Status Validated (UNII)
Record Version
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Name Type Language
VINYL CARBAMATE
Systematic Name English
NSC-133266
Code English
Classification Tree Code System Code
NCI_THESAURUS C45175
Created by admin on Sat Jun 26 08:34:52 UTC 2021 , Edited by admin on Sat Jun 26 08:34:52 UTC 2021
Code System Code Type Description
CAS
15805-73-9
Created by admin on Sat Jun 26 08:34:52 UTC 2021 , Edited by admin on Sat Jun 26 08:34:52 UTC 2021
PRIMARY
PUBCHEM
27492
Created by admin on Sat Jun 26 08:34:52 UTC 2021 , Edited by admin on Sat Jun 26 08:34:52 UTC 2021
PRIMARY
MESH
C017963
Created by admin on Sat Jun 26 08:34:52 UTC 2021 , Edited by admin on Sat Jun 26 08:34:52 UTC 2021
PRIMARY
EPA CompTox
15805-73-9
Created by admin on Sat Jun 26 08:34:52 UTC 2021 , Edited by admin on Sat Jun 26 08:34:52 UTC 2021
PRIMARY
FDA UNII
7Y2431GOM5
Created by admin on Sat Jun 26 08:34:52 UTC 2021 , Edited by admin on Sat Jun 26 08:34:52 UTC 2021
PRIMARY
NCI_THESAURUS
C29864
Created by admin on Sat Jun 26 08:34:52 UTC 2021 , Edited by admin on Sat Jun 26 08:34:52 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
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PARENT -> METABOLITE
METABOLITE -> PARENT