VINYL CARBAMATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C3H5NO2
Molecular Weight	87.0773
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)OC=C

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	87.0773
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
Tricyclic compounds containing nonenolizable cyano enones. A novel class of highly potent anti-inflammatory and cytoprotective agents.	2011-03-24	21361338
Formation and repair of tobacco carcinogen-derived bulky DNA adducts.	2010-12-20	21234336
Chemopreventive effects of pioglitazone on chemically induced lung carcinogenesis in mice.	2010-11	21045137
Cigarette smoke induces C/EBP-β-mediated activation of miR-31 in normal human respiratory epithelia and lung cancer cells.	2010-10-29	21048943
Mechanisms of lung tumorigenesis by ethyl carbamate and vinyl carbamate.	2010-05	20205516
Structure of the 1,N(2)-etheno-2'-deoxyguanosine lesion in the 3'-G(epsilon dG)T-5' sequence opposite a one-base deletion.	2010-03-30	20201499
NADPH oxidase limits innate immune responses in the lungs in mice.	2010-03-16	20300512
Alteration of microRNA expression in vinyl carbamate-induced mouse lung tumors and modulation by the chemopreventive agent indole-3-carbinol.	2010-02	19748927
Inhibition of vinyl carbamate-induced pulmonary adenocarcinoma by indole-3-carbinol and myo-inositol in A/J mice.	2010-02	19625346
Capsaicin: a novel chemopreventive molecule and its underlying molecular mechanisms of action.	2010-01-15	20071791
Triterpenoids CDDO-methyl ester or CDDO-ethyl amide and rexinoids LG100268 or NRX194204 for prevention and treatment of lung cancer in mice.	2009-12	19952361
FoxO3a gene is a target of deletion in mouse lung adenocarcinoma.	2009-10	19724863
Chiral Brønsted acid-catalyzed enantioselective three-component Povarov reaction.	2009-04-08	19334771
Inhibition of vinyl carbamate-induced lung tumors and Kras2 mutations by the garlic derivative diallyl sulfone.	2009-03-09	19101575
Structure of the 1,N2-ethenodeoxyguanosine adduct opposite cytosine in duplex DNA: Hoogsteen base pairing at pH 5.2.	2008-09	18693701
Cancer is a preventable disease that requires major lifestyle changes.	2008-09	18626751
Evidence of complete cellular repair of 1,N6-ethenoadenine, a mutagenic and potential damage for human cancer, revealed by a novel method.	2008-06	18373235
The rexinoid LG100268 and the synthetic triterpenoid CDDO-methyl amide are more potent than erlotinib for prevention of mouse lung carcinogenesis.	2008-05	18483313
Modulation by bexarotene of mRNA expression of genes in mouse lung tumors.	2008-03	17849452
Role of peroxisome proliferator-activated receptor gamma and its ligands in the treatment of hematological malignancies.	2008	18528522
A new rexinoid, NRX194204, prevents carcinogenesis in both the lung and mammary gland.	2007-10-15	17947492
Inhibition of vinyl carbamate-induced mutagenicity and clastogenicity by the garlic constituent diallyl sulfone in F1 (Big Blue x A/J) transgenic mice.	2007-08	17341656
Modulation by budesonide of a CpG endonuclease in mouse lung tumors.	2007-07	17361011
Oxidation of vinyl carbamate and formation of 1,N6-ethenodeoxyadenosine in murine lung.	2007-05	17296623
In vivo mutagenicity of vinyl carbamate and ethyl carbamate in lung and small intestine of F1 (Big Blue x A/J) transgenic mice.	2007-04-01	17205523
The synthetic triterpenoids CDDO-methyl ester and CDDO-ethyl amide prevent lung cancer induced by vinyl carbamate in A/J mice.	2007-03-15	17363558
Modulation by budesonide of DNA methylation and mRNA expression in mouse lung tumors.	2007-03-01	17163412
Inhibition of urethane-induced carcinogenicity in cyp2e1-/- in comparison to cyp2e1+/+ mice.	2007-02	17093202
Prevention of mouse lung tumors and modulation of DNA methylation by combined treatment with budesonide and R115777 (Zarnestra MT).	2007-01	16885199
Prevention of mouse lung tumors and modulation of DNA methylation by combined treatment with budesonide and R115777 (ZarnestraMT).	2006-12	16733249
Prevention of mouse lung tumors by targretin.	2006-05-01	16331605
Prevention of lung cancer progression by bexarotene in mouse models.	2006-03-02	16247446
A mouse model for tumor progression of lung cancer in ras and p53 transgenic mice.	2006-02-23	16247444
Chemoprevention: mouse colon and lung tumor bioassay and modulation of DNA methylation as a biomarker.	2005-03	15824018
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands.	2004-10-06	15453764
Interactions in the tumor-promoting activity of carbon tetrachloride, trichloroacetate, and dichloroacetate in the liver of male B6C3F1 mice.	2004-07-01	15147791
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.	2004-06-01	15172992
Carcinogen-specific targeting of chromosome 12 for loss of heterozygosity in mouse lung adenocarcinomas: implications for chromosome instability and tumor progression.	2004-04-15	14755239
Carcinogen exposure differentially modulates RAR-beta promoter hypermethylation, an early and frequent event in mouse lung carcinogenesis.	2004-04	14656941
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.	2003-11-15	14633693
Mutation analysis of vinyl carbamate or urethane induced lung tumors in rasH2 transgenic mice.	2003-04-30	12765245
Lipoxygenase and cyclooxygenase metabolism: new insights in treatment and chemoprevention of pancreatic cancer.	2003-01-07	12575899
Carcinogenic induction directs the selection of allelic losses in mouse lung tumorigenesis.	2002-11-15	12438228
Comparative prevalence, multiplicity, and progression of spontaneous and vinyl carbamate-induced liver lesions in five strains of male mice.	2002-10-10	12371669
Effect of budesonide on the methylation and mRNA expression of the insulin-like growth factor 2 and c-myc genes in mouse lung tumors.	2002-10	12325039
Chemoprevention by lipoxygenase and leukotriene pathway inhibitors of vinyl carbamate-induced lung tumors in mice.	2002-08-01	12154018
Prevention of mouse lung tumors by budesonide and its modulation of biomarkers.	2002-07	12117777
Chemopreventive effects of 2-(allylthio)pyrazine on hepatic lesion, mutagenesis and tumorigenesis induced by vinyl carbamate or vinyl carbamate epoxide.	1998-07	9683187
Vinyl carbamate epoxide, a major strong electrophilic, mutagenic and carcinogenic metabolite of vinyl carbamate and ethyl carbamate (urethane).	1993-03	8453720
Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects.	1991-03-01	1664256

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:35:07 GMT 2025` Edited by `admin` on `Mon Mar 31 18:35:07 GMT 2025`
Record UNII	7Y2431GOM5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NSC-133266

Preferred Name

English

VINYL CARBAMATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C45175