Page last updated: 2024-12-06

vinyl carbamate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Vinyl carbamate is a versatile chemical compound with potential applications in various fields. It is a reactive species that can undergo a range of chemical transformations. Notably, it has garnered interest as a potential intermediate in the synthesis of pharmaceuticals and agricultural chemicals. The unique reactivity of vinyl carbamate stems from the presence of both a vinyl group and a carbamate functionality, which enables it to participate in various reactions. While its precise synthesis methods are not widely documented, researchers have explored different strategies for its preparation. The potential effects of vinyl carbamate on biological systems are currently under investigation. Its reactivity and potential to form new compounds make it a promising candidate for drug discovery and development. Ongoing research aims to further elucidate its properties and potential applications. The study of vinyl carbamate is motivated by its potential to serve as a valuable building block in the synthesis of novel compounds with desirable biological activities. The compound's reactivity and versatility make it a promising target for exploring new therapeutic strategies. '

vinyl carbamate: promutagen & more carcinogenic analog of ethyl carbamate (urethane); structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID27492
CHEBI ID27292
MeSH IDM0069128

Synonyms (19)

Synonym
CHEBI:27292
ethenyl carbamate
nsc-133266
vinyl carbamate
carbamic acid, vinyl ester
nsc133266
15805-73-9
carbamic acid, ethenyl ester
brn 1921122
ccris 6542
nsc 133266
AKOS006273443
unii-7y2431gom5
7y2431gom5 ,
FT-0675824
DTXSID3021433
J-009471
Q27109945
ethenyl estercarbamic acid

Research Excerpts

Overview

Vinyl carbamate is a naturally occurring compound found in fermented foods and alcoholic beverages. It is a metabolite of ethyl carbamate (EC), a chemical found in alcoholic beverages and fermented foods.

ExcerptReferenceRelevance
"Vinyl carbamate (VC) is a metabolite of ethyl carbamate (EC), a chemical found in alcoholic beverages and fermented foods. "( In vivo mutagenicity of vinyl carbamate and ethyl carbamate in lung and small intestine of F1 (Big Blue x A/J) transgenic mice.
Forkert, PG; Hernandez, LG, 2007
)
2.09
"Vinyl carbamate (VC) is a metabolite of ethyl carbamate (EC), a naturally occurring compound found in fermented foods and alcoholic beverages. "( Inhibition of vinyl carbamate-induced mutagenicity and clastogenicity by the garlic constituent diallyl sulfone in F1 (Big Blue x A/J) transgenic mice.
Forkert, PG; Hernandez, LG, 2007
)
2.14
"Vinyl carbamate (VC) is a suspect metabolic intermediate in ethyl carbamate (EC) carcinogenesis. "( Tumorigenesis and genotoxicity of ethyl carbamate and vinyl carbamate in rodent cells.
Allen, JW; Backer, LC; Campbell, JA; Hatch, GG; Nesnow, S; Pereira, MA; Sharief, Y; Stead, AG; Stoner, GD, 1986
)
1.96

Treatment

ExcerptReferenceRelevance
"Vinyl carbamate-treated mice showed increased mean surface tumor counts at all time points."( Proliferative lesions of the mouse lung: progression studies in strain A mice.
Anderson, MW; Foley, JF; Gaul, BW; Hardisty, JF; Maronpot, RR; Stoner, GD,
)
0.85

Toxicity

ExcerptReferenceRelevance
" The carcinogenic and toxic possibility of EC is thought to be related to its metabolite vinyl carbamate (VC)."( Lysosomal Reacidification Ameliorates Vinyl Carbamate-Induced Toxicity and Disruption on Lysosomal pH.
Chen, W; Cui, S; Hu, D; Li, Y; Qi, J, 2020
)
1.05

Bioavailability

ExcerptReferenceRelevance
" Curcumin has long been recognized as a chemopreventive agent, but poor bioavailability and weak Nrf2 induction have prohibited clinical application."( A Curcumin Derivative That Inhibits Vinyl Carbamate-Induced Lung Carcinogenesis via Activation of the Nrf2 Protective Response.
Chapman, E; Chen, J; Jiang, T; Long, M; Ren, DM; Shen, T; Wong, PK; Zhang, DD; Zhou, B, 2015
)
0.69

Dosage Studied

The genotoxic carcinogen vinyl carbamate was dosed to C57Bl/10J strain mice for 35 weeks. The study terminated after week 59.

ExcerptRelevanceReference
"The genotoxic carcinogen vinyl carbamate was dosed to C57Bl/10J strain mice for 35 weeks, and the study terminated after week 59."( Hepatocarcinogenic effect of vinyl carbamate in the C57Bl/10J strain mouse.
Marsden, AM; Orton, TC; Willets, JM; Wright, JA, 1991
)
0.88
"The development of hepatic enzyme-altered foci (ATPase, GGTase) was investigated after dosing vinyl acetate (200 and 400 mg/kg per day, orally) to newborn rats for 3 weeks, with or without subsequent promotion by phenobarbital."( Vinyl acetate, a structural analog of vinyl carbamate, fails to induce enzyme-altered foci in rat liver.
Bolt, HM; Laib, RJ, 1986
)
0.54
" Three experiments were performed: (i) a dose-response study with vinyl carbamate-induced tumors; (ii) a limited treatment study also with vinyl carbamate and (iii) prevention of NNK-induced tumors."( Prevention of mouse lung tumors by targretin.
Alyaqoub, FS; Gunning, WT; Kramer, PM; Liu, Y; Lubet, RA; Nines, R; Pereira, MA; Steele, VE, 2006
)
0.57
" If mice were fed either the methyl ester or the ethyl amide derivative of the synthetic triterpenoid 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid (CDDO-ME and CDDO-EA, respectively), beginning 1 week after dosing with carcinogen, the number, size, and severity of lung carcinomas were markedly reduced."( The synthetic triterpenoids CDDO-methyl ester and CDDO-ethyl amide prevent lung cancer induced by vinyl carbamate in A/J mice.
Dmitrovsky, E; Gribble, GW; Honda, T; Liby, K; Risingsong, R; Royce, DB; Sporn, MB; Sporn, TA; Williams, CR; Yore, MM, 2007
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
carbamate esterAny ester of carbamic acid or its N-substituted derivatives.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (65)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (13.85)18.7374
1990's18 (27.69)18.2507
2000's27 (41.54)29.6817
2010's10 (15.38)24.3611
2020's1 (1.54)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 20.93

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index20.93 (24.57)
Research Supply Index4.25 (2.92)
Research Growth Index4.60 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (20.93)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.90%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other67 (97.10%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]