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Chemical Compound Review

Carbamat     carbamate

Synonyms: Karbamat, Carbamate ion, AG-L-17931, CHEBI:13941, CTK5D5764, ...
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Disease relevance of carbon dioxide


Psychiatry related information on carbon dioxide

  • Ganstigmine is an orally active, geneserine derived, carbamate-based acetylcholinesterase inhibitor developed for the treatment of Alzheimer's disease [6].
  • Compared with the same HFBA reaction in an organic solvent the derivatization reaction time was considerably shorter in SC-CO(2.) The described approach, combining both extraction and derivatization, simplifies the analysis of carbamate pesticides and eliminates the use of organic solvents associated with the derivatization step [7].
  • The colorimetric test of esterase activity is a useful tool to detect organophosphate and carbamate resistance in San Joaquin Valley California red scale because of its speed of testing over a wide range of months, allowing for within-season decision making by citrus growers [8].
  • Alterations of Aplysia feeding behavior following acute carbamate intoxication [9].
  • In the discussion, it is suggested that any organophosphate or carbamate pesticide and its antidote, atropine, may alter "attention" or "short-term memory" through effects on hippocampus at doses too low to induce grossly detectable peripheral symptomatology [10].

High impact information on carbon dioxide


Chemical compound and disease context of carbon dioxide


Biological context of carbon dioxide


Anatomical context of carbon dioxide

  • In intact mice, SCE levels induced by ethyl carbamate in bone marrow and alveolar macrophage cells were not significantly different whether assay followed the last of 12 (three times weekly) serial injections of 2.2 mmol/kg each or after a single injection of 2.2 mmol/kg [25].
  • Persistence of SCE-inducing DNA lesions was observed in blood, spleen, and parathymic node lymphocytes following the last of a series of 12 i.p. injections (three times weekly) of ethyl carbamate (2.2 mmol/kg) [21].
  • The present study was designed to test whether other N-unsubstituted carbamate esters of pharmacological interest (as sedatives, hypnotics, anxiolytics, and skeletal muscle relaxants) were capable of binding to CA in the same manner [23].
  • We have investigated the carbamate equilibrium of human adult hemoglobin, human cord blood hemoglobin, methemoglobin, and carbamylated hemoglobin using a stopped flow, rapid reaction pH apparatus described previously [26].
  • These cytoplasmic microtubules were entirely and reversibly disassembled by cold treatment and by either of two microtubule poisons: methyl benzimidazole carbamate and griseofulvin [27].

Associations of carbon dioxide with other chemical compounds


Gene context of carbon dioxide

  • These data show that multiple components of the cyclin D1/CDK4/p16(Ink4a)/pRb signaling pathway are frequently altered early in lung lesions of AJBL6 TGF-beta1 HT mice that are induced by ethyl carbamate as a function of progressive lung carcinogenesis, suggesting that components of this pathway may be potential targets for gene therapy [31].
  • High frequency of K-ras mutations in spontaneous and vinyl carbamate-induced lung tumors of relatively resistant B6CF1 (C57BL/6J x BALB/cJ) mice [32].
  • Both QDR1 and QDR2 were also implicated in yeast resistance to the herbicide barban (4-chloro-2-butynyl [3-chlorophenyl] carbamate), and the genes are functionally interchangeable with respect to both resistance phenotypes [33].
  • Butyrylcholinesterase (BChE), being sensitive to inhibition by some organophosphorus and carbamate pesticides, is a biomarker of toxic exposure [34].
  • Involvement of CYP2E1 and carboxylesterase enzymes in vinyl carbamate metabolism in human lung microsomes [35].

Analytical, diagnostic and therapeutic context of carbon dioxide


  1. Pyridostigmine brain penetration under stress enhances neuronal excitability and induces early immediate transcriptional response. Friedman, A., Kaufer, D., Shemer, J., Hendler, I., Soreq, H., Tur-Kaspa, I. Nat. Med. (1996) [Pubmed]
  2. Carcinogenicity of three dose levels of 1,4-Bis(4-fluorophenyl)-2-propynyl-N-cyclooctyl carbamate in male Sprague-Dawley and F344 rats. Weisburger, E.K., Ulland, B.M., Schueler, R.L., Weisburger, J.H., Harris, P.N. J. Natl. Cancer Inst. (1975) [Pubmed]
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  4. Mutagenicity of diallate, sulfallate, and triallate and relationship between structure and mutagenic effects of carbamates used widely in agriculture. De Lorenzo, F., Staiano, N., Silengo, L., Cortese, R. Cancer Res. (1978) [Pubmed]
  5. The synthetic triterpenoids CDDO-methyl ester and CDDO-ethyl amide prevent lung cancer induced by vinyl carbamate in A/J mice. Liby, K., Royce, D.B., Williams, C.R., Risingsong, R., Yore, M.M., Honda, T., Gribble, G.W., Dmitrovsky, E., Sporn, T.A., Sporn, M.B. Cancer Res. (2007) [Pubmed]
  6. Structural determinants of Torpedo californica acetylcholinesterase inhibition by the novel and orally active carbamate based anti-alzheimer drug ganstigmine (CHF-2819). Bartolucci, C., Siotto, M., Ghidini, E., Amari, G., Bolzoni, P.T., Racchi, M., Villetti, G., Delcanale, M., Lamba, D. J. Med. Chem. (2006) [Pubmed]
  7. Derivatization reactions of carbamate pesticides in supercritical carbon dioxide. King, J.W., Zhang, Z. Analytical and bioanalytical chemistry. (2002) [Pubmed]
  8. Role of esterase enzymes in monitoring for resistance of California red scale, Aonidiella aurantii (Homoptera: Diaspididae), to organophosphate and carbamate insecticides. Grafton-Cardwell, E.E., Ouyang, Y., Striggow, R.A., Christiansen, J.A., Black, C.S. J. Econ. Entomol. (2004) [Pubmed]
  9. Alterations of Aplysia feeding behavior following acute carbamate intoxication. Basso, A., Matera, L., Elia, G., Ambrosi, L., Vitiello, F., Di Benedetta, C. Boll. Soc. Ital. Biol. Sper. (1986) [Pubmed]
  10. Effects of mevinphos (Phosdrin) on unit discharge patterns in avian hippocampus. Revzin, A.M. Aviation, space, and environmental medicine. (1976) [Pubmed]
  11. Discrete steps in sensing of beta-lactam antibiotics by the BlaR1 protein of the methicillin-resistant Staphylococcus aureus bacterium. Thumanu, K., Cha, J., Fisher, J.F., Perrins, R., Mobashery, S., Wharton, C. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  12. A single dose of doxorubicin-functionalized bow-tie dendrimer cures mice bearing C-26 colon carcinomas. Lee, C.C., Gillies, E.R., Fox, M.E., Guillaudeu, S.J., Fr??chet, J.M., Dy, E.E., Szoka, F.C. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  13. Baculovirus expression of the maize mitochondrial protein URF13 confers insecticidal activity in cell cultures and larvae. Korth, K.L., Levings, C.S. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  14. Construction and characterization of a fusion protein of single-chain anti-CD20 antibody and human beta-glucuronidase for antibody-directed enzyme prodrug therapy. Haisma, H.J., Sernee, M.F., Hooijberg, E., Brakenhoff, R.H., vd Meulen-Muileman, I.H., Pinedo, H.M., Boven, E. Blood (1998) [Pubmed]
  15. 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. Pulling, L.C., Vuillemenot, B.R., Hutt, J.A., Devereux, T.R., Belinsky, S.A. Cancer Res. (2004) [Pubmed]
  16. Capecitabine, an oral fluoropyrimidine carbamate with substantial activity in advanced colorectal cancer: results of a randomized phase II study. Van Cutsem, E., Findlay, M., Osterwalder, B., Kocha, W., Dalley, D., Pazdur, R., Cassidy, J., Dirix, L., Twelves, C., Allman, D., Seitz, J.F., Schölmerich, J., Burger, H.U., Verweij, J. J. Clin. Oncol. (2000) [Pubmed]
  17. Aldicarb poisoning. A case report with prolonged cholinesterase inhibition and improvement after pralidoxime therapy. Burgess, J.L., Bernstein, J.N., Hurlbut, K. Arch. Intern. Med. (1994) [Pubmed]
  18. Mutation of beta-catenin is an early event in chemically induced mouse hepatocellular carcinogenesis. Devereux, T.R., Anna, C.H., Foley, J.F., White, C.M., Sills, R.C., Barrett, J.C. Oncogene (1999) [Pubmed]
  19. Kinetic and structural studies on the interaction of cholinesterases with the anti-Alzheimer drug rivastigmine. Bar-On, P., Millard, C.B., Harel, M., Dvir, H., Enz, A., Sussman, J.L., Silman, I. Biochemistry (2002) [Pubmed]
  20. Demonstration of a functional requirement for the carbamate nitrogen of ribulosebisphosphate carboxylase/oxygenase by chemical rescue. Smith, H.B., Hartman, F.C. Biochemistry (1991) [Pubmed]
  21. Long-term persistence of ethyl carbamate-induced sister chromatid exchanges in murine lymphocytes. Neft, R.E., Conner, M.K., Takeshita, T. Cancer Res. (1985) [Pubmed]
  22. Persistence of ethyl carbamate-induced DNA damage in vivo as indicated by sister chromatid exchange analysis. Conner, M.K., Cheng, M. Cancer Res. (1983) [Pubmed]
  23. Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. Parr, J.S., Khalifah, R.G. J. Biol. Chem. (1992) [Pubmed]
  24. Location of the ATP gamma-phosphate-binding sites on rat liver carbamoyl-phosphate synthetase I. Studies with the ATP analog 5'-p-fluorosulfonylbenzoyladenosine. Potter, M.D., Powers-Lee, S.G. J. Biol. Chem. (1992) [Pubmed]
  25. Potency of some carbamates as multiple tissue sister chromatid exchange inducers and comparison with known carcinogenic activities. Cheng, M., Conner, M.K., Alarie, Y. Cancer Res. (1981) [Pubmed]
  26. The carbamate equilibrium of alpha- and epsilon-amino groups of human hemoglobin at 37 degrees C. Gros, G., Rollema, H.S., Forster, R.E. J. Biol. Chem. (1981) [Pubmed]
  27. Physarum plasmodia do contain cytoplasmic microtubules! Salles-Passador, I., Moisand, A., Planques, V., Wright, M. J. Cell. Sci. (1991) [Pubmed]
  28. Selective carboxymethylation of the alpha-amino groups of hemoglobin. Effect on functional properties. DiDonato, A., Fantl, W.J., Acharya, A.S., Manning, J.M. J. Biol. Chem. (1983) [Pubmed]
  29. Tunneling of intermediates in enzyme-catalyzed reactions. Weeks, A., Lund, L., Raushel, F.M. Current opinion in chemical biology. (2006) [Pubmed]
  30. The carbamate reaction of glycylglycine, plasma, and tissue extracts evaluated by a pH stopped flow apparatus. Gros, G., Forster, R.E., Lin, L. J. Biol. Chem. (1976) [Pubmed]
  31. Altered expression of G1/S regulatory genes occurs early and frequently in lung carcinogenesis in transforming growth factor-beta1 heterozygous mice. Kang, Y., Ozbun, L.L., Angdisen, J., Moody, T.W., Prentice, M., Diwan, B.A., Jakowlew, S.B. Carcinogenesis (2002) [Pubmed]
  32. High frequency of K-ras mutations in spontaneous and vinyl carbamate-induced lung tumors of relatively resistant B6CF1 (C57BL/6J x BALB/cJ) mice. Massey, T.E., Devereux, T.R., Maronpot, R.R., Foley, J.F., Anderson, M.W. Carcinogenesis (1995) [Pubmed]
  33. Saccharomyces cerevisiae multidrug transporter Qdr2p (Yil121wp): localization and function as a quinidine resistance determinant. Vargas, R.C., Tenreiro, S., Teixeira, M.C., Fernandes, A.R., Sá-Correia, I. Antimicrob. Agents Chemother. (2004) [Pubmed]
  34. DNA sequence of butyrylcholinesterase from the rat: expression of the protein and characterization of the properties of rat butyrylcholinesterase. Boeck, A.T., Schopfer, L.M., Lockridge, O. Biochem. Pharmacol. (2002) [Pubmed]
  35. Involvement of CYP2E1 and carboxylesterase enzymes in vinyl carbamate metabolism in human lung microsomes. Forkert, P.G., Lee, R.P., Reid, K. Drug Metab. Dispos. (2001) [Pubmed]
  36. Chemoprevention by lipoxygenase and leukotriene pathway inhibitors of vinyl carbamate-induced lung tumors in mice. Gunning, W.T., Kramer, P.M., Steele, V.E., Pereira, M.A. Cancer Res. (2002) [Pubmed]
  37. Stereoselectivity of lipases. II. Stereoselective hydrolysis of triglycerides by gastric and pancreatic lipases. Rogalska, E., Ransac, S., Verger, R. J. Biol. Chem. (1990) [Pubmed]
  38. Site-specific mutagenesis of ribulose-1,5-bisphosphate carboxylase/oxygenase. Evidence that carbamate formation at Lys 191 is required for catalytic activity. Estelle, M., Hanks, J., McIntosh, L., Somerville, C. J. Biol. Chem. (1985) [Pubmed]
  39. Crystallization, characterization and preliminary crystallographic studies of carbamate kinase of Streptococcus faecium. Marina, A., Bravo, J., Fita, I., Rubio, V. J. Mol. Biol. (1994) [Pubmed]
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