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Chemical Compound Review

HNCO     isocyanic acid

Synonyms: isocyansaeure, isozyansaeure, Isocyanic acid, AGN-PC-0CV8QW, AG-G-99349, ...
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Disease relevance of isocyanic acid


Psychiatry related information on isocyanic acid

  • The analysis demonstrates the value of a model based approach to evaluate the cost effectiveness of surveillance programmes for isocyanate asthma, and to inform shared decision making among clinicians, patients, employers, and society [6].

High impact information on isocyanic acid

  • Carcinogenicity and pulmonary pathology associated with a single 2-hour inhalation exposure of laboratory rodents to methyl isocyanate [7].
  • This suggests that BCNU-induced, isocyanate-mediated damage to newly synthesized protein(s) may be responsible for activation of the heat shock transcription factor and increased transcription of the HSP90 and HSP70 genes [8].
  • Our results indicate that (a) bifunctional alkylation is essential for antiglioma activity of nitrosoureas and (b) myelosuppression is at least partly linked with carbamoylation but that structural entities in the carbamoylating isocyanate rather than a quantitative degree of carbamoylation determine the degree of potential myelotoxicity [9].
  • The reactions proceed via C-H bond activation, insertion of the isocyanate or the acetylene, intramolecular nucleophilic cyclization to the aldimine of the generated amido- or alkenyl-rhenium species, and reductive elimination [10].
  • Removing unfavorable electrostatic interactions at the amino terminal end of 4 and adding one H-bond acceptor by acylation with alkyl isocyanate (4 --> 7) was found to reinforce the 2.5 helical population [11].

Chemical compound and disease context of isocyanic acid


Biological context of isocyanic acid


Anatomical context of isocyanic acid


Associations of isocyanic acid with other chemical compounds

  • OBJECTIVES: It is still unclear whether antibodies to diphenylmethane diisocyanate (MDI), which are elicited in some subjects with these conditions, are specific for this type of isocyanate [22].
  • HDI-conjugated epithelial cell proteins specifically stimulated proliferation of PBMCs from subjects with isocyanate-induced asthma but not HDI-exposed nonasthmatic individuals or atopic subjects with nonisocyanate-related asthma [18].
  • Reaction kinetics were analyzed by selected reaction monitoring in LC-MS-MS using stable isotope tagging with phenyl isocyanate [23].
  • In the case of the present study, the prodrugs are 2-hydroxycarbamates for which the propinquity of the hydroxyl residue and the isocyanate group enforces a cyclization reaction [24].
  • This nitrophenol release probably involves cyclization to an oxadiazolone since 17 (R = CH3, X = OC6H4NO2-p), which cannot form an isocyanate, releases nitrophenol almost as rapidly (kobs = 0.028 min-1) [25].

Gene context of isocyanic acid

  • In summary, the cytokines studied are not detectable in peripheral blood during isocyanate inhalation challenge; soluble interleukin 2 receptor and soluble intercellular adhesion molecule 1 are both detectable but do not change significantly after a positive isocyanate challenge [26].
  • Immunologic aspects of isocyanate asthma: IL-1 beta, IL-3, IL-4, sIL2R, and sICAM-1 [26].
  • No significant differences were observed in the numbers of T-lymphocyte phenotypic markers (CD3, CD4, and CD8) between subjects with asthma (isocyanate-induced and extrinsic) and control subjects [14].
  • RESULTS: Most confirmed reports of OAD are cases of sensitizer induced occupational asthma (625 confirmed cases) followed by COPD in coal miners (414 cases), irritant induced occupational asthma (156 cases), and isocyanate asthma (54 cases) [27].
  • The sera of 62/65 workers referred for specific inhalation challenges with isocyanates were analyzed for the presence of specific antibodies to the relevant isocyanate [28].

Analytical, diagnostic and therapeutic context of isocyanic acid


  1. Lens opacities induced in rat lenses by methyl isocyanate. Harding, J.J., Rixon, K.C. Lancet (1985) [Pubmed]
  2. Respiratory effects of inhaled isocyanates. Karol, M.H. Crit. Rev. Toxicol. (1986) [Pubmed]
  3. Hypersensitivity pneumonitis (extrinsic allergic alveolitis) induced by isocyanates. Baur, X. J. Allergy Clin. Immunol. (1995) [Pubmed]
  4. Isocyanate-induced pulmonary diseases: a current perspective. Bernstein, I.L. J. Allergy Clin. Immunol. (1982) [Pubmed]
  5. Chronic hypersensitivity pneumonitis in Japan: a nationwide epidemiologic survey. Yoshizawa, Y., Ohtani, Y., Hayakawa, H., Sato, A., Suga, M., Ando, M. J. Allergy Clin. Immunol. (1999) [Pubmed]
  6. Surveillance for isocyanate asthma: a model based cost effectiveness analysis. Wild, D.M., Redlich, C.A., Paltiel, A.D. Occupational and environmental medicine. (2005) [Pubmed]
  7. Carcinogenicity and pulmonary pathology associated with a single 2-hour inhalation exposure of laboratory rodents to methyl isocyanate. Bucher, J.R., Uraih, L.C., Hildebrandt, P.K., Sauer, R.M., Seely, J.C. J. Natl. Cancer Inst. (1989) [Pubmed]
  8. Selective activation of human heat shock gene transcription by nitrosourea antitumor drugs mediated by isocyanate-induced damage and activation of heat shock transcription factor. Kroes, R.A., Abravaya, K., Seidenfeld, J., Morimoto, R.I. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  9. Chemical structure of carbamoylating groups and their relationship to bone marrow toxicity and antiglioma activity of bifunctionally alkylating and carbamoylating nitrosoureas. Ali-Osman, F., Giblin, J., Berger, M., Murphy, M.J., Rosenblum, M.L. Cancer Res. (1985) [Pubmed]
  10. Insertion of polar and nonpolar unsaturated molecules into carbon-rhenium bonds generated by C-H bond activation: synthesis of phthalimidine and indene derivatives. Kuninobu, Y., Tokunaga, Y., Kawata, A., Takai, K. J. Am. Chem. Soc. (2006) [Pubmed]
  11. N,N'-linked oligoureas as foldamers: chain length requirements for helix formation in protic solvent investigated by circular dichroism, NMR spectroscopy, and molecular dynamics. Violette, A., Averlant-Petit, M.C., Semetey, V., Hemmerlin, C., Casimir, R., Graff, R., Marraud, M., Briand, J.P., Rognan, D., Guichard, G. J. Am. Chem. Soc. (2005) [Pubmed]
  12. Isocyanate-induced asthma: results of inhalation tests with TDI, MDI and methacholine. Vogelmeier, C., Baur, X., Fruhmann, G. International archives of occupational and environmental health. (1991) [Pubmed]
  13. Borrelia burgdorferi sensu lato infection in mosquitoes from Szczecin area. Kosik-Bogacka, D.I., Ku??na-Grygiel, W., G??rnik, K. Folia biologica. (2006) [Pubmed]
  14. Activated T-lymphocytes and eosinophils in the bronchial mucosa in isocyanate-induced asthma. Bentley, A.M., Maestrelli, P., Saetta, M., Fabbri, L.M., Robinson, D.S., Bradley, B.L., Jeffery, P.K., Durham, S.R., Kay, A.B. J. Allergy Clin. Immunol. (1992) [Pubmed]
  15. The use of an immunoassay index for antibodies against isocyanate human protein conjugates and application to human isocyanate disease. Grammer, L.C., Harris, K.E., Malo, J.L., Cartier, A., Patterson, R. J. Allergy Clin. Immunol. (1990) [Pubmed]
  16. Synthesis and chromatographic separation of the glucuronides of (R)- and (S)-propranolol. Oatis, J.E., Baker, J.P., McCarthy, J.R., Knapp, D.R. J. Med. Chem. (1983) [Pubmed]
  17. Inactivation of subtilisin Carlsberg by N-((tert-butoxycarbonyl)alanylprolylphenylalanyl)-O-benzoylhydroxyl- amine: formation of a covalent enzyme-inhibitor linkage in the form of a carbamate derivative. Steinmetz, A.C., Demuth, H.U., Ringe, D. Biochemistry (1994) [Pubmed]
  18. Isocyanate-conjugated human lung epithelial cell proteins: A link between exposure and asthma? Wisnewski, A.V., Lemus, R., Karol, M.H., Redlich, C.A. J. Allergy Clin. Immunol. (1999) [Pubmed]
  19. Human cervical tissue metabolizes the tobacco-specific nitrosamine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, via alpha-hydroxylation and carbonyl reduction pathways. Prokopczyk, B., Trushin, N., Leszczynska, J., Waggoner, S.E., El-Bayoumy, K. Carcinogenesis (2001) [Pubmed]
  20. Oligomers with pendant isocyanate groups as adhesives for dentin and other tissues. Lee, C.H., Brauer, G.M. J. Dent. Res. (1989) [Pubmed]
  21. The potential impact of epidemiology on the prevention of occupational disease. Wegman, D.H. American journal of public health. (1992) [Pubmed]
  22. Specific IgG response to monomeric and polymeric diphenylmethane diisocyanate conjugates in subjects with respiratory reactions to isocyanates. Aul, D.J., Bhaumik, A., Kennedy, A.L., Brown, W.E., Lesage, J., Malo, J.L. J. Allergy Clin. Immunol. (1999) [Pubmed]
  23. Covalent adduction of human serum albumin by 4-hydroxy-2-nonenal: kinetic analysis of competing alkylation reactions. Szapacs, M.E., Riggins, J.N., Zimmerman, L.J., Liebler, D.C. Biochemistry (2006) [Pubmed]
  24. Cyclization-activated prodrugs: N-(substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates based on ring-opened derivatives of active benzoxazolones and oxazolidinones as mutual prodrugs of acetaminophen. Vigroux, A., Bergon, M., Zedde, C. J. Med. Chem. (1995) [Pubmed]
  25. Azapeptides as inhibitors and active site titrants for cysteine proteinases. Xing, R., Hanzlik, R.P. J. Med. Chem. (1998) [Pubmed]
  26. Immunologic aspects of isocyanate asthma: IL-1 beta, IL-3, IL-4, sIL2R, and sICAM-1. Grammer, L.C., Shaughnessy, M.A., Kabalin, C.S., Yarnold, P.R., Malo, J.L., Cartier, A. Allergy and asthma proceedings : the official journal of regional and state allergy societies. (1998) [Pubmed]
  27. Occupational obstructive airway diseases in Germany: Frequency and causes in an international comparison. Latza, U., Baur, X. American journal of industrial medicine. (2005) [Pubmed]
  28. Specific serum antibodies against isocyanates: association with occupational asthma. Cartier, A., Grammer, L., Malo, J.L., Lagier, F., Ghezzo, H., Harris, K., Patterson, R. J. Allergy Clin. Immunol. (1989) [Pubmed]
  29. Rates of carbamylation of specific lysyl residues in bovine alpha-crystallins. Qin, W., Smith, J.B., Smith, D.L. J. Biol. Chem. (1992) [Pubmed]
  30. A novel immunoenzymatic method for the determination of global isocyanate antibodies: comparison with ELISA. Nany, S., Pham-Huy, C., Sahui-Gnassi, A., Dutertre-Catella, H., Chanut, J.C., Claude, J.R. J. Allergy Clin. Immunol. (1992) [Pubmed]
  31. Detection of immunologically sensitized isocyanate workers by RAST and intracutaneous skin tests. Baur, X., Dewair, M., Fruhmann, G. J. Allergy Clin. Immunol. (1984) [Pubmed]
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