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N-vinyl compounds: studies on metabolism, genotoxicity, carcinogenicity

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Abstract

Several N-vinyl compounds are produced in high volumes and are widely employed in the production of copolymers and polymers used in chemical, pharmaceutical, cosmetic and food industry. Hence, information on their genotoxicity and carcinogenicity is requisite. This review presents hitherto available information on the carcinogenicity and genotoxicity of N-vinyl compounds as well as their metabolism potentially generating genotoxic and carcinogenic derivatives. The genotoxicity and carcinogenicity of the investigated N-vinyl compounds vary widely from no observed carcinogenicity tested in lifetime bioassays in two rodent species (up to very high doses) to carcinogenicity in rats at very low doses in the absence of apparent genotoxicity. Despite of the presence of the vinyl group potentially metabolized to an epoxide followed by covalent binding to DNA, genotoxicity was observed for only one of the considered N-vinyl compounds, N-vinyl carbazole. Carcinogenicity was investigated only for two, of which one, N-vinyl pyrrolidone was carcinogenic (but not genotoxic) and ranitidine was neither carcinogenic nor genotoxic. As far as investigated, neither a metabolically formed epoxide nor a therefrom derived diol has been reported for any of the considered N-vinyl compounds. It is concluded that the information collected in this review will further the understanding of the carcinogenic potentials of N-vinyl compounds and may eventually allow approaching their prediction and prevention. A suggestion how to prevent genotoxicity in designing of N-vinyl compounds is presented. However, the available information is scarce and further research especially on the metabolism of N-vinyl compounds is highly desirable.

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  1. Oesch-Tox Toxicological Consulting and Expert Opinions, 55263, Ingelheim, Germany

    F. Oesch

  2. BASF SE, Experimental Toxicology and Ecology, 67056, Ludwigshafen am Rhein, Germany

    N. Honarvar, E. Fabian & Robert Landsiedel

  3. Regulatory Toxicology of Chemicals, BASF SE, 67056, Ludwigshafen am Rhein, Germany

    F. I. Berger

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  1. F. Oesch
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  3. E. Fabian
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Correspondence to Robert Landsiedel.

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N.H., E.F., F. I. B. and R.L. are employees of BASF, a chemical company which produces and markets N-vinyl compounds; F.O. has no conflict of interest.

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Oesch, F., Honarvar, N., Fabian, E. et al. N-vinyl compounds: studies on metabolism, genotoxicity, carcinogenicity. Arch Toxicol 95, 3143–3159 (2021). https://doi.org/10.1007/s00204-021-03081-5

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