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Research ArticleArticle

METABOLISM OF NICOTINE AND COTININE BY HUMAN CYTOCHROME P450 2A13

Ziping Bao, Xiao-Yang He, Xinxin Ding, Saileta Prabhu and Jun-Yan Hong
Drug Metabolism and Disposition February 2005, 33 (2) 258-261; DOI: https://doi.org/10.1124/dmd.104.002105
Ziping Bao
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Xiao-Yang He
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Xinxin Ding
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Saileta Prabhu
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Jun-Yan Hong
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Abstract

Nicotine, a major constituent of tobacco, plays a critical role in smoking addiction. In humans, nicotine is primarily metabolized to cotinine, which is further metabolized to trans-3′-hydroxycotinine. Recently, we have demonstrated that heterologously expressed human CYP2A13 is highly active in the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), a nicotine-derived carcinogen. In the present study, CYP2A13-catalyzed NNK metabolism was found to be inhibited competitively by nicotine and N′-nitrosonornicotine (NNN), suggesting that both nicotine and NNN are also substrates of CYP2A13. We have further demonstrated that human CYP2A13 is indeed an efficient enzyme in catalyzing C-oxidation of nicotine to form cotinine, with the apparent Km and Vmax values of 20.2 μM and 8.7 pmol/min/pmol, respectively. CYP2A13 also catalyzes the 3′-hydroxylation of cotinine to form trans-3′-hydroxycotinine, with the apparent Km and Vmax values of 45.2 μM and 0.7 pmol/min/pmol, respectively. The importance of CYP2A13-catalyzed nicotine and cotinine metabolism in vivo remains to be determined.

Footnotes

  • Part of this work was supported by National Institutes of Health Grant R01-ES10048 (J.-Y.H.), R01-CA 092596 (X.D.) and National Institute of Environmental Health Sciences Center Grant ES05022.

  • Article, publication date, and citation information can be found at http://dmd.aspetjournals.org.

  • doi:10.1124/dmd.104.002105.

  • ABBREVIATIONS: P450, cytochrome P450; NNK, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone; NNN, N′-nitrosonornicotine; HPLC, high-performance liquid chromatography.

    • Received August 30, 2004.
    • Accepted November 3, 2004.
  • The American Society for Pharmacology and Experimental Therapeutics
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Drug Metabolism and Disposition: 33 (2)
Drug Metabolism and Disposition
Vol. 33, Issue 2
1 Feb 2005
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Research ArticleArticle

METABOLISM OF NICOTINE AND COTININE BY HUMAN CYTOCHROME P450 2A13

Ziping Bao, Xiao-Yang He, Xinxin Ding, Saileta Prabhu and Jun-Yan Hong
Drug Metabolism and Disposition February 1, 2005, 33 (2) 258-261; DOI: https://doi.org/10.1124/dmd.104.002105

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Research ArticleArticle

METABOLISM OF NICOTINE AND COTININE BY HUMAN CYTOCHROME P450 2A13

Ziping Bao, Xiao-Yang He, Xinxin Ding, Saileta Prabhu and Jun-Yan Hong
Drug Metabolism and Disposition February 1, 2005, 33 (2) 258-261; DOI: https://doi.org/10.1124/dmd.104.002105
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