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Nicotine Chemistry, Metabolism, Kinetics and Biomarkers

Benowitz, Neal L., Hukkanen, Janne, Jacob, Peyton·2009·Handbook of Experimental Pharmacology

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  1. Al-Delaimy WK, Crane J, Woodward A (2002) Is the hair nicotine level a more accurate biomarker of environmental tobacco smoke exposure than urine cotinine? J Epidemiol Community Health 56(1):66–71 · DOI
  2. Armitage A, Dollery C, Houseman T, Kohner E, Lewis PJ, Turner D (1978) Absorption of nicotine from small cigars. Clin Pharmacol Ther 23(2):143–151 · DOI
  3. Armstrong DW, Wang X, Ercal N (1998) Enantiomeric composition of nicotine in smokeless tobacco, medicinal products, and commercial reagents. Chirality 10:587–591 · DOI
  4. Asimus S, Hai TN, Van Huong N, Ashton M (2008) Artemisin and CYP2A6 activity in healthy subjects. Eur J Clin Pharmacol 64:283–292 · DOI
  5. Bendayan R, Sullivan JT, Shaw C, Frecker RC, Sellers EM (1990) Effect of cimetidine and ranitidine on the hepatic and renal elimination of nicotine in humans. Eur J Clin Pharmacol 38(2):165–169 · DOI
  6. Benowitz NL (1990) Clinical pharmacology of inhaled drugs of abuse: implications in understanding nicotine dependence. NIDA Res Monogr 99:12–29
  7. Benowitz NL (1996) Cotinine as a biomarker of environmental tobacco smoke exposure. Epidemiol Rev 18(2):188–204 · DOI
  8. Benowitz NL, Jacob P 3rd (1984) Daily intake of nicotine during cigarette smoking. Clin Pharmacol Ther 35(4):499–504 · DOI
  9. Benowitz NL, Jacob P 3rd (1985) Nicotine renal excretion rate influences nicotine intake during cigarette smoking. J Pharmacol Exp Ther 234(1):153–155 · DOI
  10. Benowitz NL, Jacob P 3rd (1994) Metabolism of nicotine to cotinine studied by a dual stable isotope method. Clin Pharmacol Ther 56(5):483–493 · DOI · Paper page
  11. Benowitz NL, Jacob P 3rd (2000) Effects of cigarette smoking and carbon monoxide on nicotine and cotinine metabolism. Clin Pharmacol Ther 67(6):653–659 · DOI
  12. Benowitz NL, Jacob P 3rd (2001) Trans-3′-hydroxycotinine: disposition kinetics, effects and plasma levels during cigarette smoking. Br J Clin Pharmacol 51(1):53–59 · DOI · Paper page
  13. Benowitz NL, Jacob P 3rd, Jones RT, Rosenberg J (1982a) Interindividual variability in the metabolism and cardiovascular effects of nicotine in man. J Pharmacol Exp Ther 221(2):368–372 · DOI · Paper page
  14. Benowitz NL, Kuyt F, Jacob P 3rd (1982b) Circadian blood nicotine concentrations during cigarette smoking. Clin Pharmacol Ther 32(6):758–764 · DOI
  15. Benowitz NL, Jacob P 3rd, Savanapridi C (1987) Determinants of nicotine intake while chewing nicotine polacrilex gum. Clin Pharmacol Ther 41(4):467–473 · DOI
  16. Benowitz NL, Jacob P 3rd, Fong I, Gupta S (1994) Nicotine metabolic profile in man: comparison of cigarette smoking and transdermal nicotine. J Pharmacol Exp Ther 268(1):296–303 · DOI
  17. Benowitz NL, Perez-Stable EJ, Fong I, Modin G, Herrera B, Jacob P 3rd (1999) Ethnic differences in N-glucuronidation of nicotine and cotinine. J Pharmacol Exp Ther 291(3):1196–1203 · DOI
  18. Benowitz NL, Perez-Stable EJ, Herrera B, Jacob P 3rd (2002b) Slower metabolism and reduced intake of nicotine from cigarette smoking in Chinese-Americans. J Natl Cancer Inst 94(2):108–115 · DOI
  19. Benowitz NL, Herrera B, Jacob P, 3rd (2004) Mentholated cigarette smoking inhibits nicotine metabolism. J Pharmacol Exp Ther 310:1208–1215 · DOI
  20. Benowitz NL, Lessov-Schlaggar CN, Swan GE, Jacob P 3rd (2006) Female sex and oral contraceptive use accelerate nicotine metabolism. Clin Pharmacol Ther 79(5):480–488 · DOI · Paper page
  21. Benowitz N, Bernert JT, Caraballo RS, Holiday DB, Wang J (2008a) Optimal Serum Cotinine Levels to Distinguish Cigarette Smokers and Non-Smokers within Different Racial/Ethnic Groups in the United States Between 1999–2004. Am J Epidemiol (in press) · DOI
  22. Benowitz N, Lessov-Schlaggar C, Swan G (2008b) Genetic Influences in the Variation in Renal Clearance of Nicotine and Cotinine. Clin Pharmacol Ther 84(2):243–247 · DOI
  23. Breese CR, Marks MJ, Logel J, Adams CE, Sullivan B, Collins AC, Leonard S (1997) Effect of smoking history on [3H]nicotine binding in human postmortem brain. J Pharmacol Exp Ther 282(1):7–13 · DOI · Paper page
  24. Byrd GD, Chang KM, Greene JM, deBethizy JD (1992) Evidence for urinary excretion of glucuronide conjugates of nicotine, cotinine, and trans-3′-hydroxycotinine in smokers. Drug Metab Dispos 20(2):192–197 · DOI
  25. Byrd GD, Uhrig MS, deBethizy JD, Caldwell WS, Crooks PA, Ravard A, Riggs R (1994) Direct determination of cotinine-N-glucuronide in urine using thermospray liquid chromatography/mass spectrometry. Biol Mass Spectrom 23(2):103–107 · DOI
  26. Caraballo RS, Giovino GA, Pechacek TF, Mowery PD, Richter PA, Strauss WJ, Sharp DJ, Eriksen MP, Pirkle JL, Maurer KR (1998) Racial and ethnic differences in serum cotinine levels of cigarette smokers: Third National Health and Nutrition Examination Survey, 1988–1991. JAMA 280(2):135–139 · DOI
  27. Cashman JR, Park SB, Yang ZC, Wrighton SA, Jacob P, 3rd, Benowitz NL (1992) Metabolism of nicotine by human liver microsomes: stereoselective formation of trans-nicotine N′-oxide. Chem Res Toxicol 5(5):639–646 · DOI
  28. Choi JH, Dresler CM, Norton MR, Strahs KR (2003) Pharmacokinetics of a nicotine polacrilex lozenge. Nicotine Tob Res 5(5):635–644 · DOI
  29. Collier AM, Goldstein GM, Shrewsbury RP, Davis SM, Koch GG, Zhang C-A, Benowitz NL, Lewtas J, Williams RW (1994) Cotinine elimination and its use as a biomarker in young children involuntarily exposed to environmental tobacco smoke. Indoor Environ 3:353–359
  30. Crawford EL, Weaver DA, DeMuth JP, Jackson CM, Khuder SA, Frampton MW, Utell MJ, Thilly WG, Willey JC (1998) Measurement of cytochrome P450 2A6 and 2E1 gene expression in primary human bronchial epithelial cells. Carcinogenesis 19(10):1867–1871 · DOI
  31. Dahlstrom A, Lundell B, Curvall M, Thapper L (1990) Nicotine and cotinine concentrations in the nursing mother and her infant. Acta Paediatr Scand 79(2):142–147 · DOI
  32. de Leon J, Diaz FJ, Rogers T, Browne D, Dinsmore L, Ghosheh OH, Dwoskin LP, Crooks PA (2002) Total cotinine in plasma: a stable biomarker for exposure to tobacco smoke. J Clin Psychopharmacol 22(5):496–501 · DOI
  33. Dehn DL, Claffey DJ, Duncan MW, Ruth JA (2001) Nicotine and cotinine adducts of a melanin intermediate demonstrated by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Chem Res Toxicol 14(3):275–279 · DOI
  34. Dempsey D, Jacob P, 3rd, Benowitz NL (2002) Accelerated metabolism of nicotine and cotinine in pregnant smokers. J Pharmacol Exp Ther 301(2):594–598 · DOI · Paper page
  35. Dempsey D, Tutka P, Jacob P, 3rd, Allen F, Schoedel K, Tyndale RF, Benowitz NL (2004) Nicotine metabolite ratio as an index of cytochrome P450 2A6 metabolic activity. Clin Pharmacol Ther 76:64–72 · DOI
  36. Denton TT, Zhang X, Cashman JR (2004) Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6. Biochem Pharmacol 67(4):751–756 · DOI
  37. English PB, Eskenazi B, Christianson RE (1994) Black-white differences in serum cotinine levels among pregnant women and subsequent effects on infant birthweight. Am J Public Health 84(9):1439–1443 · DOI
  38. Fant RV, Henningfield JE, Shiffman S, Strahs KR, Reitberg DP (2000) A pharmacokinetic crossover study to compare the absorption characteristics of three transdermal nicotine patches. Pharmacol Biochem Behav 67(3):479–482 · DOI
  39. Florescu A, Ferrence R, Einarson TR, Selby P, Kramer M, Woodruff S, Grossman L, Rankin A, Jacqz-Aigrain E, Koren G (2007) Reference values for hair cotinine as a biomarker of active and passive smoking in women of reproductive age, pregnant women, children, and neonates: systematic review and meta-analysis. Ther Drug Monit 29(4):437–446 · DOI
  40. Giovino G, Sidney S, Gfroerer J, O'Malley P, Allen J, Richter P, Ph DK (2004) Epidemiology of menthol cigarette use. Nicotine Tob Res 6(Suppl 1):S67–81 · DOI
  41. Gori GB, Benowitz NL, Lynch CJ (1986) Mouth versus deep airways absorption of nicotine in cigarette smokers. Pharmacol Biochem Behav 25(6):1181–1184 · DOI
  42. Gourlay SG, Benowitz NL (1996) The benefits of stopping smoking and the role of nicotine replacement therapy in older patients. Drugs Aging 9(1):8–23 · DOI
  43. Gourlay SG, Benowitz NL (1997) Arteriovenous differences in plasma concentration of nicotine and catecholamines and related cardiovascular effects after smoking, nicotine nasal spray, and intravenous nicotine. Clin Pharmacol Ther 62(4):453–463 · DOI
  44. Gow PJ, Ghabrial H, Smallwood RA, Morgan DJ, Ching MS (2001) Neonatal hepatic drug elimination. Pharmacol Toxicol 88(1):3–15 · DOI
  45. Gries JM, Benowitz N, Verotta D (1996) Chronopharmacokinetics of nicotine. Clin Pharmacol Ther 60(4):385–395 · DOI
  46. Guthrie SK, Zubieta JK, Ohl L, Ni L, Koeppe RA, Minoshima S, Domino EF (1999) Arterial/venous plasma nicotine concentrations following nicotine nasal spray. Eur J Clin Pharmacol 55(9):639–643 · DOI
  47. Hatsukami DK, Hecht SS, Hennrikus DJ, Joseph AM, Pentel PR (2003) Biomarkers of tobacco exposure or harm: application to clinical and epidemiological studies. 25–26 October 2001, Minneapolis, Minnesota. Nicotine Tob Res 5(3):387–396 · DOI
  48. Hecht SS (2003) Tobacco carcinogens, their biomarkers and tobacco-induced cancer. Nat Rev Cancer 3(10):733–744 · DOI
  49. Hecht SS, Carmella SG, Chen M, Dor Koch JF, Miller AT, Murphy SE, Jensen JA, Zimmerman CL, Hatsukami DK (1999a) Quantitation of urinary metabolites of a tobacco-specific lung carcinogen after smoking cessation. Cancer Res 59(3):590–596
  50. Hecht SS, Carmella SG, Murphy SE (1999b) Effects of watercress consumption on urinary metabolites of nicotine in smokers. Cancer Epidemiol Biomarkers Prev 8(10):907–913
  51. Hecht SS, Hochalter JB, Villalta PW, Murphy SE (2000) 2′-Hydroxylation of nicotine by cytochrome P450 2A6 and human liver microsomes: formation of a lung carcinogen precursor. Proc Natl Acad Sci USA 97(23):12493–12497 · DOI
  52. Henningfield JE, Keenan RM (1993) Nicotine delivery kinetics and abuse liability. J Consult Clin Psychol 61(5):743–750 · DOI · Paper page
  53. Henningfield JE, Stapleton JM, Benowitz NL, Grayson RF, London ED (1993) Higher levels of nicotine in arterial than in venous blood after cigarette smoking. Drug Alcohol Depend 33(1):23–29 · DOI
  54. Higashi E, Fukami T, Itoh M, Kyo S, Inoue M, Yokoi T, Nakajima M (2007) Human CYP2A6 is induced by estrogen via estrogen receptor. Drug Metab Dispos 35:1935–1941 · DOI
  55. Hukkanen J, Vaisanen T, Lassila A, Piipari R, Anttila S, Pelkonen O, Raunio H, Hakkola J (2003) Regulation of CYP3A5 by glucocorticoids and cigarette smoke in human lung-derived cells. J Pharmacol Exp Ther 304(2):745–752 · DOI
  56. Hukkanen J, Dempsey D, Jacob P, 3rd, Benowitz NL (2005a) Effect of pregnancy on a measure of FMO3 activity. Br J Clin Pharmacol 60(2):224–226 · DOI
  57. Hukkanen J, Gourlay SG, Kenkare S, Benowitz NL (2005b) Influence of menstrual cycle on cytochrome P450 2A6 activity and cardiovascular effects of nicotine. Clin Pharmacol Ther 77(3):159–169 · DOI · Paper page
  58. Hukkanen J, Jacob P 3rd, Benowitz NL (2005c) Metabolism and disposition kinetics of nicotine. Pharmacol Rev 57(1):79–115 · DOI · Paper page
  59. Hukkanen J, Jacob P 3rd, Benowitz NL (2006) Effect of grapefruit juice on cytochrome P450 2A6 and nicotine renal clearance. Clin Pharmacol Ther 80(5):522–530 · DOI
  60. Hurt RD, Dale LC, Fredrickson PA, Caldwell CC, Lee GA, Offord KP, Lauger GG, Marusic Z, Neese LW, Lundberg TG (1994) Nicotine patch therapy for smoking cessation combined with physician advice and nurse follow-up. One-year outcome and percentage of nicotine replacement. JAMA 271(8):595–600 · DOI
  61. Jacob P, 3rd, Benowitz NL (1991) Oxidative metabolism of nicotine in vivo. In: F. Adlkofer, K. Thurau (eds) Effects of nicotine on biological systems. Birkhauser Verlag, Basel, pp 35–44 · DOI
  62. Jacob P, 3rd, Shulgin AT, Benowitz NL (1990) Synthesis of (3′R, 5′S)-trans-3′-hydroxycotinine, a major metabolite of nicotine. Metabolic formation of 3′-hydroxycotinine in humans is highly stereoselective. J Med Chem 33(7):1888–1891 · DOI
  63. Jacob P, 3rd, Yu L, Shulgin AT, Benowitz NL (1999) Minor tobacco alkaloids as biomarkers for tobacco use: comparison of users of cigarettes, smokeless tobacco, cigars, and pipes. Am J Public Health 89(5):731–736 · DOI
  64. Jacob P, 3rd, Hatsukami D, Severson H, Hall S, Yu L, Benowitz NL (2002) Anabasine and anatabine as biomarkers for tobacco use during nicotine replacement therapy. Cancer Epidemiol Biomarkers Prev 11(12):1668–1673
  65. Jarvis MJ, Boreham R, Primatesta P, Feyerabend C, Bryant A (2001) Nicotine yield from machinesmoked cigarettes and nicotine intakes in smokers: evidence from a representative population survey. J Natl Cancer Inst 93(2):134–138 · DOI
  66. Johansson CJ, Olsson P, Bende M, Carlsson T, Gunnarsson PO (1991) Absolute bioavailability of nicotine applied to different nasal regions. Eur J Clin Pharmacol 41(6):585–588 · DOI
  67. Johnstone E, Benowitz N, Cargill A, Jacob R, Hinks L, Day I, Murphy M, Walton R (2006) Determinants of the rate of nicotine metabolism and effects on smoking behavior. Clin Pharmacol Ther 80(4):319–330 · DOI
  68. Kandel DB, Hu MC, Schaffran C, Udry JR, Benowitz NL (2007) Urine nicotine metabolites and smoking behavior in a multiracial/multiethnic national sample of young adults. Am J Epidemiol 165(8):901–910 · DOI
  69. Kozlowski LT, Mehta NY, Sweeney CT, Schwartz SS, Vogler GP, Jarvis MJ, West RJ (1998) Filter ventilation and nicotine content of tobacco in cigarettes from Canada, the United Kingdom, and the United States. Tob Control 7(4):369–375 · DOI
  70. Krul C, Hageman G (1998) Analysis of urinary caffeine metabolites to assess biotransformation enzyme activities by reversed-phase high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl 709(1):27–34 · DOI
  71. Kyerematen GA, Morgan M, Warner G, Martin LF, Vesell ES (1990) Metabolism of nicotine by hepatocytes. Biochem Pharmacol 40(8):1747–1756 · DOI
  72. Le Gal A, Dreano Y, Lucas D, Berthou F (2003) Diversity of selective environmental substrates for human cytochrome P450 2A6: alkoxyethers, nicotine, coumarin, N-nitrosodiethylamine, and N-nitrosobenzylmethylamine. Toxicol Lett 144(1):77–91 · DOI
  73. Lee BL, Benowitz NL, Jacob P 3rd (1987) Influence of tobacco abstinence on the disposition kinetics and effects of nicotine. Clin Pharmacol Ther 41(4):474–479 · DOI
  74. Lee BL, Jacob P 3rd, Jarvik ME, Benowitz NL (1989) Food and nicotine metabolism. Pharmacol Biochem Behav 33(3):621–625 · DOI
  75. Leete E (1983) Biosynthesis and metabolism of the tobacco alkaloids. In: Pelletier SW (ed) Alkaloids: chemical and biological perspectives. Wiley, New York, pp 85–152
  76. Leong JW, Dore ND, Shelley K, Holt EJ, Laing IA, Palmer LJ, LeSouef PN (1998) The elimination half-life of urinary cotinine in children of tobacco-smoking mothers. Pulm Pharmacol Ther 11(4):287–290 · DOI
  77. Lerman C, Tyndale R, Patterson F, Wileyto EP, Shields PG, Pinto A, Benowitz N (2006) Nicotine metabolite ratio predicts efficacy of transdermal nicotine for smoking cessation. Clin Pharmacol Ther 79(6):600–608 · DOI
  78. Lindell G, Lunell E, Graffner H (1996) Transdermally administered nicotine accumulates in gastric juice. Eur J Clin Pharmacol 51(3–4):315–318 · DOI
  79. Liston HL, Markowitz JS, DeVane CL (2001) Drug glucuronidation in clinical psychopharmacology. J Clin Psychopharmacol 21(5):500–515 · DOI
  80. MacDougall JM, Fandrick K, Zhang X, Serafin SV, Cashman JR (2003) Inhibition of human liver microsomal (S)-nicotine oxidation by (–)-menthol and analogues. Chem Res Toxicol 16(8):988–993 · DOI
  81. Madan A, Graham RA, Carroll KM, Mudra DR, Burton LA, Krueger LA, Downey AD, Czerwinski M, Forster J, Ribadeneira MD, Gan LS, LeCluyse EL, Zech K, Robertson P, Jr., Koch P, Antonian L, Wagner G, Yu L, Parkinson A (2003) Effects of prototypical microsomal enzyme inducers on cytochrome P450 expression in cultured human hepatocytes. Drug Metab Dispos 31(4):421–431 · DOI
  82. McBride JS, Altman DG, Klein M, White W (1998) Green tobacco sickness. Tob Control 7(3):294–298 · DOI
  83. McCusker K, McNabb E, Bone R (1982) Plasma nicotine levels in pipe smokers. JAMA 248(5):577–578 · DOI
  84. McKennis H, Jr., Turnbull LB, Bowman ER, Tamaki E (1963) The synthesis of hydroxycotinine and studies on its structure. J Org Chem 28:383–387 · DOI
  85. McNabb ME (1984) Chewing nicotine gum for 3 months: what happens to plasma nicotine levels? Can Med Assoc J 131(6)589–592
  86. McNabb ME, Ebert RV, McCusker K (1982) Plasma nicotine levels produced by chewing nicotine gum. JAMA 248(7):865–868 · DOI · Paper page
  87. Messina ES, Tyndale RF, Sellers EM (1997) A major role for CYP2A6 in nicotine C-oxidation by human liver microsomes. J Pharmacol Exp Ther 282(3):1608–1614 · DOI
  88. Meunier V, Bourrie M, Julian B, Marti E, Guillou F, Berger Y, Fabre G (2000) Expression and induction of CYP1A1/1A2, CYP2A6 and CYP3A4 in primary cultures of human hepatocytes: a 10-year follow-up. Xenobiotica 30(6)589–607 · DOI
  89. Molander L, Lunell E, Andersson SB, Kuylenstierna F (1996) Dose released and absolute bioavailability of nicotine from a nicotine vapor inhaler. Clin Pharmacol Ther 59(4):394–400 · DOI
  90. Molander L, Hansson A, Lunell E, Alainentalo L, Hoffmann M, Larsson R (2000) Pharmacokinetics of nicotine in kidney failure. Clin Pharmacol Ther 68(3):250–260 · DOI
  91. Molander L, Hansson A, Lunell E (2001) Pharmacokinetics of nicotine in healthy elderly people. Clin Pharmacol Ther 69(1):57–65 · DOI
  92. Munzel PA, Schmohl S, Heel H, Kalberer K, Bock-Hennig BS, Bock KW (1999) Induction of human UDP glucuronosyltransferases (UGT1A6, UGT1A9, and UGT2B7) by tbutylhydroquinone and 2,3,7,8-tetrachlorodibenzo-p-dioxin in Caco-2 cells. Drug Metab Dispos 27(5):569–573 · DOI
  93. Nakajima M, Yamamoto T, Nunoya K, Yokoi T, Nagashima K, Inoue K, Funae Y, Shimada N, Kamataki T, Kuroiwa Y (1996) Role of human cytochrome P4502A6 in C-oxidation of nicotine. Drug Metab Dispos 24(11):1212–1217 · DOI
  94. Neurath GB (1994) Aspects of the oxidative metabolism of nicotine. Clin Investig 72(3):190–195 · DOI
  95. Neurath GB, Dunger M, Orth D, Pein FG (1987) Trans-3′-hydroxycotinine as a main metabolite in urine of smokers. Int Arch Occup Environ Health 59(2):199–201 · DOI
  96. Neurath GB, Orth D, Pein FG (1991) Detection of nornicotine in human urine after infusion of nicotine. In: Adlkofer F, Thurau K (eds) Effects of nicotine on biological systems. Birkhauser Verlag, Basel, pp 45–49 · DOI
  97. Nolin TD, Frye RF, Matzke GR (2003) Hepatic drug metabolism and transport in patients with kidney disease. Am J Kidney Dis 42(5):906–925 · DOI
  98. Obach RS (2004) Potent inhibition of human liver aldehyde oxidase by raloxifene. Drug Metab Dispos 32(1):89–97 · DOI
  99. Pankow JF (2001) A consideration of the role of gas/particle partitioning in the deposition of nicotine and other tobacco smoke compounds in the respiratory tract. Chem Res Toxicol 14(11):1465–1481 · DOI
  100. Park SB, Jacob P, 3rd, Benowitz NL, Cashman JR (1993) Stereoselective metabolism of (S)-(-)-nicotine in humans: formation of trans-(S)-(-)-nicotine N-1′-oxide. Chem Res Toxicol 6(6):880–888 · DOI
  101. Patterson F, Benowitz N, Shields P, Kaufmann V, Jepson C, Wileyto P, Kucharski S, Lerman C (2003) Individual differences in nicotine intake per cigarette. Cancer Epidemiol Biomarkers Prev 12(5):468–471
  102. Patterson F, Schnoll R, Wileyto E, Pinto A, Epstein L, Shields P, Hawk L, Tyndale R, Benowitz N, Lerman C (2008) Toward Personalized Therapy for Smoking Cessation: A Randomized Placebo-controlled Trial of Bupropion. Clin Pharmacol Ther 84(3):320–325 · DOI
  103. Perez-Stable EJ, Herrera B, Jacob P 3rd, Benowitz NL (1998) Nicotine metabolism and intake in black and white smokers. JAMA 280(2):152–156 · DOI
  104. Perry RJ, Griffiths W, Dextraze P, Solomon RJ, Trebbin WM (1984) Elevated nicotine levels in patients undergoing hemodialysis. A role in cardiovascular mortality and morbidity? Am J Med 76(2):241–246 · DOI
  105. Perry DC, Davila-Garcia MI, Stockmeier CA, Kellar KJ (1999) Increased nicotinic receptors in brains from smokers: membrane binding and autoradiography studies. J Pharmacol Exp Ther 289(3):1545–1552 · DOI · Paper page
  106. Rae JM, Johnson MD, Lippman ME, Flockhart DA (2001) Rifampin is a selective, pleiotropic inducer of drug metabolism genes in human hepatocytes: studies with cDNA and oligonucleotide expression arrays. J Pharmacol Exp Ther 299(3):849–857 · DOI
  107. Rebagliato M, Bolumar F, Florey Cdu V, Jarvis MJ, Perez-Hoyos S, Hernandez-Aguado I, Avino MJ (1998) Variations in cotinine levels in smokers during and after pregnancy. Am J Obstet Gynecol 178(3):568–571 · DOI
  108. Ren Q, Murphy SE, Zheng Z, Lazarus P (2000) O-Glucuronidation of the lung carcinogen 4-(methylnitrosamino)-1- (3-pyridyl)-1-butanol (NNAL) by human UDP-glucuronosyltransferases 2B7 and 1A9. Drug Metab Dispos 28(11):1352–1360 · DOI
  109. Rose JE, Behm FM, Westman EC, Coleman RE (1999) Arterial nicotine kinetics during cigarette smoking and intravenous nicotine administration: implications for addiction. Drug Alcohol Depend 56(2):99–107 · DOI
  110. Runkel M, Bourian M, Tegtmeier M, Legrum W (1997) The character of inhibition of the metabolism of 1,2-benzopyrone (coumarin) by grapefruit juice in human. Eur J Clin Pharmacol 53(3–4):265–269 · DOI
  111. Schneider NG, Olmstead R, Mody FV, Doan K, Franzon M, Jarvik ME, Steinberg C (1995) Efficacy of a nicotine nasal spray in smoking cessation: a placebo-controlled, double-blind trial. Addiction 90(12):1671–1682 · DOI
  112. Schneider NG, Olmstead RE, Franzon MA, Lunell E (2001) The nicotine inhaler: clinical pharmacokinetics and comparison with other nicotine treatments. Clin Pharmacokinet 40(9):661–684 · DOI
  113. Selby P, Hackman R, Kapur B, Klein J, Koren G (2001) Heavily smoking women who cannot quit in pregnancy: evidence of pharmacokinetic predisposition. Ther Drug Monit 23(3):189–191 · DOI
  114. Sellers EM, Kaplan HL, Tyndale RF (2000) Inhibition of cytochrome P450 2A6 increases nicotine's oral bioavailability and decreases smoking. Clin Pharmacol Ther 68(1):35–43 · DOI
  115. Sellers EM, Ramamoorthy Y, Zeman MV, Djordjevic MV, Tyndale RF (2003) The effect of methoxsalen on nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism in vivo. Nicotine Tob Res 5(6):891–899 · DOI
  116. Shigenaga MK, Trevor AJ, Castagnoli N Jr (1988) Metabolism-dependent covalent binding of (S)-[5-3H]nicotine to liver and lung microsomal macromolecules. Drug Metab Dispos 16(3):397–402 · DOI
  117. Siegmund B, Leitner E, Pfannhauser W (1999) Determination of the nicotine content of various edible nightshades (Solanaceae) and their products and estimation of the associated dietary nicotine intake. J Agric Food Chem 47(8):3113–3120 · DOI
  118. Stepanov I, Hecht SS, Lindgren B, Jacob P 3rd, Wilson M, Benowitz NL (2007) Relationship of human toenail nicotine, cotinine, and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol to levels of these biomarkers in plasma and urine. Cancer Epidemiol Biomarkers Prev 16(7):1382–1386 · DOI
  119. Swan GE, Benowitz NL, Lessov CN, Jacob P, 3rd, Tyndale RF, Wilhelmsen K (2005) Nicotine metabolism: the impact of CYP2A6 on estimates of additive genetic influence. Pharmacogenet Genomics 15(2):115–125 · DOI
  120. Taavitsainen P, Juvonen R, Pelkonen O (2001) In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene. Drug Metab Dispos 29(3):217–222
  121. Takami K, Saito H, Okuda M, Takano M, Inui KI (1998) Distinct characteristics of transcellular transport between nicotine and tetraethylammonium in LLC-PK1 cells. J Pharmacol Exp Ther 286(2):676–680 · DOI
  122. Tateishi T, Nakura H, Asoh M, Watanabe M, Tanaka M, Kumai T, Takashima S, Imaoka S, Funae Y, Yabusaki Y, Kamataki T, Kobayashi S (1997) A comparison of hepatic cytochrome P450 protein expression between infancy and postinfancy. Life Sci 61(26):2567–2574 · DOI
  123. Tyndale RF, Sellers EM (2001) Variable CYP2A6-mediated nicotine metabolism alters smoking behavior and risk. Drug Metab Dispos 29(4 Pt 2):548–552
  124. Tyroller S, Zwickenpflug W, Richter E (2002) New sources of dietary myosmine uptake from cereals, fruits, vegetables, and milk. J Agric Food Chem 50(17):4909–4915 · DOI
  125. Urakami Y, Okuda M, Maasuda S, Saito H, Inui KI (1998) Functional characteristics and membrane locatlization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Ther 287:800–805 · DOI
  126. Voncken P, Rustemeier K, Schepers G (1990) Identification of cis-3′-hydroxycotinine as a urinary nicotine metabolite. Xenobiotica 20(12):1353–1356 · DOI
  127. Wagenknecht LE, Cutter GR, Haley NJ, Sidney S, Manolio TA, Hughes GH, Jacobs DR (1990) Racial differences in serum cotinine levels among smokers in the coronary artery risk development in (young) adults study. Am J Public Health 80(9):1053–1056 · DOI
  128. Wald NJ, Idle M, Boreham J, Bailey A (1981) Serum cotinine levels in pipe smokers: evidence against nicotine as cause of coronary heart disease. Lancet 2(8250):775–777 · DOI
  129. Wald NJ, Idle M, Boreham J, Bailey A, Van Vunakis H (1984) Urinary nicotine concentrations in cigarette and pipe smokers. Thorax 39(5):365–368 · DOI
  130. West R, Hajek P, Foulds J, Nilsson F, May S, Meadows A (2000) A comparison of the abuse liability and dependence potential of nicotine patch, gum, spray and inhaler. Psychopharmacology (Berl) 149(3):198–202 · DOI
  131. Xia XY, Peng RX, Yu JP, Wang H, Wang J (2002) In vitro metabolic characteristics of cytochrome P-450 2A6 in Chinese liver microsomes. Acta Pharmacol Sin 23(5):471–476
  132. Zevin S, Benowitz NL (1999) Drug interactions with tobacco smoking. An update. Clin Pharmacokinet 36(6):425–438 · DOI
  133. Zevin S, Jacob P 3rd, Benowitz N (1997) Cotinine effects on nicotine metabolism. Clin Pharmacol Ther 61(6):649–654 · DOI
  134. Zevin S, Schaner ME, Giacomini KM (1998) Nicotine transport in a human choriocarcinoma cell line (JAR). J Pharm Sci 87:702–706 · DOI
  135. Zevin S, Jacob P 3rd, Benowitz NL (2000) Nicotine-mecamylamine interactions. Clin Pharmacol Ther 68(1):58–66 · DOI
  136. Zhang W, Kilicarslan T, Tyndale RF, Sellers EM (2001) Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro. Drug Metab Dispos 29(6):897–902

Cited by

Metadata

Authors
Benowitz, N. L., Hukkanen, J., & Jacob, P.
Venue
Handbook of Experimental Pharmacology
Published
2009
Pages
29-60
ISSN
0171-2004
Cited by
1,179
References
7
Language
en

About these checks

Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.

Statistics and arithmetic are recomputed, not judged.

Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.

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Data sources

Bibliographic data: Semantic Scholar, OpenAlex, Crossref.

Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).

Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.