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Xenobiotica
the fate of foreign compounds in biological systems
Volume 38, 2008 - Issue 11
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Research Article

Assessing and minimizing time-dependent inhibition of cytochrome P450 3A in drug discovery: A case study with melanocortin-4 receptor agonists

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Pages 1437-1451 | Received 21 Jul 2008, Accepted 09 Sep 2008, Published online: 04 Nov 2008

References

  • Bakshi RK, Hong Q, Olson JT, Ye Z, Sebhat IK, Weinberg DH, MacNeil T, Kalyani RN, Tang R, Martin WJ, et al. 1-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid as a Tic mimetic: Application in the synthesis of potent human melanocortin-4 receptor selective agonists. Bioorganic Medicinal Chemistry Letters 2005; 15: 3430–3433
  • Carr BA, Norcross R, Fang Y, Lu P, Rodrigues AD, Shou M, Rushmore T, Booth-Genthe C. Characterization of the rhesus monkey CYP3A64 enzyme: Species comparison of CYP3A substrate specificity and kinetics using baculovirus-expressed recombinant enzymes. Drug Metabolism Disposition 2006; 34: 1703–1712
  • Centers for Disease Control and Prevention (CDC). Prevalence of overweight and obesity among adults with diagnosed diabetes. United States. 2004, 1988–1994 and 1999–2002 (available at: http://www.cdc.gov/mmwr/preview/mmwrhtml/mm5345a2.htm)
  • Chen Q, Ngui JS, Doss GA, Wang RW, Cai X, DiNinno FP, Blizzard TA, Hammond ML, Stearns RA, Evens SD, et al. Cytochrome P450 3A4-mediated bioactivation of raloxifene: Irreversible enzyme inhibition and thiol adduct formation. Chemical Research in Toxicology 2002; 15: 907–914
  • Chiba M, Hensleigh M, Lin JH. Hepatic and intestinal metabolism of indinavir, an HIV protease inhibitor, in rat and human liver microsomes: Major role of CYP3A. Biochemical Pharmacology 1997; 53: 1187–1195
  • Fan W, Boston BA, Kesterson RA, Hruby VJ, Cone RD. Role of melanocortinergic neurons in feeding and the agouti obesity syndrome. Nature 1997; 385: 165–168
  • Franklin MR. Inhibition of mixed function oxidations by substrates forming reduced cytochrome P-450 metabolic-intermediate complexes. Pharmacology and Therapeutics A 1977; 2: 227–245
  • Franklin MR. Cytochrome P450 metabolic intermediate complexes from macrolide antibiotics and related compounds. Methods in Enzymology 1991; 206: 559–573
  • Huszar D, Lynch CA, Fairchild-Huntress V, Dunmore JH, Fang Q, Berkemeier LR, Gu W, Kesterson RA, Boston BA, Cone RD, et al. Targeted disruption of the melanocortin-4 receptor results in obesity in mice. Cell 1997; 88: 131–141
  • Mayhew BS, Jones DR, Hall SD. An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metabolism and Disposition 2000; 28: 1031–1037
  • Mei Q, Tang C, Assang C, Slaughter D, Rodrigues DA, Rushmore TH, Shou M. Role of a potent inhibitory monoclonal antibody to cytochrome P450 3A4 in assessment of human drug metabolism. Journal of Pharmacology and Experimental Therapeutics 1999; 291: 749–759
  • Nargund RP, Strack AM, Fong TM. Melanocortin-4 receptor (MC4R) agonists for the treatment of obesity. Journal of Medicinal Chemistry 2006; 49: 4035–4043
  • Park A, Kosareff NM, Kim JS, De Lijser HJP. Quinone-sensitized steady-state photolysis of acetophenone oximes under aerobic conditions: Kinetics and product studies. Photochemistry and Photobiology 2006; 82: 110–118
  • Raucy JL, Lasker JM. Isolation of P450 enzymes from human liver. Methods in Enzymology 1991; 206: 557–587
  • Silverman RB. Mechanism-based enzyme inactivation: Chemistry and enzymology. CRC Press, Boca Raton, FL 1988, Vols 1 and 2
  • Tang W, Stearns RA. Heterotropic cooperativity of cytochrome P450 3A4 and potential drug–drug interactions. Current Drug Metabolism 2001; 2: 185–198
  • Venkatakrishnan K, Obach RS. Drug–drug interaction via mechanism-based cytochrome P450 inactivation: Points to consider for risk assessment from in vitro data and clinical pharmacologic evaluation. Current Drug Metabolism 2007; 8: 449–462
  • Waley SG. Kinetics of suicide substrates: Practical procedures for determining parameters. Biochemical Journal 1985; 227: 843–849
  • Wang RW, Newton DJ, Liu N, Atkins WM, Lu AYH. In vitro drug–drug interaction patterns are substrate dependent. Drug Metabolism and Disposition 2000; 28: 360–366
  • Watkins PB, Wrighton SA, Schuetz EG, Maurel P, Guzelian PS. Macrolide antibiotics inhibit the degradation of the glucocorticoid-responsive cytochrome P-450p in rat hepatocytes in vivo and in primary monolayer culture. Journal of Biological Chemistry 1986; 261: 6264–6271
  • Zhang Z, Chen Q, Li Y, Doss GA, Bean BJ, Ngui JS, Elipe MS, Kim S, Wu JY, DiNinno F, et al. In vitro bioactivation of dihydrobenzoxathiin selective estrogen receptor modulators by cytochrome P450 3A4 in human liver microsomes: Formation of reactive iminium and quinone type metabolites. Chemical Research in Toxicology 2005; 18: 675–685

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