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http://dx.doi.org/10.4062/biomolther.2021.102

Inhibition of Cytochrome P450 Enzymes by Drugs-Molecular Basis and Practical Applications  

Guengerich, F. Peter (Department of Biochemistry, Vanderbilt University School of Medicine)
Publication Information
Biomolecules & Therapeutics / v.30, no.1, 2022 , pp. 1-18 More about this Journal
Abstract
Drug-drug interactions are a major cause of hospitalization and deaths related to drug use. A large fraction of these is due to inhibition of enzymes involved in drug metabolism and transport, particularly cytochrome P450 (P450) enzymes. Understanding basic mechanisms of enzyme inhibition is important, particularly in terms of reversibility and the use of the appropriate parameters. In addition to drug-drug interactions, issues have involved interactions of drugs with foods and natural products related to P450 enzymes. Predicting drug-drug interactions is a major effort in drug development in the pharmaceutical industry and regulatory agencies. With appropriate in vitro experiments, it is possible to stratify clinical drug-drug interaction studies. A better understanding of drug interactions and training of physicians and pharmacists has developed. Finally, some P450s have been the targets of drugs in some cancers and other disease states.
Keywords
Cytochrome P450; CYP; Drug-drug interactions; P450 inhibition; Enzyme inhibition;
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1 Boscaro, M., Barzon, L. and Sonino, N. (2000) The diagnosis of Cushing's syndrome: atypical presentations and laboratory shortcomings. Arch. Int. Med. 160, 3045-3053.   DOI
2 Child, S. A. and Guengerich, F. P. (2020) Multistep binding of the nonsteroidal inhibitors orteronel and seviteronel to human cytochrome P450 17A1 and relevance to inhibition of enzyme activity. J. Med. Chem. 63, 6513-6522.   DOI
3 Correia, M. A. and Hollenberg, P. F. (2015) Inhibition of cytochrome P450 enzymes. In Cytochrome P450: Structure, Mechanism, and Biochemistry (4th ed.) (P. R. Ortiz de Montellano, ed.), pp. 177-259. Springer, New York.
4 Dresser, G. K., Spence, J. D. and Bailey, D. G. (2000) Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition. Clin. Pharmacokinet. 38, 41-57.   DOI
5 Franklin, M. R. and Buening, M. K. (1974) The formation of complexes absorbing at 455 nm form cytochrome P450 and metabolites of compounds related to SKF 525A. Drug Metab. Dispos. 2, 386-390.
6 Goosen, T. C., Cillie, D., Bailey, D. G., Yu, C., He, K., Hollenberg, P. F., Woster, P. M., Cohen, L., Williams, J. A., Rheeders, M. and Dijkstra, H. P. (2004) Bergamottin contribution to the grapefruit juicefelodipine interaction and disposition in humans. Clin. Pharmacol. Ther. 76, 607-617.   DOI
7 Guengerich, F. P. (1990a) Mechanism-based inactivation of human liver microsomal cytochrome P-450 IIIA4 by gestodene. Chem. Res. Toxicol. 3, 363-371.   DOI
8 Guengerich, F. P., McCarty, K. D. and Chapman, J. G. (2021) Stepwise binding of inhibitors to human cytochrome P450 17A1 and relevance to kinetics of inhibition of androgen biosynthesis. J. Biol. Chem. 297, 100969.   DOI
9 He, K., Iyer, R., Hayes, R. N., Sinz, M. W., Woolf, T. F. and Hollenberg, P. F. (1998) Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem. Res. Toxicol. 11, 252-259.   DOI
10 Kuhl, H., Jung-Hoffmann, C. and Heidt, F. (1988) Alterations in the serum levels of gestodene and SHBG during 12 cycles of treatment with 30 mg ethinylestradiol and 75 mg gestodene. Contraception 38, 477-486.   DOI
11 Lepesheva, G. I. and Waterman, M. R. (2007) Sterol 14α-demethylase cytochrome P450 (CYP51), a P450 in all biological kingdoms. Biochim. Biophys. Acta 1770, 467-477.   DOI
12 Lin, H. L., Zhang, H. M. and Hollenberg, P. F. (2018) Formation of both heme and apoprotein adducts contributes to the mechanism-based inactivation of human CYP2J2 by 17α-ethynylestradiol. Drug Metab. Dispos. 46, 813-822.   DOI
13 Petrunak, E. M., Rogers, S. A., Aube, J. and Scott, E. E. (2017) Structural and functional evaluation of clinically relevant inhibitors of steroidogenic cytochrome P450 17A1. Drug Metab. Dispos. 45, 635-645.   DOI
14 Ekroos, M. and Sjogren, T. (2006) Structural basis for ligand promiscuity in cytochrome P450 3A4. Proc. Natl. Acad. Sci. U.S.A. 103, 13682-13687.   DOI
15 Eng, H., Tseng, E., Cerny, M. A., Goosen, T. C. and Obach, R. S. (2021) Cytochrome P450 3A time-dependent inhibition assays are too sensitive for identification of drugs causing clinically significant drug-drug interactions: a comparison of human liver microsomes and hepatocytes and definition of boundaries for inactivation rate constants. Drug Metab. Dispos. 49, 442-450.   DOI
16 Alyamani, M., Li, Z. F., Upadhyay, S. K., Anderson, D. J., Auchus, R. J. and Sharifi, N. (2017) Development and validation of a novel LC-MS/MS method for simultaneous determination of abiraterone and its seven steroidal metabolites in human serum: innovation in separation of diastereoisomers without use of a chiral column. J. Steroid Biochem. Mol. Biol. 172, 231-239.   DOI
17 Paine, M. F., Criss, A. B. and Watkins, P. B. (2005) Two major grapefruit juice components differ in time to onset of intestinal CYP3A4 inhibition. J. Pharmacol. Exp. Ther. 312, 1151-1160.   DOI
18 Paine, M. F., Shen, D. D. and McCune, J. S. (2018) Recommended approaches for pharmacokinetic natural product-drug interaction research: a NaPDI Center commentary. Drug Metab. Dispos. 46, 1041-1045.   DOI
19 Parkinson, A., Ogilvie, B. W., Buckley, D. B., Kazmi, F. and Parkinson, O. (2019) Biotransformation of xenobiotics. In Casarett and Doull's Toxicology: The Basic Science of Poisons (6th ed.) (C. D. Klaassen, ed.), pp. 193-399. McGraw Hill, New York.
20 Paulsen-Sorman, U. B., Jonsson, K. H. and Lindeke, B. G. A. (1984) Cytochrome P-455 nm complex formation in the metabolism of phenylalkylamines. 8. Stereoselectivity in metabolic intermediary complex formation with a series of chiral 2-substituted 1-phenyl-2-aminoethanes. J. Med. Chem. 27, 342-346.   DOI
21 Rangno, R. (1997) Terfenadine therapy: can we justify the risks? Can. Med. Assoc. J. 157, 37-38.
22 Rendic, S. and Guengerich, F. P. (2015) Survey of human oxidoreductases and cytochrome P450 enzymes involved in the metabolism of xenobiotic and natural chemicals. Chem. Res. Toxicol. 28, 38-42.   DOI
23 Flockhart, D. A. (2007) Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine. Available from: https://drug-interactions.medicine.iu.edu/ [accessed 2021 Aug 27].
24 Mostaghel, E. A. and Nelson, P. S. (2008) Intracrine androgen metabolism in prostate cancer progression: mechanisms of castration resistance and therapeutic implications. Best Pract. Res. Clin. Endocrinol. Metab. 22, 243-258.   DOI
25 Chu, J. W., Matthias, D. F., Belanoff, J., Schatzberg, A., Hoffman, A. R. and Feldman, D. (2001) Successful long-term treatment of refractory Cushing's disease with high-dose mifepristone (RU 486). J. Clin. Endocrinol. Metab. 86, 3568-3573.   DOI
26 Mansuy, D., Battioni, J. P. and Chottard, J. C. (1979) Preparation of a porphyrin-iron-carbene model for the cytochrome P450 complexes obtained upon metabolic oxidation of the insecticide synergists of the 1,3-benzodioxole series. J. Am. Chem. Soc. 101, 3971-3973.   DOI
27 Bailey, D. G., Dresser, G. and Arnold, J. M. (2013) Grapefruit-medication interactions: forbidden fruit or avoidable consequences? Can. Med. Assoc. J. 185, 309-316.   DOI
28 Emmerich, J., van Koppen, C. J., Burkhart, J. L., Hu, Q., Siebenburger, L., Boerger, C., Scheuer, C., Laschke, M. W., Menger, M. D. and Hartmann, R. W. (2017) Lead optimization generates CYP11B1 inhibitors of pyridylmethyl isoxazole type with improved pharmacological profile for the treatment of Cushing's disease. J. Med. Chem. 60, 5086-5098.   DOI
29 Guengerich, F. P. (2019b) Cytochrome P450 research and The Journal of Biological Chemistry. J. Biol. Chem. 294, 1671-1680.   DOI
30 Ortiz de Montellano, P. R., Kunze, K. L., Yost, G. S. and Mico, B. A. (1979) Self-catalyzed destruction of cytochrome P-450: covalent binding of ethynyl sterols to prosthetic heme. Proc. Natl. Acad. Sci. U.S.A. 76, 746-749.   DOI
31 Omura, T. and Sato, R. (1962) A new cytochrome in liver microsomes. J. Biol. Chem. 237, 1375-1376.
32 Palovaara, S., Kivisto, K. T., Tapanainen, P., Manninen, P., Neuvonen, P. J. and Laine, K. (2000) Effect of an oral contraceptive preparation containing ethinylestradiol and gestodene on CYP3A4 activity as measured by midazolam 1'-hydroxylation. Br. J. Clin. Pharmacol. 50, 333-337.   DOI
33 Petrunak, E. M., DeVore, N. M., Porubsky, P. R. and Scott, E. E. (2014) Structures of human steroidogenic cytochrome P450 17A1 with substrates. J. Biol. Chem. 289, 32952-32964.   DOI
34 Rendic, S. and Guengerich, F. P. (2012) Contributions of human enzymes in carcinogen metabolism. Chem. Res. Toxicol. 25, 1316-1383.   DOI
35 Ryan, K. J. (1959) Biological aromatization of steroids. J. Biol. Chem. 234, 268-272.   DOI
36 Segel, I. H. (1975) Enzyme Kinetics. Wiley, New York.
37 Sellers, E. M., Kaplan, H. L. and Tyndale, R. F. (2000) Inhibition of cytochrome P450 2A6 increases nicotine's oral bioavailability and decreases smoking. Clin. Pharmacol. Ther. 68, 35-43.   DOI
38 Shinkyo, R. and Guengerich, F. P. (2011) Inhibition of human cytochrome P450 3A4 by cholesterol. J. Biol. Chem. 286, 18426-18433.   DOI
39 Fekry, M. I., Xiao, Y., Berg, J. Z. and Guengerich, F. P. (2019) A role for the orphan human cytochrome P450 2S1 in polyunsaturated fatty acid w-1 hydroxylation using an untargeted metabolomic approach. Drug Metab. Dispos. 47, 1325-1332.   DOI
40 Fahmi, O. A., Hurst, S., Plowchalk, D., Cook, J., Guo, F., Youdim, K., Dickins, M., Phipps, A., Darekar, A., Hyland, R. and Obach, R. S. (2009) Comparison of different algorithms for predicting clinical drug-drug interactions, based on the use of CYP3A4 in vitro data: predictions of compounds as precipitants of interaction. Drug Metab. Dispos. 37, 1658-1666.   DOI
41 Friggeri, L., Hargrove, T. Y., Rachakonda, G., Williams, A. D., Wawrzak, Z., Di Santo, R., De Vita, D., Waterman, M. R., Tortorella, S., Villalta, F. and Lepesheva, G. I. (2014) Structural basis for rational design of inhibitors targeting Trypanosoma cruzi sterol 14α-demethylase: two regions of the enzyme molecule potentiate its inhibition. J. Med. Chem. 57, 6704-6717.   DOI
42 Guengerich, F. P. and Kim, D. H. (1990) In vitro inhibition of dihydropyridine oxidation and aflatoxin B1 activation in human liver microsomes by naringenin and other flavonoids. Carcinogenesis 11, 2275-2279.   DOI
43 Schmiedlin-Ren, P., Edwards, D. J., Fitzsimmons, M. E., He, K., Lown, K. S., Woster, P. M., Rahman, A., Thummel, K. E., Fisher, J. M., Hollenberg, P. F. and Watkins, P. B. (1997) Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents. Drug Metab. Dispos. 25, 1228-1233.
44 Emmerich, J., Hu, Q., Hanke, N. and Hartmann, R. W. (2013) Cushing's syndrome: development of highly potent and selective CYP11B1 inhibitors of the (pyridylmethyl)pyridine type. J. Med. Chem. 56, 6022-6032.   DOI
45 Friggeri, L., Hargrove, T. Y., Wawrzak, Z., Guengerich, F. P. and Lepesheva, G. I. (2019) Validation of human sterol 14α-demethylase (CYP51) druggability: structure-guided design, synthesis and evaluation of stoichiometric, functionally irreversible inhibitors. J. Med. Chem. 62, 10391-10401.   DOI
46 Hardy, K. D., Wahlin, M. D., Papageorgiou, I., Unadkat, J. D., Rettie, A. E. and Nelson, S. D. (2014) Studies on the role of metabolic activation in tyrosine kinase inhibitor-dependent hepatotoxicity: induction of CYP3A4 enhances the cytotoxicity of lapatinib in HepaRG cells. Drug Metab. Dispos. 42, 162-171.   DOI
47 Guengerich, F. P. (1988) Oxidation of 17α-ethynylestradiol by human liver cytochrome P-450. Mol. Pharmacol. 33, 500-508.
48 Guengerich, F. P. (1989) Characterization of human microsomal cytochrome P-450 enzymes. Annu. Rev. Pharmacol. Toxicol. 29, 241-264.   DOI
49 Guengerich, F. P. (1990b) Inhibition of oral contraceptive steroid-metabolizing enzymes by steroids and drugs. Am. J. Obstet. Gynecol. 163, 2159-2163.   DOI
50 Guengerich, F. P. (2014) Cytochrome P450-mediated drug interactions and cardiovascular toxicity: the Seldane to Allegra transformation. In Predictive ADMET: Integrated Approaches in Drug Discovery and Development (J. Wang and L. Urban, Ed.), pp. 523-534. Wiley, New York.
51 Albertolle, M. E., Glass, S. M., Trefts, E. and Guengerich, F. P. (2019) Isotopic tagging of oxidized and reduced cysteines (iTORC) for detecting and quantifying sulfenic acids, disulfides, and free thiols in cells. J. Biol. Chem. 294, 6522-6530.   DOI
52 Malhotra, S., Bailey, D. G., Paine, M. F. and Watkins, P. B. (2001) Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins. Clin. Pharmacol. Ther. 69, 14-23.   DOI
53 Obach, R. S., Walsky, R. L., Venkatakrishnan, K., Houston, J. B. and Tremaine, L. M. (2005) In vitro cytochrome P450 inhibition data and the prediction of drug-drug interactions: qualitative relationships, quantitative predictions, and the rank-order approach. Clin. Pharmacol. Ther. 78, 582-592.   DOI
54 Abeles, R. H. and Maycock, A. L. (1976) Suicide enzyme inactivators. Acct. Chem. Res. 9, 313-319.   DOI
55 Albertolle, M. E., Kim, D., Nagy, L. D., Yun, C. H., Pozzi, A., Savas, U., Johnson, E. F. and Guengerich, F. P. (2017) Heme-thiolate sulfenylation of human cytochrome P450 4A11 functions as a redox switch for catalytic inhibition. J. Biol.Chem. 292, 11230-11242.   DOI
56 Albertolle, M. E., Phan, T. T. N., Pozzi, A. and Guengerich, F. P. (2018) Sulfenylation of human liver and kidney microsomal cytochromes P450 and other drug-metabolizing enzymes as a response to redox alteration. Mol. Cell. Proteomics 17, 889-900.   DOI
57 Attard, G., Reid, A. H., Auchus, R. J., Hughes, B. A., Cassidy, A. M., Thompson, E., Oommen, N. B., Folkerd, E., Dowsett, M., Arlt, W. and de Bono, J. S. (2012) Clinical and biochemical consequences of CYP17A1 inhibition with abiraterone given with and without exogenous glucocorticoids in castrated men with advanced prostate cancer. J. Clin. Endocrinol. Metab. 97, 507-516.   DOI
58 Silverman, R. B. (1995) Mechanism-based enzyme inactivators. Methods Enzymol. 249, 240-283.   DOI
59 Yano, J. K., Wester, M. R., Schoch, G. A., Griffin, K. J., Stout, C. D. and Johnson, E. F. (2004) The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05 A resolution. J. Biol. Chem. 279, 38091-38094.   DOI
60 Shou, M. and Dai, R. (2008) Analysis of in vitro cytochrome P450 inhibition in drug discovery and development. In Drug Metabolism in Drug Design and Development (D. Zhang, M. Zhu and W. G. Humphreys, Eds.), pp. 513-544. Wiley, Hoboken, NJ.
61 Thompson, D. and Oster, G. (1996) Use of terfenadine and contraindicated drugs. JAMA 275, 1339-1341.   DOI
62 Woosley, R. L., Chen, Y., Freiman, J. P. and Gillis, R. A. (1993) Mechanism of the cardiotoxic actions of terfenadine. JAMA 269, 1532-1536.   DOI
63 Uno, S., Sakurai, K., Nebert, D. W. and Makishima, M. (2014) Protective role of cytochrome P450 1A1 (CYP1A1) against benzo[a] pyrene-induced toxicity in mouse aorta. Toxicology 316, 34-42.   DOI
64 Ward, S. and Back, D. J. (1993) Metabolism of gestodene in human liver cytosol and microsomes in vitro. J. Steroid Biochem. Mol. Biol. 46, 235-243.   DOI
65 Williams, R. T. (1947) Detoxication Mechanisms (1st ed.). Wiley, New York.
66 Woosley, R. L. (1996) Cardiac actions of antihistamines. Annu. Rev. Pharmacol. Toxicol. 36, 233-252.   DOI
67 Yano, J. K., Denton, T. T., Cerny, M. A., Zhang, X., Johnson, E. F. and Cashman, J. R. (2006) Synthetic inhibitors of cytochrome P-450 2A6: inhibitory activity, difference spectra, mechanism of inhibition, and protein cocrystallization. J. Med. Chem. 49, 6987-7001.   DOI
68 Yin, L. N., Lucas, S., Maurer, F., Kazmaier, U., Hu, Q. Z. and Hartmann, R. W. (2012) Novel imidazol-1-ylmethyl substituted 1,2,5,6-tetra-hydropyrrolo 3,2,1-i,j quinolin-4-ones as potent and selective CYP11B1 inhibitors for the treatment of Cushing's syndrome. J. Med. Chem. 55, 6629-6633.   DOI
69 Guengerich, F. P. (2020) A history of the role of cytochrome P450 enzymes in the toxicity of drugs. Toxicol. Res. 37, 1-23.   DOI
70 Guengerich, F. P. (2019a) Kinetic modeling of steady-state situations in cytochrome P450 enzyme reactions. Drug Metab. Dispos. 47, 1232-1239.   DOI
71 Guengerich, F. P., McCarty, K. D. and Chapman, J. G. (2020) Kinetics of cytochrome P450 3A4 inhibition by heterocyclic drugs defines a general sequential multistep binding process. J. Biol. Chem. 296, 100223.   DOI
72 Halpert, J. and Neal, R. A. (1980) Inactivation of purified rat liver cytochrome P-450 by chloramphenicol. Mol. Pharmacol. 17, 427-431.
73 Hecker, M., Haurand, M., Ullrich, V. and Terao, S. (1986) Spectral studies on structure-activity relationships of thromboxane synthase inhibitors. Eur. J. Biochem. 157, 217-223.   DOI
74 Honig, P. K., Woosley, R. L., Zamani, K., Conner, D. P. and Cantilena, L. R., Jr. (1992) Changes in the pharmacokinetics and electrocardiographic pharmacodynamics of terfenadine with concomitant administration of erythromycin. Clin. Pharmacol. Ther. 52, 231-238.   DOI
75 Kramlinger, V. M., Alvarado Rojas, M., Kanamori, T. and Guengerich, F. P. (2015) Cytochrome P450 3A enzymes catalyze the O6-demethylation of thebaine, a key step in endogenous mammalian morphine biosynthesis. J. Biol. Chem. 290, 20200-20210.   DOI
76 Kuby, S. A. (1991) A Study of Enzymes, Vol. I, Enzyme Catalysis, Kinetics, and Substrate Binding (Vol. 7). CRC Press, Boca Raton, FL.
77 Kuhl, H., Jung-Hoffmann, C. and Wiegratz, I. (1995) Gestodene-containing contraceptives. Clin. Obstet. Gynecol. 38, 829-840.   DOI
78 Johnson, K. A. (2019) Kinetic Anaylsis for the New Enzymology (1st ed.). KinTek, Austin, TX.
79 Lepesheva, G. I., Nes, W. D., Zhou, W., Hill, G. C. and Waterman, M. R. (2004) CYP51 from Trypanosoma brucei is obtusifoliol-specific. Biochemistry 43, 10789-10799.   DOI
80 Guengerich, F. P., Brian, W. R., Iwasaki, M., Sari, M. A., Baarnhielm, C. and Berntsson, P. (1991) Oxidation of dihydropyridine calcium channel blockers and analogues by human liver cytochrome P-450 IIIA4. J. Med. Chem. 34, 1838-1844.   DOI
81 Lidegaard, O., Nielsen, L. H., Skovlund, C. W., Skjeldestad, F. E. and Lokkegaard, E. (2011) Risk of venous thromboembolism from use of oral contraceptives containing different progestogens and oestrogen doses: Danish cohort study, 2001-9. BMJ 343, d6423.   DOI
82 Bailey, D. G., Freeman, D. J., Melendez, L. J., Kreeft, J. H., Edgar, B. and Carruthers, S. G. (1993) Quinidine interaction with nifedipine and felodipine: pharmacokinetic and pharmacodynamic evaluation. Clin. Pharmacol. Ther. 53, 354-359.   DOI
83 Auchus, R. J. and Miller, W. L. (2015) P450 enzymes in steroid processing. In Cytochrome P450: Structure, Mechanism, and Biochemistry (4th ed.) (P. R. Ortiz de Montellano, ed.), pp. 851-879. Springer, New York.
84 Bailey, D. G., Edgar, B., Spence, J. D., Munzo, C. and Arnold, J. M. O. (1990) Felodipine and nifedipine interactions with grapefruit juice. Clin. Pharmacol. Ther. 47, 180.
85 Bailey, D. G., Spence, J. D., Munoz, C. and Arnold, J. M. O. (1991) Interaction of citrus juices with felodipine and nifedipine. Lancet 337, 268-269.   DOI
86 Bhutani, P., Joshi, G., Raja, N., Bachhav, N., Rajanna, P. K., Bhutani, H., Paul, A. T. and Kumar, R. (2021) US FDA approved drugs from 2015-June 2020: a perspective. J. Med. Chem. 64, 2339-2381.   DOI
87 Bjornsson, T. D., Callaghan, J. T., Einolf, H. J., Fischer, V., Gan, L., Grimm, S., Kao, J., King, S. P., Miwa, G., Ni, L., Kumar, G., McLeod, J., Obach, R. S., Roberts, S., Roe, A., Shah, A., Snikeris, F., Sullivan, J. T., Tweedie, D., Vega, J. M., Walsh, J. and Wrighton, S. A. (2003a) The conduct of in vitro and in vivo drug-drug interaction studies: a Pharmaceutical Research and Manufacturers of America (PhRMA) perspective. Drug Metab. Dispos. 31, 815-832.   DOI
88 Chen, L., Krekels, E. H. J., Verweij, P. E., Bui, J. B., Knibbe, C. A. J. and Bruggemann, R. J. M. (2020) Pharmacokinetics and pharmacodynamics of posaconazole. Drugs 80, 671-695.   DOI
89 Bjornsson, T. D., Callaghan, J. T., Einolf, H. J., Fischer, V., Gan, L., Grimm, S., Kao, J., King, S. P., Miwa, G., Ni, L., Kumar, G., McLeod, J., Obach, S. R., Roberts, S., Roe, A., Shah, A., Snikeris, F., Sullivan, J. T., Tweedie, D., Vega, J. M., Walsh, J. and Wrighton, S. A. (2003b) The conduct of in vitro and in vivo drug-drug interaction studies: a PhRMA perspective. J. Clin. Pharmacol. 43, 443-469.   DOI
90 Bolt, H. M., Bolt, M. and Kappus, H. (1977) Interaction of rifampicin treatment with pharmacokinetics and metabolism of ethinyloestradiol in man. Acta Endocrinol. 85, 189-197.   DOI
91 Cheong, E. J. Y., Nair, P. C., Neo, R. W. Y., Tu, H. T., Lin, F., Chiong, E., Esuvaranathan, K., Fan, H., Szmulewitz, R. Z., Peer, C. J., Figg, W. D., Chai, C. L. L., Miners, J. O. and Chan, E. C. Y. (2020) Slow-, tightbinding inhibition of CYP17A1 by abiraterone redefines its kinetic selectivity and dosing regimen. J. Pharmacol. Exp. Ther. 374, 438-451.   DOI
92 Conney, A. H. (2003) Enzyme induction and dietary chemicals as approaches to cancer chemoprevention: the Seventh DeWitt S. Goodman Lecture. Cancer Res. 63, 7005-7031.
93 DeVore, N. M. and Scott, E. E. (2012) Structures of cytochrome P450 17A1 with prostate cancer drugs abiraterone and TOK-001. Nature 482, 116-119.   DOI
94 Dixon, M. and Webb, E. C. (1964) Enzymes (2nd ed.). Longman's, Green, London.
95 Edgar, B., Bailey, D. G., Bergstrand, R., Johnsson, G. and Lurje, L. (1990) Formulation dependent interaction between felodipine and grapefruit juice. Clin. Pharmacol. Ther. 47, 181.
96 FDA (2012) Guidance for Industry Drug Interaction Studies - Study Design, Data Analysis, Implications for Dosing, and Labeling Recommendations. U.S. Department of Health and Human Services Food and Drug Administration, Center for Drug Evaluation and Research (CDER), February 2012 Clinical Pharmacology, Silver Spring, MD.
97 Zhu, Y., Wang, F., Li, Q., Zhu, M., Du, A., Tang, W. and Chen, W. (2014) Amlodipine metabolism in human liver microsomes and roles of CYP3A4/5 in the dihydropyridine dehydrogenation. Drug Metab. Dispos. 42, 245-249.   DOI
98 Yu, J. J., Zhou, Z., Tay-Sontheimer, J., Levy, R. H. and RagueneauMajlessi, I. (2018) Risk of clinically relevant pharmacokinetic-based drug-drug interactions with drugs approved by the US Food and Drug Administration between 2013 and 2016. Drug Metab. Dispos. 46, 835-845.   DOI
99 Yun, C. H., Okerholm, R. A. and Guengerich, F. P. (1993) Oxidation of the antihistaminic drug terfenadine in human liver microsomes. Role of cytochrome P-450 3A(4) in N-dealkylation and C-hydroxylation. Drug Metab. Dispos. 21, 403-409.
100 Zhang, D., Flint, O., Wang, L., Gupta, A., Westhouse, R. A., Zhao, W., Raghavan, N., Caceres-Cortes, J., Marathe, P., Shen, G., Zhang, Y., Allentoff, A., Josephs, J., Gan, J., Borzilleri, R. and Humphreys, W. G. (2012) Cytochrome P450 11A1 bioactivation of a kinase inhibitor in rats: use of radioprofiling, modulation of metabolism, and adrenocortical cell lines to evaluate adrenal toxicity. Chem. Res. Toxicol. 25, 556-571.   DOI
101 Moore, L. G., Goodwin, B., Jones, S. A., Wisely, G. B., Serabjit-Singh, C. J., Wilson, T. M., Collins, J. L. and Kliewer, S. A. (2000) St. John's wort induces hepatic drug metabolism through activation of the pregnane X receptor. Proc. Natl. Acad. Sci. U.S.A. 97, 7500-7502.   DOI
102 Lin, H. L., Kenaan, C. and Hollenberg, P. F. (2012) Identification of the residue in human CYP3A4 that is covalently modified by bergamottin and the reactive intermediate that contributes to the grapefruit juice effect. Drug Metab. Dispos. 40, 998-1006.   DOI
103 Lingappan, K., Jiang, W., Wang, L., Wang, G., Couroucli, X. I., Shivanna, B., Welty, S. E., Barrios, R., Khan, M. F., Nebert, D. W., Roberts, L. J. and Moorthy, B. (2014) Mice deficient in the gene for cytochrome P450 (CYP)1A1 are more susceptible than wild-type to hyperoxic lung injury: evidence for protective role of CYP1A1 against oxidative stress. Toxicol. Sci. 141, 68-77.   DOI
104 Montane, E., Arellano, A. L., Sanz, Y., Roca, J. and Farre, M. (2018) Drug-related deaths in hospital inpatients: a retrospective cohort study. Br. J. Clin. Pharmacol. 84, 542-552.   DOI
105 Mueller, G. C. and Miller, J. A. (1948) The metabolism of 4-dimethylaminoazobenzene by rat liver homogenates. J. Biol. Chem. 176, 535-544.   DOI
106 Ortiz de Montellano, P. R. (2015) Cytochrome P450: Structure, Mechanism, and Biochemistry (4th ed.). Springer, New York.
107 Zimmerlin, A., Trunzer, M. and Faller, B. (2011) CYP3A time-dependent inhibition risk assessment validated with 400 reference drugs. Drug Metab. Dispos. 39, 1039-1046.   DOI
108 Omura, T. and Sato, R. (1964) The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239, 2370-2378.   DOI