과제정보
Thanks are extended to K. Trisler for assistance in preparation of the manuscript. P450 research in the author's laboratory is supported by National Institutes of Health grant R01 GM118122. The content is solely the responsibility of the author and does not necessarily represent the official view of the National Institutes of Health.
참고문헌
- Abeles, R. H. and Maycock, A. L. (1976) Suicide enzyme inactivators. Acct. Chem. Res. 9, 313-319. https://doi.org/10.1021/ar50105a001
- 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. https://doi.org/10.1074/jbc.M117.792200
- 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. https://doi.org/10.1074/mcp.RA117.000382
- 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. https://doi.org/10.1074/jbc.AC118.007225
- 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. https://doi.org/10.1016/j.jsbmb.2016.04.002
- 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. https://doi.org/10.1210/jc.2011-2189
- 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.
- 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.
- 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. https://doi.org/10.1016/0140-6736(91)90872-M
- 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. https://doi.org/10.1038/clpt.1993.32
- 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. https://doi.org/10.1503/cmaj.120951
- 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. https://doi.org/10.1021/acs.jmedchem.0c01786
- 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. https://doi.org/10.1124/dmd.31.7.815
- 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. https://doi.org/10.1177/0091270003252519
- 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. https://doi.org/10.1530/acta.0.0850189
- 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. https://doi.org/10.1001/archinte.160.20.3045
- 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. https://doi.org/10.1007/s40265-020-01306-y
- 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. https://doi.org/10.1124/jpet.120.265868
- 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. https://doi.org/10.1021/acs.jmedchem.9b01849
- 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. https://doi.org/10.1210/jc.86.8.3568
- 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.
- 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.
- 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. https://doi.org/10.1038/nature10743
- Dixon, M. and Webb, E. C. (1964) Enzymes (2nd ed.). Longman's, Green, London.
- 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. https://doi.org/10.2165/00003088-200038010-00003
- 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.
- 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. https://doi.org/10.1073/pnas.0603236103
- 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. https://doi.org/10.1021/jm400240r
- 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. https://doi.org/10.1021/acs.jmedchem.7b00437
- 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. https://doi.org/10.1124/dmd.121.000356
- 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. https://doi.org/10.1124/dmd.108.026252
- 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.
- 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. https://doi.org/10.1124/dmd.119.089086
- 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].
- 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.
- 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. https://doi.org/10.1021/jm500739f
- 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. https://doi.org/10.1021/acs.jmedchem.9b01485
- 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. https://doi.org/10.1016/j.clpt.2004.08.019
- Guengerich, F. P. (1988) Oxidation of 17α-ethynylestradiol by human liver cytochrome P-450. Mol. Pharmacol. 33, 500-508.
- Guengerich, F. P. (1989) Characterization of human microsomal cytochrome P-450 enzymes. Annu. Rev. Pharmacol. Toxicol. 29, 241-264. https://doi.org/10.1146/annurev.pa.29.040189.001325
- Guengerich, F. P. (1990a) Mechanism-based inactivation of human liver microsomal cytochrome P-450 IIIA4 by gestodene. Chem. Res. Toxicol. 3, 363-371. https://doi.org/10.1021/tx00016a015
- Guengerich, F. P. (1990b) Inhibition of oral contraceptive steroid-metabolizing enzymes by steroids and drugs. Am. J. Obstet. Gynecol. 163, 2159-2163. https://doi.org/10.1016/0002-9378(90)90557-n
- 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. https://doi.org/10.1093/carcin/11.12.2275
- 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. https://doi.org/10.1021/jm00110a012
- 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.
- Guengerich, F. P. (2019a) Kinetic modeling of steady-state situations in cytochrome P450 enzyme reactions. Drug Metab. Dispos. 47, 1232-1239. https://doi.org/10.1124/dmd.119.088732
- Guengerich, F. P. (2019b) Cytochrome P450 research and The Journal of Biological Chemistry. J. Biol. Chem. 294, 1671-1680. https://doi.org/10.1074/jbc.tm118.004144
- Guengerich, F. P. (2020) A history of the role of cytochrome P450 enzymes in the toxicity of drugs. Toxicol. Res. 37, 1-23. https://doi.org/10.1007/s43188-020-00056-z
- 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. https://doi.org/10.1074/jbc.RA120.016855
- 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. https://doi.org/10.1016/j.jbc.2021.100969
- Halpert, J. and Neal, R. A. (1980) Inactivation of purified rat liver cytochrome P-450 by chloramphenicol. Mol. Pharmacol. 17, 427-431.
- 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. https://doi.org/10.1124/dmd.113.054817
- 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. https://doi.org/10.1021/tx970192k
- 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. https://doi.org/10.1111/j.1432-1033.1986.tb09659.x
- 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. https://doi.org/10.1038/clpt.1992.135
- Johnson, K. A. (2019) Kinetic Anaylsis for the New Enzymology (1st ed.). KinTek, Austin, TX.
- 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. https://doi.org/10.1074/jbc.M115.665331
- Kuby, S. A. (1991) A Study of Enzymes, Vol. I, Enzyme Catalysis, Kinetics, and Substrate Binding (Vol. 7). CRC Press, Boca Raton, FL.
- 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. https://doi.org/10.1016/0010-7824(88)90088-1
- Kuhl, H., Jung-Hoffmann, C. and Wiegratz, I. (1995) Gestodene-containing contraceptives. Clin. Obstet. Gynecol. 38, 829-840. https://doi.org/10.1097/00003081-199538040-00018
- 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. https://doi.org/10.1021/bi048967t
- 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. https://doi.org/10.1016/j.bbagen.2006.07.018
- 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. https://doi.org/10.1136/bmj.d6423
- 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. https://doi.org/10.1124/dmd.112.044560
- 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. https://doi.org/10.1124/dmd.118.080903
- 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. https://doi.org/10.1093/toxsci/kfu106
- 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. https://doi.org/10.1067/mcp.2001.113185
- 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. https://doi.org/10.1021/ja00508a048
- 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. https://doi.org/10.1111/bcp.13471
- 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. https://doi.org/10.1073/pnas.130155097
- 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. https://doi.org/10.1016/j.beem.2008.01.003
- Mueller, G. C. and Miller, J. A. (1948) The metabolism of 4-dimethylaminoazobenzene by rat liver homogenates. J. Biol. Chem. 176, 535-544. https://doi.org/10.1016/S0021-9258(19)52671-0
- 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. https://doi.org/10.1016/j.clpt.2005.09.004
- Omura, T. and Sato, R. (1962) A new cytochrome in liver microsomes. J. Biol. Chem. 237, 1375-1376.
- 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. https://doi.org/10.1016/S0021-9258(20)82244-3
- Ortiz de Montellano, P. R. (2015) Cytochrome P450: Structure, Mechanism, and Biochemistry (4th ed.). Springer, New York.
- 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. https://doi.org/10.1073/pnas.76.2.746
- 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. https://doi.org/10.1124/jpet.104.076836
- 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. https://doi.org/10.1124/dmd.117.079962
- 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. https://doi.org/10.1046/j.1365-2125.2000.00271.x
- 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.
- 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. https://doi.org/10.1021/jm00369a018
- 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. https://doi.org/10.1074/jbc.M114.610998
- 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. https://doi.org/10.1124/dmd.117.075317
- Rangno, R. (1997) Terfenadine therapy: can we justify the risks? Can. Med. Assoc. J. 157, 37-38.
- Rendic, S. and Guengerich, F. P. (2012) Contributions of human enzymes in carcinogen metabolism. Chem. Res. Toxicol. 25, 1316-1383. https://doi.org/10.1021/tx300132k
- 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. https://doi.org/10.1021/tx500444e
- Ryan, K. J. (1959) Biological aromatization of steroids. J. Biol. Chem. 234, 268-272. https://doi.org/10.1016/S0021-9258(18)70286-X
- 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.
- Segel, I. H. (1975) Enzyme Kinetics. Wiley, New York.
- 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. https://doi.org/10.1067/mcp.2000.107651
- Shinkyo, R. and Guengerich, F. P. (2011) Inhibition of human cytochrome P450 3A4 by cholesterol. J. Biol. Chem. 286, 18426-18433. https://doi.org/10.1074/jbc.M111.240457
- 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.
- Silverman, R. B. (1995) Mechanism-based enzyme inactivators. Methods Enzymol. 249, 240-283. https://doi.org/10.1016/0076-6879(95)49038-8
- Thompson, D. and Oster, G. (1996) Use of terfenadine and contraindicated drugs. JAMA 275, 1339-1341. https://doi.org/10.1001/jama.1996.03530410053033
- 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. https://doi.org/10.1016/j.tox.2013.12.005
- 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. https://doi.org/10.1016/0960-0760(93)90299-C
- Williams, R. T. (1947) Detoxication Mechanisms (1st ed.). Wiley, New York.
- Woosley, R. L., Chen, Y., Freiman, J. P. and Gillis, R. A. (1993) Mechanism of the cardiotoxic actions of terfenadine. JAMA 269, 1532-1536. https://doi.org/10.1001/jama.1993.03500120070028
- Woosley, R. L. (1996) Cardiac actions of antihistamines. Annu. Rev. Pharmacol. Toxicol. 36, 233-252. https://doi.org/10.1146/annurev.pa.36.040196.001313
- 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. https://doi.org/10.1074/jbc.C400293200
- 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. https://doi.org/10.1021/jm060519r
- 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. https://doi.org/10.1021/jm3003872
- 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. https://doi.org/10.1124/dmd.117.078691
- 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.
- 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. https://doi.org/10.1021/tx200524d
- 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. https://doi.org/10.1124/dmd.113.055400
- 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. https://doi.org/10.1124/dmd.110.037911