Mechanisms and significance of inhibitory drug interactions involving cytochrome P450 enzymes (Review)

International Journal of Molecular Medicine

Volumn 3, Issue 3, 1999, Pages 227-238

  Murray, Michael ^a  

^a UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Cytochrome p450; Drug interactions; Enzyme inactivation; Mechanismbased inhibition; Metabolite intermediate complexation; Structure function relationships

Indexed keywords

CYTOCHROME P450; DRUG; ENZYME INHIBITOR;

ANIMAL; CHEMISTRY; CLASSIFICATION; DRUG ANTAGONISM; DRUG COMBINATION; DRUG INTERACTION; ENZYME SPECIFICITY; ENZYMOLOGY; HUMAN; LIVER; METABOLISM; PROTEIN CONFORMATION; REVIEW;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; DRUG INTERACTIONS; DRUG THERAPY, COMBINATION; ENZYME INHIBITORS; HUMANS; LIVER; PHARMACEUTICAL PREPARATIONS; PROTEIN CONFORMATION; SUBSTRATE SPECIFICITY;

EID: 0033086126     PISSN: 11073756     EISSN: None     Source Type: Journal    
DOI: 10.3892/ijmm.3.3.227     Document Type: Article

References (142)

1. Ryan DE and Levin W: Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacol Ther 45: 153-229, 1990.
2. Nelson DR, Koymans L, Kamataki T, Stegeman JJ, Feyereisen R, Waxman DJ, Waterman MR, Gotoh O, Coon MJ, Estabrook R\V, Gunsalus IC and Nebert DW: P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics 6: 1-42, 1996.
3. Ortiz de Montellano PR (ed): Oxygen activity and reactivity. In: Cytochrome P450: Structure, Mechanism and Biochemistry. 2nd edition. Plenum Press, New York, pp245-302, 1995.
4. Gonzalez FJ: The molecular biology of cytochrome P450s. Pharmacol Rev 40: 243-288, 1989.
5. Wood AW, Levin W, Lu AYH, Yagi H, Hemandez O, Jerina DM and Conney AH: Metabolism of benzo(a)pyrene and benzo(a)pyrene derivatives to mutagenic products by highly purified hepatic microsomal enzymes. J Biol Chem 251: 4882-4890, 1976.
6. Shimada T, Yun CH, Yamazaki H, Gautier JC, Beaune PH and Guengerich FP: Characterization of human lung microsomal cytochrome P-450 1A1 and its role in the oxidation of chemical carcinogens. Mol Pharmacol 41: 856-864, 1992.
7. Patten C, Thomas PE, Guy R, Lee M, Gonzalez FJ, Guengerich FP and Yang CS: Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes. Chem ResToxicol6:511-518, 1993.
8. Spaldin V, Madden S, Pool WF, Woolf TF and Park BK: The effect of enzyme inhibition on the metabolism and activation of tacrine by human liver microsomes. Br J Clin Pharmacol 38: 15-22, 1994.
9. Bertilsson L, Carrillo JA, Dahl ML, Llerena A, Alm C, Bondesson U, Lindstrom L, Rodriguez de la Rubia I, Ramos S and Benitez J: Clozapine disposition covaries with CYP1A2 activity determined by a caffeine test. Br J Clin Pharmacol 38: 471-473, 1994.
10. Gu L, Gonzalez FJ, Kalow W and Tang BK: Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1. Pharmacogenetics 2: 73-77, 1992.
11. Tang BK and Kalow W: Assays for CYP1A2 by testing in vivo metabolism of caffeine in humans. Methods Enzymol 272: 124-131, 1996.
12. Shimada T, Yamazaki H, Mimura M, Inui Y and Guengerich FP: Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270:414-423, 1994.
13. Vainer JL and Chouinard G: Interaction between caffeine and clozapine. J Clin Psychopharmacol 14: 284-285, 1994.
14. Odom-White A and de Leon J: Clozapine levels and caffeine. J Clin Psychiatry 57: 175-176, 1996.
15. Kunze KL and Trager WF: Isoform-selective mechanism-based inhibition of human P450 1A2 by furafylline. Chem Res Toxicol 6: 649-656, 1993.
16. Yamazaki H, Inui Y, Yun CH, Mimura M, Gucngcrich FP and Shimada T: Cylochrome P450 2E1 and 2A6 enzymes as major catalysts for metabolic activation of N-nitrosodialkylamines and tobacco-related nitrosamines in human liver microsomes. Carcinogenesis 13: 1789-1794, 1992.
17. Kimonen T, Juvonen RO, Alhava E and Fasanen M: The inhibition of CYP enzymes in mouse and human liver by pilocarpine. Br J Pharmacol 114: 832-836, 1995.
18. Maenpaa J, Juvonen R, Raunio H, Rautio A and Pelkonen O: Metabolic interactions of methoxsalen and coumarin in humans and mice. Biochem Pharmacol 48: 1363-1369, 1994.
19. Chang TKH, Gonzalez FJ and Waxman DJ: Evaluation of triacetyloleandomycin, a-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch Biochem Biophys 311: 437-442, 1994.
20. Levin W, Thomas PE, Ryan DE and Wood AW: Isozyme specificity of testosterone 7α-hydroxylation in rat hepatic microsomes: is cytochrome P-450a the sole catalyst? Arch Biochem Biophys 258: 630-635, 1987.
21. Yun CH, Shimada T and Guengerich FP: Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol Pharmacol 40: 679-685, 1991.
22. Ryan DE, Thomas PE, Korzeniowski D and Levin W: Separation and characterization of highly purified forms of liver microsomal "cytochrome P-450 from rats treated with polychlorinated biphenyls, phenobarbital, and 3-methylcholanthrene. J Biol Chem254: 1365-1374, 1979.
23. Yamano S, Nhamburo PT, Aoyama T, Meyer UA, Inaba T, Kalow W, Gelboin HV, McBride OW and Gonzalez FJ: cDNA cloning and sequence and cDNA-directed expression of human P450 IIB1: identification of a normal and two variant cDNAs derived from the CYP2B locus on chromosome 19 and differential expression of the IIB mRNAs in human liver. Biochemistry 28: 7340-7348, 1989.
24. Stevens JC, White RB, Hsu SH and Martinet M: Human liver CYP2B6-catalyzed hydroxylation of RP 73401. J Pharmacol ExpTher282: 1389-1395, 1997.
25. Mimura M, Baba T, Yamazaki Y, Ohmori S, Inui Y, Gonzalez FJ, ' Guengerich FP and Shimada T: Characterization of cytochrome P450 2B6 in human liver microsomes. Drug Metab Dispos 21: 1048-1056, 1993.
26. Watkins PB, Wrighton SA, Maurel P, Schuetz EG, MendezPicon G, Parker GA and Guzelian PS: Identification of an inducible form of cytochrome P-450 in human liver. Proc Natl Acad Sci USA 82: 6310-6314, 1985.
27. Heimark LD, Gibaldi M, Trager WF, O'Reilly RA and Goulart DA: The mechanism of the warfarin-rifampicin drug interaction in humans. Clin Pharmacol Ther 42: 388-394, 1987.
28. Rahman A, Korzekwa KR, Grogan J, Gonzalez FJ and Harris JW: Selective biotransformation of taxol to 6α-hydroxytaxol by human cytochrome P450 2C8. Cancer Res 54: 5543-5546, 1994.
29. Leo MA, Lasker JM, Raucy JL, Kirn CI, Black M and Lieber CS: Metabolism of retinol and retinoic acid by human liver cytochrome P450IIC8. Arch Biochem Biophys 269: 305-312, 1989.
30. Knodell RG, Hall SD, Wilkinson GR and Guengerich FP: Hepatic metabolism of tolbutamide: characterization of the form of cytochrome P-450 involved in methyl hydroxylation and relationship to HI vivo disposition. J Pharmacol Exp Ther 241: 1112-1119, 1987.
31. Veronese ME, Mackenzie PI, Doecke CJ, McManus ME, Miners JO and Birkett DJ: Tolbutamide and phenytoin hydroxylations by cDNA-expressed human liver cytochrome P450 2C9. Biochem Biophys Res Commun 175: 1112-1118, 1991.
32. Miners JO, Rees DL, Valente L, Veronese ME and Birkett DJ: Human hepatic P450 2C9 catalyzes the rate-limiting pathway of torsemide metabolism. J Pharmacol Exp Ther 272: 1076-1081, 1995.
33. Leemann T, Transon C and Dayer P: Cytochrome P450TB (CYP2C): a major monooxygenase catalyzing diclofenac 4′-hydroxylation in human liver. Life Sci 52: 29-34, 1993.
34. Wrighton SA, Stevens JC, Becker GW and VandenBranden M: Isolation and characterization of human liver cytochrome P450 2C19: correlation between 2C19 and S-mephenytoin 4′-hydroxylation. Arch Biochem Biophys 306: 240-245, 1993.
35. Andersson T, Regårdh CG, Dahl-Puustinen ML and Bertilsson L: Slow omeprazole metabolizers are also poor S-mephenytoin hydroxylators. Ther Drug Monit 12: 415-416, 1990.
36. Gram LF, Guentert TW, Grange S, Vitisen K and Brøsen K: Moclobemide, a substrate of CYP2C19 and an inhibitor of CYP2C19, CYP2D6, and CYP1A2: a panel study. Clin Pharmacol Ther 57: 670-677, 1995.
37. Birkett DJ, Rees D, Andersson T, Gonzalez FJ and Miners JO: In vitro proguanil activation to cycloguanil by human liver microsomes is mediated by CYP3A isoforms as well as by S-mephenytoin hydroxylase. Br J Clin Pharmacol 37:413-420, 1994.
38. Mahgoub AA, Idle JR, Dring LG, Lancaster R and Smith RL: Polymorphic hydroxylation of debrisoquine in man. Lancet ii: 584, 1977.
39. Larrey D, Distelrath LM, Dannan GA, Wilkinson GR and Guengerich FP: Purification and characterization of the rat liver microsomal cytochrome P-450 involved in the 4-hydroxylation of debrisoquine, a prototype for genetic variation in oxidative drug metabolism. Biochemistry 23: 2787-2795, 1984.
40. Distelrath LM and Guengerich FP: Characterization of a human liver cytochrome P-450 involved in the oxidation of debrisoquine and other drugs using antibodies raised to the analogous rat enzyme. Proc Natl Acad Sci USA 79: 3735-3741, 1984.
41. McGourty JC, Silas JH, Fleming JJ, McBurney A and Ward JW: Pharmacokinetics and beta-blocking effects of timolol in poor and extensive metabolizers of debrkoquin. Clin Pharmacol Ther 38: 409-413, 1985.
42. Mellstrom B, Sawe J, Bertilsson L and Sjoqvist F: Amitriptyline metabolism: association with debrisoquin hydroxylation in non-smokers. Clin Pharmacol Ther 39: 369-371, 1986.
43. Dayer P, Desmeules J, Leemann T and Stribemi R: Bioactivation of the narcotic drug codeine in human liver is mediated by the polymorphic monooxygenase catalyzing debrisoquine 4-hydroxylation. Biochem Biophys Res Commun 152: 411-416, 1988.
44. Gonzalez FJ, Skoda RC, Kimura S, Umeno M, Zanger UM, Nebert DW, Gelboin HV, Hardwick JP and Meyer UA: Characterization of the common genetic defect in humans deficient in debrisoquine metabolism. Nature 331: 442-446, 1988.
45. Tyndale R, Aoyama T, Broly F, Matsunaga T, Inaba T, Kalow W, Gelboin HV, Meyer UA and Gonzalez FJ: Identification of a new variant CYP2D6 allele lacking the codon encoding Lys-281: possible association with the poor metabolizer phenotype. Pharmacogenetics 1:26-32, 1991.
46. Armstrong M, Idle JR and Daly AK: A polymorphic CfoI site in exon 6 of the human cytochrome P450 CYP2D6 gene detected by the polymerase chain reaction. Hum Genet 91: 616-617, 1993.
47. Daly AK, Steen VM, Fairbrother KS and Idle JR: CYP2D6 multiallelism. Methods Enzymol 272: 199-210, 1996.
48. Guengerich FP, Kim DH and Iwasaki M: Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol 4: 168-179, 1991.
49. Kharasch ED, Armstrong AS, Gunn K, Artry A, Cox K and Karol MD: Clinical sevoflurane metabolism and disposition. II. The role of P450 2E1 in fluoride and hexafluoroisopropanol formation. Anesthesiology 82: 1379-1388, 1995.
50. Spracklin DK, Hankins DC, Fisher JM, Thummel KE and Kharasch ED: P450 2E1 is the principal catalyst of human halothane metabolism in vitro. 3 Pharmacol Exp Ther 281: 400-411, 1997.
51. Koop DR: Hydroxylation of p-nitrophenol by rabbit ethanolinducible cytochrome P450 isozyme 3A. Mol Pharmacol 29: 399-404, 1986.
52. Peter R, Bocker RG, Beaune PH, Iwasaki M, Guengerich FP and Yang CS: Hydroxylation of chlorzoxazone as a specific probe for human liver cytochrome P-450 IIE1. Chem Res Toxicol 3: 566-573, 1990.
53. Zerilli A, Ratanasavanh D, Lucas D, Goasduff T, Dreano Y, Menard C, Picart D and Berthou F: Both cytochromes P450 2E1 and 3A are involved in the O-hydroxylation of p-nitrophenol, a catalytic activity known to be specific for P450 2E1. Chem Res Toxicol 10: 1205-1212, 1997.
54. Ono S, Hatanaka T, Hotta H, Tsusui M, Satoh T and Gonzalez FJ: Chlorzoxazone is metabolized by human CYP1A2 as well as human CYP2E1. Pharmacogenetics 5: 143-150, 1995.
55. Gorski JC, Jones DR, Wrighton SA and Hall SD: Contribution of human CYP3A subfamily members to the 6-hydroxylation of chlorzoxazone. Xenobiotica 27: 243-256, 1997.
56. Koop DR: Oxidative and reductive metabolism by cytochrome P450 2EI. FASEB J 6: 724-730, 1992.
57. Favrcau LV, Malchoff DM, Mole JE and Schenkman JB: Responses to insulin by two forms of rat hepatic microsomal cytochrome P450 that undergo major (RLM6) and minor (RLM5b) elevations in diabetes. J Biol Chem 262: 14319-14326, 1987.
58. Yoo JSH, Ning SM, Pantuk EJ and Yang CS: Regulation of hepatic microsomal cytochrome P450IIE1 by dietary lipids and carbohydrates in rats. J Nutr 121: 959-965, 1991.
59. Johansson I, Ekstrom G, Scholte B, Puzycki D, Jornvall H and Ingelman-Sundberg M: Ethanol-, fasting- and acetone-inducible cytochromes P450 in rat liver: regulation and characteristics of enzymes belonging to the IIB and IIE gene subfamilies. Biochemistry 27: 1925-1934, 1987.
60. Koop DE and Tiemey DJ: Multiple mechanisms in the regulation of ethanol-inducible cytochrome P450IIE1. Bioessays 12: 429-435, 1991.
61. Ronis MJJ, Johansson I, Hultenby K, Lagercrantz J, Glaumann H and Ingelman-Sundberg M: Acetone-regulated synthesis and degradation of cytochrome P450 IIE1 and IIB1 in rat liver. Eur J Biochem 198: 383-389, 1991.
62. Song BJ, Gelboin HV, Park SS, Yang CS and Gonzalez FJ: Complementary DNA and protein sequences of ethanol-inducible rat and human cytochrome P450s: transcriptional and post-transcriptional regulation of the rat enzyme. J Biol Chem 261: 16689-16697, 1986.
63. Badger TM, Huang J, Ronis MJJ and Lumpkin CK: Induction of cytochrome P450 2E1 during chronic ethanol exposure occurs .via transcription of the CYP2E1 gene when blood alcohol concentrations are high. Biochem Biophys Res Commun 190: 780-785, 1993.
64. Martini R, Ingelman-Sundberg M and Murray M: Pretranslational and posttranslational regulation of rat hepatic CYPs 3A2 and 2E1 by disulfiram. Biochem Pharmacol 54: 1323-1329, 1997.
65. Guengerich FP, Martin MV, Beaune PH, Kremers P, Wolff T and Waxman DJ: Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation: a prototype for genetic polymorphism in oxidative drug metabolism. J Biol Chem 261: 5051-5060, 1986.
66. Wrighton SA and Van den Branden M: Isolation and characterization of human fetal liver cytochrome P450HLp2: a third member of the P450III gene family. Arch Biochem Biophys 268: 144-151, 1989.
67. Kitada M, Kamataki T, Itahashi K, Rikihisa T, Kalo R and Kanakubo Y: Purification and properties of cytochrome P-450 from homogenates of human fetal livers. Arch Biochem Biophys 241:275-280, 1985.
68. Wrighton SA, Ring BJ, Watkins PB and Van den Branden M: Identification of a polymorphically expressed member of the human cytochrome P-450III family. Mol Pharmacol 36: 97-105, 1989.
69. Komori M, Nishio K, Kitada M, Shiramatsu K, Muroya K, Soma M, Nagashima K and Kamataki T: Fetus-specific expression of a form of cytochrome P-450 in human livers. Biochemistry 29:4430-4433, 1990.
70. Comalbert J, Fabre I, Fabre G, Dalet I, Derancourt J, Cano JP and Maurel P: Metabolism of cyclosporin A. IV. Purification and identification of the rifampicin-inducible human liver cytochrome P450 (cyclosporin A oxidase) as a product of P4501IIA gene subfamily. Drug Metab Dispos 17: 197-207, 1989.
71. Brian WR, Sari MA, Iwasaki M, Shimada T, Kaminsky LS and Guengerich FP: Catalytic activities of human liver cytochrome P4501IIA4 expressed in Saccharomyces cerevisiae. Biochemistry 29: 11280-11292, 1990.
72. Harris JW, Rahman A, Kim BR, Guengerich FP and Collins JM: Metabolism of taxol by hepatic microsomes and liver slices: participation of cytochrome P450 3A4 and an unknown P450 enzyme. Cancer Res 54:4026-4035, 1994.
73. Ren S, Yang JS, Kalhorn TF and Slattery JT: Oxidation of cyclophosphamide to 4-hydroxycyclophosphamide in human liver microsomes. Cancer Res 57: 4229-4235, 1997.
74. Sutton DS, Butler AM, Nadin L and Murray M: Role of CYP3A4 in human hepatic diltiazem N-demethylation: inhibition of CYP3A4 activity by oxidized diltiazem metabolites. J Pharmacol Exp Ther 282: 294-300, 1997.
75. Transon C, Leemann T and Dayer P: In vitro comparative inhibition profiles of major human drug metabolizing P450s (CYP2C9, CYP2D6 and CYP3A4) by HMG-CoA reductase inhibitors. Eur J Clin Pharmacol 50: 209-215, 1996.
76. Szklarz GD and Halpert JR: Use of homology modelling in conjunction with site-directed mutagcnesis for analysis of structure-function relationships of mammalian cytochromes P450. Life Sci 61: 2507-2520, 1997.
77. Von Wachenfeldt C and Johnson EF: Structures of eukaryotic cytochrome P450 enzymes. In: Cytochrome P450: Structure, Mechanism and Biochemistry. 2nd edition. Ortiz de Montellano PR (ed). Plenum Press, New York, pp183-223, 1995.
78. Gotoh O: Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding sequences. J Biol Chem 267: 83-90, 1992.
79. Ellis SW, Hayhurst GP, Smith G, Lightfoot T, Wong MMS, Simula AP, Ackland MJ, Stemberg MJE, Lennard MS, Tucker GT and Wolf CR: Evidence that aspartic acid 301 is a critical substrate-contact residue in the active site of cytochrome P450 2D6. J Biol Chem 270: 29055-29058, 1995.
80. Koymans L, Vermeulen NPE, van Acker SABE, te Koppele JM, Heykants JJP, Lavrijsen K, Meuldermans W and Donne-Op den Kelder GM: A predictive model for substrates of cytochrome P450-debrisoquine (2D6). Chem Res Toxicol 5: 211-219, 1992.
81. Lewis DFV, Eddershaw PJ, Goldfarb PS and Tarbit MH: Molecular modelling of cytochrome P4502D6 (CYP2D6) based on an alignment with CYP102: structural studies on specific CYP2D6 substrates. Xenobiotica 27: 319-340, 1997.
82. De Groot MJ, Vermeulen NPE, Kramer JD, van Acker FAA, Donne-Op den Kelder GM: A three-dimensional protein model for human cytochrome P450 2D6 based on the crystal structures of P450 101, P450 102, and P450 108. Chem Res Toxicol 9: 1079-1091, 1996.
83. Shou M, Grogan J, Mancewicz JA, Krausz KW, Gonzalez FJ, Gelboin HV and Korzekwa KR: Activation of CYP3A4: evidence for the simultaneous binding of two substrates in a cytochrome P450 active site. Biochemistry 33: 6450-6455, 1994.
84. Korzekwa KR, Krishnamachary N, Shou M, Ogai A, Panse RA, Rettie AE, Gonzalez FJ and Tracy TS: Evaluation of atypical cytochrome P450 kinetics with two-substrate models: evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites. Biochemistry 37: 4137-4147, 1998.
85. Harlow GR and Halpert JR: Analysis of human cytochrome P450 3A4 cooperativity: construction and characterization of a site-directed mutant that displays hyperbolic steroid hydroxylation kinetics. Proc Natl Acad Sci USA 95: 6636-6641, 1998.
86. Ibeanu GC, Ghanayem BI, Linko P, Li L, Pederson LG and Goldstein JA: Identification of residues 99, 220, and 221 of human cytochrome P450 2C19 as key determinants of omeprazole activity. J Biol Chem 271: 12496-12501, 1996.
87. Jones JP, He M, Trager WF and Rettie AE: Three-dimensional quantitative structure-activity relationship for inhibitors of cytochrome P4502C9. Drug Metab Dispos 24: 1-6, 1996.
88. Jones BC, Hawksworth G, Home VA, Newlands A, Morsman J, Tute MS and Smith DA: Putative active site template model for cytochrome P4502C9 (tolbutamide hydroxylase). Drug Metab Dispos 24: 260-266, 1996.
89. Murray M and Reidy GF: Selectivity in the inhibition of mammalian cytochromes P-450 by chemical agents. Pharmacol Rev 42: 85-101, 1990.
90. Wilkinson CF, Hetnarski K, Cantwell GP and Di Carlo FJ: Structure-activity relationships in the effects of 1-alkylimidazoles on microsomal oxidation in vitro and in vivo. Biochem Pharmacol 23:2377-2386, 1974.
91. Orme-Johnson NR and Orme-Johnson WH: Detection and quantitation of free cytochrome P-450 and cytochrome P-450 complexes by EPR spectroscopy. Methods Enzymol 52: 252-257, 1978.
92. Murray M, Ryan AJ and Little PJ: Inhibition of rat hepatic microsomal aminopyrine N-demethylase activity by benzimidazole derivatives. Quantitative structure-activity relationships. J Med Chem 25: 887-892, 1982.
93. Dickins M and Bridges JW: The relationship between the binding of 2-n-alkylbenzimidazoles to rat hepatic microsomal cytochrome P-450 and the inhibition of monoxygenation. Biochem Pharmacol 31: 1315-1320, 1982.
94. Murray M and Wilkinson CF: Interactions of nitrogen heterocycles with cytochrome P-450 and monooxygenase activity. Chem Biol Interact 50: 267-275, 1984.
95. Murray M and Zaluzny L: Comparative effects of antithrombitic and antimycotic TV-substituted imidazoles on rat hepatic microsomal steroid and xenobiotic hydroxylases in vitro. Biochem Pharmacol 37:415-420, 1988.
96. Ono S, Hatanaka T, Hotta H, Satoh T, Gonzalez FJ and Tsutsui M: Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica 26: 681-693, 1996.
97. Tsao SC, Dickinson TH and Abemethy DR: Metabolite inhibition of parent drug biotransformation. Studies of diltiazem. Drug Metab Dispos 18: 180-182, 1990.
98. Ring BJ, Binkley SN, Roskos L and Wrighton SA: Effect of fluoxetine, norfluoxetine, sertraline and desmethyl sertraline on human CYP3A catalyzed 1′-hydroxy midazolam formation in vitro. J Pharmacol Exp Ther 275: 1131-1135, 1995.
99. Von Moltke LL, Greenblatt DJ, Harmatz JS, Duan SX, Harrel LM, Cotreau-Bibbo MM, Pritchard GA, Wright CE and Shader RI: Triazolam biotransformation by human liver microsomes in vitro: effects of metabolic inhibitors and clinical confirmation of a predicted interaction with ketoconazole. J Pharmacol Exp Ther 276: 370-379, 1996.
100. Wouters W, van Dun J, Dillen A, Coene MC, Cools W and De Coster R: Effects of liarozole, a new antitumoral compound, on retinoic acid-induced inhibition of cell growth and on retinoic acid metabolism in MCF-7 human breast cancer cells. Cancer Res 52: 2841-2846, 1992.
101. Vanden Bossche HV, Moereels H and Koymans LM: Aromatase inhibitors: mechanisms for non-steroidal inhibitors. Breast Cancer Res Treat 30: 43-55, 1994.
102. Wouters W, Snoeck E and De Coster R: Vorozole, a specific non-steroidal aromatase inhibitor. Breast Cancer Res Treat 30: 89-94, 1994.
103. Smith CL, Hampton EM, Pederson JA, Pennington LR and Bourne D\V: Clinical and medicoeconomic impact of the cyclbsporine-diltiazem interaction in renal transplant recipients. Pharmacotherapy 14: 471-481, 1994.
104. Ortiz de Montellano PR arid Correia MA: Inhibition of cytochrome P450 enzymes. In: Cytochrome P450: Structure, Mechanism and Biochemistry. 2nd edition. Ortiz de Montellano PR (ed). Plenum Press, New York, pp305-364, 1995.
105. Ortiz de Montellano PR, Yost GS, Mico B A, Dinizo SE, Correia MA and Kumbara H: Destruction of cytochrome P-450 by 2-isopropyl-4-pentenamide and methyl 2-isopropyl-4pentenoate: mass spectrometric characterization of prosthetic heme adducts and non-participation of epoxide metabolites. Arch Biochem Biophys 197: 524-533, 1979.
106. Sharma U, Roberts ES and Hollenbcrg PF: Inactivation of cytochrome P4502B1 by the monoamine oxidase inhibitors R-(-)-deprenyl and clorgyline. Drug Metab Dispos 24: 669-675, 1996.
107. Guengerich FP: Mechanism-based inactivation of human liver cytochrome P-450 IIIA4 by gestodene. Chem Res Toxicol 3: 363-371, 1990.
108. Guengerich FP: Oxidation of 17α-ethynylestradiol by human liver cytochrome P-450. Mol Pharmacol 33: 500-508, 1988.
109. Ortiz de Montellano PR, Beilan HS and Mathews JM: Alkylation of the prosthetic heme in cytochrome P-450 during oxidative metabolism of the sedative-hypnotic ethchlorvynol. J Med Chem 25:1174-1179, 1982.
110. Lunetta JM, Sugiyama K and Correia MA: Secobarbital-mediated inactivation of rat liver cytochrome P-450b: a mechanistic reappraisal. Mol Pharmacol 35: 10-17, 1989.
111. Decker CJ, Rashed MS, Baillie TA, Maltby D and Correia MA: Oxidative metabolism of spironolactone: evidence for the involvement of electrophilic thiosteroid species in drug-mediated destruction of rat hepatic cytochrome P-450. Biochemistry 28: 5128-5136, 1989.
112. Halpert JR, Hammond D and Neal RA: Inactivation of purified rat liver cytochrome P-450 during the metabolism of parathion (diethyl p-nitrophenyl phosphorothioate). J Biol Chem 255: 1080-1089, 1980.
113. Butler AM and Murray M: Inhibition and inactivation of constitutive cytochromes P450 in rat liver by parathion. Mol Pharmacol 43: 902-908, 1993.
114. Lopez-Garcia MO, Dansette PM and Mansuy D: Thiophene derivatives as new mechanism-based inhibitors of cytochrome P450: inactivation of yeast-expressed human liver P450 2C9 by tienilic acid. Biochemistry 33: 166-175, 1993.
115. Bond EJ and DeMatteis FA: Biochemical changes in rat liver after administration of carbon disulphide, with particular reference to microsomal changes. Biochem Pharmacol 18: 2531-2549, 1969.
116. Brady JF, Ishizaki H, Fukuto JM, Lin MC, Fadel A, Gapac JM and Yang CS: Inhibition of cytochrome P-450 2EI by diallyl sulfide and its metabolites. Chem Res Toxicol 4: 642-647, 1991.
117. Halpert J and Neal R A: Inactivation of purified rat liver cytochrome P-450 by chloramphenicol. Mol Pharmacol 17: 427-434, 1980.
118. Halpert J: Covalent modification of lysine during the suicide inactivation of rat liver cytochrome P-450 by chloramphenicol. Biochem Pharmacol 30: 875-881, 1981.
119. Tinel M, Belghiti J, Descatoire V, Ampuyal G, Letteron P, Geneve J, Larrey D and Pessayre D: Inactivation of human liver cytochrome P-450 by the drug methoxsalen and other psoralen derivatives. Biochem Pharmacol 36: 951-955, 1987.
120. Mansuy D, Rouer E, Bacot C, Gans P, Chottard JC and Leroux JP: Interaction of aliphatic W-hydroxylamines with microsomal cytochrome P450: nature of the different derived complexes and inhibitory effects on monoxygenases activities. Biochem Pharmacol 27: 1229-1237, 1978.
121. Lindeke B, Paulsen U and Anderson E: Cytochrome P-455 complex formation in the metabolism of phenylalkylamines-IV. Spectral evidences for metabolic conversion of methamphetamine to N-hydroxyamphetamine. Biochem Pharmacol 28: 3629-3635, 1979.
122. Bast A and Noordhoek J: Spectral interaction of orphenadrine and its metabolites with oxidised and reduced hepatic microsomal cytochrome P-450 in the rat. Biochem Pharmacol 31: 2745-2753, 1982.
123. Periti P, Mazzei T, Mini E and Novelli A: Pharmacokinetic drug interactions of macrolides. Clin Pharmacokinet 23: 106-131, 1992.
124. Azanza JR, Catalan M, Alvarez MP, Sadaba B, Honorato J, Llorens R and Harreros J: Possible interaction between cyclosporin and josamycin: a description of three cases. Clin Pharmacol Ther 51: 572-575, 1992.
125. Gharbi-Benarous J, Delaforge M, Jankowski CK and Girault JP: A comparative NMR study between the macrolide antibiotic roxithromycin and erythromycin A with different biological properties. J Med Chem 34: 1117-1125, 1991.
126. Ohmori S, Ishii I, Kuriya SI, Taniguchi T, Rikihisa T, Hirose S, Kanakubo Y and Kitada M: Effects of clarithromycin and its metabolites on the mixed function oxidase system in hepatic microsomes of rats. Drug Metab Dispos 21: 358-363, 1993.
127. Labout JJM, Thijssen CT, Keijser GGJ and Hespe W: Difference between single and multiple dose pharmacokinetics of orphenadrine in man. Eur J Clin Pharmacol 21: 343-350, 1982.
128. Reidy GF, Mehta I and Murray M: Inhibition of oxidative drug metabolism by orphenadrine: in vitro and in vivo evidence for isozyme-specific complexation of cytochrome P-450 and inhibition kinetics. Mol Pharmacol 35: 736-743, 1989.
129. Guo Z, Raeissi S, White RB and Stevens JC: Orphenadrine and methimazole inhibit multiple P450 enzymes in human liver microsomes. Drug Metab Dispos 25: 390-393, 1997.
130. Ekins S, Van den Branden M, Ring BJ and Wrighton SA: Examination of purported probes of human CYP2B6. Pharmacogenetics 7: 165-179, 1997.
131. Murray M and Field SL: Inhibition and metabolite complexation of rat hepatic microsomal cytochrome P450 by tricyclic antidepressants. Biochem Pharmacol 43: 2065-2071, 1992.
132. Murray M: Metabolite intermediate complexation of microsomal cytochrome P450 2C11 in male rat liver by nortriptyline. Mol Pharmacol 42: 931-938, 1992.
133. Bensoussan C, Delaforge M and Mansuy D: Particular ability of cytochromes P450 3A to form inhibitory P450-iron-metabolite complexes upon metabolic oxidation of aminodrugs. Biochem Pharmacol 49: 591-602, 1995.
134. Wilkinson CF, Murray M and Marcus CB: Interactions of methylenedioxyphenyl compounds with cytochrome P-450 and effects on microsomal oxidation. Rev Biochem Toxicol 6: 27-63, 1984.
135. Yu LS, Wilkinson CF and Anders MW: Generation of carbon monoxide during the microsomal metabolism of methylenedioxyphenyl compounds. Biochem Pharmacol 29: 1113-1122, 1980.
136. Anders MW, Sunram JM and Wilkinson CF: Mechanism of the metabolism of 1,3-benzodioxoles to carbon monoxide. Biochem Pharmacol 35: 577-580, 1984.
137. Murray M, Wilkinson CF, Marcus C and Dube CE: Structure-activity relationships in the interactions of alkoxymethylenedioxyphenylbenzene derivatives with rat hepatic microsomal mixedfunction oxidases in vivo. Mol Pharmacol 24: 129-136, 1983.
138. Murray M, Hetnarski K and Wilkinson CF: Selective inhibitory interactions of alkoxymethylenedioxybenzenes toward monooxygenase activity in rat hepatic microsomes. Xenobiotica 15: 369-379, 1985.
139. Baurnann P, Meyer JW, Amey M, Baettig D, Bryois C, Jonzier-Perey M, Koeb L, Monney C and Woggon B: Dextromethorphan and mephenytoin phenotyping of patients treated with thioridazine or amitriptylinc. Ther Drug Monit 14: 1-8, 1992.
140. Masimirembwa CM, Hasler JA and Johansson I: Inhibitory effects of antiparasitic drugs on P450 2D6. Eur J Clin Pharmacol 48:35-38, 1995.
141. Frye RF, Matzke GR, Adedoyin A, Porter JA and Branch RA: Validation of the five-drug 'Pittsburgh cocktail' approach for assessment of selective regulation of drug-metabolizing enzymes. Clin Pharmacol Ther 62: 365-376, 1997.
142. Eagling VA, Back DJ and Barry MG: Differential inhibition of P450 isoforms by the protease inhibitors ritonavir, saquinavir and indinavir. Br J Clin Pharrnacol 44: 190-194, 1997.