654
Views
33
CrossRef citations to date
0
Altmetric
Research Article

Cytochrome P450 Inactivation by Pharmaceuticals and Phytochemicals: Therapeutic Relevance

Pages 101-147 | Published online: 09 Oct 2008

REFERENCES

  • Abernethy D. R., Greenblatt D. J., Shader R. I. Imipramine-cimetidine interaction: impairment of clearance and enhanced absolute bioavailability. J. Pharmacol. Exp. Ther. 1984; 229: 702–705
  • Abreo K., LaBarre J. Suprofen, acute renal failure, and hematuria. Ann. Intern. Med. 1986; 105: 799
  • Alderman J., Preskorn S. H., Greenblatt D. J., Harrison W., Penenberg D., Allison J., Chung M. Desipramine pharmacokinetics when coadministered with paroxetine or sertraline in extensive metabolizers. J. Clin. Psychopharmacol. 1997; 17: 284–291
  • Almeida J. C., Grimsley E. W. Coma from the health food store: interaction between kava and alprazolam. Ann. Intern. Med. 1996; 125: 940–941
  • Alvarez-Diez T. M., Zheng J. Mechanism-based inactivation of cytochrome P450 3A4 by 4-ipomeanol. Chem. Res. Toxicol. 2004; 17: 150–157
  • Amsterdam J. D., Brunswick D. J., Potter L., Kaplan M. J. Cimetidine-induced alterations in desipramine plasma concentrations. Psychopharmacol. (Berl). 1984; 83: 373–375
  • Anderson T. F., Voorhees J. J. Psoralen photochemotherapy of cutaneous disorders. Annu. Rev. Pharmacol. Toxicol. 1980; 20: 235–257
  • Anderson P., Bondesson U., de Faire U. Pharmacokinetics of verapamil in patients with hypertension. Eur J Clin Pharmacol. 1986; 31: 155–163
  • Askmark H., Wiholm B. E. Epidemiology of adverse reactions to carbamazepine as seen in a spontaneous reporting system. Acta. Neurol. Scand. 1990; 81: 131–140
  • Bajpai M., Roskos L. K., Shen D. D., Levy R. H. Roles of cytochrome P4502C9 and cytochrome P4502C19 in the stereoselective metabolism of phenytoin to its major metabolite. Drug Metab. Dispos. 1996; 24: 1401–1403
  • Beier R.C. Natural pesticides and bioactive components in foods. Rev. Environ. Contam. Toxicol. 1990; 113: 47–137
  • Benowitz N. L., Nguyen T. L., Jones R. T., Herning R. I., Bachman J. Metabolic and psychophysiologic studies of cannabidiol-hexobarbital interaction. Clin. Pharmacol. Ther. 1980; 28: 115–120
  • Bensoussan C., Delaforge M., Mansuy D. Particular ability of cytochromes P450 3A to form inhibitory P450-iron-metabolite complexes upon metabolic oxidation of aminodrugs. Biochem. Pharmacol. 1995; 49: 591–602
  • Bertelsen K. M., Venkatakrishnan K., Von Moltke L. L., Obach R. S., Greenblatt D. J. Apparent mechanism-based inhibition of human CYP2D6 in vitro by paroxetine: comparison with fluoxetine and quinidine. Drug Metab. Dispos. 2003; 31: 289–293
  • Bestervelt L. L., Vaz A. D., Coon M. J. Inactivation of ethanol-inducible cytochrome P450 and other microsomal P450 isozymes by trans-4-hydroxy-2-nonenal, a major product of membrane lipid peroxidation. Proc. Natl. Acad. Sci. USA 1995; 92: 3764–3768
  • Blobaum A. L. Mechanism-based inactivation and reversibility: is there a new trend in the inactivation of cytochrome p450 enzymes?. Drug Metab Dispos. 2006; 34: 1–7
  • Blumenthal M. German Federal Institute for Drugs and Medical. The Complete German Commission E Monographs: Therapeutic Guide to Herbal Medicines, W. R. Busse, C. Riggins, R. Rister. American Botanical Council, Boston 1998, (trans Klein, S.).
  • Bochner F., Hooper W. D., Sutherland J. M., Eadie M. J., Tyrer J. H. The renal handling of diphenylhydantoin and 5-(p-hydroxyphenyl)-5-phenylhydantoin. Clin. Pharmacol. Ther. 1973; 14: 791–796
  • Bourdi M., Larrey D., Nataf J., Bernuau J., Pessayre D., Iwasaki M., Guengerich F. P., Beaune P. H. Anti-liver endoplasmic reticulum autoantibodies are directed against human cytochrome P-450IA2. A specific marker of dihydralazine-induced hepatitis. J. Clin. Invest. 1990; 85: 1967–1973
  • Bornheim L. M., Everhart E. T., Li J., Correia M. A. Characterization of cannabidiol-mediated cytochrome P450 inactivation. Biochem. Pharmacol. 1993; 45: 1323–1331
  • Brady J. F., Ishizaki H., Fukuto J. M., Lin M. C., Fadel A., Gapac J. M., Yang C. S. Inhibition of cytochrome P-450 2E1 by diallyl sulfide and its metabolites. Chem. Res. Toxicol. 1991; 4: 642–647
  • Bumpus N. N., Kent U. M., Hollenberg P. F. Metabolism of efavirenz and 8‐hydroxyefavirenz by P450 2B6 leads to inactivation by two distinct mechanisms. J. Pharmacol. Exp. Ther. 2006; 318: 345–351
  • Cadepond F., Ulmann A., Baulieu E. E. RU486 (mifepristone): mechanisms of action and clinical uses. Annu. Rev. Med. 1997; 48: 129–156
  • Cai Y., Bennett D., Nair R. V., Ceska O., Ashwood-Smith M. J., DiGiovanni J. Inhibition and inactivation of murine hepatic ethoxy- and pentoxyresorufin O-dealkylase by naturally occurring coumarins. Chem. Res. Toxicol. 1993; 6: 872–879
  • Cai Y., Baer-Dubowska W., Ashwood-Smith M. J., Ceska O., Tachibana S., DiGiovanni J. Mechanism-based inactivation of hepatic ethoxyresorufin O-dealkylation activity by naturally occurring coumarins. Chem. Res. Toxicol. 1996; 9: 729–736
  • Chan J. D. Pharmacokinetic drug interactions of vinca alkaloids: summary of case reports. Pharmacother. 1998; 18: 1304–1307
  • Chan W. K., Delucchi A. B. Resveratrol, a red wine constituent, is a mechanism-based inactivator of cytochrome P450 3A4. Life Sci. 2000; 67: 3103–3112
  • Chang T. K., Chen J., Lee W. B. Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: evidence for mechanism-based inactivation of CYP1A2. J. Pharmacol. Exp. Ther. 2001; 299: 874–882
  • Chatterjee P., Franklin M. R. Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components. Drug Metab. Dispos. 2003; 31: 1391–1397
  • Chen L., Mohr S. N., Yang C. S. Decrease of plasma and urinary oxidative metabolites of acetaminophen after consumption of watercress by human volunteers. Clin. Pharmacol. Ther. 1996; 60: 651–660
  • Chen Q., Ngui J. S., Doss G. A., Wang R. W., Cai X., DiNinno F. P., Blizzard T. A., Hammond M. L., Stearns R. A., Evans D. C., Baillie T. A., Tang W. Cytochrome P450 3A4‐mediated bioactivation of raloxifene: irreversible enzyme inhibition and thiol adduct formation. Chem. Res. Toxicol. 2002; 15: 907–914
  • Cheng C. L., Smith D. E., Carver P. L., Cox S. R., Watkins P. B., Blake D. S., Kauffman C. A., Meyer K. M., Amidon G. L., Stetson P. L. Steady-state pharmacokinetics of delavirdine in HIV-positive patients: effect on erythromycin breath test. Clin. Pharmacol. Ther. 1997; 61: 531–543
  • Chiba M., Nishime J. A., Lin J. H. Potent and selective inactivation of human liver microsomal cytochrome P-450 isoforms by L-754,394, an investigational human immune deficiency virus protease inhibitor. J. Pharmacol. Exp. Ther. 1995; 275: 1527–1534
  • Chu S., Wilson D. S., Deaton R. L., Mackenthun A. V., Eason C. N., Cavanaugh J. H. Single- and multiple-dose pharmacokinetics of clarithromycin, a new macrolide antimicrobial. J. Clin. Pharmacol. 1993; 33: 719–726
  • Chun Y. J., Ryu S. Y., Jeong T. C., Kim M. Y. Mechanism-based inhibition of human cytochrome P450 1A1 by rhapontigenin. Drug Metab. Dispos. 2001; 29: 389–393
  • Chung F. L., Morse M. A., Eklind K. I., Lewis J. Quantitation of human uptake of the anticarcinogen phenethyl isothiocyanate after a watercress meal. Cancer Epidemiol. Biomarkers Prev. 1992; 1: 383–388
  • Clarke S. E., Ayrton A. D., Chenery R. J. Characterization of the inhibition of P4501A2 by furafylline. Xenobiotica 1994; 24: 517–526
  • Colburn W. A., Di Santo A. R., Gibaldi M. Pharmacokinetics of erythromycin on repetitive dosing. J. Clin. Pharmacol. 1977; 17: 592–600
  • Coni E., Di Benedetto R., Di Pasquale M., Masella R., Modesti D., Mattei R., Carlini E. A. Protective effect of oleuropein, an olive oil biophenol, on low density lipoprotein oxidizability in rabbits. Lipids 2000; 35: 45–54
  • Cook D. L., Atkins W. M. Enhanced detoxication due to distributive catalysis and toxic thresholds: a kinetic analysis. Biochem. 1997; 36: 10801–10806
  • Coon M. J. Cytochrome P450: nature's most versatile biological catalyst. Annu. Rev. Pharmacol. Toxicol. 2005; 45: 1–25
  • Cooper D. Y., Levin S., Narasimhulu S., Rosenthal O. Photochemical action spectrum of the terminal oxidase of mixed function oxidase systems. Science 1965; 147: 400–402
  • Creemers G. J., Lund B., Verweij J. Topoisomerase I inhibitors: topotecan and irenotecan. Cancer Treat. Rev. 1994; 20: 73–96
  • Dreyer D. L., Huey P. F. Coumarins of Citrus macroptera. Phytochem. 1973; 12: 3011–3013
  • Decker C. J., Rashed M. S., Baillie T. A., Maltby D., Correia M. A. Oxidative metabolism of spironolactone: evidence for the involvement of electrophilic thiosteroid species in drug-mediated destruction of rat hepatic cytochrome P450. Biochem. 1989; 28: 5128–5136
  • Dekhuijzen P. N., Koopmans P. P. Pharmacokinetic profile of zafirlukast. Clin. Pharmacokinet. 2002; 41: 105–114
  • Dharmaratne H. R., Nanayakkara N. P., Khan I. A. Kavalactones from Piper methysticum, and their 13C NMR spectroscopic analyses. Phytochem. 2002; 59: 429–433
  • Edelson R., Berger C., Gasparro F., Jegasothy B., Heald P., Wintroub B., Vonderheid E., Knobler R., Wolff K., Plewig G., et al. Treatment of cutaneous T-cell lymphoma by extracorporeal photochemotherapy. Preliminary results. N Engl J Med. 1987; 316: 297–303
  • Egner P. A., Kensler T. W., Prestera T., Talalay P., Libby A. H., Joyner H. H., Curphey T. J. Regulation of phase 2 enzyme induction by oltipraz and other dithiolethiones. Carcinogenesis 1994; 15: 177–181
  • Eisenberg D. M., Davis R. B., Ettner S. L., Appel S., Wilkey S., Van Rompay M., Kessler R. C. Trends in alternative medicine use in the United States, 1990–1997: results of a follow-up national survey. J. Am. Med. Assoc. 1998; 280: 1569–1575
  • Ernest C. S., Hall S. D., Jones D. R. Mechanism-based inactivation of CYP3A by HIV protease inhibitors. J. Pharmacol. Exp. Ther. 2005; 312: 583–591
  • Esterbauer H., Zollner H., Lang J. Metabolism of the lipid peroxidation product 4‐hydroxynonenal by isolated hepatocytes and by liver cytosolic fractions. Biochem. J. 1985; 228: 363–373
  • Esterbauer H., Zollner H. Methods for determination of aldehydic lipid peroxidation products. Free Radic. Biol. Med. 1989; 7: 197–203
  • Evans G. H., Shand D. G. Disposition of propranolol. V. Drug accumulation and steady-state concentrations during chronic oral administration in man. Clin. Pharmacol. Ther. 1973; 14: 487–493
  • Faber M. S., Fuhr U. Time response of cytochrome P450 1A2 activity on cessation of heavy smoking. Clin. Pharmacol. Ther. 2004; 76: 178–184
  • Fabre G., Julian B., Saint-Aubert B., Joyeux H., Berger Y. Evidence for CYP3A-mediated N-deethylation of amiodarone in human liver microsomal fractions. Drug Metab. Dispos. 1993; 21: 978–985
  • Flora K., Hahn M., Rosen H., Benner K. Milk thistle (Silybum marianum) for the therapy of liver disease. Am J Gastroenterol. 1998; 93: 139–143
  • Fontana E., Dansette P. M., Poli S. M. Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity. Curr. Drug Metab. 2005; 6: 413–454
  • Friguet B., Stadtman E. R., Szweda L. I. Modification of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. Formation of cross-linked protein that inhibits the multicatalytic protease. J. Biol. Chem. 1994; 269: 21639–21643
  • Funck-Brentano C., Jacqz-Aigrain E., Leenhardt A., Roux A., Poirier J. M., Jaillon P. Influence of amiodarone on genetically determined drug metabolism in humans. Clin. Pharmacol. Ther. 1991; 50: 259–266
  • Funck-Brentano C., Becquemont L., Kroemer H. K., Buhl K., Knebel N. G., Eichelbaum M., Jaillon P. Variable disposition kinetics and electrocardiographic effects of flecainide during repeated dosing in humans: contribution of genetic factors, dose-dependent clearance, and interaction with amiodarone. Clin. Pharmacol. Ther. 1994; 55: 256–269
  • Furst S. M., Sukhai P., McClelland R. A., Uetrecht J. P. Covalent binding of carbamazepine oxidative metabolites to neutrophils. Drug Metab. Dispos. 1995; 23: 590–594
  • Galetin A., Burt H., Gibbons L., Houston J. B. Prediction of time-dependent CYP3A4 drug-drug interactions: impact of enzyme degradation, parallel elimination pathways, and intestinal inhibition. Drug Metab. Dispos. 2006; 34: 166–175
  • Gannett P. M., Iversen P., Lawson T. The mechanism of inhibition of cytochrome P450IIE1 by dihydrocapsaicin. Bioorg. Chem. 1990; 18: 185–198
  • Gill J., Heel R. C., Fitton A. Amiodarone. An overview of its pharmacological properties, and review of its therapeutic use in cardiac arrhythmias. Drugs 1992; 43: 69–110
  • Ghanbari F., Rowland-Yeo K., Bloomer J. C., Clarke S. E., Lennard M. S., Tucker G. T., Rostami-Hodjegan A. A critical evaluation of the experimental design of studies of mechanism based enzyme inhibition, with implications for in vitro-in vivo extrapolation. Curr. Drug Metab. 2006; 7: 315–334
  • Goosen T. C., Mills D. E., Hollenberg P. F. Effects of benzyl isothiocyanate on rat and human cytochromes P450: identification of metabolites formed by P450 2B1. J. Pharmacol. Exp. Ther. 2001; 296: 198–206
  • Gordon W. P., Forte A. J., McMurtry R. J., Gal J., Nelson S. D. Hepatotoxicity and pulmonary toxicity of pennyroyal oil and its constituent terpenes in the mouse. Toxicol. Appl. Pharmacol. 1982; 65: 413–424
  • Gorski J. C., Jones D. R., Haehner-Daniels B. D., Hamman M. A., O'Mara E. M., Hall S. D. The contribution of intestinal and hepatic CYP3A to the interaction between midazolam and clarithromycin. Clin. Pharmacol. Ther. 1998; 64: 133–143
  • Greenblatt D. J., Preskorn S. H., Cotreau M. M., Horst W. D., Harmatz J. S. Fluoxetine impairs clearance of alprazolam but not of clonazepam. Clin. Pharmacol. Ther. 1992; 52: 479–486
  • Guengerich F. P. Oxidation of 17 alpha-ethynylestradiol by human liver cytochrome P-450. Mol. Pharmacol. 1988; 33: 500–508
  • Guengerich F. P. Mechanism-based inactivation of human liver microsomal cytochrome P‐450 IIIA4 by gestodene. Chem. Res. Toxicol. 1990; 3: 363–371
  • Guengerich F. P. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 2001; 14: 611–650
  • Guengerich F. P. Cytochromes P450, drugs, and diseases. Mol. Interv. 2003; 3: 194–204
  • Guengerich F. P. Cytochrome P450: what have we learned and what are the future issues?. Drug Metab. Rev. 2004; 36: 159–197
  • Guengerich F. P. Cytochrome P450s and other enzymes in drug metabolism and toxicity. AAPS J. 2006; 8: E101–E111
  • Guo Z., Smith T. J., Wang E., Eklind K. I., Chung F. L., Yang C. S. Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3‐pyridyl)-1-butanone metabolism and the modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis 1993; 14: 1167–1173
  • Gurley B. J., Gardner S. F., Hubbard M. A., Williams D. K., Gentry W. B., Cui Y., Ang C. Y. Cytochrome P450 phenotypic ratios for predicting herb-drug interactions in humans. Clin. Pharmacol. Ther. 2002; 72: 276–287
  • Gurley B. J., Gardner S. F., Hubbard M. A., Williams D. K., Gentry W. B., Khan I. A., Shah A. In vivo effects of goldenseal, kava kava, black cohosh, and valerian on human cytochrome P450 1A2, 2D6, 2E1, and 3A4/5 phenotypes. Clin. Pharmacol. Ther. 2005; 77: 415–426
  • Ha-Duong N. T., Dijols S., Macherey A. C., Goldstein J. A., Dansette P. M., Mansuy D. Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochem. 2001; 40: 12112–12122
  • Hallifax D., Houston J. B. Binding of drugs to hepatic microsomes: comment and assessment of current prediction methodology with recommendation for improvement. Drug Metab Dispos. 2006; 34: 724–726
  • Halpert J., Balfour C., Miller N. E., Morgan E. T., Dunbar D., Kaminsky L. S. Isozyme selectivity of the inhibition of rat liver cytochromes P-450 by chloramphenicol in vivo. Mol. Pharmacol. 1985; 28: 290–296
  • Hanioka N., Ozawa S., Jinno H., Tanaka-Kagawa T., Nishimura T., Ando M., Sawada J. J. Interaction of irinotecan (CPT-11) and its active metabolite 7-ethyl-10-hydroxycamptothecin (SN-38) with human cytochrome P450 enzymes. Drug Metab. Dispos. 2002; 30: 391–396
  • Harleton E., Webster M., Bumpus N. N., Kent U. M., Rae J. M., Hollenberg P. F. Metabolism of N, N′, N″-triethylenethiophosphoramide by CYP2B1 and CYP2B6 results in the inactivation of both isoforms by two distinct mechanisms. J. Pharmacol. Exp. Ther. 2004; 310: 1011–1019
  • Harvey A. T., Preskorn S. H. Fluoxetine pharmacokinetics and effect on CYP2C19 in young and elderly volunteers. J. Clin. Psychopharmacol. 2001; 21: 161–166
  • He K., Falick A. M., Chen B., Nilsson F., Correia M. A. Identification of the heme adduct and an active site peptide modified during mechanism-based inactivation of rat liver cytochrome P450 2B1 by secobarbital. Chem. Res. Toxicol. 1996; 9: 614–622
  • He K., He Y. A., Szklarz G. D., Halpert J. R., Correia M. A. Secobarbital-mediated inactivation of cytochrome P450 2B1 and its active site mutants. Partitioning between heme and protein alkylation and epoxidation. J. Biol. Chem. 1996; 271: 25864–25872
  • He K., Iyer K. R., Hayes R. N., Sinz M. W., Woolf T. F., Hollenberg P. F. Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem. Res. Toxicol. 1998; 11: 252–259
  • He K., Woolf T. F., Hollenberg P. F. Mechanism-based inactivation of cytochrome P‐450‐3A4 by mifepristone (RU486). J. Pharmacol. Exp. Ther. 1999; 288: 791–797
  • Hemeryck A., Lefebvre R. A., De Vriendt C., Belpaire F. M. Paroxetine affects metoprolol pharmacokinetics and pharmacodynamics in healthy volunteers. Clin. Pharmacol. Ther. 2000; 67: 283–291
  • Heimark L. D., Wienkers L., Kunze K., Gibaldi M., Eddy A. C., Trager W. F., O'Reilly R. A., Goulart D. A. The mechanism of the interaction between amiodarone and warfarin in humans. Clin. Pharmacol. Ther. 1992; 51: 398–407
  • Hirsch A., Saccar C., McGeady S. J. Interaction between theophylline and amiodarone. Ann. Allergy 1993; 70: 68
  • Hodgson E., Philpot R. M. Interaction of methylenedioxyphenyl (1,3-benzodioxole) compounds with enzymes and their effects on mammals. Drug Metab. Rev. 1974; 3: 231–301
  • Hollenberg P. F. Characteristics and common properties of inhibitors, inducers, and activators of CYP enzymes. Drug Metab Rev. 2002; 34: 17–35
  • Huitema A. D., Kerbusch T., Tibben M. M., Rodenhuis S., Beijnen J. H. Reduction of cyclophosphamide bioactivation by thioTEPA: critical sequence-dependency in high-dose chemotherapy regimens. Cancer Chemother. Pharmacol. 2000; 46: 119–127
  • Hutzler J. M., Steenwyk R. C., Smith E. B., Walker G. S., Wienkers L. C. Mechanism-based inactivation of cytochrome P450 2D6 by 1-[(2-ethyl-4-methyl-1H-imidazol-5-yl)methyl]-4-[4-(trifluoromethyl)-2-pyridinyl]piperazine: kinetic characterization and evidence for apoprotein adduction. Chem. Res. Toxicol. 2004; 17: 174–184
  • Iba M. M., Mannering G. J. NADPH- and linoleic acid hydroperoxide-induced lipid peroxidation and destruction of cytochrome P-450 in hepatic microsomes. Biochem. Pharmacol. 1987; 36: 1447–1455
  • Ingelman-Sundberg M. Genetic polymorphisms of cytochrome P450 2D6 (CYP2D6): clinical consequences, evolutionary aspects and functional diversity. Pharmacogenom. J. 2005; 5: 6–13
  • Issekutz B., Lichtneckert I., Nagy H. Effect of capsaicin and histamine on heat regulation. Arch. Int. Pharmacodyn. Ther. 1950; 81: 35–46
  • Ito K., Hallifax D., Obach R. S., Houston J. B. Impact of parallel pathways of drug elimination and multiple cytochrome P450 involvement on drug-drug interactions: CYP2D6 paradigm. Drug Metab Dispos. 2005; 33: 837–844
  • Ivie G. W., Holt D. L., Ivey M. C. Natural toxicants in human foods: psoralens in raw and cooked parsnip root. Science 1981; 213: 909–910
  • Jang G. R., Benet L. Z. Antiprogestin-mediated inactivation of cytochrome P450 3A4. Pharmacol. 1998; 56: 150–157
  • Jeppesen U., Gram L. F., Vistisen K., Loft S., Poulsen H. E., Brosen K. Dose-dependent inhibition of CYP1A2, CYP2C19 and CYP2D6 by citalopram, fluoxetine, fluvoxamine and paroxetine. Eur. J. Clin. Pharmacol. 1996; 51: 73–78
  • Jhamandas K., Yaksh T. L., Harty G., Szolcsanyi J., Go V. L. Action of intrathecal capsaicin and its structural analogues on the content and release of spinal substance P: selectivity of action and relationship to analgesia. Brain Res. 1984; 306: 215–225
  • Jin L., Baillie T. A. Metabolism of the chemoprotective agent diallyl sulfide to glutathione conjugates in rats. Chem. Res. Toxicol. 1997; 10: 318–327
  • Jung-Hoffmann C., Kuhl H. Interaction with the pharmacokinetics of ethinylestradiol and progestogens contained in oral contraceptives. Contraception 1989; 40: 299–312
  • Jushchyshyn M. I., Kent U. M., Hollenberg P. F. The mechanism-based inactivation of human cytochrome P450 2B6 by phencyclidine. Drug Metab. Dispos. 2003; 31: 46–52
  • Jushchyshyn M. I., Wahlstrom J. L., Hollenberg P. F., Wienkers L. C. Mechanism of inactivation of human cytochrome P450 2B6 by phencyclidine. Drug Metab. Dispos. 2006; 34: 1523–1529
  • Kalgutkar A. S., Vaz A. D., Lame M. E., Henne K. R., Soglia J., Zhao S. X., Abramov Y. A., Lombardo F., Collin C., Hendsch Z. S., Hop C. E. Bioactivation of the nontricyclic antidepressant nefazodone to a reactive quinone-imine species in human liver microsomes and recombinant cytochrome P450 3A4. Drug Metab. Dispos. 2005; 33: 243–253
  • Kalgutkar A. S., Soglia J. R. Minimising the potential for metabolic activation in drug discovery. Expert Opin. Drug Metab. Toxicol. 2005; 1: 91–142
  • Kalgutkar A. S., Obach R. S., Maurer T. S. Mechanism-based inactivation of cytochrome P450 enzymes: chemical mechanisms, structure-activity relationships and relationship to clinical drug-drug interactions and idiosyncratic adverse drug reactions. Curr. Drug Metab. 2007; 8: 407–447
  • Kapetanovic I. M., Torchin C. D., Thompson C. D., Miller T. A., McNeilly P. J., Macdonald T. L., Kupferberg H. J., Perhach J. L., Sofia R. D., Strong J. M. Potentially reactive cyclic carbamate metabolite of the antiepileptic drug felbamate produced by human liver tissue in vitro. Drug Metab. Dispos. 1998; 26: 1089–1095
  • Kassahun K., Skordos K., McIntosh I., Slaughter D., Doss G. A., Baillie T. A., Yost G. S. Zafirlukast metabolism by cytochrome P450 3A4 produces an electrophilic alpha, beta-unsaturated iminium species that results in the selective mechanism-based inactivation of the enzyme. Chem. Res. Toxicol. 2005; 18: 1427–1437
  • Kaul S., Shukla U. A., Barbhaiya R. H. Nonlinear pharmacokinetics of nefazodone after escalating single and multiple oral doses. J. Clin. Pharmacol. 1995; 35: 830–839
  • Keledjian J., Duffield P. H., Jamieson D. D., Lidgard R. O., Duffield A. M. Uptake into mouse brain of four compounds present in the psychoactive beverage kava. J. Pharm. Sci. 1988; 77: 1003–1006
  • Kensler T. W., Egner P. A., Dolan P. M., Groopman J. D., Roebuck B. D. Mechanism of protection against aflatoxin tumorigenicity in rats fed 5-(2-pyrazinyl)-4-methyl-1,2-dithiol-3-thione (oltipraz) and related 1,2-dithiol-3-thiones and 1,2-dithiol-3-ones. Cancer Res. 1987; 47: 4271–4277
  • Kensler T. W., Groopman J. D., Eaton D. L., Curphey T. J., Roebuck B. D. Potent inhibition of aflatoxin-induced hepatic tumorigenesis by the monofunctional enzyme inducer 1,2‐dithiole-3-thione. Carcinogenesis 1992; 13: 95–100
  • Kent U. M., Roberts E. S., Chun J., Hodge K., Juncaj J., Hollenberg P. F. Inactivation of cytochrome P450 2E1 by tert-butylisothiocyanate. Chem. Res. Toxicol. 1998; 11: 1154–1161
  • Kent U. M., Juschyshyn M. I., Hollenberg P. F. Mechanism-based inactivators as probes of cytochrome P450 structure and function. Curr. Drug Metab. 2001; 2: 215–243
  • Kent U. M., Mills D. E., Rajnarayanan R. V., Alworth W. L., Hollenberg P. F. Effect of 17-alpha-ethynylestradiol on activities of cytochrome P450 2B (P450 2B) enzymes: characterization of inactivation of P450s 2B1 and 2B6 and identification of metabolites. J. Pharmacol. Exp. Ther. 2002; 300: 549–558
  • Kent U. M., Aviram M., Rosenblat M., Hollenberg P. F. The licorice root derived isoflavan glabridin inhibits the activities of human cytochrome P450S 3A4, 2B6, and 2C9. Drug Metab. Dispos. 2002; 30: 709–715
  • Khan K. K., He Y. Q., Domanski T. L., Halpert J. R. Midazolam oxidation by cytochrome P450 3A4 and active-site mutants: an evaluation of multiple binding sites and of the metabolic pathway that leads to enzyme inactivation. Mol. Pharmacol. 2002a; 61: 495–506
  • Khan K. K., He Y. Q., Correia M. A., Halpert J. R. Differential oxidation of mifepristone by cytochromes P450 3A4 and 3A5: selective inactivation of P450 3A4. Drug Metab. Dispos. 2002b; 30: 985–990
  • Khojasteh-Bakht S. C., Koenigs L. L., Peter R. M., Trager W. F., Nelson S. D. (R)‐(+)‐Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. Drug Metab. Dispos. 1998; 26: 701–704
  • Knudsen J. B., Bastain W., Sefton C. M., Allen J. G., Dickinson J. P. Pharmacokinetics of ticlopidine during chronic oral administration to healthy volunteers and its effects on antipyrine pharmacokinetics. Xenobiotica 1992; 22: 579–589
  • Kobayashi Y., Sridar C., Kent U. M., Puppali S. G., Rimoldi J. M., Zhang H., Waskell L., Hollenberg P. F. Structure-activity relationship and elucidation of the determinant factor(s) responsible for the mechanism-based inactivation of cytochrome P450 2B6 by substituted phenyl diaziridines. Drug Metab Dispos. 2006; 34: 2102–2110
  • Koenigs L. L., Trager W. F. Mechanism-based inactivation of P450 2A6 by furanocoumarins. Biochem. 1998; 37: 10047–10061
  • Koenigs L. L., Trager W. F. Mechanism-based inactivation of cytochrome P450 2B1 by 8‐methoxypsoralen and several other furanocoumarins. Biochem. 1998; 37: 13184–13193
  • Koudriakova T., Iatsimirskaia E., Utkin I., Gangl E., Vouros P., Storozhuk E., Orza D., Marinina J., Gerber N. Metabolism of the human immunodeficiency virus protease inhibitors indinavir and ritonavir by human intestinal microsomes and expressed cytochrome P4503A4/3A5: mechanism-based inactivation of cytochrome P4503A by ritonavir. Drug Metab Dispos. 1998; 26: 552–561
  • Kraner J. C., Morgan E. T., Halpert J. R. Selective suppression of rat hepatic cytochrome P450 2C11 by chloramphenicol. J. Pharmacol. Exp. Ther. 1994; 270: 1367–1372
  • Kroemer H. K., Echizen H., Heidemann H., Eichelbaum M. Predictability of the in vivo metabolism of verapamil from in vitro data: contribution of individual metabolic pathways and stereoselective aspects. J. Pharmacol. Exp. Ther. 1992; 260: 1052–1057
  • Kuehl P., Zhang J., Lin Y., Lamba J., Assem M., Schuetz J., Watkins P. B., Daly A., Wrighton S. A., Hall S. D., Maurel P., Relling M., Brimer C., Yasuda K., Venkataramanan R., Strom S., Thummel K., Boguski M. S., Schuetz E. Sequence diversity in CYP3A promoters and characterization of the genetic basis of polymorphic CYP3A5 expression. Nat. Genet. 2001; 27: 383–391
  • Kunze K. L., Trager W. F. Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem. Res. Toxicol. 1993; 6: 649–656
  • Kuo C. L., Vaz A. D., Coon M. J. Metabolic activation of trans-4-hydroxy-2-nonenal, a toxic product of membrane lipid peroxidation and inhibitor of P450 cytochromes. J. Biol. Chem. 1997; 272: 22611–22616
  • Lakhanpal S., Donehower R. C., Rowinsky E. K. Phase II study of 4-ipomeanol, a naturally occurring alkylating furan, in patients with advanced hepatocellular carcinoma. Invest. New Drugs. 2001; 19: 69–76
  • Laganiere S., Davies R. F., Carignan G., Foris K., Goernert L., Carrier K., Pereira C., McGilveray I. Pharmacokinetic and pharmacodynamic interactions between diltiazem and quinidine. Clin. Pharmacol. Ther. 1996; 60: 255–264
  • Langouet S., Furge L. L., Kerriguy N., Nakamura K., Guillouzo A., Guengerich F.P. Inhibition of human cytochrome P450 enzymes by 1,2-dithiole-3-thione, oltipraz and its derivatives, and sulforaphane. Chem. Res. Toxicol. 2000; 13: 245–252
  • Leclercq I., Desager J. P., Horsmans Y. Inhibition of chlorzoxazone metabolism, a clinical probe for CYP2E1, by a single ingestion of watercress. Clin. Pharmacol. Ther. 1998; 64: 144–149
  • Lemberger L., Rowe H., Bosomworth J. C., Tenbarge J. B., Bergstrom R. F. The effect of fluoxetine on the pharmacokinetics and psychomotor responses of diazepam. Clin. Pharmacol. Ther. 1988; 43: 412–419
  • Letteron P., Descatoire V., Larrey D., Tinel M., Geneve J., Pessayre D. Inactivation and induction of cytochrome P-450 by various psoralen derivatives in rats. J. Pharmacol. Exp. Ther. 1986; 238: 685–692
  • Licad-Coles E., He K., Yin H., Correia M. A. Cytochrome P450 2C11: Escherichia coli expression, purification, functional characterization, and mechanism-based inactivation of the enzyme. Arch. Biochem. Biophys. 1997; 338: 35–42
  • Lillibridge J. H., Amore B. M., Slattery J. T., Kalhorn T. F., Nelson S. D., Finnell R. H., Bennett G. D. Protein-reactive metabolites of carbamazepine in mouse liver microsomes. Drug Metab. Dispos. 1996; 24: 509–514
  • Lin H. L., Kent U. M., Hollenberg P. F. The grapefruit juice effect is not limited to cytochrome P450 (P450) 3A4: evidence for bergamottin-dependent inactivation, heme destruction, and covalent binding to protein in P450s 2B6 and 3A5. J. Pharmacol. Exp. Ther. 2005; 313: 154–164
  • López-Garcia M. P., Dansette P. M., Mansuy D. Thiophene derivatives as new mechanism-based inhibitors of cytochromes P-450: inactivation of yeast-expressed human liver cytochrome P-450 2C9 by tienilic acid. Biochemistry 1994; 33: 166–175
  • Lu P., Schrag M. L., Slaughter D. E., Raab C. E., Shou M., Rodrigues A. D. Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab. Dispos. 2003; 31: 1352–1360
  • Ma Q., Okusanya O. O., Smith P. F., Dicenzo R., Slish J. C., Catanzaro L. M., Forrest A., Morse G. D. Pharmacokinetic drug interactions with non-nucleoside reverse transcriptase inhibitors. Expert Opin. Drug Metab. Toxicol. 2005; 1: 473–485
  • Macdonald T. L., Gutheim W. G., Martin R. B., Guengerich F. P. Oxidation of substituted N, N-dimethylanilines by cytochrome P-450: estimation of the effective oxidation-reduction potential of cytochrome P-450. Biochemistry 1989; 28: 2071–2017
  • Madden S., Maggs J. L., Park B. K. Bioactivation of carbamazepine in the rat in vivo. Evidence for the formation of reactive arene oxide(s). Drug Metab. Dispos. 1996; 24: 469–479
  • Madeira M., Levine M., Chang T. K. H, Mirfazaelian A., Bellward G. D. The effect of cimetidine on dextromethorphan o-demethylase activity of human liver microsomes and recombinant cyp2d6. Drug Metab. Dispos. 2004; 32: 460–467
  • Masubuchi Y., Horie T. Mechanism-based inactivation of cytochrome P450s 1A2 and 3A4 by dihydralazine in human liver microsomes. Chem. Res. Toxicol. 1999; 12: 1028–1032
  • Masubuchi Y., Nakano T., Ose A., Horie T. Differential selectivity in carbamazepine-induced inactivation of cytochrome P450 enzymes in rat and human liver. Arch. Toxicol. 2001; 75: 538–543
  • Masubuchi Y., Ose A., Horie T. Mechanism-based inactivation of CYP2C11 by diclofenac. Drug Metab. Dispos. 2001; 29: 1190–1195
  • Masubuchi Y., Ose A., Horie T. Diclofenac-induced inactivation of CYP3A4 and its stimulation by quinidine. Drug Metab. Dispos. 2002; 30: 1143–1148
  • Mathews J. M., Etheridge A. S., Black S. R. Inhibition of human cytochrome P450 activities by kava extract and kavalactones. Drug Metab. Dispos. 2002; 30: 1153–1157
  • Mayhew B. S., Jones D. R., Hall S. D. An in vitro model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab. Dispos. 2000; 28: 1031–1037
  • McGinnity D. F., Berry A. J., Kenny J. R., Grime K., Riley R. J. Evaluation of time-dependent cytochrome P450 inhibition using cultured human hepatocytes. Drug Metab. Dispos. 2006; 34: 1291–1300
  • McTavish D., Sorkin E. M. Verapamil. An updated review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in hypertension. Drugs 1989; 38: 19–76
  • Michos N., Zulliger H. W., Barkworth M. F., Johnson K. J., Rehm K. D., Toberich H., Klein G. Suprofen sustained release kinetics in healthy male volunteers. 1st communication: a single dose open crossover bioavailability study of suprofen sustained release tablets versus capsules. Arzneimittelforschung 1986; 36: 941–948
  • Miller R. R., Porter J., Greenblatt D. J. Clinical importance of the interaction of phenytoin and isoniazid: a report from the Boston Collaborative Drug Surveillance Program. Chest 1979; 75: 356–358
  • Miller D. D., Sawyer J. B., Duffy J. P. Cimetidine's effect on steady-state serum nortriptyline concentrations. Drug Intell. Clin. Pharm. 1983; 17: 904–905
  • Miller J. W., Skerjanec A., Knadler M. P., Ghosh A., Allerheiligen S. R. Divergent effects of raloxifene HCI on the pharmacokinetics and pharmacodynamics of warfarin. Pharm. Res. 2001; 18: 1024–1028
  • Millward M. J., Cantwell B. M., Lien E. A., Carmichael J., Harris A.L. Intermittent high-dose tamoxifen as a potential modifier of multidrug resistance. Eur. J. Cancer 1992; 28A: 805–810
  • Mitscher L. A., Drake S., Gollapudi S. R., Harris J. A., Shankel D. M. Isolation and identification of higher plant agents active in antimutagenic assay systems: Glycyrrhiza glabra. Basic Life Sci. 1986; 39: 153–165
  • Modly C. E., Das M., Don P. S., Marcelo C. L., Mukhtar H., Bickers D. R. Capsaicin as an in vitro inhibitor of benzo(a)pyrene metabolism and its DNA binding in human and murine keratinocytes. Drug Metab. Dispos. 1986; 14: 413–416
  • Monahan B. P., Ferguson C. L., Killeavy E. S., Lloyd B. K., Troy J., Cantilena L. R. Torsades de pointes occurring in association with terfenadine use. J. Am. Med. Assoc. 1990; 264: 2788–2790
  • Montamat S. C., Abernethy D. R. Calcium antagonists in geriatric patients: diltiazem in elderly persons with hypertension. Clin. Pharmacol. Ther. 1989; 45: 682–691
  • Mori Y., Sakai Y., Kuroda N., Yokoya F., Toyoshi K., Horie M., Baba S. Further structural analysis of urinary metabolites of suprofen in the rat. Drug Metab. Dispos. 1984; 12: 767–771
  • Munns A. J., De Voss J. J., Hooper W. D., Dickinson R. G., Gillam E. M. Bioactivation of phenytoin by human cytochrome P450: characterization of the mechanism and targets of covalent adduct formation. Chem. Res. Toxicol. 1997; 10: 1049–1058
  • Murray M., Reidy G. F. In vitro formation of an inhibitory complex between an isosafrole metabolite and rat hepatic cytochrome P-450 PB-B. Drug Metab. Dispos. 1989; 17: 449–454
  • Murray M., Reidy G. F. Selectivity in the inhibition of mammalian cytochromes P-450 by chemical agents. Pharmacol. Rev. 1990; 42: 85–101
  • Nakajima M., Yoshida R., Shimada N., Yamazaki H., Yokoi T. Inhibition and inactivation of human cytochrome P450 isoforms by phenethyl isothiocyanate. Drug Metab. Dispos. 2001; 29: 1110–1113
  • Narimatsu S., Arai T., Watanabe T., Masubuchi Y., Horie T., Suzuki T., Ishikawa T., Tsutsui M., Kumagai Y., Cho A. K. Covalent binding of a reactive metabolite derived from propranolol and its active metabolite 4-hydroxypropranolol to hepatic microsomal proteins of the rat. Chem. Res. Toxicol. 1997; 10: 289–295
  • Narimatsu S., Arai T., Masubuchi Y., Horie T., Hosokawa M., Ueno K., Kataoka H., Yamamoto S., Ishikawa T., Cho A. K. Inactivation of rat cytochrome P450 2D enzyme by a further metabolite of 4-hydroxypropranolol, the major and active metabolite of propranolol. Biol. Pharm. Bull. 2001; 24: 988–994
  • Nicolau D. P., Uber W. E., Crumbley A. J., Strange C. Amiodarone-cyclosporine interaction in a heart transplant patient. J. Heart Lung Transplant 1992; 11: 564–568
  • Nolan P. E., Marcus F. I., Hoyer G. L., Bliss M., Gear K. Pharmacokinetic interaction between intravenous phenytoin and amiodarone in healthy volunteers. Clin. Pharmacol. Ther. 1989; 46: 43–50
  • Obach R. S., Walsky R. L., Venkatakrishnan K., Gaman E. A., Houston J. B., Tremaine L. M. The utility of in vitro cytochrome P450 inhibition data in the prediction of drug-drug interactions. J. Pharmacol. Exp. Ther. 2006; 316: 336–348
  • Ochs H. R., Greenblatt D. J., Roberts G. M., Dengler H. J. Diazepam interaction with antituberculosis drugs. Clin. Pharmacol. Ther. 1981; 29: 671–678
  • Ochs H. R., Greenblatt D. J., Knuchel M. Differential effect of isoniazid on triazolam oxidation and oxazepam conjugation. Br. J. Clin. Pharmacol. 1983; 16: 743–746
  • O'Donnell J. P., Dalvie D. K., Kalgutkar A. S., Obach R. S. Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. Drug Metab. Dispos. 2003; 31: 1369–1377
  • Offman E. M., Freeman D. J., Dresser G. K., Munoz C., Bend J. R., Bailey D. G. Red wine‐cisapride interaction: comparison with grapefruit juice. Clin. Pharmacol. Ther. 2001; 70: 17–23
  • Ogilvie B. W., Zhang D., Li W., Rodrigues A. D., Gipson A. E., Holsapple J., Toren P., Parkinson A. Glucuronidation converts gemfibrozil to a potent, metabolism-dependent inhibitor of CYP2C8: implications for drug-drug interactions. Drug Metab. Dispos. 2006; 34: 191–197
  • Ohno Y., Hisaka A., Suzuki H. General framework for the quantitative prediction of CYP3A4-mediated oral drug interactions based on the AUC increase by coadministration of standard drugs. Clin Pharmacokinet. 2007; 46: 681–696
  • Ohyama K., Nakajima M., Suzuki M., Shimada N., Yamazaki H., Yokoi T. Inhibitory effects of amiodarone and its N-deethylated metabolite on human cytochrome P450 activities: prediction of in vivo drug interactions. Br. J. Clin. Pharmacol. 2000; 49: 244–253
  • O'Reilly R. A., Trager W. F., Rettie A. E., Goulart D. A. Interaction of amiodarone with racemic warfarin and its separated enantiomorphs in humans. Clin. Pharmacol. Ther. 1987; 42: 290–294
  • Ortiz de Montellano P. R., Mathews J. M. Autocatalytic alkylation of the cytochrome P‐450 prosthetic haem group by 1-aminobenzotriazole. Isolation of an NN-bridged benzyne-protoporphyrin IX adduct. Biochem. J. 1981; 195: 761–764
  • Ortiz De Montellano P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry2nd, Paul R. Ortiz De Montellano. Plenum Press, New York 1995
  • Ortiz De Montellano P. R. Cytochrome P450: Structure, Mechanism, and Biochemistry2nd, Paul R. Ortiz De Montellano. Kluwer Academic/Plenum Publishers, New York 2005
  • Paddack G. L., Wahl R. C., Holman R. E., Schorr W. J., Lacher J. W. Acute renal failure associated with ticrynafen. J. Am. Med. Assoc. 1980; 243: 764–765
  • Pathak M. A., Daniels F., Fitzpatrick T. B. The presently known distribution of furocoumarins (psoralens) in plants. J. Invest. Dermatol. 1962; 39: 225–239
  • Pellock J. M., Brodie M. J. Felbamate: 1997 update. Epilepsia 1997; 38: 1261–1264
  • Pirisi F. M., Cabras P., Cao C. F., Migliorini M., Muggelli M. Phenolic compounds in virgin olive oil. 2. Reappraisal of the extraction, HPLC separation, and quantification procedures. J. Agric. Food Chem. 2000; 48: 1191–1196
  • Poet T. S., Brendel K., Halpert J. R. Inactivation of cytochromes P450 2B protects against cocaine-mediated toxicity in rat liver slices. Toxicol. Appl. Pharmacol. 1994; 126: 26–32
  • Polasek T. M., Elliot D. J., Lewis B. C., Miners J. O. Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. J. Pharmacol. Exp. Ther. 2004; 311: 996–1007
  • Polasek T. M., Miners J. O. Quantitative prediction of macrolide drug-drug interaction potential from in vitro studies using testosterone as the human cytochrome P4503A substrate. Eur. J. Clin. Pharmacol. 2006; 62: 203–208
  • Potkin S. G., Thyrum P. T., Alva G., Carreon D., Yeh C., Kalali A., Arvanitis L. A, the Pharmacokinetic Study Group. Effect of fluoxetine and imipramine on the pharmacokinetics and tolerability of the antipsychotic quetiapine. J. Clin. Psychopharmacol. 2002; 22: 174–182
  • Premdas P. D., Bowers R. J., Forkert P. G. Inactivation of hepatic CYP2E1 by an epoxide of diallyl sulfone. J. Pharmacol. Exp. Ther. 2000; 293: 1112–1120
  • Racha J.K., Rettie A.E., Kunze K.L. Mechanism-based inactivation of human cytochrome P450 1A2 by furafylline: detection of a 1:1 adduct to protein and evidence for the formation of a novel imidazomethide intermediate. Biochem. 1998; 37: 7407–7419
  • Reilly C. A., Ehlhardt W. J., Jackson D. A., Kulanthaivel P., Mutlib A. E., Espina R. J., Moody D. E., Crouch D. J., Yost G. S. Metabolism of capsaicin by cytochrome P450 produces novel dehydrogenated metabolites and decreases cytotoxicity to lung and liver cells. Chem Res Toxicol. 2003; 16: 336–349
  • Reimann I. W., Klotz U., Siems B., Frolich J. Cimetidine increases steady state plasma levels of propranolol. Br. J. Clin. Pharmacol. 1981; 12: 785–790
  • Rendic S. Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002; 34: 83–448
  • Richter T., Murdter T. E., Heinkele G., Pleiss J., Tatzel S., Schwab M., Eichelbaum M., Zanger U. M. Potent mechanism-based inhibition of human CYP2B6 by clopidogrel and ticlopidine. J. Pharmacol. Exp. Ther. 2004; 308: 189–197
  • Richter T., Schwab M., Eichelbaum M., Zanger U.M. Inhibition of human CYP2B6 by N, N′, N”triethylenethiophosphoramide is irreversible and mechanism-based. Biochem. Pharmacol. 2005; 69: 517–524
  • Ritchie L. D., Grant S. M. Tamoxifen-warfarin interaction: the Aberdeen hospitals drug file. Br. Med. J. 1989; 298: 1253
  • Rosenblat M., Belinky P., Vaya J., Levy R., Hayek T., Coleman R., Merchav S., Aviram M. Macrophage enrichment with the isoflavan glabridin inhibits NADPH oxidase-induced cell-mediated oxidation of low density lipoprotein. A possible role for protein kinase C. J. Biol. Chem. 1999; 274: 13790–13799
  • Rota C., Barr D. P., Martin M. V., Guengerich F. P., Tomasi A., Mason R. P. Detection of free radicals produced from the reaction of cytochrome P-450 with linoleic acid hydroperoxide. Biochem. J. 1997; 328: 565–571
  • Ruze P. Kava-induced dermopathy: a niacin deficiency?. Lancet 1990; 335: 1442–1445
  • Samigun, Mulyono, Santoso B. Lowering of theophylline clearance by isoniazid in slow and rapid acetylators. Br. J. Clin. Pharmacol. 1990; 29: 570–573
  • Sahali-Sahly Y., Balani S. K., Lin J. H., Baillie T. A. In vitro studies on the metabolic activation of the furanopyridine L-754,394, a highly potent and selective mechanism-based inhibitor of cytochrome P450 3A4. Chem. Res. Toxicol. 1996; 9: 1007–1012
  • Schaefer W. H., Harris T. M., Guengerich F. P. Characterization of the enzymatic and nonenzymatic peroxidative degradation of iron porphyrins and cytochrome P-450 heme. Biochem. 1985; 24: 3254–3263
  • Schauenstein E., Esterbauer H. Formation and properties of reactive aldehydes. Ciba. Found. Symp. 1978; 67: 225–244
  • Schellens J. H., van der Wart J. H., Brugman M., Breimer D. D. Influence of enzyme induction and inhibition on the oxidation of nifedipine, sparteine, mephenytoin and antipyrine in humans as assessed by a “cocktail” study design. J. Pharmacol. Exp. Ther. 1989; 249: 638–645
  • 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., Watkins P. B. Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents. Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins. Drug Metab. Dispos. 1997; 25: 1228–1233
  • Sellers E. M., Ramamoorthy Y., Zeman M. V., Djordjevic M. V., Tyndale R. F. The effect of methoxsalen on nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) metabolism in vivo. Nicotine Tob. Res. 2003; 5: 891–899
  • Sharma U., Roberts E. S., Kent U. M., Owens S. M., Hollenberg P. F. Metabolic inactivation of cytochrome P4502B1 by phencyclidine: immunochemical and radiochemical analyses of the protective effects of glutathione. Drug Metab. Dispos. 1997; 25: 243–250
  • Sindrup S. H., Brøsen K., Gram L. F., Hallas J., Skjelbo E., Allen A., Allen G. D., Cooper S. M., Mellows G., Tasker T. C., et al. The relationship between paroxetine and the sparteine oxidation polymorphism. Clin Pharmacol Ther. 1992; 51: 278–287
  • Silverman R. B. Mechanism-based enzyme inactivators. Methods Enzymol. 1995; 249: 240–283
  • Smith T. J., Guo Z., Li C., Ning S. M., Thomas P. E., Yang C. S. Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res. 1993; 53: 3276–3282
  • Snyder K. R., Sparano N., Malinowski J. M. Raloxifene hydrochloride. Am. J. Health Syst. Pharm. 2000; 57: 1669–1675
  • Sofowora G. G., Choo E. F., Mayo G., Shyr Y., Wilkinson G. R. In vivo inhibition of human CYP1A2 activity by oltipraz. Cancer Chemother. Pharmacol. 2001; 47: 505–510
  • Sridar C., Kent U. M., Notley L. M., Gillam E. M., Hollenberg P. F. Effect of tamoxifen on the enzymatic activity of human cytochrome CYP2B6. J. Pharmacol. Exp. Ther. 2002; 301: 945–952
  • Sridar C., Goosen T. C., Kent U. M., Williams J. A., Hollenberg P. F. Silybin inactivates cytochromes P450 3A4 and 2C9 and inhibits major hepatic glucuronosyltransferases. Drug Metab. Dispos. 2004; 32: 587–594
  • Sridar C., Kobayashi Y., Brevig H., Kent U. M., Puppali S. G., Rimoldi J. M., Hollenberg P. F. Synthesis of substituted phenyl diaziridines and characterization as mechanism-based inactivators of human cytochrome P450 2B6. Drug Metab Dispos. 2006; 34: 1849–1855
  • Steiner E., Spina E. Differences in the inhibitory effect of cimetidine on desipramine metabolism between rapid and slow debrisoquin hydroxylators. Clin. Pharmacol. Ther. 1987; 42: 278–282
  • Stupans I., Murray M., Kirlich A., Tuck K. L., Hayball P. J. Inactivation of cytochrome P450 by the food-derived complex phenol oleuropein. Fd. Chem. Toxicol. 2001; 39: 1119–1124
  • Steward D. J., Haining R. L., Henne K. R., Davis G., Rushmore T. H., Trager W. F., Rettie A. E. Genetic association between sensitivity to warfarin and expression of CYP2C9*3. Pharmacogenetics 1997; 7: 361–367
  • Su T., Bao Z., Zhang Q. Y., Smith T. J., Hong J. Y., Ding X. Human cytochrome P450 CYP2A13: predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 2000; 60: 5074–5079
  • Sweetman S. C., Blake P. S., McGlashan J. M., Parsons A.V. Martindale: The Extra Pharmacopeia33rd. Pharmaceutical Press, London 2002; 1101
  • Szweda L. I., Uchida K., Tsai L., Stadtman E. R. Inactivation of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. Selective modification of an active-site lysine. J. Biol. Chem. 1993; 268: 3342–3347
  • Thomassen D., Slattery J. T., Nelson S. D. Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. J. Pharmacol. Exp. Ther. 1988; 244: 825–829
  • Thompson G. A. The Regulation of Membrane Lipid Metabolism, G.A. Thomspon. CRC Press, Boca Raton, Florida 1980; 1–17
  • Toda N., Usui H., Nishino N., Fujiwara M. Cardiovascular effects of capsaicin in dogs and rabbits. J. Pharmacol. Exp. Ther. 1972; 181: 512–521
  • Uchida K., Stadtman E. R. Covalent attachment of 4-hydroxynonenal to glyceraldehyde-3‐phosphate dehydrogenase. A possible involvement of intra- and intermolecular cross-linking reaction. J. Biol. Chem. 1993; 268: 6388–6393
  • Usia T., Watabe T., Kadota S., Tezuka Y. Mechanism-based inhibition of CYP3A4 by constituents of Zingiber aromaticum. Biol. Pharm. Bull. 2005; 28: 495–499
  • Usia T., Watabe T., Kadota S., Tezuka Y. Metabolite-cytochrome P450 complex formation by methylenedioxyphenyl lignans of Piper cubeba: mechanism-based inhibition. Life Sci. 2005; 76: 2381–2391
  • Vaccaro E., Giorgi M., Longo V., Mengozzi G., Gervasi P. G. Inhibition of cytochrome p450 enzymes by enrofloxacin in the sea bass (Dicentrarchus labrax). Aquat. Toxicol. 2003; 62: 27–33
  • Vanden Bossche H., Koymans L., Moereels H. P450 inhibitors of use in medical treatment: focus on mechanisms of action. Pharmacol Ther. 1995; 67: 79–100
  • van Erp N. P., Baker S. D., Zhao M., Rudek M. A., Guchelaar H. J., Nortier J. W., Sparreboom A., Gelderblom H. Effect of milk thistle (Silybum marianum) on the pharmacokinetics of irinotecan. Clin. Cancer Res. 2005; 11: 7800–7806
  • Vaya J., Belinky P. A., Aviram M. Antioxidant constituents from licorice roots: isolation, structure elucidation and antioxidative capacity toward LDL oxidation. Free Radic. Biol. Med. 1997; 23: 302–313
  • Venkatakrishnan K., Obach R. S. In vitro-in vivo extrapolation of CYP2D6 inactivation by paroxetine: prediction of nonstationary pharmacokinetics and drug interaction magnitude. Drug Metab. Dispos. 2005; 33: 845–852
  • Venkatakrishnan K., Obach R. S. Drug-drug interactions via mechanism-based cytochrome P450 inactivation: points to consider for risk assessment from in vitro data and clinical pharmacologic evaluation. Curr. Drug Metab. 2007; 8: 449–462
  • von Weymarn L. B., Zhang Q. Y., Ding X., Hollenberg P. F. Effects of 8-methoxypsoralen on cytochrome P450 2A13. Carcinogenesis 2005; 26: 621–629
  • von Weymarn L. B., Chun J. A., Hollenberg P. F. Effects of benzyl and phenethyl isothiocyanate on P450s 2A6 and 2A13: potential for chemoprevention in smokers. Carcinogenesis 2006; 27: 782–790
  • Voorman R. L., Maio S. M., Payne N. A., Zhao Z., Koeplinger K. A., Wang X. Microsomal metabolism of delavirdine: evidence for mechanism-based inactivation of human cytochrome P450 3A. J. Pharmacol. Exp. Ther. 1998; 287: 381–388
  • Walsky RL, Obach RS. Validated assays for human cytochrome P450 activities. Drug Metab. Dispos. 2004; 32: 647–660
  • Wang Y. H., Jones D. R., Hall S. D. Prediction of cytochrome P450 3A inhibition by verapamil enantiomers and their metabolites. Drug Metab. Dispos. 2004; 32: 259–266
  • Wang Y. H., Jones D. R., Hall S. D. Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab. Dispos. 2005; 33: 664–671
  • Weber W. W., Hein D. W. Clinical pharmacokinetics of isoniazid. Clin. Pharmacokinet. 1979; 4: 401–422
  • Wen X., Wang J. S., Neuvonen P. J., Backman J. T. Isoniazid is a mechanism-based inhibitor of cytochrome P450 1A2, 2A6, 2C19 and 3A4 isoforms in human liver microsomes. Eur. J. Clin. Pharmacol. 2002; 57: 799–804
  • Wenzel S. E., Kamada A. K. Zileuton: the first 5-lipoxygenase inhibitor for the treatment of asthma. Ann. Pharmacother. 1996; 30: 858–864
  • Whittington H. G., Grey L. Possible interaction between disulfiram and isoniazid. Am. J. Psych. 1969; 125: 1725–1729
  • Williams J. A., Hyland R., Jones B. C., Smith D. A., Hurst S., Goosen T. C., Peterkin V., Koup J. R., Ball S. E. Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab. Dispos. 2004; 32: 1201–1208
  • Winkler P., Lindner W., Esterbauer H., Schauenstein E., Schaur R. J., Khoschsorur G. A. Detection of 4-hydroxynonenal as a product of lipid peroxidation in native Ehrlich ascites tumor cells. Biochim. Biophys. Acta 1984; 796: 232–237
  • Winkler P., Schaur R. J., Schauenstein E. Selective promotion of ferrous ion-dependent lipid peroxidation in Ehrlich ascites tumor cells by histidine as compared with other amino acids. Biochim. Biophys. Acta 1984; 796: 226–231
  • Wiseman L. R., Markham A. Irinotecan. A review of its pharmacological properties and clinical efficacy in the management of advanced colorectal cancer. Drugs 1996; 52: 606–623
  • Wright J. M., Stokes E. F., Sweeney V. P. Isoniazid-induced carbamazepine toxicity and vice versa: a double drug interaction. N. Engl. J. Med. 1982; 307: 1325–1327
  • Yang J., Jamei M., Yeo K. R., Tucker G. T., Rostami-Hodjegan A. Kinetic values for mechanism-based enzyme inhibition: assessing the bias introduced by the conventional experimental protocol. Eur. J. Pharm. Sci. 2005; 26: 334–340
  • Yang J., Jamei M., Yeo K. R., Tucker G. T., Rostami-Hodjegan A. Theoretical assessment of a new experimental protocol for determining kinetic values describing mechanism (time)-based enzyme inhibition. Eur. J. Pharm. Sci. 2007; 31: 232–241
  • Yao K., Falick A. M., Patel N., Correia M. A. Cumene hydroperoxide-mediated inactivation of cytochrome P450 2B1. Identification of an active site heme-modified peptide. J. Biol. Chem. 1993; 268: 59–65
  • Zhao X. J., Jones D. R., Wang Y. H., Grimm S. W., Hall S. D. Reversible and irreversible inhibition of CYP3A enzymes by tamoxifen and metabolites. Xenobiotica 2002; 32: 863–878
  • Zhao P., Kunze K. L., Lee C.A. Evaluation of time-dependent inactivation of CYP3A in cryopreserved human hepatocytes. Drug Metab. Dispos. 2005; 33: 853–861
  • Zhou S., Koh H. L., Gao Y., Gong Z. Y., Lee E. J. Herbal bioactivation: the good, the bad and the ugly. Life Sci. 2004; 74: 935–968
  • Zhou S., Chan E., Lim L. Y., Boelsterli U. A., Li S. C., Wang J., Zhang Q., Huang M., Xu A. Therapeutic drugs that behave as mechanism-based inhibitors of cytochrome P450 3A4. Curr. Drug Metab. 2004; 5: 415–442
  • Zhou S., Yung Chan S., Cher Goh B., Chan E., Duan W., Huang M., McLeod H. L. Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin. Pharmacokinet. 2005; 44: 279–304
  • Zdravkovic M., Olsen A. K., Christiansen T., Schulz R., Taub M. E., Thomsen M. S., Rasmussen M. H., Ilondo M. M. A clinical study investigating the pharmacokinetic interaction between NN703 (tabimorelin), a potential inhibitor of CYP3A4 activity, and midazolam, a CYP3A4 substrate. Eur. J. Clin. Pharmacol. 2003; 58: 683–688

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.