Abstract
Induction and inhibition of cytochrome P450 enzymes are mechanisms that underly some of the more serious drug-drug interactions; it is therefore pertinent that the structure, distribution and essential roles of cytochromes P450 are reviewed.
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Acocella G, Bonollo L, Garimoldi M, Mainardi M, Tenconi LT, Nicolis FB (1972) Kinetics of rifampicin and isoniazid administered alone and in combination to normal subjects and patients with liver disease. Gut 13:47–53
Adebayo GI (1988) Interaction between phenytoin and theophylline in healthy volunteers. Clin Exp Pharmacol Physiol 15:883–887
Ahmad SR (1992) USA antihistamine alert. Lancet 340:542
Alvares AP, Schilling G, Levin W, Kuntzman R (1967) Studies on the induction of CO-binding pigments in liver microsomes by phenobarbital and 3-methylcholanthrene. Biochem Biophys Res Commun 29:521–526
Angle M, Huff PS, Lea JW (1991) Interactions between oral contraceptives and therapeutic drugs. Outlook 9:1–6
Aring E (1993) Extrahepatic microsomal forms: lung microsomal cytochrome P450 isozymes. In: Schenkman JB, Greim H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 373–386
Armstrong G, Beg MF, Scahill S (1991) Warfarin potentiated by proguanil. Br Med J 3034:789
Axelrod J (1955) The enzymatic demethylation of ephedrine. J Pharmacol Exp Ther 114:430–438
Ayesh R, Idle JR, Ritchie JC, Crothers MJ, Hetzel MR (1984) Metabolic oxidation phenotypes as markers for susceptibility to lung cancer. Nature 311:169–170
Barbeau A, Cloutier T, Roy M, Plasse L, Paris S, Poirier J (1985) Ecogenetics of Parkinson’s disease: 4-hydroxylation of debrisoquine. Lancet II:1213–1216
Bertilsson L, Dengler HJ, Eichelbaum M, Schultz HU (1980) Pharmacogenetic covariation of defective N-oxidation of sparteine and 4-hydroxylation of debrisoquine. Eur J Clin Pharmacol 17:153–155
Birnbaum LS (1993) Changes in cytochrome P450 in senescence. In: Schenkman JB, Greim H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 477–492
Black SD (1993) Cytochrome P450 structure and function. In: Schenkam JB, Greim H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 156–168
Booth CD (1993) A drug interaction between danazol and warfarin. Pharm J 250:439–440
Brodie BB, Axelrod J, Cooper JR, Gaudette LE, La Due BN, Mitowa C, Udenfriend S (1955) Detoxification of drugs and other foreign compounds by liver microsomes. Science 121:603–604
Brooks BA, McBride OW, Dolphin CT, Farrall M, Scambler PJ, Gonzalez FJ, Idle JR (1988) The gene CYP3 encoding P45PCN1 (nifedipine oxidase) is tightly linked to the gene COLIA2 encoding collagen type I alpha on 7q21-p22.1. Am J Hum Genet 43:280–284
Brosen K, Gram LF (1989) Clinical significance of the sparteine/debrisoquine oxidation polymorphism. Eur J Clin Pharmacol 36:537–547
Cadle RM, Zenon GJ III, Rodríguez-Barradas MC, Hamill RJ (1994) Fluconazole induced symptomatic phenytoin toxicity. Ann Pharmacother 28:191–195
Cashman JR, Hanks D, Weiner RI (1987) Epoxy derivatives of arachidonic acid are potent stimulators of prolactin secretion. Neuroendocrinology 46:245–251
Castel JM, Cappiello E, Leopaldi D, Latini R (1990) Rifampicin lowers plasma concentrations of propafenone and its antiarrhythmic effect. Br J Clin Pharmacol 30:155
Committee on Safety of Medicines (1989) Serious interaction between tamoxifen and warfarin. Committee on Safety of Medicines, London (Current problems, no 26)
Conney AH (1967) Pharmacological implications of microsomal enzyme induction. Pharmacol Rev 19:317–366
Conney AH, Miller EC, Miller J A (1956) The metabolism of methylated aminoazo dyes. V. Evidence for induction of enzyme synthesis in the rat by 3-methylcholanthrene. Cancer Res 16:450–459
Conney AH, Miller EC, Miller JA (1957) Substrate-induced synthesis and other properties of benzpyrenehydroxylase in rat liver. J Biol Chem 228:753–766
Consumers’ Association (1993) Fluoroquinolones reviewed. Drug Ther Bull 31(18):69–72
Crespi CL, Penman BW, Gelboin HV, Gonzalez FJ (1991) A tobacco smoke-derived nitrosamine 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone is activated by multiple human cytochrome P450s including the polymorphic human cytochrome P4502D6. Carcinogenesis 12:1197–1201
Daly AK, Idle JR (1993) Genetics: animal and human cytochrome P450 polymorphisms. In: Schenkman JB, Grein H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 433–446
Damani LA (1988) The flavin-containing monooxygenase as an amine oxidase. In: Gorrod JW, Oelschlager H, Caldwell J (eds) Metabolism of xenobiotics. Taylor and Francis, London, pp 59–70
D’Arcy PF (1984a) Tobacco smoking and drugs: a clinically important interaction? Drug Intell Clin Pharm 18:302–307
D’Arcy PF (1984b) Vaccine-drug interactions. Drug Intell Clin Pharm 18:697–700
D’Arcy PF (1986) Drug interactions with oral contraceptives. Drug Intell Clin Pharm 20:353–362
D’Arcy PF, Merkus FWHM (1981) Alcohol and drug interactions. Pharm Int 2:273–280
Davis GC, Williams AC, Markey SP, Ebert MH, Caine ED, Reichert CM, Kopin IJ (1979) Chronic parkinsonism secondary to intravenous injection of meperidine analogues. Psychiatry Res 1:249–254
Dayer P, Balant L, Courvoisier F, Kupfer A, Kubli A, Georgia A, Fabre J (1982) The genetic control of bufuralol metabolism in man. Eur J Drug Metab Pharmacokinet 7:73–77
Dean WL, Gray RD (1982) Relationship between state of aggregation and catalytic activity for cytochrome P-450 LM2 and NADPH-cytochrome P-450 reductase. J Biol Chem 257:14679–14685
DeWaziers I, Cugnenc P, Yang CS, Leroux JP, Beaune P (1990) Cytochrome P-450 isozymes, epoxide hydrolase and glutathione transferase in rat and human hepatic and extrahepatic tissues. J Pharmacol Exp Ther 253:387–394
Dillard ML, Fink RM, Parkerson R (1992) Ciprofloxacin-phenytoin interaction. Ann Pharmacother 26:263
Eichelbaum M, Spannbrucker N, Steincke B, Dengler HJ (1979) Defective N-oxidation of sparteine in man: a new pharmacogenetic defect. Eur J Clin Pharmacol 17:153–155
Elofsson S-A, Gamberale F, Hindmarsh T, Iregren A, Isaksson A, Johnsson I, Knave B, Lydahl E, Mindus P, Persson HE, Philipson B, Steby M, Struwe G, Söderman E, Wennberg A, Widen L (1980) Exposure to organic solvents. A cross-sectional epidemiological investigation on occupationally-exposed car and industry spray painters with special reference to the nervous system. Scand J Work Environ Health 6:239–273
Estabrook RW (1979) Concluding remarks. In: Estabrook RW, Lindenlaub E (eds) The induction of drug metabolism. Schattauer, Stuttgart, pp 643–645 (Symposia Medica Hoechst, vol 14)
Evans DAP, Mahgoub A, Sloan TP, Idle JR, Smith RL (1980) A family and population study of the genetic polymorphism of debrisoquine oxidation in a British white population. J Med Genet 17:102–105
Gannon RH, Anderson ML (1992) Fluconazole-nortriptyline drug interaction. Ann Pharmacother 26:1456–1457
Gelehrter TD (1979) Enzyme induction in mammals — an overview. In: Estabrook RW, Lindenlaub E (eds) The induction of drug metabolism. Schattauer, Stuttgart, pp 7–24
Gonzalez FJ (1993) Cytochrome P450 in humans. In: Schenkman JB, Greim H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 239–257
Gorrie M, Beaman M, Nicholls A, Blackwell P (1994) Allopurinol interaction with cyclosporin. Br Med J 308:113
Griffin JP, D’Arcy PF, Speirs CJ (1988) A manual of adverse drug interactions, 4th edn. Wright, London
Guengerich FP, Kim DH (1990) In vitro inhibition of dihydropyridine oxidation and aflatoxin activation in human liver microsomes by naringin and other flavonoids. Carcinogenesis 11:2275–2279
Guengerich FP, Marin MV, Beaune PH, Kremers P, Wolff T, Waxman DJ (1986) 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
Gupta A, Sexton RC, Rudney H (1986) Modulation of regulatory oxysterol formation and low density lipoprotein suppression of 3-hydroxy-3-methyl glutaryl coenzyme A (HMG-Coa) reductase activity by ketoconazole. A role for cytochrome P450 in the regulation of HMG-Coa reductase in rat intestinal epithelia cells. J Biol Chem 261:8348–8356
Horowitz HW, Jorde UP, Wormser GP (1992) Drug interactions in use of dapsone for Pneumocystis carinii prophylaxis. Lancet 339:747
Hoyumpa AM Jr, Schenker S (1982) Major drug interactions: effect of liver disease, alcohol and nutrition. Ann Rev Med 33:113–149
Jassal SV (1991) Warfarin potentiation by glibenclamide. Br Med J 303:789
Kolmodin B, Azarnoff DL, Sjöqvist F (1969) Effect of environmental factors on drug metabolism: decreased plasma half-life of aminopyrine in workers exposed to chlorinated hydrocarbon insecticides. Clin Pharmacol Ther 10:638–642
Langhoff E, Madsen S (1983) Rapid metabolism of cyclosporin and prednisone in kidney transplant patients receiving tuberculostatic treatment. Lancet II:1031
Le Goascogne C, Röbel P, Gouezow M, Snanes N, Baulieu E-E, Waterman M (1987) Neurosteroids: cytochrome P450 in the rat brain. Science 237:1212–1214
Lindeil TJ, Ellinger R, Warren JT, Sundheimer D, O’Malley AF (1977) The effect of acute and chronic phénobarbital treatment on the activity of rat liver deoxyribonuclease acid-dependent ribonucleic acid polymerases. Mol Pharmacol 13:426–434
Lodwick R, McConkey B, Brown AM (1987) Life threatening interaction between tamoxifen and warfarin. Br Med J 295:1141
Lu AYH, Coon M J (1968) Role of hemoprotein P450 in fatty acid ω-hydroxylation in a soluble enzyme from liver microsomes. J Biol Chem 243:1331–1332
Mahgoub A, Idle JR, Dring LG, Lancaster R, Smith RL (1977) Polymorphic hydroxylation of debrisoquine in man. Lancet 11:584–586
Maizlish NA, Langolf GD, Whitehead LW, Fine LJ, Alberts JW, Goldberg J, Smith P (1985) Behavioral evaluation of workers exposed to mixtures of organic solvents. Br J Ind Med 43:257–262
Mallov JS (1976) MBK neuropathy among spray painters. JAMA 235:1455–1457
Maltony C, Ciliberti A, Caretti D (1982) Experimental contributions in identifying brain potential carcinogens in the petrochemical industry. Ann NY Acad Sei 381:216–249
Matsubara S, Yamamoto S, Sogawa K, Yokotani N, Fujii-Kuriyama Y, Haniu M, Shively JE, Gotoh O, Kusunose E, Kusunose M (1987) cDNA cloning and inducible expression during pregnancy of the mRNA for rabbit pulmonary prostaglandin ω-hydroxylase (cytochrome P-450P2). J Biol Chem 262:13366–13371
McFadden JP, Pontin JE, Powles AV, Fry L, Idle JR (1989) Cyclosporin decreased nifedipine metabolism. Br Med J 299:1224
McManus ME, Boobis AR, Pacifici GM, Frempang RY, Brodie MJ, Kahn GC, Whyte C, Davies DS (1980) Xenobiotic metabolism in the human lung. Life Sei 26:481–487
Meeks ML, Mahaffey KW, Katz MD (1992) Danazol increases the anticoagulant effects of warfarin. Ann Pharmacother 26:641–642
Mönig H, Baese C, Heidemann HT, Ohnhaus EE, Schulte HM (1990) Effect of oral contraceptive steroids on the pharmacokinetics of phenprocoumon. Br J Clin Pharmacol 30:115–116
Müller GC, Miller JA (1953) The metabolism of methylated aminoazo dyes. II. Oxidative demethylation by rat liver homogenates. J Biol Chem 202:579–587
Murphy RC, Falk JR, Lumni S, Yadagari P, Zirrolli JA, Balazy M, Masferrer JL, Abraham NG, Schwartzman ML (1988) 12(R)-Hydroxyeicosatrienoic acid: a vasodilator cytochrome P450-dependent arachidonate metabolite from bovine corneal epithelium. J Biol Chem 263:17197–17202
Nebert DW, Gonzalez EJ (1985) Cytochrome P-450 gene expression and regulation. Trends Pharmacol Sei 6:160–164
Noticeboard (1992) Warning about astemizole. Lancet 340:1155
Oates S, Shah RR, Idle JR, Smith RL (1982) Genetic polymorphism of phenformin 4-hydroxylation. Clin Pharmacol Ther 32:81–89
Pantuck EJ, Hsiao KC, Kuntzman R, Conney AH (1975) Intestinal metabolism of phenacetin in the rat: effect of charcoal-broiled beef and rat chow. Science 187:744–745
Parke DV (1975) Induction of the drug-metabolising enzymes. In: Parke DV (ed) Enzyme-induction. Plenum, London, p 207
Parke DV (1979) The responsiveness of cells to various drug inducers. In: Estabrook RW, Lindenlaub E (eds) The induction of drug metabolism. Schattauer, Stuttgart, pp 105–111
Philpot RM, Wolf CR (1981) The properties and distribution of the enzymes of pulmonary cytochrome P450 dependent monooxygenase systems. In: Hodgson E, Bend JR, Philpot RM (eds) Reviews in biochemical toxicology, vol 3. Elsevier, Amsterdam, pp 51–76
Philpot RM, Aring E, Fouts JR (1975) Reconstitution of the rabbit pulmonary microsomal mixed-function oxidase system from solubilized components. Drug Metab Dispos 3:118–126
Posner HS, Mitoma C, Udenfriend S (1961) Enzymatic hydroxylation of aromatic compounds. II. Further studies of the properties of the microsomal hydroxylating system. Arch Biochem Biophys 94:269–279
Remmer H, Merker HJ (1963) Drug induced changes in the liver endoplasmic reticulum: association with drug metabolizing enzymes. Science 14:1657–1658
Rennert H, Fischer RT, Alkvarez JG, Trzaskos JM, Strauss JM (1990) Generation of regulatory oxysterols: 26-hydroxylation of cholesterol by ovarian mitochondria. Endocrinology 127:738–746
Sacerdoti D, Abraham NG, McGiff JC, Schwartzman ML (1988) Renal cytochrome P450-dependent metabolism of arachidonic acid in spontaneously hypertensive rats. Biochem Pharmacol 37:521–527
Schenkman JB (1993) Historical background and description of the cytochrome P450 monooxygenase system. In: Schenkman JB, Greim H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 3–13
Schmucker DL, Woodhouse KW, Wang RK, Wynne H, James OF, McManus M, Kremers P (1990) Effects of age and gender on in vitro properties of human liver microsomal monooxygenases. Clin Pharmacol Ther 48:365–374
Seat TL, Ceklum CL, Back DJ (1991) Possible potentiation of warfarin by fluconazole. Ann Pharmacother 24:1177–1178
Serpa MD, Cossolias J, McCreevy MJ (1992) Moricizine-warfarin: a possible drug interaction. Ann Pharmacother 26:127
Shaeffer MS, Collier D, Sorrell MF (1994) Interaction between FK 506 and erythromycin. Ann Pharmacother 28:280–281
Shimada T, Guengerich FP (1989) Evidence for cytochrome P-450NF, the nifedipine oxidase, being the principal enzyme involved in the bioactivation of aflatoxins in human liver. Proc Natl Acad Sei USA 86:462–465
Sladek NE, Mannering GJ (1966) Evidence for a new P-450 hemoprotein in hepatic microsomes from methylcholanthrene treated rats. Biochem Biophys Res Commun 24:668–674
Snyder GD, Capdevila J, Chacos N, Manna S, Flack JR (1983) Action of luteinizing hormone-releasing hormone: involvement of novel arachidonic acid metabolites. Proc Natl Acad Sei USA 80:3504–3507
Soto J, Sacrisän JA, Arellano F, Mazas J (1991) Possible theophylline-amiodarone interaction. Ann Pharmacother 24:1115
Srivastava SP, Seth PK (1983) 7-Ethoxycoumarin O-deethylase activity in rat brain microsomes. Biochem Pharmacol 32:3657–3660
Staum JM (1990) Enzyme induction: rifampicin-disopyramide interaction. Ann Pharmacother 24:701–703
Strobel HW, Stralka DJ, Hammond DK, White T (1993) Extrahepatic microsomal forms: gastrointestinal cytochromes P450, assessment and evaluation. In: Schenkman JB, Greim H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 363–371
Tenni P, Laiich DL, Byrne MJ (1989) Life threatening interaction between tamoxifen and warfarin. Br Med J 298:93
Timbrell JA (1993) Biotransformation of xenobiotics. In: Ballantyne B, Marrs T, Turner P (eds) General and applied toxicology, vol 1. Macmillan, Basingstoke, pp 89–119
Tisdel KA, Israel D SA, Kolb KW (1994) Warfarin-felbamate interaction: first report. Ann Pharmacother 28:805
Tjia JF, Back DJ, Breckenridge AM (1989) Calcium channel antagonists and cyclosporin metabolism: in vitro studies with human liver microsomes. Br J Clin Pharmacol 28:362–365
Volk B, Amelized Z, Anagnostopoulos J, Knoth R, Oesch F (1988) First evidence of cytochrome P450 induction in the mouse brain by phenytoin. Neurosci Lett 84:219–224
Warner A, Gustafsson J-A (1993) Extrahepatic microsomal forms: brain cytochrome P450. In: Schenkman JB, Greim H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 387–397
Warner M, Tollet P, Carlström K, Gustafsson J-Ä (1989) Endocrine regulation of cytochrome P450 in the rat brain and pituitary gland. J Endocrinol 122:341–349
Watkins PB, Wrighton PB, Schuetz EG, Molowa DT, Guzelian PS (1987) Identification of glucocorticoid-inducible cytochromes P-450 in the intestinal mucosa of rats and man. J Clin Invest 80:1029–1036
Wattenberg LW, Leon JL (1962) Histochemical demonstration of reduced pyridine nucleotide dependent poly cyclic hydrocarbon metabolizing systems. J Histochem Cytochem 10:412–420
Wattenberg LW, Leong JL, Strand PJ (1962) Benzpyrene hydroxylase activity in the gastrointestinal tract. Cancer Res 22:1120–1125
Williams DE, Hale SE, Okita RT, Masters BSS (1984) A progtaglandin ω-hydroxylase cytochrome P-450 (P-450PGω) purified from lungs of pregnant rabbits. J Biol Chem 259:14600–14608
Williams RT (1959) Detoxification mechanisms. Cunningham, London
Wolff T, Strobl G, Greim H (1993) Structural models for substrates and inhibitors of cytochrome P450 enzymes. In: Schenkman JB, Greim H (eds) Cytochrome P450. Springer, Berlin Heidelberg New York, pp 195–207
Woodcock BG, Kirsten R, Nelson K, Rietbrock S, Hopf R, Kaltenbach M (1991) A reduction in verapamil concentrations with phenytoin. N Engl J Med 325: 1179
Zeigler DM (1984) Metabolic oxygenation of organic nitrogen and sulphur compounds. In: Mitchell JR, Horning MG (eds) Drug metabolism and drug toxicity. Raven, New York, pp 33–53
Zeigler DM (1985) Molecular basis for N-oxygenation of sec-and tert-amines. In: Gorrod JW, Damani LA (eds) Biological oxidation of nitrogen in organic molecules. Ellis Horwood, Chichester, pp 45–52
Zornberg GL, Bodkin JA, Cohen BA (1991) Severe adverse interactions between pethidine and selegiline. Lancet 337:246
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D’Arcy, P.F. (1996). Drug Interactions and Drug-Metabolising Enzymes. In: D’Arcy, P.F., McElnay, J.C., Welling, P.G. (eds) Mechanisms of Drug Interactions. Handbook of Experimental Pharmacology, vol 122. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-61015-8_5
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DOI: https://doi.org/10.1007/978-3-642-61015-8_5
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