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Xenobiotica
the fate of foreign compounds in biological systems
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Research Article

Microsomal prediction of in vivo clearance and associated interindividual variability of six benzodiazepines in humans

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Pages 603-625 | Received 14 Mar 2005, Published online: 22 Sep 2008

References

  • Abernethy DR, Greenblatt DJ, Divoll M, Smith RB, Shader RI. 1984. The influence of obesity on the pharmacokinetics of oral alprazolarn and triazolam. Clinical Pharmacokinetics 9:177–183.
  • Allonen H, Ziegler G, Klotz U. 1981. Midazolam kinetics. Clinical Pharmacology and Therapy 30:653–661.
  • Andersson T, Miners JO, Veronese ME, Birkett DJ. 1994. Diazepam metabolism by human liver microsomes is mediated by both 5-mephenytoin hydroxylase and CYP3A isoforms. British Journal of Clinical Pharmacology 38:131–137.
  • Andrews J, Paskaleva E, Galetin A, Houston JB. 2003. Pharmacogenomics and predictive drug metabolism. In: Pharmacogenomics Workshop, Annual Human Genome Meeting, Cancun, Mexico, 27 April-2 May.
  • Bareggi SR, Pirola R, Truci G, Leva S, Smirne S. 1988. Effect of after-dinner administration on the pharmacokinetics of oral flunitrazepam and loprazolam. Journal of Clinical Pharmacology 28:371–375.
  • Benet LZ. 1996. In: Hardman JG, Molinoff PB, Ruddon RW, Gilman AG, editors. Pharmacokinetics, Goodman and Gilman's the pharmacological basis of therapeutics. New York: McGraw-Hill. p 14.
  • Bjornsson TD, Callaghan JT, Einolf HJ, Fischer V, Gan L, Grimm S, Kao J, King SP, Miwa G, Ni L, et al. 2003. The conduct of in vitro and in vivo drug-drug interaction studies: A pharmaceutical research and manufacturers of America (PhRMA) perspective. Drug Metabolism and Disposition 31:815–832.
  • Boxenbaum HG, Posmanter HN, Macasieb T, Geitner KA, Weinfeld RE, Moore JD, Darragh A, O'Kelly DA, Weissman L, Kaplan SA. 1978. Pharmacokinetics of flunitrazepam following single- and multiple-dose oral administration to healthy human subjects. Journal of Pharmacokinetics and Biopharmacology 6:283–293.
  • Carlile DJ, Hakooz N, Bayliss MK, Houston JB. 1999. Microsomal prediction of in vivo clearance of CYP2C9 substrates in humans. British Journal of Clinical Pharmacology 47:625–635.
  • Chien JY, Mohutsky MA, Wrighton SA. 2003. Physiological approaches to the prediction of drug-drug interactions in study populations. Current Drug Metabolism 4:347–356.
  • Chun AH, Carrigan PJ, Hoffman DJ, Kershner RP, Stuart JD. 1977. Effect of antacids on absorption of clorazepate. Clinical Pharmacology and Therapy 22:329–335.
  • Ciraulo DA, Barnhill JG, Boxenbaum HG, Greenblatt DJ, Smith RB. 1986. Pharmacokinetics and clinical effects of alprazolam following single and multiple oral doses in patients with panic disorder. Journal of Clinical Pharmacology 26:292–298.
  • Crevoisier C, Eckert M, Heizmann P, Thumeysen DJ, Ziegler WH. 1981. Relation between the clinical effect and the pharmacokinetics of midazolam following i.m. and i.v. administration/2nd comm.: Pharmacokinetical aspects. Arzneim-Forsch/Drug Research 31:2211–2215.
  • Derry CL, Kroboth PD, Pittenger AL, Kroboth FJ, Corey SE, Smith RB. 1995. Pharmacokinetics and pharmacodynamics of triazolam after two intermittent doses in obese and normal-weight men. Journal of Clinical Psychopharmacology 15:197–205.
  • Divoll M, Greenblatt DJ, Ochs HR, Shader RI. 1983. Absolute bioavailability of oral and intramuscular diazepam: effects of age and sex. Anaesthesia and Analg 62:1–8.
  • Drouet-Coassolo C, Iliadis A, Coassolo P, Antoni M, Cano JP. 1990. Pharmacokinetics of flunitrazepam following single dose oral administration in liver disease patients compared with healthy volunteers. Fundamentals of Clinical Pharmacology 4:643–651.
  • Easterbrook J, Lu C, Sakai Y, Li AP. 2001. Effects of organic solvents on the activities of cytochromes P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes. Drug Metabolism and Disposition 29:141–144.
  • Ellinwood EH Jr, Heatherly DG, Nikaido AM, Bjornsson TD, Kilts C. 1985. Comparative pharmacokinetics and pharmacodynamics of lorazepam, alprazolam and diazepam. Psychopharmacology 86:392–399.
  • Fleishaker JC, Phillips JP, Eller MG, Smith RB. 1989. Pharmacokinetics and pharmacodynamics of alprazolam following single and multiple oral doses of a sustained-release formulation. Journal of Clinical Pharmacology 29:543–549.
  • Floyd MD, Gervasini G, Masica AL, Mayo G, George AL Jr, Bhat K, Kim RB, Wilkinson GR. 2003. Genotype-phenotype associations for common CYP3A4 and CYP3A5 variants in the basal and induced metabolism of midazolam in European- and African-American men and women. Pharmacogenetics 13:595–606.
  • Friedman H, Greenblatt DJ, Burstein ES, Harmatz JS, Shader RI. 1986. Population study of triazolam pharmacokinetics. British Journal of Clinical Pharmacology 22:639–642.
  • Friedman H, Redmond DE Jr, Greenblatt DJ. 1991. Comparative pharmacokinetics of alprazolam and lorazepam in humans and in African Green Monkeys. Psychopharmacology 104:103–105.
  • Galetin A, Brown C, Hallifax D, Ito K, Houston JB. 2004. Utility of recombinant enzyme kinetics in prediction of human clearance - impact of variability, CYP3A5 and CYP2C19 on CYP3A4 substrates. Drug Metabolism and Disposition 32:1411–1420.
  • Galetin A, Clarke SE, Houston JB. 2003. Multisite kinetic analysis of interactions between prototypical CYP3A4 subgroup substrates: Midazolam, testosterone and nifedipine. Drug Metabolism and Disposition 31:1108–1116.
  • Garzone PD, Kroboth PD. 1989. Pharmacokinetics of the newer benzodiazepines. Clinical Pharmacokinetics 16:337–364.
  • Gorski JC, Hall SD, Jones DR, Vandenbranden M, Wrighton SA. 1994. Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochemical Pharmacology 47:1643–1653.
  • Gorski JC, Jones DR, Hamman MA, Wrighton SA, Hall SD. 1999. Biotransformation of alprazolam by members of the human cytochrome P4503A subfamily. Xenobiotica 29:931–944.
  • Grahnén A, et al. 1991. British Journal of Clinical Pharmacology 31:89–92.
  • Greenblatt DJ, Harmatz JS, Shader RI. 1978. Factors influencing diazepam pharmacokinetics: Age, sex and liver disease. International Journal of Clinical Pharmacology 16:177–179.
  • Greenblatt DJ, Allen MD, Harmatz JS, Shader RI. 1980. Diazepam disposition determinants. Clinical Pharmacology and Therapy 27:301–312.
  • Greenblatt DJ, Divoll M, Abernethy DR, Moschitto U, Smith RB, Shader RI. 1983. Alprazolam kinetics in the elderly. Relation to antipyrine disposition. Archives of General Psychiatry 40:287–290.
  • Greenblatt DJ, Abernethy DR, Locniskar A, Harmatz JS, Limjuco RA, Shader RI. 1984. Effect of age, gender, and obesity on midazolam kinetics. Anaesthesiology 61:27–35.
  • Greenblatt DJ, Harmatz JS, Dorsey C, Shader RI. 1988. Comparative single-dose kinetics and dynamics of lorazepam, alprazolam, prazepam, and placebo. Clinical Pharmacology and Therapy 44:326–334.
  • Greenblatt DJ, et al. 1988. Desmethyldiazepam pharmacokinetics: studies following intravenous and oral desmethyldiazepam, oral clorazepate, and intravenous diazepam. Journal of Clinical Pharmacology 28:853–859.
  • Greenblatt DJ, Wright CE. 1993. Clinical pharmacokinetics of alprazolam. Therapeutic implications. Clinical Pharmacokinetics 24:453–471.
  • Greenblatt DJ, Wright CE, von Moltke LL, Harmatz JS, Ehrenberg BL, Harrel LM, Corbett K, Couniham M, Tobias S, Shader RI. 1998. Ketoconazole inhibition of triazolam and alprazolam clearance: Differential kinetic and dynamic consequences. Clinical Pharmacology and Therapy 64:237–247.
  • Greenblatt DJ, von Moltke LL, Harmatz JS, Durol AL, Daily JP, Graf JA, Mertzanis P, Hoffman JL, Shader RI. 2000. Alprazolarn-ritonavir interaction: Implications for product labelling. Clinical Pharmacology and Therapy 67:335–341.
  • Guentert TW. 1984. Pharmacokinetics of benzodiazepines and of their metabolites. In: Bridges JW, Chasseaud LF, editors. Progress in Drug Metabolism. London: Taylor & Francis. 8:241–386.
  • Heizmann P, Eckert M, Ziegler WH. 1983. Pharmacokinetics and bioavailability of midazolam in man. British Journal of Clinical Pharmacology 16:43S–49S.
  • Hesse LM, Venkatakrishnan K, Von Moltke LL, Shader RI, Greenblatt DJ. 2001. CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam. Drug Metabolism and Disposition 29:133–140.
  • Hirota N, Ito K, Iwatsubo T, Green CE, Tyson CA, Shimada N, Suzuki H, Sugiyama Y. 2001. In vitro/in vivo scaling of alprazolam metabolism by CYP3A4 and CYP3A5 in humans. Biopharmaceutics and Drug Disposition 22:53–71.
  • Houston JB, Galetin A. 2003. Progress towards prediction of human pharmacokinetic parameters from in vitro technologies. Drug Metabolism Reviews 35:393–415.
  • Houston JB, Kenworthy KE. 2000. In vitro-in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metabolism and Disposition 28:246–254.
  • Hustert E, Haberl M, Burk O, Wolbold R, He YQ, Klein K, Nuessler AC, Neuhaus P, Klattig J, Eiselt R, et al. 2001. The genetic determinants of CYP3A5 polymorphism. Pharmacogenetics 11:773–779.
  • Ito K, Houston JB. 2004. Prediction of human drug clearance from in vitro and preclinical data using physiologically-based and empirical approaches. Pharmaceutical Research 22:102–111.
  • Kangas L, Kanto J, Pakkanen A. 1982. A pharmacokinetic and pharmacodynamic study of flunitrazepam. International Journal of Clinical Pharmacology and Therapy Toxicology 20:585–588.
  • Kanto J, Kangas L, Aaltonen L, Hilke H. 1981. Effect of age on the pharmacokinetics and sedative of flunitrazepam. International Journal of Clinical Pharmacology and Therapy Toxicology 19:400–404.
  • Kenworthy K, Bloomer JC, Clarke SE, Houston JB. 1999. CYP3A4 drug interactions: Correlation of ten in vitro probe substrates. British Journal of Clinical Pharmacology 48:716–727.
  • Kirkwood C, Moore A, Hayes P, De Vane CL, Pelonero A. 1991. Influence of menstrual cycle and gender on alprazolam pharmacokinetics. Clinical Pharmacology and Therapy 50:404–409.
  • Klotz U, Arvela P, Rosenkranz B. 1985. Famotidine, a new H2-receptor antagonist, does not affect hepatic elimination of diazepam or tubular secretion of procainamide. European Journal of Clinical Pharmacology 28:671–675.
  • Kroboth PD, Smith RB, Stoehr GP, Juhl RP. 1985. Pharmacodynamic evaluation of the benzodiazepine-oral contraceptive interaction. Clinical Pharmacology and Therapy 38:525–532.
  • Kroboth PD, McAuley JW, Derry CL. 1995a. Time-dependent sensitization to triazolam? An observation in three studies. Journal of Clinical Psychopharmacology 15:192–196.
  • Kroboth PD, McAuley JW, Kroboth FJ, Bertz RJ, Smith RB. 1995b. Triazolam pharmacokinetics after intravenous, oral, and sublingual administration. Journal of Clinical Psychopharmacology 15:259–262.
  • Kuehl P, Zhang J, Lin Y, Lamba J, Assem M, Schuetz J, Watkins PB, Daly A, Wrighton SA, Hall SD, et al. 2001. Sequence diversity in CYP3A4 promoters and characterization of the genetic basis of polymorphic CYP3A5 expression. Nature Genetics 27:383–391.
  • Kupferschmidt HHT, Ha HR, Ziegler WH, Meier PJ, Krahenbuhl S. 1995. Interaction between grapefruit juice and midazolam in humans. Clinical Pharmacology and Therapy 58:20–28.
  • Lamba JK, Lin YS, Schuetz EG, Thummel KE. 2002. Genetic contribution to variable human CYP3A-mediated metabolism. Advanced Drug Delivery Reviews 54:1271–1294.
  • Lin K-M, Lau JK, Smith R, Phillips P, Antal E, Poland RE. 1988. Comparison of alprazolam plasma levels in normal Asian and Caucasian male volunteers. Psychopharmacology 96:365–369.
  • Lin YS, Dowling ALS, Quigley SD, Farin FM, Zhang J, Lamba J, Schuetz EG, Thummel KE. 2002. Co-regulation of CYP3A4 and CYP3A5 and contribution to hepatic and intestinal metabolism of midazolam. Molecular Pharmacology 62:162–172.
  • Lown KS, Thummel KE, Benedict PE, Shen DD, Turgeon DK, Berent S, Watkins PB. 1995. The erythromycin breath test predicts the clearance of midazolam. Clinical Pharmacology and Therapy 57:16–24.
  • Lu J-F, et al. 1993. Acta Pharmacologica Sinica 14:485–488.
  • Luurila H, et al. 1996. Pharmacology and Toxicology 78:117–122.
  • Ma JD, Nafziger AN, Bertino JS. 2004. Genetic polymorphisms of cytochrome P450 enzymes and the effect on interindividual, pharmacokinetics variability in extensive metabolizers. Journal of Clinical Pharmacology 44:447–456.
  • Macklon AF, Barton M, James O, Rawlins MD. 1980. The effect of age on the pharmacokinetics of diazepam. Clinical Science 59:479–483.
  • MacLeod SM, Giles HG, Bengert B, Liu FF, Sellers EM. 1979. Age- and gender-related differences in diazepam pharmacokinetics. Journal of Clinical Pharmacology 19:15–19.
  • McGowan WAW, Dundee JW, Clarke RSJ, Howard PJ. 1980. Comparison of the subjective effects and plasma concentrations following oral and I.M. administration of flunitrazepam in patients. British Journal of Anaesthesiology 52:447–451.
  • Nestorov I, Gueorguieva I, Jones H, Houston JB, Rowland M. 2002. Incorporating measures of variability and uncertainty into prediction of in vivo hepatic clearance from in vitro data. Drug Metabolism and Disposition 30:276–282.
  • Obach RS. 1999. Prediction of human clearance of twenty-nine drugs from hepatic microsomal intrinsic clearance data: An examination of in vitro half-life approach and non-specific binding to microsomes. Drug Metabolism and Disposition 27:1350–1359.
  • Ochs HR, Greenblatt DJ, Kaschell HJ, Klehr U, Divoll M, Abernethy DR. 1981. Diazepam kinetics in patients with renal insufficiency or hyperthyroidism. British Journal of Clinical Pharmacology 12:829–832.
  • Ochs HR, Steinhaus E, Locniskar A, Knuchel M, Greenblatt DJ. 1982. Desmethyldiazepam kinetics after intravenous, intramuscular, and oral administration of clorazepate dipotassium. Klinik Wochenschr 60:411–415.
  • Ochs HR, Greenblatt DJ, Verburg-Ochs B, Locniskar A. 1984. Comparative single-dose kinetics of oxazolam, prazepam, and clorazepate: Three precursors of desmethyldiazepam. Journal of Clinical Pharmacology 24:446–451.
  • Ochs HR, Rauh HW, Greenblatt DJ, Kaschell HJ. 1984. Clorazepate dipotassium and diazepam in renal insufficiency: Serum concentrations and protein binding of diazepam and desmethyldiazepam. Nephron 37:100–104.
  • Ozdemir V, Kalowa W, Tang BK, Paterson AD, Walker SE, Edrenyi L, Kashuba AD. 2000. Evaluation of the genetic component of variability in CYP3A4 activity: A repeated drug administration method. Pharmacogenetics 10:373–388.
  • Patki KC, Von Moltke LL, Greenblatt DJ. 2003. In vitro metabolism of midazolam, triazolam, nifedipine and testosterone by human liver microsomes and recombinant cytochromes P450: Role of CYP3A4 and CYP3A5. Drug Metabolism and Disposition 31:938–944.
  • Pearce RE, McIntyre CJ, Madan A, Sanzgiri U, Draper AJ, Bullock PL, Cook DC, Burton LA, Latham J, Nevins C, et al. 1996. Effects of freezing, thawing and storing human liver microsomes on cytochrome P450 activity. Archives of Biochemistry and Biophysics 331:145–169.
  • Pentikainen PJ, Valisalmi L, Himberg JJ, Crevoisier C. 1989. Pharmacokinetics of midazolam following intravenous and oral administration in patients with chronic liver disease and in healthy subjects. Journal of Clinical Pharmacology 29:272–277.
  • Schrag ML, Wienkers LC. 2001. Triazolam substrate inhibition: Evidence of competition for heme-bound reactive oxygen within the CYP3A4 active site. Drug Metabolism and Disposition 29:70–75.
  • Shou M, Mei Q, Ettore W JR, Dai R, Baillie T, Rushmore TH. 1999. Sigmoidal kinetic model for two cooperative substrate-binding sites in a cytochrome P450 3A4 active site: An example of the metabolism of diazepam and its derivatives. Biochemical Journal 340:845–853.
  • Smith MT, Eadie MJ, Brophy TO. 1981. The pharmacokinetics of midazolam in man. European Journal of Clinical Pharmacology 19:271–278.
  • Smith RB, Kroboth PD, Vanderlugt JT, Phillips JP, Juhl RP. 1984. Pharmacokinetics and pharmacodynamics of alprazolam after oral and IV administration. Psychopharmacology 84:452–456.
  • Smith RB, Kroboth PD, Varner PD. 1987. Pharmacodynamics of triazolam after intravenous administration. Journal of Clinical Pharmacology 27:971–979.
  • Smith RB, Kroboth PD. 1987. Influence of dosing regimen on alprazolam and metabolite serum concentrations and tolerance to sedative and psychomotor effects. Psychopharmacology 93:105–112.
  • Stoehr GP, Kroboth PD, Juhl RP, Wender DB, Phillips JP, Smith RB. 1984. Effect of oral contraceptives on triazolarn, temazepam, alprazolam, and lorazepam kinetics. Clinical Pharmacology and Therapy 36:683–690.
  • Thummel KE, Wilkinson GR. 1998. In vitro and in vivo drug interactions involving CYP3A. Annual Review of Pharmacology and Toxicology 38:389–430.
  • Thummel KE, O'Shea D, Paine ME, Shen DD, Kunze KL,, Perkins JD, Wilkinson GR. 1996. Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-meditated metabolism. Clinical Pharmacology and Therapy 59:491–502.
  • Tateishi T, Watanabe M, Moriya H, Yamaguchi S, Sato T, Kobayashi S. 1999. No ethnic difference between Caucasian and Japanese hepatic samples in the expression frequency of CYP3A5 and CYP3A7 proteins. Biochemical Pharmacology 57:935–939.
  • Thummel KE, Shen DD, Podoll TD, Kunze KL,, Trager WE, Bachi CE, March CL, McVicar JP, Barr DM, Perkins JD. 1994. Use of midazolam as a cytochrome P450 3A probe: II. Characterization of inter-and intra-individual hepatic CYP3A variability after liver transplantation. Journal of Pharmacology and Experimental Therapeutics 271:557–566.
  • Tucker GT, Houston JB, Huang S-M. 2001. Optimising drug development: Strategies to assess drug metabolism/transporter interaction potential - toward a consensus. British Journal of Clinical Pharmacology 52:107–117.
  • Vanakoski J, Idanpaan-Heikkila jj, Olkkola KT, Seppala T. 1996. Effects of heat exposure in a Finnish sauna on the pharmacokinetics and metabolism of midazolam. European Journal of Clinical Pharmacology 51:335-338. Vanderveen RP, et al. 1991. Clinical Pharmacology 10:539–543.
  • Vinik HR, Reyes JG, Greenblatt DJ, Abernethy DR, Smith LR. 1983. The pharmacokinetics of midazolam in chronic renal failure patients. Anaesthesiology 59:390–394.
  • Wandel C, Witte JS, Hall JM, Stein CM, Wood All, Wilkinson GR 2000. CYP3A activity in African American and European American men: Population differences and functional effect of the CYP3A4*1B 5'-promoter region polymorphism. Clinical Pharmacology and Therapeutics 68:82–91.
  • Wedlund PJ. 2000. The CYP2C19 enzyme polymorphism. Pharmacology 61:174–183.
  • Westlind-Johnsson A, Malmebo S, Johansson A, Otter C, Andersson TB, Johansson I, Edwards RJ, Boobis AR, Ingelman-Sundberg M. 2003. Comparative analysis of CYP3A expression in human liver suggests only a minor role for CYP3A5 in drug metabolism. Drug Metabolism and Disposition 31:755–761.
  • Williams JA, Ring BJ, Cantrell VE, Jones DR, Eckstein J, Ruterbories K, Hamman MA, Hall SD, Wrighton SA. 2002. Comparative metabolic capabilities of CYP3A4, CYP3A5 and CYP3A7. Drug Metabolism and Disposition 30:883–891.
  • Wilson ZE, Rostami-Hodjegan A, Burn JL, Tooley A, Boyle J, Ellis SW, Tucker GT. 2003. Inter-individual variability in levels of human microsomal protein and hepatocellularity per gram of liver. British Journal of Clinical Pharmacology 56:433–440.
  • Xie H-G, Wood All, Kim RB, Stein CM, Wilkinson GR. 2004. Genetic variability in CYP3A5 and its possible consequences. Pharmacogenomics 5:243–272.

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