Molecular and physical mechanisms of first-pass extraction

Drug Metabolism and Disposition

Volumn 27, Issue 2, 1999, Pages 161-166

  Hall, Stephen D ^d,f   Thummel, Kenneth E ^a   Watkins, Paul B ^b   Lown, Kenneth S ^b   Benet, Leslie Z ^c   Paine, Mary F ^a   Mayo, Robert R ^b   Turgeon, D Kim ^b   Bailey, David G ^g   Fontana, Robert J ^b   Wrighton, Steven A ^e  

^a UNIVERSITY OF WASHINGTON   (United States)

^b UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^e ELI LILLY AND COMPANY   (United States)

^f WISHARD MEMORIAL HOSPITAL   (United States)

^g NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; GLYCOPROTEIN P;

CONFERENCE PAPER; DRUG ADSORPTION; DRUG BIOAVAILABILITY; DRUG ELIMINATION; FIRST PASS EFFECT; INTESTINE CELL; PRIORITY JOURNAL; SYMPOSIUM;

EID: 0032949332     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Conference Paper

References (39)

1. Bech-Hanson NT, Till JE and Ling V (1976) Pleiotropic phenotype of colchicine-resistant CHO cells: Cross-resistance and collateral sensitivity. J Cell Physiol 88:23-32.
2. Chang T, Benet LZ and Hebert MF (1996) The effect of water-soluble vitamin E on cyclosporine pharmacokinetics in healthy volunteers. Clin Pharmacol Ther 59:297-303.
3. Dundee JW, Halliday NJ, Harper KW and Brogden RN (1984) Midazolam. A review of its pharmacological properties and therapeutic use. Drugs 28:519-543.
4. Edgar G, Regardh CG, Johnsson O, Johansson L, Lundborg P, Lofberg I and Ronn O (1985) Felodipine kinetics in healthy men. Clin Pharmacol Ther 38:205-211.
5. Gomez DY, Wacher VJ, Tomlanovich SJ, Hebert MF and Benet LZ (1995) The effects of ketoconazole on the intestinal metabolism and bioavailability of cyclosporine. Clin Pharmacol Ther 58:15-19.
6. Guengerich FP, Brian WR, Iwasaki M, Sari M-A, Baarnhielm C and Berntsson P (1991) Oxidation of dihydropyridine calcium channel blockers and analogues by human liver cytochrome P450 IIIA4. J Med Chem 34:1838-1844.
7. Guengerich FP, Martin MV, Beaune PH, Kremers P, Wolff T and 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.
8. Hebert MF, Roberts JP, Prueksaritanont T and Benet LZ (1992) Bioavailability of cyclosporine with concomitant rifampin administration is markedly less than predicted by hepatic enzyme induction. Clin Pharmacol Ther 52:453-457.
9. 14C-midazolam in humans following oral dosing. Arzneim-Forsch/Drug Res 31:2220-2223.
10. Hofsli E and Nissen-Meyer J (1989) Reversal of drug resistance by erythromycin: Erythromycin increases the accumulation of actinomycin D and doxorubicin in multidrug-resistant cells. Int J Cancer 44:149-154.
11. Hsing S, Gatmaitan Z and Arias IM (1992) The function of Gp170, the multidrug-resistance gene product, in the brush border of rat intestinal mucosa. Gastroenterology 102:879-885.
12. Iwatsubo T, Hirota N, Ooie T, Suzuki H, Shimada N, Chiba K, Ishizaki T, Green CE, Tyson CA and Sugiyama Y (1997) Prediction of in vivo drug metabolism in the human liver from in vitro data of metabolism. Pharmacol Ther 73:147-171.
13. Kim RB, Fromm MF, Wandel C, Leake B, Wood AJJ and Roden DM (1998) The drug transporter P-glycoprotein limits oral absorption and brain entry of HIV-1 protease inhibitors. J Clin Invest 101:289-294.
14. Kolars JC, Awni WM, Merion RM and Watkins PB (1991) First-pass metabolism of cyclosporin by the gut. Lancet 338:1488-1490.
15. Kolars JC, Schmiedlin-Ren P, Schuetz JD, Fang C and Watkins PB (1992) Identification of rifampin-inducible P450IIIA4 (CYP3A4) in human small bowel enterocytes. J Clin Invest 90:1871-1878.
16. Kronbach T, Mathys D, Umeno M, Gonzalez FJ and Meyer UA (1989) Oxidation of midazolam and triazolam by human liver cytochrome P450IIIA4. Mol Pharmacol 36:89-96.
17. Lown KS, Bailey DG, Fontana RJ, Janardan SK, Adair CH, Fortlage LA, Brown MB, Guo W and Watkins PB (1997) Grapefruit juice increases felodipine oral availability in humans by decreasing intestinal CYP3A protein expression. J Clin Invest 99:2545-2553.
18. Lown KS, Fontana RJ, Schmiedlin-Ren P, Turgeon DK and Watkins PB (1995) Interindividual variation in intestinal mdr1: Lack of short term diet effects. Gastroenterology 108:A737.
19. Lown KS, Kolars JC, Thummel KE, Barnett JL, Kunze KL, Wrighton SA and Watkins PB (1994) Interpatient heterogeneity in expression of CYP3A4 and CYP3A5 in small bowel. Lack of prediction by the erythromycin breath test. Drug Metab Dispos 22:947-955.
20. Lown KS, Mayo RR, Leichtman AB, Hsiao H-L, Turgeon DK, Schmiedlin-Ren P, Brown MB, Guo W, Rossi SJ, Benet LZ and Watkins PB (1997) Role of intestinal P-glycoprotein (mdr1) in interpatient variation in the oral bioavailability of cyclosporin A. Clin Pharmacol Ther 62:248-60.
21. Mechetner EB and Roninson IB (1992) Efficient inhibition of P-glycoprotein-mediated multi-drug resistance with a monoclonal antibody. Proc Natl Acad Sci USA 89:5824-5828.
22. Paine MF, Shen DD, Kunze KL, Perkins JD, Marsh CL, McVicar JP, Barr DM, Gillies BS and Thummel KE (1996) First-pass metabolism of midazolam by the human intestine. Clin Pharmacol Ther 60:14-24.
23. Regardh CG, Edgar B, Olsson R, Kendall M. Collste P and Shansky C (1989) Pharmacokineucs of felodipine in patients with liver disease. Eur J Clin Pharmacol 36:437-439.
24. Roninson IB (1992) From amplification to function: The case of the MDR1 gene. Mutat Res Rev Genet Toxicol 276:151-161.
25. Saeki T, Ueda K, Tanigawara Y, Hori R and Komano T (1993a) P-glycoprotein-mediated transcellular transport of MDR-reversing agents. FEBS Lett 324:99-102.
26. Saeki T, Ueda K, Tanigawara Y, Hori R and Komano T (1993b) Human P-glycoprotein transports cyclosporin A and FK506. J Biol Chem 268:6077-6080.
27. Saitoh H and Aungst BJ (1995) Possible involvement of multiple P-glycoprotein-mediated efflux systems in the transport of verapamil and other organic cations across rat intestine. Pharm Res 12:1304-1310.
28. Schmeidlin-Ren P, Edwards DJ, Fitzsimmons ME, He K, Lown KS, Woster PM, Rahman A, Thummel KE, Fisher JM, Hollenberg PF and Watkins PB (1997) Mechanisms of enhanced oral availability of CYP3A4 substrates by grapefruit constituents: Decreased enterocyte CYP3A4 concentration and mechanism-based inactivation by furanocoumarins. Drug Metab Dispos 25:1228-1233
29. Shimada T, Yamazaki H, Mimura M, Inui Y and Guengerich FP (1994) Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians. J Pharmacol Exp Ther 270:414-423.
30. Siegsmund MJ, Cardarelli C, Aksentijevich I, Sugimoto Y, Pastan I and Gottesman MM (1994) Ketoconazole effectively reverses multidrug resistance in highly resistant KB cells. J Urol 151:485-491.
31. Thiebaut F, Tsuruo T, Hamada H, Gottesman MM, Pastan I and Willingham MC (1987) Cellular localization of the multidrug-resistance gene product P-glycoprotein in normal human tissues. Proc Natl Acad Sci USA 84:7735-7738.
32. Thummel KE, O'Shea D, Paine MF, Shen DD, Kunze KL, Perkins JD and Wilkinson GR (1996) Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clin Pharmacol Ther 59:491-502.
33. Ueda K, Okamura N, Hirai M, Tanigawara Y, Saeki T, Kioka N, Komano T and Hori R (1992) Human P-glycoprotein transports cortisol, aldosterone, and dexamethasone, but not progesterone. J Biol Chem 267:24248-24252.
34. Wacher VJ, Wu C-Y and Benet LZ (1995) Overlapping substrate specificities and tissue distribution of cytochrome P450 3A and P-glycoprotein: Implications for drug delivery and activity in cancer chemotherapy. Mol Carcinog 13:129-134.
35. Wang SX, Sutfin TA, Baamhielm C and Regardh CG (1989) Contribution of the intestine to the first-pass metabolism of felodipine in the rat. J Pharmacol Exp Ther 250:632-636.
36. Watkins PB (1994) Noninvasive tests of CYP3A enzymes. Pharmacogenetics 4:171-184.
37. Watkins PB, Wrighton SA, Schuetz EG, Molowa DT and Guzelian PS (1987) Identification of glucocorticoid-inducible cytochromes P-450 in the intestinal mucosa of rats and man. J Clin Invest 80:1029-1036.
38. Wille RT, Lown KS, Huszczo UR, Schmiedlin-Ren P and Watkins PB (1997) Short term effect of medications on CYP3A4 and P-glycoprotein expression in human intestinal mucosa. Gastroenterology 112:A419.
39. Wu C-Y, Benet LZ, Hebert MF, Gupta SK, Rowland M, Gomez DY and Wacher VJ (1995) Differentiation of absorption and first-pass gut and hepatic metabolism in humans: Studies with cyclosporine. Clin Pharmacol Ther 58:492-497.