Identification of the transporters involved in the hepatobiliary transport and intestinal efflux of methyl 1-(3,4-dimethoxyphenyl)-3-(3-ethylvaleryl)-4- hydroxy-6,7,8-trimethoxy-2-naphthoate (S-8921) glucuronide, a pharmacologically active metabolite of S-8921

Drug Metabolism and Disposition

Volumn 36, Issue 8, 2008, Pages 1553-1561

  Sakamoto, Shingo ^a,b   Kusuhara, Hiroyuki ^b   Horie, Kazutoshi ^a   Takahashi, Kohji ^a   Baba, Takahiko ^a   Ishizaki, Jun ^a   Sugiyama, Yuichi ^b  

^a SHIONOGI AND CO LTD   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 (3,4 DIMETHOXYPHENYL) 3 (3 ETHYLVALERYL) 4 HYDROXY 6,7,8 TRIMETHOXY 2 NAPHTHOIC ACID GLUCURONIDE; 1 (3,4 DIMETHOXYPHENYL) 3 (3 ETHYLVALERYL) 4 HYDROXY 6,7,8 TRIMETHOXY 2 NAPHTHOIC ACID METHYL ESTER; GLUCURONIDE; MULTIDRUG RESISTANCE PROTEIN 2; ORGANIC ANION TRANSPORTER; ORGANIC ANION TRANSPORTER 2; ORGANIC ANION TRANSPORTING POLYPEPTIDE 1B1; ORGANIC ANION TRANSPORTING POLYPEPTIDE 1B3; PROTEIN SLC10A2; S 8921G; SODIUM DEPENDENT BILE ACID TRANSPORTER; SODIUM TAUROCHOLATE COTRANSPORTING POLYPEPTIDE; TAUROCHOLIC ACID;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BILIARY EXCRETION; BINDING SITE; CELL STRAIN; CONTROLLED STUDY; CRYOPRESERVATION; DRUG BILE LEVEL; DRUG BLOOD LEVEL; DRUG GLUCURONIDATION; DRUG IDENTIFICATION; DRUG LIVER LEVEL; DRUG METABOLISM; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG TARGETING; DRUG TRANSPORT; DRUG UPTAKE; HUMAN; HUMAN CELL; HYPERBILIRUBINEMIA; HYPOCHOLESTEROLEMIA; INTESTINE ABSORPTION; INTESTINE SECRETION; JEJUNUM; LIVER CELL; LIVER CLEARANCE; LIVER METABOLISM; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; SODIUM TRANSPORT;

ANIMALS; ATP-BINDING CASSETTE TRANSPORTERS; BILIARY TRACT; BLOTTING, WESTERN; CARBON RADIOISOTOPES; CELLS, CULTURED; DOGS; GLUCURONIDES; HEPATOCYTES; HUMANS; INTESTINES; LIVER; MALE; NAPHTHOLS; ORGANIC ANION TRANSPORTERS; RATS; RATS, SPRAGUE-DAWLEY;

MUS; RATTUS;

EID: 47949116498     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.020511     Document Type: Article

References (27)

1. Adachi Y, Suzuki H, Schinkel AH, and Sugiyama Y (2005) Role of breast cancer resistance protein (Bcrp1/Abcg2) in the extrusion of glucuronide and sulfate conjugates from enterocytes to intestinal lumen. Mol Pharmacol 67:923-928.
2. Akita H, Suzuki H, and Sugiyama Y (2001) Sinusoidal efflux of taurocholate is enhanced in Mrp2-deficient rat liver. Pharm Res 18:1119-1125.
3. +/bile acid cotransporter. J Clin Invest 93:1326-1331.
4. Hagenbuch B and Meier PJ (2003) The superfamily of organic anion transporting polypeptides. Biochim Biophys Acta 1609:1-18.
5. +/Bile acid cotransporter by S-8921 reduces serum cholesterol and prevents atherosclerosis in rabbits. Arterioscler Thromb Vasc Biol 18:1304-1311.
6. Hirano M, Maeda K, Hayashi H, Kusuhara H, and Sugiyama Y (2005) Bile salt export pump (BSEP/ABCB11) can transport a nonbile acid substrate, pravastatin. J Pharmacol Exp Ther 314:876-882.
7. Hirano M, Maeda K, Shitara Y, and Sugiyama Y (2004) Contribution of OATP2 (OATP1B1) and OATP8 (OATP1B3) to the hepatic uptake of pitavastatin in humans. J Pharmacol Exp Ther 311:139-146.
8. Ho RH, Tirona RG, Leake BF, Glaeser H, Lee W, Lemke CJ, Wang Y, and Kim RB (2006) Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics. Gastroenterology 130:1793-1806.
9. Jonker JW, Buitelaar M, Wagenaar E, Van Der Valk MA, Scheffer GL, Scheper RJ, Plosch T, Kuipers F, Elferink RP, Rosing H, et al. (2002) The breast cancer resistance protein protects against a major chlorophyll-derived dietary phototoxin and protoporphyria. Proc Natl Acad Sci U S A 99:15649-15654.
10. Konig J, Cui Y, Nies AT, and Keppler D (2000) A novel human organic anion transporting polypeptide localized to the basolateral hepatocytes membrane. Am J Physiol 278:G156-G164.
11. Kusuhara H and Sugiyama Y (2001) Drug-drug interactions involving the membrane transport process, in Drug-Drug Interactions (Rodrigues D ed) pp 123-188, Marcel Dekker, New York.
12. Lowry OH, Rosebrough NJ, Farr AL, and Randall RJ (1951) Protein measurement with the folin phenol reagent. J Biol Chem 193:265-275.
13. +-taurocholate cotransporting polypeptide (NTCP), organic anion transporting polypeptide (OATP) 1B1 (OATP-C), and OATP1B3 (OATP8). Mol Pharm 3:70-77.
14. Maher JM, Slitt AL, Cherrington NJ, Cheng X, and Klaassen CD (2005) Tissue distribution and hepatic and renal ontogeny of the multidrug resistance-associated protein (Mrp) family in mice. Drug Metab Dispos 33:947-955.
15. Mottino AD, Hoffman T, Jennes L, and Vore M (2000) Expression and localization of multidrug resistant protein mrp2 in rat small intestine. J Pharmacol Exp Ther 293:717-723.
16. Packard CJ and Shepherd J (1982) The hepatobiliary axis and lipoprotein metabolism: effects of bile acid sequestrants and ileal bypass surgery. J Lipid Res 23:1081-1098.
17. Rost D, Mahner S, Sugiyama Y, and Stremmel W (2002) Expression and localization of the multidrug resistance-associated protein 3 in rat small and large intestine. Am J Physiol 282:G720-G726.
18. Sakamoto S, Kusuhara H, Miyata K, Shimaoka H, Kanazu T, Matsuo Y, Nomura K, Okamura N, Hara S, Horie K, et al. (2007) Glucuronidation converting S-8921 to a potent ASBT inhibitor, resulting in a hypocholesterolemic action. J Pharmacol Exp Ther 322:1-9.
19. Sasaki M, Suzuki H, Ito K, Abe T, and Sugiyama Y (2002) Transcellular transport of organic anions across a double-transfected Madin-Darby canine kidney II cell monolayer expressing both human organic anion-transporting polypeptide (OATP2/SLC21A6) and multidrug resistance-associated protein 2 (MRP2/ABCC2). J Biol Chem 277:6497-6503.
20. Shepherd J, Cobbe SM, Ford I, Isles CG, Lorimer AR, MacFarlane PW, Mckillop JH, and Packaed CJ (1995) Prevention of coronary heart disease with pravastatin in men with hypercholesterolemia. West of Scotland Coronary Prevention Study Group. N Engl J Med 333:1301-1307.
21. Shitara Y, Li AP, Kato Y, Lu C, Ito K, Itoh T, and Sugiyama Y (2003) Function of uptake transporters for taurocholate and estradiol-17β-D- glucuronide in cryopreserved human hepatocytes. Drug Metab Pharmacokinet 18:33-41.
22. Shoji T, Suzuki H, Kusuhara H, Watanabe Y, Sakamoto S, and Sugiyama Y (2004) ATP-dependent transport of organic anions into isolated basolateral membrane vesicles from rat intestine. Am J Physiol 287:G749-G756.
23. Yamaguchi T, Nakajima Y, Mizobuchi M, Inazawa K, Kanazu T, Kadono K, Ohkawa T, and Iwatani K (1998) Disposition and metabolism of the new hypocholesterolemic compound S-8921 in rats and dogs. Arzneimittelforschung 48:995-1006.
24. Zamek-Gliszczynski MJ, Nezasa K, Tian X, Bridges AS, Lee K, Belinsky MG, Kruh GD, and Brouwer KL (2006a) Evaluation of the role of multidrug resistance-associated protein (Mrp) 3 and Mrp4 in hepatic basolateral excretion of sulfate and glucuronide metabolites of acetaminophen, 4-methylumbelliferone, and harmol in Abcc3-/- and Abcc4-/- mice. J Pharmacol Exp Ther 319:1485-1491.
25. Zamek-Gliszczynski MJ, Nezasa K, Tian X, Kalvass JC, Patel NJ, Raub TJ, and Brouwer KL (2006b) The important role of Bcrp (Abcg2) in the biliary excretion of sulfate and glucuronide metabolites of acetaminophen, 4-methylumbelliferone, and harmol in mice. Mol Pharmacol 70:2127-2133.
26. Zelcer N, van de Wetering K, de Waart R, Scheffer GL, Marschall HU, Wielinga PR, Kuil A, Kunne C, Smith A, van der Valk M, et al. (2006) Mice lacking Mrp3 (Abcc3) have normal bile salt transport, but altered hepatic transport of endogenous glucuronides. J Hepatol 44:768-775.
27. Zelcer N, van de Wetering K, Hillebrand M, Sarton E, Kuil A, Wielinga PR, Tephly T, Dahan A, Beijnen JH, and Borst P (2005) Mice lacking multidrug resistance protein 3 show altered morphine pharmacokinetics and morphine-6-glucuronide antinociception. Proc Natl Acad Sci U S A 102:7274-7279.