Species difference in the inhibitory potentials of non-steroidal anti-inflammatory drugs on the hepatic sulfation and glucuronidation of bioactive flavonoids: Differential observations among common inhibition parameters

Xenobiotica

Volumn 44, Issue 5, 2014, Pages 417-431

  Fong, Sophia Yui Kau ^a   Zuo, Zhong ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Human; Liver cytosols; Liver microsomes; Rat; SULT; UGT

Indexed keywords

BAICALEIN; DICLOFENAC; DIFLUNISAL; FENOPROFEN; FLAVONOID; FLURBIPROFEN; IBUPROFEN; INDOMETACIN; KETOPROFEN; KETOROLAC; MEFENAMIC ACID; NAPROXEN; NIFLUMIC ACID; NONSTEROID ANTIINFLAMMATORY AGENT; OROXYLIN A; PIROXICAM; SULINDAC; WOGONIN; 5,7-DIHYDROXY-6-METHOXY-2-PHENYLCHROMEN-4-ONE; FLAVANONE DERIVATIVE;

ANIMAL CELL; ARTICLE; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG GLUCURONIDATION; DRUG POTENCY; DRUG SULFATION; HUMAN; HUMAN CELL; HUMAN VERSUS ANIMAL COMPARISON; IC 50; LIVER CYTOSOL; LIVER MICROSOME; MALE; NONHUMAN; RAT; SPECIES DIFFERENCE; ANIMAL; CHEMISTRY; COMPARATIVE STUDY; CYTOSOL; DOSE RESPONSE; DRUG EFFECTS; IC50; LIVER; METABOLISM;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CYTOSOL; DOSE-RESPONSE RELATIONSHIP, DRUG; FLAVANONES; FLAVONOIDS; HUMANS; INHIBITORY CONCENTRATION 50; LIVER; MICROSOMES, LIVER; RATS; SPECIES SPECIFICITY;

EID: 84898769262     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2013.851431     Document Type: Article

References (55)

1. Boobis AR, Sesardic D, Murray BP, et al. (1990). Species variation in the response of the cytochrome P-450-dependent monooxygenase system to inducers and inhibitors. Xenobiotica 20:1139-61.
2. Chu X, Korzekwa K, Elsby R, et al. (2013). Intracellular drug concentrations and transporters: measurement, modeling, and implications for the liver. Clin Pharmacol Ther 94:126-41.
3. Cornish-Bowden A. (1974). A simple graphical method for determining the inhibition constants of mixed, uncompetitive and non-competitive inhibitors. Biochem J 137:143-4.
4. Crook PR, Willis JV, Kendall MJ, et al. (1982). The pharmacokinetics of diclofenac sodium in patients with active rheumatoid disease. Eur J Clin Pharmacol 21:331-4.
5. Davies E, Avery GS. (1971). Ibuprofen: a review of its pharmacological properties and therapeutic efficacy in rheumatic disorders. Drugs 2:416-46.
6. Dunn RT, Klaassen CD. (1998). Tissue-specific expression of rat sulfotransferase messenger RNAs. Drug Metab Dispos 26:598-604.
7. Eagling VA, Tjia JF, Back DJ. (1998). Differential selectivity of cytochrome P450 inhibitors against probe substrates in human and rat liver microsomes. Br J Clin Pharmacol 45:107-14.
8. Fong YK, Li CR, Wo SK, et al. (2012). In vitro and in situ evaluation of herb-drug interactions during intestinal metabolism and absorption of Baicalein. J Ethnopharmacol 141:742-53.
9. Gaganis P, Miners JO, Knights KM. (2007). Glucuronidation of fenamates: kinetic studies using human kidney cortical microsomes and recombinant UDP-glucuronosyltransferase (UGT) 1A9 and 2B7. Biochem Pharmacol 73:1683-91.
10. Gamage N, Barnett A, Hempel N, et al. (2006). Human sulfotransferases and their role in chemical metabolism. Toxicol Sci 90:5-22.
11. Herman RJ, Loewen GR, Antosh DM, et al. (1994). Analysis of polymorphic variation in drug metabolism: III. Glucuronidation and sulfation of diflunisal in man. Clin Invest Med 17:297-307.
12. Honma W, Kamiyama Y, Yoshinari K, et al. (2001). Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. Drug Metab Dispos 29:274-81.
13. Houin G, Tremblay D, Bree F, et al. (1983). The pharmacokinetics and availability of niflumic acid in humans. Int J Clin Pharmacol Ther Toxicol 21:130-4.
14. Insel PA. (1990). Analgesic-antipyretics and antiinflammatory agents: drugs employed in the treatment of rheumatoid arthritis and gout. In: Gillman AG, Rall TW, Nies AS, Taylor P, eds. Goodman and Gillman's: the pharmacological basis of therapeutics. 8th ed. New York: Pergamon Press, 638-81.
15. Kaneko T, Chiba H, Horie N, et al. (2009). Effect of Scutellariae Radix ingredients on prostaglandin E2 production and COX-2 expression by LPS-activated macrophage. In Vivo 23:577-81.
16. Kiang TKL, Ensom MHH, Chang TKH. (2005). UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol Ther 106: 97-132.
17. Kim YH, Jeong DW, Paek IB, et al. (2006). Liquid chromatography with tandem mass spectrometry for the simultaneous determination of baicalein, baicalin, oroxylin A and wogonin in rat plasma. J Chromatogr B 844:261-7.
18. King CD, Green MD, Rios GR, et al. (1996). The glucuronidation of exogenous and endogenous compounds by stably expressed rat and human UDP-glucuronosyltransferase 1.1. Arch Biochem Biophys 332: 92-100.
19. Kotani A, Kojima S, Hakamata H, Kusu F. (2006). HPLC with electrochemical detection to examine the pharmacokinetics of baicalin and baicalein in rat plasma after oral administration of a Kampo medicine. Anal Biochem 350:99-104.
20. Krippendorff B-F, Neuhaus R, Lienau P, et al. (2009). Mechanism-based inhibition: deriving KI and kinact directly from time-dependent IC50 values. J Biomol Screening 14:913-23.
21. Kulkarni KH, Wang S, Hu M. (2006). Gender difference affects metabolism of isoflavones in rat intestinal and liver microsomes. 14th North American International Society for the Study of Xenobiotics Meeting. Rio Grande, PR.
22. Lahoz A, Gombau L, Donato MT, et al. (2006). In vitro ADME medium/high-throughput screening in drug preclinical development. Mini-Rev Med Chem 6:1053-62.
23. Lam W, Loi C-M, Atherton J, et al. (2007). Application of in-line liquid chromatography-accurate radioisotope counting-mass spectrometry (LC-ARC-MS) to evaluate metabolic profile of [3H]-mefenamic acid in rat plasma. Drug Metab Lett 1:179-88.
24. Lee BH, Lee SJ, Kang TH, et al. (2000). Baicalein: an in vitro antigenotoxic compound from Scutellaria baicalensis. Planta Med 66:70-1.
25. Li CR, Zhang L, Lin G, Zuo Z. (2011). Identification and quantification of baicalein, wogonin, oroxylin A and their major glucuronide conjugated metabolites in rat plasma after oral administration of Radix scutellariae product. J Pharm Biomed Anal 54:750-8.
26. Li CR, Zhang L, Wo SK, et al. (2012). Pharmacokinetic interactions among major bioactive components in Radix Scutellariae via metabolic competition. Biopharm Drug Dispos 33:487-500.
27. Mackenzie PI, Walter Bock K, Burchell B, et al. (2005). Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677-85.
28. Mano Y, Usui T, Kamimura H. (2006). In vitro inhibitory effects of nonsteroidal anti-inflammatory drugs on 4-methylumbelliferone glucuronidation in recombinant human UDP-glucuronosyltransferase 1A9-potent inhibition by niflumic acid. Biopharm Drug Dispos 27:1-6.
29. Mano Y, Usui T, Kamimura H. (2007). Inhibitory potential of nonsteroidal anti-inflammatory drugs on UDP-glucuronosyltransferase 2B7 in human liver microsomes. Eur J Clin Pharmacol 63:211-16.
30. Mano Y, Usui T, Kamimura H. (2008). Species differences in inhibition potential of nonsteroidal anti-inflammatory drugs against estradiol 3bglucuronidation between rats, dogs, and humans. J Pharm Sci 97: 2805-10.
31. Martignoni M, Groothuis GM, de Kanter R. (2006). Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opin Drug Metabol Toxicol 2:875-94.
32. McEvoy GK. (2003). Nonsteroidal anti-inflammatory agents. AHFS drug handbook. Bethesda: American Society of Health-System Pharmacists, 1902-2021.
33. Montvale NJ. (1999). Physicians' desk reference. Medical Economics Co.
34. Obach RS, Walsky RL, Venkatakrishnan K, et al. (2006). The utility of in vitro cytochrome P450 inhibition data in the prediction of drug-drug interactions. J Pharmacol Exp Ther 316:336-48.
35. Pai TG, Suiko M, Sakakibara Y, Liu M-C. (2001). Sulfation of flavonoids and other phenolic dietary compounds by the human cytosolic sulfotransferases. Biochem Biophys Res Commun 285: 1175-9.
36. Pfeiffer E, Treiling CR, Hoehle SI, Metzler M. (2005). Isoflavones modulate the glucuronidation of estradiol in human liver microsomes. Carcinogenesis 26:2172-8.
37. Pritchard M, Fournel-Gigleux S, Siest G, et al. (1994). A recombinant phenobarbital-inducible rat liver UDP-glucuronosyltransferase (UDPglucuronosyltransferase 2B1) stably expressed in V79 cells catalyzes the glucuronidation of morphine, phenols, and carboxylic acids. Mol Pharmacol 45:42-50.
38. Rao SI, Duffel MW. (1991). Inhibition of aryl sulfotransferase by carboxylic acids. Drug Metab Dispos: Biological Fate Chem 19: 543-5.
39. Riches Z, Stanley EL, Bloomer JC, Coughtrie MWH. (2009). Quantitative evaluation of the expression and activity of five major sulfotransferases (SULTs) in human tissues: the SULT "Pie". Drug Metab Dispos 37:2255-61.
40. Scott G, Nierenberg D. (1992). Pharmacokinetic data for commonly used drugs. In: Melmon KL, Morelli HF, Hoffman BB, Nierenberg DW, eds. Clinical pharmacology. Basic principles in therapeutics. 3rd ed. New York: McGraw-Hill, 1029-72.
41. Small RE, Cox SR, Adams WJ. (1990). Influence of H2 receptor antagonists on the disposition of flurbiprofen enantiomers. J Clin Pharmacol 30:660-4.
42. Su YL, Huang Y, Chen ZY. (2004). Isolation and elucidation of antioxidant constituents from acetone extract in root of Scutellaria rehderiana. China J Chin Mater Med 29:863-4.
43. Vietri M, De Santi C, Pietrabissa A, et al. (2000a). Inhibition of human liver phenol sulfotransferase by nonsteroidal anti-inflammatory drugs. Eur J Clin Pharmacol 56:81-7.
44. Vietri M, Pietrabissa A, Mosca F, Pacifici GM. (2000b). Mycophenolic acid glucuronidation and its inhibition by non-steroidal antiinflammatory drugs in human liver and kidney. Eur J Clin Pharmacol 56:659-64.
45. Williamson G, Barron D, Shimoi K, Terao J. (2005). In vitro biological properties of flavonoid conjugates found in vivo. Free Radical Res 39: 457-69.
46. Yang CH, Tang L, Lv C, et al. (2011). Sulfation of selected monohydroxyflavones by sulfotransferases in vitro: a species and gender comparison. J Pharm Pharmacol 63:967-70.
47. Yang X, Gandhi Y, Duignan D, Morris M. (2009). Prediction of biliary excretion in rats and humans using molecular weight and quantitative structure-pharmacokinetic relationships. AAPS J 11: 511-25.
48. Yuan R, Parmelee T, Balian JD, et al. (1999). In vitro metabolic interaction studies: experience of the Food and Drug Administration. Clin Pharmacol Ther 66:9-15.
49. Yuen AW, Land G, Weatherley BC, Peck AW. (1992). Sodium valproate acutely inhibits lamotrigine metabolism. Br J Clin Pharmacol 33: 511-13.
50. Zhai S, Dai R, Friedman FK, Vestal RE. (1998). Comparative inhibition of human cytochromes P450 1A1 and 1A2 by flavonoids. Drug Metab Dispos 26:989-92.
51. Zhang D, Chando TJ, Everett DW, et al. (2005). In vitro inhibition of UDP glucuronosyltransferases bu Atazanavir and other HIV protease inhibitiors and the relationship of this propertu to in vivo bilirubin glucuronidation. Drug Metab Dispos 33:1729-39.
52. Zhang H, Cui D, Wang B, et al. (2007a). Pharmacokinetic drug interactions involving 17a-ethinylestradiol. Clin Pharmacokinet 46: 133-57.
53. Zhang L, Li C, Lin G, et al. (2011). Hepatic metabolism and disposition of baicalein via the coupling of conjugation enzymes and transporters-in vitro and in vivo evidences. AAPS J 13:378-89.
54. Zhang L, Lin G, Zuo Z. (2007b). Involvement of UDP- glucuronosyltransferases in the extensive liver and intestinal first-pass metabolism of flavonoid baicalein. Pharm Res 24:81-9.
55. Zhou Q, Zheng Z, Xia B, et al. (2010). Use of isoform-specific UGT metabolism to determine and describe rates and profiles of glucuronidation of wogonin and oroxylin A by human liver and intestinal microsomes. Pharm Res 27:1568-83.