Differences in the disposition of silymarin between patients with nonalcoholic fatty liver disease and chronic hepatitis C

Drug Metabolism and Disposition

Volumn 39, Issue 12, 2011, Pages 2182-2190

  Schrieber, Sarah J ^a,j   Hawke, Roy L ^a   Wen, Zhiming ^b   Smith, Philip C ^b   Reddy, K Rajender ^d   Wahed, Abdus S ^e   Belle, Steven H ^e   Afdhal, Nezam H ^f   Navarro, Victor J ^g   Meyers, Catherine M ^h   Doo, Edward ⁱ   Fried, Michael W ^c  

^a University of North Carolina   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

^c UNIVERSITY OF NORTH CAROLINA SCHOOL OF MEDICINE   (United States)

^d UNIVERSITY OF PENNSYLVANIA   (United States)

^e UNIVERSITY OF PITTSBURGH GRADUATE SCHOOL OF PUBLIC HEALTH   (United States)

^f BETH ISRAEL DEACONESS MEDICAL CENTER   (United States)

^g THOMAS JEFFERSON UNIVERSITY   (United States)

^h NATIONAL INSTITUTES OF HEALTH   (United States)

ⁱ NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^j CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

more..

Author keywords

[No Author keywords available]

Indexed keywords

FLAVONOLIGNAN; ISOSILYBIN A; ISOSILYBIN B; PLACEBO; SILICRISTIN; SILIDIANIN; SILYBIN A; SILYBIN B; SILYMARIN; UNCLASSIFIED DRUG;

ABDOMINAL PAIN; ADULT; AREA UNDER THE CURVE; ARTICLE; BLOOD SAMPLING; CLINICAL ARTICLE; COHORT ANALYSIS; CONTROLLED STUDY; DIZZINESS; DRUG ACCUMULATION; DRUG BLOOD LEVEL; DRUG DISPOSITION; DRUG DOSE COMPARISON; DRUG EFFICACY; DRUG ELIMINATION; DRUG HALF LIFE; DRUG INDUCED HEADACHE; DRUG METABOLISM; FEMALE; GASTROINTESTINAL TOXICITY; HEPATITIS C; HUMAN; MALE; MAXIMUM PLASMA CONCENTRATION; NONALCOHOLIC FATTY LIVER; PHASE 1 CLINICAL TRIAL; PRIORITY JOURNAL; RANDOMIZED CONTROLLED TRIAL; RESPIRATORY TRACT INFECTION; SINGLE DRUG DOSE; STEADY STATE; TIME TO MAXIMUM PLASMA CONCENTRATION; TREATMENT DURATION; TREATMENT RESPONSE;

ADULT; AREA UNDER CURVE; FATTY LIVER; FEMALE; HALF-LIFE; HEPATITIS C, CHRONIC; HUMANS; MALE; MIDDLE AGED; SILYMARIN;

HEPATITIS C VIRUS; SILYBUM MARIANUM;

EID: 81855217432     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.111.040212     Document Type: Article

References (37)

1. Abenavoli L, Capasso R, Milic N, and Capasso F (2010) Milk thistle in liver diseases: past, present, future. Phytother Res 24:1423-1432.
2. Borst P, Zelcer N, and van de Wetering K (2006) MRP2 and 3 in health and disease. Cancer Lett 234:51-61. (Pubitemid 43343940)
3. Chalasani N, Deeg MA, and Crabb DW (2004) Systemic levels of lipid peroxidation and its metabolic and dietary correlates in patients with nonalcoholic steatohepatitis. Am J Gastroenterol 99:1497-1502. (Pubitemid 39193189)
4. Chalon SA, Desager JP, Desante KA, Frye RF, Witcher J, Long AJ, Sauer JM, Golnez JL, Smith BP, Thomasson HR, et al. (2003) Effect of hepatic impairment on the pharmacokinetics of atomoxetine and its metabolites. Clin Pharmacol Ther 73:178-191. (Pubitemid 36269669)
5. Chandra P and Brouwer KL (2004) The complexities of hepatic drug transport: current knowledge and emerging concepts. Pharm Res 21:719-735. (Pubitemid 39011292)
6. Cheng Q, Aleksunes LM, Manautou JE, Cherrington NJ, Scheffer GL, Yamasaki H, and Slitt AL (2008) Drug-metabolizing enzyme and transporter expression in a mouse model of diabetes and obesity. Mol Pharm 5:77-91. (Pubitemid 351300037)
7. Congiu M, Mashford ML, Slavin JL, and Desmond PV (2002) UDP glucuronosyltransferase mRNA levels in human liver disease. Drug Metab Dispos 30:129-134. (Pubitemid 34106530)
8. Congiu M, Mashford ML, Slavin JL, and Desmond PV (2009) Coordinate regulation of metabolic enzymes and transporters by nuclear transcription factors in human liver disease. J Gastroenterol Hepatol 24:1038-1044.
9. Day CP and James OF (1998) Steatohepatitis: a tale of two "hits"? Gastroenterology 114:842-845.
10. Fisher CD, Lickteig AJ, Augustine LM, Ranger-Moore J, Jackson JP, Ferguson SS, and Cherrington NJ (2009) Hepatic cytochrome P450 enzyme alterations in humans with progressive stages of nonalcoholic fatty liver disease. Drug Metab Dispos 37:2087-2094.
11. Flora K, Hahn M, Rosen H, and Benner K (1998) Milk thistle (Silybum marianum) for the therapy of liver disease. Am J Gastroenterol 93:139-143. (Pubitemid 29063954)
12. Freedman ND, Curto TM, Morishima C, Seeff LB, Goodman ZD, Wright EC, Sinha R, Everhart JE, and HALT-C Trial Group (2011) Silymarin use and liver disease progression in the Hepatitis C Antiviral Long-Term Treatment against Cirrhosis trial. Aliment Pharmacol Ther 33:127-137.
13. Galli A, Svegliati-Baroni G, Ceni E, Milani S, Ridolfi F, Salzano R, Tarocchi M, Grappone C, Pellegrini G, Benedetti A, et al. (2005) Oxidative stress stimulates proliferation and invasiveness of hepatic stellate cells via a MMP2-mediated mechanism. Hepatology 41:1074 -1084.
14. Geier A, Dietrich CG, Grote T, Beuers U, Prüfer T, Fraunberger P, Matern S, Gartung C, Gerbes AL, and Bilzer M (2005) Characterization of organic anion transporter regulation, glutathione metabolism and bile formation in the obese Zucker rat. J Hepatol 43:1021-1030. (Pubitemid 41627988)
15. György I, Antus S, Blázovics A, and Földiák G (1992) Substituent effects in the free radical reactions of silybin: radiation-induced oxidation of the flavonoid at neutral pH. Int J Radiat Biol 61:603-609.
16. Hawke RL, Schrieber SJ, Soule TA, Wen Z, Smith PC, Reddy KR, Wahed AS, Belle SH, Afdhal NH, Navarro VJ, et al. (2010) Silymarin ascending multiple oral dosing phase I study in noncirrhotic patients with chronic hepatitis C. J Clin Pharmacol 50:434-449.
17. Jain SK, Pemberton PW, Smith A, McMahon RF, Burrows PC, Aboutwerat A, and Warnes TW (2002) Oxidative stress in chronic hepatitis C: not just a feature of late stage disease. J Hepatol 36:805-811. (Pubitemid 35177411)
18. Jančová P, Siller M, Anzenbacherová E, Křen V, Anzenbacher P, and Simánek V (2011) Evidence for differences in regioselective and stereoselective glucuronidation of silybin diastereomers from milk thistle (Silybum marianum) by human UDP-glucuronosyltransferases. Xenobiotica 41:743-751.
19. Kim NC, Graf TN, Sparacino CM, Wani MC, and Wall ME (2003) Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum). Org Biomol Chem 1:1684-1689.
20. Koruk M, Taysi S, Savas MC, Yilmaz O, Akcay F, and Karakok M (2004) Oxidative stress and enzymatic antioxidant status in patients with nonalcoholic steatohepatitis. Ann Clin Lab Sci 34:57-62. (Pubitemid 38280304)
21. Lang I (2006) Phase I/II clinical trial to explore silymarin in chronic liver diseases. Gastroenterol Hepatol News 131:990.
22. Leslie EM, Deeley RG, and Cole SP (2005) Multidrug resistance proteins: role of P-glycoprotein, MRP1, MRP2, and BCRP (ABCG2) in tissue defense. Toxicol Appl Pharmacol 204:216 -237.
23. Lickteig AJ, Fisher CD, Augustine LM, Aleksunes LM, Besselsen DG, Slitt AL, Manautou JE, and Cherrington NJ (2007) Efflux transporter expression and acetaminophen metabolite excretion are altered in rodent models of nonalcoholic fatty liver disease. Drug Metab Dispos 35:1970-1978. (Pubitemid 47481594)
24. Medina J and Moreno-Otero R (2005) Pathophysiological basis for antioxidant therapy in chronic liver disease. Drugs 65:2445-2461. (Pubitemid 41697314)
25. Miranda SR, Lee JK, Brouwer KL, Wen Z, Smith PC, and Hawke RL (2008) Hepatic metabolism and biliary excretion of silymarin flavonolignans in isolated perfused rat livers: role of multidrug resistance-associated protein 2 (Abcc2). Drug Metab Dispos 36:2219-2226.
26. Ogasawara K, Terada T, Katsura T, Hatano E, Ikai I, Yamaoka Y, and Inui K (2010) Hepatitis C virus-related cirrhosis is a major determinant of the expression levels of hepatic drug transporters. Drug Metab Pharmacokinet 25:190-199.
27. Richardson TA, Sherman M, Kalman D, and Morgan ET (2006) Expression of UDP-glucuronosyltransferase isoform mRNAs during inflammation and infection in mouse liver and kidney. Drug Metab Dispos 34:351-353. (Pubitemid 43290891)
28. Schinkel AH and Jonker JW (2003) Mammalian drug efflux transporters of the ATP binding cassette (ABC) family: an overview. Adv Drug Deliv Rev 55:3-29. (Pubitemid 36078452)
29. Schrieber SJ, Wen Z, Vourvahis M, Smith PC, Fried MW, Kashuba AD, and Hawke RL (2008) The pharmacokinetics of silymarin is altered in patients with hepatitis C virus and nonalcoholic fatty liver disease and correlates with plasma caspase-3/7 activity. Drug Metab Dispos 36:1909-1916.
30. Sookoian S, Castaño G, Gianotti TF, Gemma C, and Pirola CJ (2009) Polymorphisms of MRP2 (ABCC2) are associated with susceptibility to nonalcoholic fatty liver disease. J Nutr Biochem 20:765-770.
31. Sridar C, Goosen TC, Kent UM, Williams JA, and Hollenberg PF (2004) Silybin inactivates cytochromes P450 3A4 and 2C9 and inhibits major hepatic glucuronosyltransferases. Drug Metab Dispos 32:587-594. (Pubitemid 38668150)
32. Strader DB, Bacon BR, Lindsay KL, La Brecque DR, Morgan T, Wright EC, Allen J, Khokar MF, Hoofnagle JH, and Seeff LB (2002) Use of complementary and alternative medicine in patients with liver disease. Am J Gastroenterol 97:2391-2397.
33. van de Steeg E, Wagenaar E, van der Kruijssen CM, Burggraaff JE, de Waart DR, Elferink RP, Kenworthy KE, and Schinkel AH (2010) Organic anion transporting polypeptide 1a/1b-knockout mice provide insights into hepatic handling of bilirubin, bile acids, and drugs. J Clin Invest 120:2942-2952.
34. Wagner M, Halilbasic E, Marschall HU, Zollner G, Fickert P, Langner C, Zatloukal K, Denk H, and Trauner M (2005) CAR and PXR agonists stimulate hepatic bile acid and bilirubin detoxification and elimination pathways in mice. Hepatology 42:420-430. (Pubitemid 41061095)
35. Wen Z, Dumas TE, Schrieber SJ, Hawke RL, Fried MW, and Smith PC (2008) Pharmacokinetics and metabolic profile of free, conjugated, and total silymarin flavonolignans in human plasma after oral administration of milk thistle extract. Drug Metab Dispos 36:65-72.
36. Wu CP, Calcagno AM, Hladky SB, Ambudkar SV, and Barrand MA (2005) Modulatory effects of plant phenols on human multidrug-resistance proteins 1, 4 and 5 (ABCC1, 4 and 5). FEBS J 272:4725-4740. (Pubitemid 41366995)
37. 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.