Novel mechanisms of nonsteroidal anti-inflammatory drug-induced renal toxicity

Expert Opinion on Drug Metabolism and Toxicology

Volumn 1, Issue 3, 2005, Pages 399-408

  Knights, Kathleen M ^a   Tsoutsikos, Paraskevi ^a   Miners, John O ^a  

^a FLINDERS UNIVERSITY   (Australia)

Author keywords

acyl glucuronides; arachidonic acid; cyclooxygenase; cytochrome P450; lipoxygenase; nephrotoxicity; NSAIDs; renal metabolism; uridine 5 diphosphate glucuronosyltransferases

Indexed keywords

ARACHIDONIC ACID; NONSTEROID ANTIINFLAMMATORY AGENT; PROSTAGLANDIN SYNTHASE;

ANIMAL; CHEMICALLY INDUCED DISORDER; HUMAN; KIDNEY; KIDNEY DISEASE; METABOLISM; PATHOLOGY; PHYSIOLOGY; REVIEW;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ARACHIDONIC ACID; HUMANS; KIDNEY; KIDNEY DISEASES; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES;

EID: 33747824468     PISSN: 17425255     EISSN: 17447607     Source Type: Journal    
DOI: 10.1517/17425255.1.3.399     Document Type: Review

References (69)

1. WHELTON A: Nephrotoxicity of nonsteroidal anti-inflammatory drugs: physiologic foundations and clinical implications. Am. J. Med. (1999) 106(5B):13S-24S. (Pubitemid 29268660)
2. WHELTON A, HAMILTON CW: Nonsteroidal anti-inflammatory drugs: Effects on kidney function. J. Clin. Pharmacol. (1991) 31:588-598.
3. BENNETT HH: The effects of nonsteroidal anti-inflammatory drugs on renal function. Physician Assistant (2002) 26(2):38-42.
4. WINDER CV: Experimental observations of flufenamic, mefenamic, and meclofenamic acids. I. Pharmacology. Annals. Phys. Med. (1966) Suppl. 1:7-16.
5. HARDY TL: N-phenylanthranilic acid: an agent for inducing and studying renal papillary necrosis in the rat. Br. J. Exp. Pathol. (1970) 51(4):348-355.
6. ROBERTSON CE, FORD MJ, VAN SOMEREN V, DLUGOLECKA M, PRESCOTT LF: Mefenamic acid nephropathy. Lancet (1980) 2(8188):232-233. (Pubitemid 10084828)
7. BREZIN JH, KATZ SM, SCHWARTZ AB, CHINITZ JL: Reversible renal failure and nephrotic syndrome associated with nonsteroidal anti-inflammatory drugs. NEJM (1979) 301(23):1271-1273. (Pubitemid 10199255)
8. BRASH AR: Arachidonic acid as a bioactive molecule. J. Clin. Invest. (2001) 107(11):1339-1345. (Pubitemid 32522025)
9. PARENTE L, PERRETTI M: Advances in the pathophysiology of constitutive and inducible cyclooxygenases: two enzymes in the spotlight. Biochem. Pharmacol. (2003) 65:153-159. (Pubitemid 36015818)
10. SIMMONS DL, BOTTING RM, HLA T: Cyclooxygenase isozymes: the biology of prostaglandin synthesis and inhibition. Pharmacol. Rev. (2004) 56:387-437. (Pubitemid 39096597)
11. NANTEL F, MEADOWS E, DENIS D, CONNOLLY B, METTERS KM, GIAID A: Immunolocalization of cyclooxygenase-2 in the macula densa of human elderly. FEBS Letters (1999) 457:475-477. (Pubitemid 29414746)
12. KOMHOFF M, GRONE HJ, KLEIN T, SEYBERTH HW, NUSING RM: Localization of cyclooxygenase-1 and -2 in adult and fetal human kidney: implication for renal function. Am. J. Physiol. Renal. (1997) 272:F460-F468.
13. HARRIS RC, MCKANNA JA, AKAI Y et al.: Cyclooxygenase-2 is associated with the macula densa of rat kidney and increases with salt restriction. J. Clin. Invest. (1994) 94:2504-2510. (Pubitemid 24379628)
14. MINERS JO, SMITH PA, SORICH MJ, McKINNON RA, MACKENZIE PI: Predicting human drug glucuronidation parameters: application of in vitro and in silico modelling approaches. Ann. Rev. Pharmacol. Toxicol. (2002) 44:1-25. (Pubitemid 38268090)
15. PRITCHARD M, FOURNEL-GIGLEUX S, SIEST G, MACKENZIE P, MAGDALOU J: A recombinant phenobarbital-inducible rat liver UDP-glucuronosyltransferase (UDPglucuronosyltransferase 2B1) stably expressed in V79 cells catalyses the glucuronidation of morphine, phenols and carboxylic acids. Mol. Pharmacol. (1994) 45(1):42-50.
16. JUDE AR, LITTLE JM, FREEMAN JP et al.: Linoleic acid diols are novel substrates for human UDP-glucuronosyltransferases. Arch. Biochem. Biophys. (2000) 380:294-302. (Pubitemid 30659099)
17. JUDE AR, LITTLE JM, CZERNIK PJ, TEPHLY TR, GRANT DF, RADOMINSKA-PANDYA A: Glucuronidation of linoleic acid diols by human microsomal and recombinant UDPglucuronosyltransferases: identification of UGT2B7 as the major isoform involved. Arch. Biochem. Biophys. (2001) 389:176-186. (Pubitemid 32881943)
18. JUDE AR, LITTLE JM, BULL AW, PODGORSKI I, RADOMINSKAPANDYA A: 13-Hydroxy- and 13- oxooctadecadienoic acids: novel substrates for human UDP-glucuronosyltransferases. Drug Metab. Dispos. (2001) 29:652-655. (Pubitemid 32374565)
19. SONKA J, LITTLE J, SAMOKYSZYN V, RADOMINSKA-PANDYA A: Glucuronidation of arachidonic acid, 20- hydroxy-eicosatetraenoic acid and prostaglandin E2 by human hepatic and intestinal UDP-glucuronosyltransferases and recombinant UGT2B7. Proceedings of the 11th North American ISSX Meeting, USA. Drug Metab. Rev. (2002) 34(Suppl. 1):194.
20. IMIG JD: Eicosanoid regulation of renal vasculature. Am. J. Physiol. (2000) 279:F965-F981.
21. WHEELAN P, HANKIN JA, BILIR B, GUENETTE D, MURPHY RC: Metabolic transformations of leukotriene B4 in primary cultures of human hepatocytes. JPET (1999) 288:326-334. (Pubitemid 29113507)
22. BERRY KA, BORGEA P, GOSSELIN J, FLAMAND L, MURPHY RC: Urinary metabolites of leukotriene B4 in the human subject. J. Biol. Chem. (2003) 278(27):24449-24460. (Pubitemid 37548596)
23. TURGEON D, CHOUINARD S, BELANGER P, et al.: Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases. J. Lipid Res. (2003) 44:1182-1191. (Pubitemid 37279636)
24. TUKEY RH, STRASSBURG CP: Human UDP-glucuronosyltransferases, metabolism, expression and disease. Ann. Rev. Pharmacol. Toxicol. (2000) 40:581-616. (Pubitemid 30340694)
25. TURGEON D, CARRIER JS, LEVESQUE E, HUM DW, BELANGER A: Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolising UGT2B subfamily members. Endocrinology (2001) 142:778-787. (Pubitemid 32222427)
26. BEAULIEU M, LEVESQUE E, HUM DW, BELANGER A: Isolation and characterization of a human orphan UDPglucuronosyltransferase, UGT2B11. Biochem. Biophys. Res. Commun. (1998) 248:44-50. (Pubitemid 28418184)
27. ROMAN RJ: P450 metabolites of arachidonic acid in the control of cardiovascular function. Physiol. Rev. (2002) 82:131-185. (Pubitemid 34654217)
28. PRAKASH C, ZHANG JY, FALCK JR, CHAUHAN K, BLAIR IA: 20- Hydroxyeicosatetraenoic acid is excreted as a glucuronide conjugate in human urine. Biochem. Biophys. Res. Comm. (1992) 185(2):728-733.
29. LITTLE JM, KURKELA M, SONKA J et al.: Glucuronidation of oxidised fatty acids and prostaglandins B1 and E2 by human hepatic and recombinant UDPglucuronosyltransferases (UGT). J. Lipid Res. (2004) 45(9):1694-1703. (Pubitemid 39296209)
30. CAO Y, PEARMAN AT, ZIMMERMAN GA, MCINTYRE TM, PRESCOTT SM: Intracellular unesterified arachidonic acid signals apoptosis. Proc. Natl. Acad. Sci. (2000) 97(21):11280-11285.
31. MORAN JH, NOWAK G, GRANT DF: Analysis of the toxic effects of linoleic acid, 12,13-cis-epoxyoctadecenoic acid, and 12,13-dihydroxyoctadecenoic acid in rabbit renal cortical mitochondria. Toxicol. Appl. Pharmacol. (2001) 172(2):150-161. (Pubitemid 32373137)
32. MORAN JH, WEISE R, SCHNELLMANN RG, FREEMAN JP, GRANT DF: Cytotoxicity of linoleic acid diols to renal proximal tubular cells. Toxicol. Appl. Pharmacol. (1997) 146(1):53-59. (Pubitemid 27406396)
33. VANE JR: Towards a better aspirin. Nat. New Biol. (1994) 367:215-216.
34. MEADE EA, SMITH WL, DEWITT DL: Differential inhibition of prostaglandin endoperoxide synthase (cyclooxygenase) isozymes by aspirin and other non-steroidal anti-inflammatory drugs. J. Biol. Chem. (1993) 268(9):6610-6614. (Pubitemid 23099364)
35. MITCHELL JA, AKARASEREENONT P, THIEMERMANN C, FLOWER RJ, VANE JR: Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc. Natl. Acad. Sci. (1994) 90:11693-11697.
36. GIERSE JK, HAUSER SD, CREELY DP et al.: Expression and selective inhibition of the constitutive and inducible forms of human cyclo-oxygenase. Biochem. J. (1995) 305:479-484.
37. BRATER DC, HARRIS C, REDFERN JS, GERTZ BJ: Renal effects of COX-2 selective inhibitors. Am. J. Nephrol. (2001) 21:1-15. (Pubitemid 32238607)
38. KRAMER BK, KAMMERL MC, KOMHOFF M: Renal cyclooxygenase-2 (COX-2) physiological, pathophysiological, and clinical implications. Kidney Blood Press. Res. (2004) 27:43-62. (Pubitemid 38186474)
39. PERAZELLA MA, TRAY K: Selective COX-2 inhibitors: a pattern of nephrotoxicity similar to traditional nonsteroidal anti-inflammatory drugs. Am. J. Med. (2001) 111:64-67. (Pubitemid 32635263)
40. AHMAD SR, KORTEPETER C, BRINKER A, CHEN M, BEITZ J: Renal failure associated with the use of celecoxib and rofecoxib. Drug Safety (2002) 25(7):537-544. (Pubitemid 34827919)
41. GAMBORO G, PERAZELLA MA: Adverse renal effects of anti-inflammatory agents: evaluation of selective and nonselective cyclooxygenase inhibitors. J. Int. Med. (2003) 253:643-652. (Pubitemid 36649096)
42. SANDHU GK, HEYNEMAN CA: Nephrotoxic potential of selective cyclooxygenase-2 inhibitors. Ann Pharmacother. (2004) 38:700-704. (Pubitemid 38352237)
43. MCGURK KA, BRIERLY CH, BURCHELL B: Drug glucuronidation by human renal UDPglucuronosyltransferases. Biochem. Pharmacol. (1998) 55(7):1005-1012. (Pubitemid 28167722)
44. BOWALGAHA K, MINERS JO: The glucuronidation of mycophenolic acid by human liver, kidney and jejunum microsomes. Br. J. Clin. Pharmacol. (2001) 52:605-609.
45. JIN C, MINERS JO, LILLYWHITE KJ, MACKENZIE PI: Complementary deoxyribonucleic acid cloning and expression of human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs. J. Phamacol. Exp. Ther. (1993) 264(1):475-479. (Pubitemid 23309239)
46. KING C, TANG W, NGUI J, TEPHLY T, BRAUN M: Characterization of rat and human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of diclofenac. Toxicol. Sci. (2001) 61(1):49-53. (Pubitemid 32409686)
47. SAKAGUCHI K, GREEN M, STOCK N, REGER TS, ZUNIC J, KING C: Glucuronidation of carboxylic acid containing compounds by UDPglucuronosyltransferase isoforms. Arch. Biochem. Biophys. (2004) 424(2):219-225. (Pubitemid 38401955)
48. TSOUTSIKOS P, MINERS JO, KNIGHTS KM: Glucuronidation of fenamates by human renal and recombinant UDP-glucuronosyltransferases (UGT). Proceedings of the 8th World Conference on Clinical Pharmacology and Therapeutics, Australia. Clin. Exp. Physiol. Pharmacol. (2004) 31(Suppl. 1):A142.
49. KNIGHTS KM, TSOUTSIKOS P, BOWALGAHA K, ELLIOT DJ, MINERS JO: Kinetic characterisation of S-naproxen glucuronidation by human kidney cortical microsomes and recombinant UGT1A9 and UGT2B7. Proceedings of the 7th International ISSX Meeting, Canada. Drug Metab. Rev. (2004) 36(Suppl. 1):135.
50. CARROLL MA, KEMP R, CHENG MK, MCGIFF JC: Regulation of preglomerular microvascular 20-hydroxyeicosatetraenoic acid levels. Med. Sci. Monitor (2001) 7(4):567-572. (Pubitemid 32691729)
51. TSOUTSIKOS, P MINERS JO, STAPLETON A, et al.: Evidence that unsaturated fatty acids are potent inhibitors of renal UDP-glucuronosyltransferases (UGT): kinetic studies using human kidney cortical microsomes and recombinant UGt1A9 and UGT2B7. Biochem. Pharmacol. (2004) 67:191-199. (Pubitemid 37518547)
52. LASKER JM, CHEN WB, WOLF I, BLOSWICK BP, WILSON PD, POWELL PK: Formation of 20- hydroxyeicosatetraenoic acid, a vasoactive and natriuretic eicosanoid, in human kidney. Role of CYP4F2 and CYP4A11. J. Biol. Chem. (2000) 275(6):4118-4126. (Pubitemid 30094644)
53. PAULSON SK, ZHANG JY, JESSEN SM et al.: Comparison of celecoxib metabolism and excretion in mouse, rabbit, dog, cynomolgus monkey and rhesus monkey. Xenobiotica (2000) 30(70):731-744. (Pubitemid 30623545)
54. ZHANG JY, YUAN JJ, WANG Y-F, BIBLE RH, BREAU AP: Pharmacokinetics and metabolism of a COX-2 inhibitor, valdecoxib, in mice. DMD (2003) 31:491-501. (Pubitemid 36378528)
55. ZHANG JY, ZHAN J, COOK CS, INGS RM, BREAU AP: Involvement of human UGT2B7 and 2B15 in rofecoxib metabolism. DMD (2003) 31:652-658. (Pubitemid 36444175)
56. MURRAY MD, BRATER DC: Renal toxicity of the nonsteroidal antiinflammatory drugs. Ann. Rev. Pharmacol. Toxicol. (1993) 32:435-465. (Pubitemid 23116014)
57. FOSTER RT, JAMALI F, RUSSELL AS, ALBALLA SR: Pharmacokinetics of ketoprofen enantiomers in young and elderly arthritic patients following single and multiple doses. J. Pharm. Sci. (1988) 77(3):191-195.
58. GRUBB NG, RUDY DW, BRATER DC, HALL SD: Stereoselective pharmacokinetics of ketoprofen and ketoprofen glucuronide in end-stage renal disease: evidence for a ?futile cycle? of elimination. Br. J. Clin. Pharmacol. (1999) 48:494-500. (Pubitemid 29454228)
59. DICKINSON RG, KING AR Studies on the reactivity of acyl glucuronides - II. Interaction of diflunisal acyl glucuronide and its isomers with human serum albumin in vitro. Biochem. Pharmacol. (1991) 42:2301-2306.
60. SALLUSTIO BC, SABORDO L, EVANS AM, NATION RL: Hepatic disposition of electrophilic acyl glucuronide conjugates. Curr. Drug Metab. (2000) 1:163-180.
61. MCGURK KA, REMMEL RP, HOSAGRAHARA VP, TOSH D, BURCHELL B: Reactivity of mefenamic acid 1-O-acyl glucuronide with proteins in vitro and ex vivo. DMD (1996) 24(8):842-849. (Pubitemid 26274740)
62. ZHOU S, CHAN E, DUAN W, HUANG W, CHEN Y-Z: Drug bioactivation, covalent binding to target proteins and toxicity relevance. Drug Metab. Rev. (2005) 37(1):41-213. (Pubitemid 40259715)
63. TERRIER N, BENOIT E, SENAY C, et al.: Human and rat liver UDPglucuronosyltransferase are targets of ketoprofen acylglucuronide. Mol. Pharmacol. (1999) 56:226-234. (Pubitemid 29309832)
64. WHELTON A, STURMER T, PORTER GA: Non-steroidal antiinflammatory drugs. In: Clinical nephrotoxins, 2nd edn. ME De Broe, GA Porter, WM Bennett, GA Verpooten (Eds), Kluwer Academic Publishers, Dordrecht, Germany (2003):280-306.
65. FIORUCCI S, MELI R, BUCCI M, CIRINO G: Dual inhibitors of cyclooxygenase and 5-lipoxygenase. A new avenue in anti-inflammatory therapy? Biochem. Pharmacol. (2001) 62:1433-1438. (Pubitemid 33145286)
66. CELOTTI F, LAUFER S: Antiinflammatory drugs: new multitarget compounds to face an old problem. The dual inhibition concept. Pharmacol. Res. (2001) 43(5):429-436. (Pubitemid 32578858)
67. BERTOLINI A, OTTANI A, SANDRINI M: Dual acting antiinflammatory drugs: A reappraisal. Pharmacol. Res. (2001) 44(6):437-450. (Pubitemid 34014322)
68. GAMBARO G: Strategies to safely interfere with prostanoid activity while avoiding adverse renal effects: could COX-2 and COX-LOX dual inhibition be the answer? Nephrol. Dial. Transplant (2002) 17:1159-1162. (Pubitemid 34812056)
69. http://www.tga.gov.au