Amide hydrolysis of a novel chemical series of microsomal prostaglandin e synthase-1 inhibitors induces kidney toxicity in the rat

Drug Metabolism and Disposition

Volumn 41, Issue 3, 2013, Pages 634-641

  Bylund, Johan ^a,b   Annas, Anita ^a   Hellgren, Dennis ^a   Bjurström, Sivert ^a   Andersson, Hakan ^a   Svanhagen, Alexander ^a  

^a ASTRAZENECA R AND D   (Sweden)

^b UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AZ 0908; AZ 4270; AZ 4284; AZ 7847; CREATININE; PROSTAGLANDIN E SYNTHASE 1 INHIBITOR; PROSTAGLANDIN SYNTHASE INHIBITOR; UNCLASSIFIED DRUG; UREA;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; AREA UNDER THE CURVE; ARTICLE; CONTROLLED STUDY; CREATININE BLOOD LEVEL; FEMALE; HISTOPATHOLOGY; HUMAN; HUMAN CELL; HYDROLYSIS; LIVER CELL; MALE; MAXIMUM PLASMA CONCENTRATION; NEPHROTOXICITY; NONHUMAN; PRIORITY JOURNAL; RAT; TOXICITY TESTING; TOXICOKINETICS; UREA BLOOD LEVEL;

ANIMALS; BIOTRANSFORMATION; DOGS; DRUG DESIGN; ENZYME INHIBITORS; FEMALE; HEPATOCYTES; HUMANS; HYDROLYSIS; INTRAMOLECULAR OXIDOREDUCTASES; KIDNEY; KIDNEY DISEASES; MALE; METABOLOMICS; RATS; RATS, SPRAGUE-DAWLEY; RATS, WISTAR; SULFONAMIDES; TOXICITY TESTS;

EID: 84874063962     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.112.048983     Document Type: Article

References (20)

1. Bancroft JD and Gamble M (2008) Theory and Practice of Histological Techniques, 6th ed, Churchill Livingstone, Edinburgh. Briem S, Martinsson S, Bueters T, and Skoglund E (2007) Combined approach for highthroughput preparation and analysis of plasma samples from exposure studies. Rapid Commun Mass Spectrom 21:1965-1972.
2. Bylund J, Ek ME, Kers A, Nordvall G, Ohberg L, Viklund J, von Berg S, Holenz J, Narhi K, Sohn D, and Johansson MH (2009) inventors, AstraZeneca AB, assignee. Bis-(sulfonylamino) derivatives in therapy 065. U.S. patent 2009/0131468 A1. 2009 May 21.
3. Depré M, Ehrich E, Van Hecken A, De Lepeleire I, Dallob A, Wong P, Porras A, Gertz BJ, and De Schepper PJ (2000) Pharmacokinetics, COX-2 specificity, and tolerability of supratherapeutic doses of rofecoxib in humans. Eur J Clin Pharmacol 56:167-174.
4. Fleck C, Nguyen TT, and Bräunlich H (1988) Relation between renal and hepatic excretion of drugs. XI. Excretion of sulfonamides with various physico-chemical properties of different ages-influence of nephrectomy or bile duct ligation. Exp Pathol 35:115-127.
5. Floby E, Johansson J, Hoogstraate J, Hewitt NJ, Hill J, and Sohlenius-Sternbeck A-K (2009) Comparison of intrinsic metabolic clearance in fresh and cryopreserved human hepatocytes. Xenobiotica 39:656-662.
6. Gnann JW, Jr, Barton NH, and Whitley RJ (1983) Acyclovir: mechanism of action, pharmacokinetics, safety and clinical applications. Pharmacotherapy 3:275-283.
7. Hein R, Brunkhorst R, Thon WF, Schedel I, and Schmidt RE (1993) Symptomatic sulfadiazine crystalluria in AIDS patients: a report of two cases. Clin Nephrol 39:254-256.
8. Huntjens DR, Danhof M, and Della Pasqua OE (2005) Pharmacokinetic- pharmacodynamic correlations and biomarkers in the development of COX-2 inhibitors. Rheumatology (Oxford) 44:846-859.
9. Huntjens DR, Spalding DJ, Danhof M, and Della Pasqua OE (2006) Correlation between in vitro and in vivo concentration-effect relationships of naproxen in rats and healthy volunteers. Br J Pharmacol 148:396-404.
10. Iyer JP, Srivastava PK, Dev R, Dastidar SG, and Ray A (2009) Prostaglandin E2 synthase inhibition as a therapeutic target. Expert Opin Ther Targets 13:849-865.
11. Jonsson O, Palma Villar R, Nilsson LB, Norsten-Höög C, Brogren J, Eriksson M, Königsson K, and Samuelsson A (2012) Capillary microsampling of 25 ml blood for the determination of toxicokinetic parameters in regulatory studies in animals. Bioanalysis 4:661-674.
12. Nilsson A, Forngren B, Bjurström S, Goodwin RJA, Basmaci E, Gustafsson I, Annas A, Hellgren D, Svanhagen A,, Andrén PE, and Lindberg J (2012) In situ mass spectrometry imaging and ex vivo characterization of renal crystalline deposits induced in multiple preclinical drug toxicology studies. PLoS ONE 7:e47353.
13. Perazella MA (1999) Crystal-induced acute renal failure. Am J Med 106:459-465.
14. Samuelsson B, Morgenstern R, and Jakobsson PJ (2007) Membrane prostaglandin E synthase-1: a novel therapeutic target. Pharmacol Rev 59:207-224.
15. Sohlenius-Sternbeck A-K, Afzelius L, Prusis P, Neelissen J, Hoogstraate J, Johansson J, Floby E, Bengtsson A, Gissberg O, and Sternbeck J, et al. (2010) Evaluation of the human prediction of clearance from hepatocyte and microsome intrinsic clearance for 52 drug compounds. Xenobiotica 40:637-649.
16. Testa B and Krämer SD (2007) The biochemistry of drug metabolism-an introduction: part 3. Reactions of hydrolysis and their enzymes. Chem Biodivers 4:2031-2122.
17. Wang M and FitzGerald GA (2010) Cardiovascular biology of microsomal prostaglandin E synthase-1. Trends Cardiovasc Med 20:189-195.
18. Xu D, Rowland SE, Clark P, Giroux A, Côté B, Guiral S, Salem M, Ducharme Y, Friesen RW, and Méthot N, et al. (2008) MF63 [2-(6-chloro-1H-phenanthro[9,10-d]imidazol-2-yl)-isophthalonitrile], a selective microsomal prostaglandin E synthase-1 inhibitor, relieves pyresis and pain in preclinical models of inflammation. J Pharmacol Exp Ther 326:754-763.
19. Yang X, Gandhi YA, Duignan DB, and Morris ME (2009) Prediction of biliary excretion in rats and humans using molecular weight and quantitative structure-pharmacokinetic relationships. AAPS J 11:511-525.
20. Yarlagadda SG and Perazella MA (2008) Drug-induced crystal nephropathy: an update. Expert Opin Drug Saf 7:147-158.