Phospho-ibuprofen (MDC-917) is a novel agent against colon cancer: Efficacy, metabolism, and pharmacokinetics in mouse models

Journal of Pharmacology and Experimental Therapeutics

Volumn 337, Issue 3, 2011, Pages 876-886

  Xie, Gang ^a   Sun, Yu ^a   Nie, Ting ^a   Mackenzie, Gerardo G ^a   Huang, Liqun ^a   Kopelovich, Levy ^b   Komninou, Despina ^c   Rigas, Basil ^a  

^a STONY BROOK UNIVERSITY   (United States)

^b NATIONAL CANCER INSTITUTE   (United States)

^c Medicon Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXYPHOSPHOIBUPROFEN; 2 HYDROXYPHOSPHOIBUPROFEN; ANTINEOPLASTIC AGENT; CARBOXYIBUPROFEN; CARBOXYPHOSPHOIBUPROFEN; DRUG METABOLITE; IBUPROFEN; IBUPROFEN DERIVATIVE; IBUPROFEN GLUCURONIDE; MDC 917; PHOSPHOIBUPROFEN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER CELL; CANCER INHIBITION; CANCER MODEL; COLON CANCER; CONTROLLED STUDY; DRUG ABSORPTION; DRUG DISTRIBUTION; DRUG EFFICACY; DRUG ELIMINATION; DRUG HALF LIFE; DRUG METABOLISM; DRUG SAFETY; DRUG TISSUE LEVEL; DRUG TRANSFORMATION; FEMALE; HUMAN; HUMAN CELL; HYDROLYSIS; IN VITRO STUDY; LIVER MICROSOME METABOLISM; MAXIMUM PLASMA CONCENTRATION; MOUSE; NONHUMAN; OXIDATION; PLASMA CONCENTRATION-TIME CURVE; PRIORITY JOURNAL; SINGLE DRUG DOSE; TIME TO MAXIMUM PLASMA CONCENTRATION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; COLONIC NEOPLASMS; ESTERASES; FEMALE; HT29 CELLS; HUMANS; IBUPROFEN; MICE; MICE, NUDE; MICROSOMES, LIVER; PHOSPHORIC ACID ESTERS; TUMOR CELLS, CULTURED; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 79956188691     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.111.180224     Document Type: Article

References (31)

1. American Cancer Society (2008) Cancer Facts and Figures 2008. American Cancer Society Atlanta, GA.
2. Antonicelli L and Tagliabracci A (1995) Asthma death induced by ibuprofen. Monaldi Arch Chest Dis 50:276-278.
3. Bajrami B, Zhao L, Schenkman JB, and Rusling JF (2009) Rapid LC-MS drug metabolite profiling using microsomal enzyme bioreactors in a parallel processing format. Anal Chem 81:9921-9929.
4. Chang SY, Li W, Traeger SC, Wang B, Cui D, Zhang H, Wen B, and Rodrigues AD (2008) Confirmation that cytochrome P450 2C8 (CYP2C8) plays a minor role in (S)-(+)- and (R)-(-)-ibuprofen hydroxylation in vitro. Drug Metab Dispos 36:2513-2522.
5. Coussens LM and Werb Z (2002) Inflammation and cancer. Nature 420:860-867. (Pubitemid 36019639)
6. Hamman MA, Thompson GA, and Hall SD (1997) Regioselective and stereoselective metabolism of ibuprofen by human cytochrome P450 2C. Biochem Pharmacol 54:33-41. (Pubitemid 27353220)
7. Harris RE, Beebe-Donk J, Doss H, and Burr Doss D (2005) Aspirin, ibuprofen, and other non-steroidal anti-inflammatory drugs in cancer prevention: a critical review of non-selective COX-2 blockade (review). Oncol Rep 13:559-583.
8. Harris RE, Namboodiri KK, and Farrar WB (1996) Nonsteroidal antiinflammatory drugs and breast cancer. Epidemiology 7:203-205. (Pubitemid 26068056)
9. Hosokawa M, Maki T, and Satoh T (1990) Characterization of molecular species of liver microsomal carboxylesterases of several animal species and humans. Arch Biochem Biophys 277:219-227. (Pubitemid 20098389)
10. Huang L, Mackenzie G, Ouyang N, Sun Y, Xie G, Johnson F, Komninou D, and Rigas B (2011) The novel phospho-non-steroidal anti-inflammatory drugs, OXT-328, MDC-22 and MDC-917, inhibit adjuvant-induced arthritis in rats. Br J Pharmacol 162:1521-1533.
11. Imai T, Yoshigae Y, Hosokawa M, Chiba K, and Otagiri M (2003) Evidence for the involvement of a pulmonary first-pass effect via carboxylesterase in the disposition of a propranolol ester derivative after intravenous administration. J Pharmacol Exp Ther 307:1234-1242. (Pubitemid 37494247)
12. Johnson CH, Wilson ID, Harding JR, Stachulski AV, Iddon L, Nicholson JK, and Lindon JC (2007) NMR spectroscopic studies on the in vitro acyl glucuronide migration kinetics of Ibuprofen ((+/-)-(R,S)-2-(4-isobutylphenyl) propanoic acid), its metabolites, and analogues. Anal Chem 79:8720-8727. (Pubitemid 350171385)
13. Kepp DR, Sidelmann UG, and Hansen SH (1997) Isolation and characterization of major phase I and II metabolites of ibuprofen. Pharm Res 14:676-680. (Pubitemid 27220290)
14. Kremers P, Beaune P, Cresteil T, de Graeve J, Columelli S, Leroux JP, and Gielen JE (1981) Cytochrome P-450 monooxygenase activities in human and rat liver microsomes. Eur J Biochem 118:599-606.
15. Kuehl GE, Lampe JW, Potter JD, and Bigler J (2005) Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos 33:1027-1035. (Pubitemid 41002785)
16. Lanza FL (1984) Endoscopic studies of gastric and duodenal injury after the use of ibuprofen, aspirin, and other nonsteroidal anti-inflammatory agents. Am J Med 77:19-24.
17. Li B, Sedlacek M, Manoharan I, Boopathy R, Duysen EG, Masson P, and Lockridge O (2005) Butyrylcholinesterase, paraoxonase, and albumin esterase, but not carboxylesterase, are present in human plasma. Biochem Pharmacol 70:1673-1684. (Pubitemid 41540360)
18. Liu D, Zheng X, Tang Y, Zi J, Nan Y, Wang S, Xiao C, Zhu J, and Chen C (2010) Metabolism of tanshinol borneol ester in rat and human liver microsomes. Drug Metab Dispos 38:1464-1470.
19. Mackenzie GG, Sun Y, Huang L, Xie G, Ouyang N, Gupta RC, Johnson F, Komninou D, Kopelovich L, and Rigas B (2010) Phospho-sulindac (OXT-328), a novel sulindac derivative, is safe and effective in colon cancer prevention in mice. Gastroenterology 139:1320-1332.
20. Marnett LJ (1995) Aspirin and related nonsteroidal anti-inflammatory drugs as chemopreventive agents against colon cancer. Prev Med 24:103-106.
21. Martignoni M, Groothuis GM, and de Kanter R (2006) Species differences between mouse, rat, dog, monkey and human CYP-mediated drug metabolism, inhibition and induction. Expert Opin Drug Metab Toxicol 2:875-894. (Pubitemid 44911538)
22. Mathijssen RH, Verweij J, de Bruijn P, Loos WJ, and Sparreboom A (2002) Effects of St. John's wort on irinotecan metabolism. J Natl Cancer Inst 94:1247-1249. (Pubitemid 34993875)
23. McElwee NE, Veltri JC, Bradford DC, and Rollins DE (1990) A prospective, population-based study of acute ibuprofen overdose: complications are rare and routine serum levels not warranted. Ann Emerg Med 19:657-662. (Pubitemid 20180908)
24. Meier CR, Schmitz S, and Jick H (2002) Association between acetaminophen or nonsteroidal antiinflammatory drugs and risk of developing ovarian, breast, or colon cancer. Pharmacotherapy 22:303-309. (Pubitemid 34205168)
25. Piazza GA, Keeton AB, Tinsley HN, Gary BD, Whitt JD, Mathew B, Thaiparambil J, Coward L, Gorman G, Li Y, et al. (2009) A novel sulindac derivative that does not inhibit cyclooxygenases but potently inhibits colon tumor cell growth and induces apoptosis with antitumor activity. Cancer Prev Res (Phila) 2:572-580.
26. Riley TR 3rd and Smith JP (1998) Ibuprofen-induced hepatotoxicity in patients with chronic hepatitis C: a case series. Am J Gastroenterol 93:1563-1565.
27. Rudy AC, Knight PM, Brater DC, and Hall SD (1991) Stereoselective metabolism of ibuprofen in humans: administration of R-, S- and racemic ibuprofen. J Pharmacol Exp Ther 259:1133-1139.
28. Seifert A, Tatzel S, Schmid RD, and Pleiss J (2006) Multiple molecular dynamics simulations of human p450 monooxygenase CYP2C9: the molecular basis of substrate binding and regioselectivity toward warfarin. Proteins 64:147-155. (Pubitemid 43830993)
29. Ulrich CM, Bigler J, and Potter JD (2006) Non-steroidal anti-inflammatory drugs for cancer prevention: promise, perils and pharmacogenetics. Nat Rev Cancer 6:130-140. (Pubitemid 43361545)
30. Xie G, Liu M, Zhu H, and Lei B (2008) Esterase SeE of Streptococcus equi ssp. equi is a novel nonspecific carboxylic ester hydrolase. FEMS Microbiol Lett 289:181-186.
31. Zheng Z, Fang JL, and Lazarus P (2002) Glucuronidation: an important mechanism for detoxification of benzo[a]pyrene metabolites in aerodigestive tract tissues. Drug Metab Dispos 30:397-403. (Pubitemid 34263824)