Species differences in hydrolase activities toward OT-7100 responsible for different bioavailability in rats, dogs, monkeys and humans

References

• Boogaard PJ, Van Elburg PA, De Kloe KP, Watson WP, Van Sittert NJ. Metabolic inactivation of 2-oxiranylmethyl 2-ethyl-2,5-dimethylhexanoate (C10GE) in skin, lung and liver of human, rat and mouse. Xenobiotica 1999; 29: 987–1006
   PubMed Web of Science ®Google Scholar
• Boxenbaum H. Interspecies variation in liver weight, hepatic blood flow, and antipyrine intrinsic clearance: Extrapolation of data to benzodiazepines and phenytoin. Journal of Pharmacokinetics and Biopharmaceutics 1980; 8: 165–176
   PubMedGoogle Scholar
• Campbell CJ, Chantrell LJ, Eastmond R. Purification and partial characterization of rat intestinal cefuroxime axetil esterase. Biochemical Pharmacology 1987; 36: 2317–2324
   PubMedGoogle Scholar
• Cook CS, Karabatsos PJ, Schoenhard GL, Karim A. Species dependent esterase activities for hydrolysis of an anti-HIV prodrug glycovir and bioavailability of active SC-48334. Pharmaceutical Research 1995; 12: 1158–1164
   PubMed Web of Science ®Google Scholar
• Fitzsimmons ML, Collins JM. Selective biotransformation of the human immunodeficiency virus protease inhibitor Saquinavir by human small-intestinal cytochrome P4503A4. Potential contribution to high first-pass metabolism. Drug Metabolism and Disposition 1997; 25: 256–266
   PubMed Web of Science ®Google Scholar
• Hashizume T, Imaoka S, Mise M, Terauchi Y, Fujii T, Miyazaki H, Kamataki T, Funae Y. Involvement of CYP2J2 and CYP4F12 in the metabolism of ebastine in human intestinal microsomes. Journal Pharmacology and Experimental Therapeutics 2001; 300: 298–304
   Google Scholar
• Hosokawa M, Endo T, Fujisawa M, Hara S, Iwata N, Sato Y, Satoh T. Interindividual variation in carboxylesterase levels in human liver microsomes. Drug Metabolism and Disposition 1995; 23: 1022–1027
   PubMed Web of Science ®Google Scholar
• Hosokawa M, Maki T, Satoh T. Characterization of molecular species of liver microsomal carboxylesterases of several animal species and humans. Archives of Biochemistry and Biophysics 1990; 277: 219–227
   PubMed Web of Science ®Google Scholar
• Hosokawa M, Suzuki K, Takahashi D, Mori M, Satoh T, Chiba K. Purification, molecular cloning, and functional expression of dog liver microsomal acyl-CoA hydrolase: A member of the carboxylesterase multigene family. Archives of Biochemistry and Biophysics 2001; 389: 245–253
   PubMed Web of Science ®Google Scholar
• Imai T, Yoshigae Y, Hosokawa M, Chiba K, Otagiri M. Evidence for the involvement of a pulmonary first-pass effect via carboxylesterase in the disposition of a propranolol ester derivative after intravenous administration. Journal of Pharmacology and Experimental Therapeutics 2003; 307: 1234–1242
   PubMed Web of Science ®Google Scholar
• Inaba M, Ohnishi Y, Ishii H, Tanioka Y, Yoshida Y, Sudoh K, Hakusui H, Mizuno N, Ito K, Sugiyama Y. Pharmacokinetics of CPT-11 in rhesus monkeys. Cancer Chemotherapy and Pharmacology 1998; 41: 103–108
   PubMedGoogle Scholar
• Inoue M, Morikawa M, Tsuboi M, Sugiura M. Species difference and characterization of intestinal esterase on the hydrolyzing activity of ester-type drugs. Japanese Journal of Pharmacology 1979; 29: 9–16
   PubMedGoogle Scholar
• Lin JH. Species similarities and differences in pharmacokinetics. Drug Metabolism and Disposition 1995; 23: 1008–1021
   PubMed Web of Science ®Google Scholar
• Lin JH, Chiba M, Baillie TA. Is the role of the small intestine in first-pass metabolism overemphasized?. Pharmacological Reviews 1999; 51: 135–158
   PubMed Web of Science ®Google Scholar
• Lowry OH, Rosebrough NJ, Farr AL, Randall RJ. Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry 1951; 193: 264–275
   Web of Science ®Google Scholar
• Miki S, Yoshinaga N, Iwamoto T, Yasuda T, Sato S. Antinociceptive effect of the novel compound OT-7100 in a diabetic neuropathy model. European Journal of Pharmacology 2001; 430: 229–234
   PubMedGoogle Scholar
• Morgan EW, Yan B, Greenway D, Parkinson A. Regulation of two rat liver microsomal carboxylesterase isozymes: Species differences, tissue distribution, and the effects of age, sex, and xenobiotic treatment of rats. Archives of Biochemistry and Biophysics 1994a; 315: 513–526
   PubMed Web of Science ®Google Scholar
• Morgan EW, Yan B, Greenway D, Peterson DR, Parkinson A. Purification and characterization of two rat liver microsomal carboxylesterases (hydrolase A and B). Archives of Biochemistry and Biophysics 1994b; 31: 495–512
   Google Scholar
• Satoh T. Role of carboxylesterases in xenobiotic metabolism. Reviews in biochemical toxicology, JR Bend, E Hodgson, RM Philpot. Elsevier, New York, NY 1987; 155–181
   Google Scholar
• Satoh T, Hosokawa M. The mammalian carboxylesterases: From molecules to functions. Annual Review of Pharmacology and Toxicology 1998; 38: 257–288
   PubMed Web of Science ®Google Scholar
• Thummel KE, Kunze KL, Shen DD. Enzyme-catalyzed processes of first-pass hepatic and intestinal drug extraction. Advanced Drug Delivery Reviews 1997; 27: 99–127
   PubMed Web of Science ®Google Scholar
• Thummel KE, O'Shea D, Paine MF, Shen DD, Kunze KL, Perkins JD, Wilkinson GR. Oral first-pass elimination of midazolam involves both gastrointestinal and hepatic CYP3A-mediated metabolism. Clinical Pharmacology and Therapeutics 1996; 59: 491–502
   PubMed Web of Science ®Google Scholar
• Yamaoka K, Nakagawa T, Uno T. Statistical moments in pharmacokinetics. Journal of Pharmacokinetics and Biopharmaceutics 1978; 6: 547–558
   PubMedGoogle Scholar
• Yan B, Matoney L, Yang D. Human carboxylesterases in term placentae: Enzymatic characterization, molecular cloning and evidence for the existence of multiple forms. Placenta 1999; 20: 599–607
   PubMed Web of Science ®Google Scholar
• Yasuda T, Iwamoto T, Ohara M, Sato S, Kohri H, Noguchi K, Senba E. The novel analgesic compound OT-7100 (5-nButyl-7-(3,4,5,-trimethoxybenzoylamino)pyrazolo[1,5-a]pyrimidine) attenuates mechanical nociceptive responses in animal models of acute and peripheral neuropathic hyperalgesia. Japanese Journal of Pharmacology 1999; 79: 65–73
   PubMedGoogle Scholar
• Yasuda T, Okamoto K, Iwamoto T, Miki S, Yoshinaga N, Sato S, Noguchi K, Senba E. A novel analgesic compound OT-7100 attenuates nociceptive responses in animal models of inflammatory and neuropathic hyperalgesia: A possible involvement of adenosinergic anti-nociception. Japanese Journal of Pharmacology 2001; 87: 214–225
   PubMedGoogle Scholar
• Zhang QY, Dunbar D, Ostrowska A, Zeisloft S, Yang J, Kaminsky LS. Characterization of human small intestinal cytochromes P-450. Drug Metabolism and Disposition 1999; 27: 804–809
   PubMed Web of Science ®Google Scholar
• Zhang W, Xu G, McLeod HL. Comprehensive evaluation of carboxylesterase-2 expression in normal human tissues using tissue array analysis. Applied Immunohistochemistry and Molecular Morphology 2002; 10: 374–380
   Web of Science ®Google Scholar
• Zhu W, Song L, Zhang H, Matoney L, Lecluyse E, Yan B. Dexamethasone differentially regulates expression of carboxylesterase genes in humans and rats. Drug Metabolism and Disposition 2000; 28: 186–191
   PubMed Web of Science ®Google Scholar