Pharmacokinetics, oral bioavailability and metabolism of a novel isoquinolinone-based melatonin receptor agonist in rats

References

• Artursson P, Karlsson J. (1991). Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 175:880–885.
   PubMed Web of Science ®Google Scholar
• Balsam A, Sexton F, Borges M, Ingbar SH. (1983). Formation of diiodotyrosine from thyroxine. Ether-link cleavage, an alternate pathway of thyroxine metabolism. J Clin Invest 72:1234–1245.
   PubMed Web of Science ®Google Scholar
• Barrenetxe J, Delagrange P, Martínez JA. (2004). Physiological and metabolic functions of melatonin. J Physiol Biochem 60:61–72.
   PubMed Web of Science ®Google Scholar
• Bendz LM, Scates AC. (2010). Melatonin treatment for insomnia in pediatric patients with attention-deficit/hyperactivity disorder. Ann Pharmacother 44:185–191.
   PubMed Web of Science ®Google Scholar
• Bogaards JJ, Bertrand M, Jackson P, Oudshoorn MJ, Weaver RJ, van Bladeren PJ, Walther B. (2000). Determining the best animal model for human cytochrome P450 activities: a comparison of mouse, rat, rabbit, dog, micropig, monkey and man. Xenobiotica 30:1131–1152.
   PubMed Web of Science ®Google Scholar
• Bruyère A, Declevès X, Bouzom F, Proust L, Martinet M, Walther B, Parmentier Y. (2009). Development of an optimized procedure for the preparation of rat intestinal microsomes: comparison of hepatic and intestinal microsomal cytochrome P450 enzyme activities in two rat strains. Xenobiotica 39:22–32.
   PubMed Web of Science ®Google Scholar
• Cavallo A, Ris MD, Succop P, Jaskiewicz J. (2005). Melatonin treatment of pediatric residents for adaptation to night shift work. Ambul Pediatr 5:172–177.
   PubMedGoogle Scholar
• Davies B, Morris T. (1993). Physiological parameters in laboratory animals and humans. Pharm Res 10:1093–1095.
   PubMed Web of Science ®Google Scholar
• DeMuro RL, Nafziger AN, Blask DE, Menhinick AM, Bertino JS Jr. (2000). The absolute bioavailability of oral melatonin. J Clin Pharmacol 40:781–784.
   PubMed Web of Science ®Google Scholar
• Di L, Kerns EH, Hong Y, Chen H. (2005). Development and application of high throughput plasma stability assay for drug discovery. Int J Pharm 297:110–119.
   PubMed Web of Science ®Google Scholar
• Di WL, Kadva A, Johnston A, Silman R. (1997). Variable bioavailability of oral melatonin. N Engl J Med 336:1028–1029.
   PubMed Web of Science ®Google Scholar
• Dolder CR, Nelson M, Snider M. (2008). Agomelatine treatment of major depressive disorder. Ann Pharmacother 42:1822–1831.
   PubMed Web of Science ®Google Scholar
• Ekmekcioglu C. (2006). Melatonin receptors in humans: biological role and clinical relevance. Biomed Pharmacother 60:97–108.
   PubMed Web of Science ®Google Scholar
• Galli-Carminati G, Deriaz N, Bertschy G. (2009). Melatonin in treatment of chronic sleep disorders in adults with autism: a retrospective study. Swiss Med Wkly 139:293–296.
   PubMed Web of Science ®Google Scholar
• Hill SM, Frasch T, Xiang S, Yuan L, Duplessis T, Mao L. (2009). Molecular mechanisms of melatonin anticancer effects. Integr Cancer Ther 8:337–346.
   PubMed Web of Science ®Google Scholar
• Hu Y, Chan KH, He X, New DC, Wong YH. (2012) Synthesis and functional characterization of substituted isoquinolinones as a novel class of subtype-selective melatoninergic ligands. In press.
   Google Scholar
• Kennaway DJ, Rowe SA. (1995). Melatonin binding sites and their role in seasonal reproduction. J Reprod Fertil Suppl 49:423–435.
   PubMedGoogle Scholar
• Li Y, Yuan H, Yang K, Xu W, Tang W, Li X. (2010). The structure and functions of P-glycoprotein. Curr Med Chem 17:786–800.
   PubMed Web of Science ®Google Scholar
• Lin JH, Chiba M, Baillie TA. (1999). Is the role of the small intestine in first-pass metabolism overemphasized? Pharmacol Rev 51:135–158.
   PubMed Web of Science ®Google Scholar
• Lipartiti M, Franceschini D, Zanoni R, Gusella M, Giusti P, Cagnoli CM, Kharlamov A, Manev H. (1996). Neuroprotective effects of melatonin. Adv Exp Med Biol 398:315–321.
   PubMedGoogle Scholar
• Mor M, Rivara S, Pala D, Bedini A, Spadoni G, Tarzia G. (2010). Recent advances in the development of melatonin MT(1) and MT(2) receptor agonists. Expert Opin Ther Pat 20:1059–1077.
   PubMed Web of Science ®Google Scholar
• Nelson RJ, Demas GE. (1997). Role of melatonin in mediating seasonal energetic and immunologic adaptations. Brain Res Bull 44:423–430.
   PubMed Web of Science ®Google Scholar
• Pouton CW. (2006). Formulation of poorly water-soluble drugs for oral administration: physicochemical and physiological issues and the lipid formulation classification system. Eur J Pharm Sci 29:278–287.
   PubMed Web of Science ®Google Scholar
• Qureshi SA, Buttar HS. (1989). A comparative study of the pharmacokinetics of propranolol and its major metabolites in the rat after oral and vaginal administration. Xenobiotica 19:883–890.
   PubMed Web of Science ®Google Scholar
• Rivara S, Vacondio F, Fioni A, Silva C, Carmi C, Mor M, Lucini V, Pannacci M, Caronno A, Scaglione F, Gobbi G, Spadoni G, Bedini A, Orlando P, Lucarini S, Tarzia G. (2009). N-(Anilinoethyl)amides: design and synthesis of metabolically stable, selective melatonin receptor ligands. ChemMedChem 4:1746–1755.
   PubMed Web of Science ®Google Scholar
• Rosenthal NE, Sack DA, Jacobsen FM, James SP, Parry BL, Arendt J, Tamarkin L, Wehr TA. (1986). Melatonin in seasonal affective disorder and phototherapy. J Neural Transm Suppl 21:257–267.
   PubMedGoogle Scholar
• Routledge PA, Shand DG. (1979). Clinical pharmacokinetics of propranolol. Clin Pharmacokinet 4:73–90.
   PubMed Web of Science ®Google Scholar
• Scheer FA, Czeisler CA. (2005). Melatonin, sleep, and circadian rhythms. Sleep Med Rev 9:5–9.
   PubMed Web of Science ®Google Scholar
• Semak I, Korik E, Antonova M, Wortsman J, Slominski A. (2008). Metabolism of melatonin by cytochrome P450s in rat liver mitochondria and microsomes. J Pineal Res 45:515–523.
   PubMed Web of Science ®Google Scholar
• Skene DJ, Arendt J. (2007). Circadian rhythm sleep disorders in the blind and their treatment with melatonin. Sleep Med 8:651–655.
   PubMed Web of Science ®Google Scholar
• Srinivasan V, Spence DW, Pandi-Perumal SR, Trakht I, Cardinali DP. (2008). Jet lag: therapeutic use of melatonin and possible application of melatonin analogs. Travel Med Infect Dis 6:17–28.
   PubMedGoogle Scholar
• Sträuber H, Müller RH, Babel W. (2003). Evidence of cytochrome P450-catalyzed cleavage of the ether bond of phenoxybutyrate herbicides in Rhodococcus erythropolis K2-3. Biodegradation 14:41–50.
   PubMed Web of Science ®Google Scholar
• Tan DX, Reiter RJ, Manchester LC, Yan MT, El-Sawi M, Sainz RM, Mayo JC, Kohen R, Allegra M, Hardeland R. (2002). Chemical and physical properties and potential mechanisms: melatonin as a broad spectrum antioxidant and free radical scavenger. Curr Top Med Chem 2:181–197.
   PubMedGoogle Scholar
• von Gall C, Stehle JH, Weaver DR. (2002). Mammalian melatonin receptors: molecular biology and signal transduction. Cell Tissue Res 309:151–162.
   PubMed Web of Science ®Google Scholar
• Wang Q, Rager JD, Weinstein K, Kardos PS, Dobson GL, Li J, Hidalgo IJ. (2005). Evaluation of the MDR-MDCK cell line as a permeability screen for the blood-brain barrier. Int J Pharm 288:349–359.
   PubMed Web of Science ®Google Scholar
• Zhu J, Hu Y, Ho MK, Wong YH. (2011). 3-Methoxylphenylpropyl amides as novel receptor subtype-selective melatoninergic ligands: characterization of physicochemical and pharmacokinetic properties. Xenobiotica 41:35–45.
   PubMed Web of Science ®Google Scholar
• Zlotos DP. (2005). Recent advances in melatonin receptor ligands. Arch Pharm (Weinheim) 338:229–247.
   PubMed Web of Science ®Google Scholar