Pharmacokinetic properties of newly synthesized retinoid X receptor agonists possessing a 6-[N-ethyl-N-(3-alkoxy-4-isopropylphenyl)amino]nicotinic acid skeleton in rats

References

• Germain P, Chambon P, Eichele G, Evans RM, Lazar MA, Leid M et al. (2006). International Union of Pharmacology. LXIII. Retinoid X receptors. Pharmacol Rev, 58:760–772.
   PubMed Web of Science ®Google Scholar
• Giguère V. (1999). Orphan nuclear receptors: from gene to function. Endocr Rev, 20:689–725.
   PubMed Web of Science ®Google Scholar
• Mangelsdorf DJ, Thummel C, Beato M, Herrlich P, Schütz G, Umesono K et al. (1995). The nuclear receptor superfamily: the second decade. Cell, 83:835–839.
   PubMed Web of Science ®Google Scholar
• Altucci L, Gronemeyer H. (2001). Nuclear receptors in cell life and death. Trends Endocrinol Metab, 12:460–468.
   PubMed Web of Science ®Google Scholar
• Shintani M, Nishimura H, Yonemitsu S, Ogawa Y, Hayashi T, Hosoda K et al. (2001). Troglitazone not only increases GLUT4 but also induces its translocation in rat adipocytes. Diabetes, 50:2296–2300.
   PubMed Web of Science ®Google Scholar
• Singh Ahuja H, Liu S, Crombie DL, Boehm M, Leibowitz MD, Heyman RA et al. (2001). Differential effects of rexinoids and thiazolidinediones on metabolic gene expression in diabetic rodents. Mol Pharmacol, 59:765–773.
   PubMed Web of Science ®Google Scholar
• Bischoff ED, Heyman RA, Lamph WW. (1999). Effect of the retinoid X receptor-selective ligand LGD1069 on mammary carcinoma after tamoxifen failure. J Natl Cancer Inst, 91:2118.
   PubMed Web of Science ®Google Scholar
• Leibowitz MD, Ardecky RJ, Boehm MF, Broderick CL, Carfagna MA, Crombie DL et al. (2006). Biological characterization of a heterodimer-selective retinoid X receptor modulator: potential benefits for the treatment of type 2 diabetes. Endocrinology, 147:1044–1053.
   PubMed Web of Science ®Google Scholar
• Mukherjee R, Davies PJ, Crombie DL, Bischoff ED, Cesario RM, Jow L et al. (1997). Sensitization of diabetic and obese mice to insulin by retinoid X receptor agonists. Nature, 386:407–410.
   PubMed Web of Science ®Google Scholar
• Pinaire JA, Reifel-Miller A. (2007). Therapeutic potential of retinoid x receptor modulators for the treatment of the metabolic syndrome. PPAR Res, 2007:94156.
   PubMed Web of Science ®Google Scholar
• Duvic M, Martin AG, Kim Y, Olsen E, Wood GS, Crowley CA et al.; Worldwide Bexarotene Study Group. (2001). Phase 2 and 3 clinical trial of oral bexarotene (Targretin capsules) for the treatment of refractory or persistent early-stage cutaneous T-cell lymphoma. Arch Dermatol, 137:581–593.
   PubMed Web of Science ®Google Scholar
• Duvic M, Hymes K, Heald P, Breneman D, Martin AG, Myskowski P et al.; Bexarotene Worldwide Study Group. (2001). Bexarotene is effective and safe for treatment of refractory advanced-stage cutaneous T-cell lymphoma: multinational phase II–III trial results. J Clin Oncol, 19:2456–2471.
   PubMed Web of Science ®Google Scholar
• Davies PJ, Berry SA, Shipley GL, Eckel RH, Hennuyer N, Crombie DL et al. (2001). Metabolic effects of rexinoids: tissue-specific regulation of lipoprotein lipase activity. Mol Pharmacol, 59:170–176.
   PubMed Web of Science ®Google Scholar
• Sharma V, Hays WR, Wood WM, Pugazhenthi U, St Germain DL, Bianco AC et al. (2006). Effects of rexinoids on thyrotrope function and the hypothalamic–pituitary–thyroid axis. Endocrinology, 147:1438–1451.
   PubMed Web of Science ®Google Scholar
• Kagechika H, Shudo K. (2005). Synthetic retinoids: recent developments concerning structure and clinical utility. J Med Chem, 48:5875–5883.
   PubMed Web of Science ®Google Scholar
• Takamatsu K, Takano A, Yakushiji N, Morishita K, Matsuura N, Makishima M et al. (2008). Reduction of lipophilicity at the lipophilic domain of RXR agonists enables production of subtype preference: RXRalpha-preferential agonist possessing a sulfonamide moiety. ChemMedChem, 3:454–460.
   PubMed Web of Science ®Google Scholar
• Haugen BR, Jensen DR, Sharma V, Pulawa LK, Hays WR, Krezel W et al. (2004). Retinoid X receptor gamma-deficient mice have increased skeletal muscle lipoprotein lipase activity and less weight gain when fed a high-fat diet. Endocrinology, 145:3679–3685.
   PubMed Web of Science ®Google Scholar
• Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. (2001). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev, 46:3–26.
   PubMed Web of Science ®Google Scholar
• Takamatsu K, Takano A, Yakushiji N, Morohashi K, Morishita K, Matsuura N et al. (2008). The first potent subtype-selective retinoid X receptor (RXR) agonist possessing a 3-isopropoxy-4-isopropylphenylamino moiety, NEt-3IP (RXRalpha/beta-dual agonist). ChemMedChem, 3:780–787.
   PubMed Web of Science ®Google Scholar
• Aiba T, Takehara Y, Okuno M, Hashimoto Y. (2003). Poor correlation between intestinal and hepatic metabolic rates of CYP3A4 substrates in rats. Pharm Res, 20:745–748.
   PubMed Web of Science ®Google Scholar
• Komura H, Iwaki M. (2005). Pharmacokinetics and metabolism of metoprolol and propranolol in the female DA and female Wistar rat: the female DA rat is not always an animal model for poor metabolizers of CYP2D6. J Pharm Sci, 94:397–408.
   PubMed Web of Science ®Google Scholar
• Easterbrook J, Lu C, Sakai Y, Li AP. (2001). Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes. Drug Metab Dispos, 29:141–144.
   PubMed Web of Science ®Google Scholar
• Brown HS, Chadwick A, Houston JB. (2007). Use of isolated hepatocyte preparations for cytochrome P450 inhibition studies: comparison with microsomes for Ki determination. Drug Metab Dispos, 35:2119–2126.
   PubMed Web of Science ®Google Scholar
• Kobayashi S, Murray S, Watson D, Sesardic D, Davies DS, Boobis AR. (1989). The specificity of inhibition of debrisoquine 4-hydroxylase activity by quinidine and quinine in the rat is the inverse of that in man. Biochem Pharmacol, 38:2795–2799.
   PubMed Web of Science ®Google Scholar
• Kotegawa T, Laurijssens BE, Von Moltke LL, Cotreau MM, Perloff MD, Venkatakrishnan K et al. (2002). In vitro, pharmacokinetic, and pharmacodynamic interactions of ketoconazole and midazolam in the rat. J Pharmacol Exp Ther, 302:1228–1237.
   PubMed Web of Science ®Google Scholar
• Sugita O, Sawada Y, Sugiyama Y, Iga T, Hanano M. (1981). Prediction of drug–drug interaction from in vitro plasma protein binding and metabolism. A study of tolbutamide–sulfonamide interaction in rats. Biochem Pharmacol, 30:3347–3354.
   PubMed Web of Science ®Google Scholar
• Kato R, Fujiwara A, Kawai T, Moriguchi J, Nakagawa M, Tsukura Y et al. (2008). Changes in digoxin pharmacokinetics treated with lipopolysaccharide in Wistar rats. Biol Pharm Bull, 31:1221–1225.
   PubMed Web of Science ®Google Scholar
• Braunschweig J, Stäubli M, Studer H. (1987). Interactions of amiodarone with digoxin in rats. Br J Pharmacol, 92:553–559.
   PubMed Web of Science ®Google Scholar
• Davies B, Morris T. (1993). Physiological parameters in laboratory animals and humans. Pharm Res, 10:1093–1095.
   PubMed Web of Science ®Google Scholar
• Wilkinson GR. (2001). Pharmacokinetics. In: Hardman JG, Limbird LE, Gilman AG, eds. The Pharmacological Basis of Therapeutics, 10th edition. New York: McGraw-Hill, pp. 3–29.
   Google Scholar
• Rowland M, Tozer TN. (1995). Distribution. In: Rowland M, Tozer TN, eds. Clinical Pharmacokinetics, 3rd edition. Baltimore: Williams & Wilkins, pp. 137–155.
   Google Scholar
• Fu LW, Yang LY, Chen WP, Lin CY. (1997). Cyclosporin pharmacokinetics following administration of capsules and Neoral in paediatric patients with lupus nephritis. Br J Clin Pharmacol, 44:125–127.
   PubMed Web of Science ®Google Scholar
• Venkataram S, Rogers JA. (1988). Characteristics of drug–phospholipid coprecipitates. II: Bioavailability studies of griseofulvin in rats. J Pharm Sci, 77:933–936.
   PubMed Web of Science ®Google Scholar
• Spina E, Avenoso A, Campo GM, Scordo MG, Caputi AP, Perucca E. (1997). Effect of ketoconazole on the pharmacokinetics of imipramine and desipramine in healthy subjects. Br J Clin Pharmacol, 43:315–318.
   PubMed Web of Science ®Google Scholar
• Okabe H, Mizukami A, Taguchi M, Aiba T, Yasuhara M, Hashimoto Y. (2003). The increased intestinal absorption rate is responsible for the reduced hepatic first-pass extraction of propranolol in rats with cisplatin-induced renal dysfunction. J Pharm Pharmacol, 55:479–486.
   PubMed Web of Science ®Google Scholar
• Fukino K, Sasaki Y, Hirai S, Nakamura T, Hashimoto M, Yamagishi F et al. (2008). Effects of N-acetyltransferase 2 (NAT2), CYP2E1 and glutathione-S-transferase (GST) genotypes on the serum concentrations of isoniazid and metabolites in tuberculosis patients. J Toxicol Sci, 33:187–195.
   PubMed Web of Science ®Google Scholar
• Vree TB, van den Biggelaar-Martea M, Verwey-van Wissen CP. (1993). Determination of indomethacin, its metabolites and their glucuronides in human plasma and urine by means of direct gradient high-performance liquid chromatographic analysis. Preliminary pharmacokinetics and effect of probenecid. J Chromatogr, 616:271–282.
   PubMed Web of Science ®Google Scholar
• Yamazaki H, Komatsu T, Takemoto K, Shimada N, Nakajima M, Yokoi T. (2001). Rat cytochrome p450 1A and 3A enzymes involved in bioactivation of tegafur to 5-fluorouracil and autoinduced by tegafur in liver microsomes. Drug Metab Dispos, 29:794–797.
   PubMed Web of Science ®Google Scholar