Effect of PVP K30 and/or l-Arginine on Stability Constant of Etoricoxib–HPβCD Inclusion Complex: Preparation and Characterization of Etoricoxib–HPβCD Binary System

REFERENCES

• F. Acartürk, Ö. Ki¸slal, and N. Çelebi. (1992). The effect of some natural polymers on the solubility and dissolution characteristics of nifedipine. Int. J. Pharm. 85:1–6.
   Web of Science ®Google Scholar
• N. G. B. Agrawal, and A. G. Porras. (2001). Dose proportionality of oral etoricoxib, a highly selective cyclooxygenase-2 inhibitor, in healthy volunteers. J. Clin. Pharmacol. 41:1106–1110.
   PubMed Web of Science ®Google Scholar
• S. M. Ali, F. Asmat, A. Maheshwari, and M. Koketsu. (2005). Complexation of fluoxetine hydrochloride with β-cyclodextrin. A proton magnetic resonance study in aqueous solution. Il Farmaco 60:445–449.
   PubMedGoogle Scholar
• S. M. Ali, A. Maheshwari, and F. Asmat. (2004). Complexation of roxatidine acetate hydrochloride with β-cyclodextrin; NMR spectroscopic study. Pharmazie 8:653–655.
   Google Scholar
• R. J. Bergaron, and R. Rowan. (1976). The molecular disposition of sodium p-nitrophenolate in the cavities of cycloheptaamylose and cyclohexaamylose in solution. Bioorg. Chem. 5:423–436.
   Google Scholar
• S. Berge, L. Bighley, and D. C. Monkhouse. (1977). Pharmaceutical salts. J. Pharm. Sci. 66:1–19.
   PubMed Web of Science ®Google Scholar
• G. P. Bettinetti, A. Gazzania, P. Mura, F. Giordano, and M. Setti. (1992). The thermal behaviour and dissolution properties of naproxen in combinations with chemically modified β-cyclodextrins. Drug Dev. Ind. Pharm. 18:39–53.
   Web of Science ®Google Scholar
• G. P. Bettinetti, F. Melani, P. Mura, R. Monnanni, and F. Giordano. (1991). Carbon-13 nuclear magnetic resonance study of naproxen interaction with cyclodextrin in solution. J. Pharm. Sci. 80:1162–1169.
   PubMed Web of Science ®Google Scholar
• M. E. Brewster, and T. Loftsson. (2007). Cyclodextrins as pharmaceutical solubilizers. Adv. Drug Deliv. Rev. 59:645–666.
   PubMed Web of Science ®Google Scholar
• B. Cappello, C. Carmignani, M. Iervolino, M. Immacolata la Rotonda, and M. F. Saettone. (2001). Solubilization of tropicamide by hydroxypropyl-β-cyclodextrin and water-soluble polymers: In vitro: In vivo studies. Int. J. Pharm. 213:75–81.
   PubMed Web of Science ®Google Scholar
• C. Chen, F. Chen, A. Wu, H. Hsu, I. Kang, and H. Cheng. (1996). Effect of hydroxypropyl-β-cyclodextrin on the solubility, photostability and in vitro permeability of alkannimshikonin enantiomers. Int. J. Pharm. 141:171–178.
   Web of Science ®Google Scholar
• M. Cirri, F. Maestrelli, G. Corti, S. Furlanetto, and P. Mura. (2006). Simultaneous effect of cyclodextrin complexation, pH, and hydrophilic polymers on naproxen solubilization. J. Pharm. Biomed. Anal. 42:126–131.
   PubMed Web of Science ®Google Scholar
• D. J. Cochrane, B. Jarvis, and G. M. Keating. (2002). Etoricoxib. Drugs 62:2637–2651.
   PubMed Web of Science ®Google Scholar
• G. Dollo, P. Corre, M. Chollet, F. Chevanne, M. Bertault, J. Burgot, and R. Verge. (1999). Improvement in solubility and dissolution rate of 1,2-dithiole-3-thiones upon complexation with β-cyclodextrin and its hydroxypropyl and sulfobutyl ether-7 derivatives. J. Pharm. Sci. 88:889–895.
   PubMed Web of Science ®Google Scholar
• N. Erden, and N. Celebi. (1988). A study of inclusion complex of naproxen with β-cyclodextrin. Int. J. Pharm. 48:83–89.
   Web of Science ®Google Scholar
• M. T. Esclusa-Diaz, M. Gayo-Otero, M. B. Perez-Marcos, J. L. Vila-Jato, and J. J. Torres-Labandeira. (1996). Preparation and evaluation of ketoconazole-β-cyclodextrin multicomponent complexes. Int. J. Pharm. 142:183–187.
   Web of Science ®Google Scholar
• E. Fenyvesi, M. Vikmon, J. J. SzemanSzejtli, P. Ventura, and M. Pasini (1994). In T. Osa (Ed.), Enhancement of drug solubilizing capacity of hydroxy-propyl-β-cyclodextrin by tertiary complex formation. Proceeding of Seventh International Symposium on Cyclodextrins ( pp. 414–418). Tokyo: Academic Society of Japan.
   Google Scholar
• C. M. Fernandes, M. T. Vieira, and F. J. B. Veiga. (2002). Physicochemical characterization and in vitro dissolution behavior of nicardipine–cyclodextrins inclusion compounds. Eur. J. Pharm. Sci. 15:79–88.
   PubMed Web of Science ®Google Scholar
• J. L. Ford. (1986). The current status of solid dispersions. Pharm. Acta Helv. 61:69–88.
   PubMedGoogle Scholar
• K. H. Fromming, and J. Szejtli (1994). Cyclodextrins in pharmacy. Dordrecht: Kluwer Academic.
   Google Scholar
• A. H. Goldberg, M. Gribaldi, J. L. Kanig, and M. Myersohn. (1966). Increasing dissolution rates and gastrointestinal absorption of drugs IV: Chloramphenicol-urea system. J. Pharm. Sci. 55:1205–1211.
   PubMed Web of Science ®Google Scholar
• T. Higuchi, and K. A. Connors. (1965). Phase-solubility techniques. Adv. Anal. Chem. Instrum. 4:117–212.
   Google Scholar
• S. Ismail. (1991). Interaction of anti-convulsant drugs with alpha and beta-cyclodextrins I. Methsumide. STP Pharm. Sci. 1:321–325.
   Google Scholar
• K. A. Khan. (1975). The concept of dissolution efficiency. J. Pharm. Pharmacol. 27:48–49.
   PubMed Web of Science ®Google Scholar
• D. Laveneziana, R. Speranza, P. Raulli, and G. Paredi. (1996). Ibuprofen-arginine in the management of pain. Clin. Drug. Investig. 11:1–7.
   Web of Science ®Google Scholar
• G. S. Lazaro, O. P. Ferreira, and I. F. Gimeneza. (2007). Inclusion complexes of pyrimethamine in 2-hydroxypropyl-β-cyclodextrin: Characterization, phase solubility and molecular modeling. Bioorg. Med. Chem. 15:5752–5759.
   PubMed Web of Science ®Google Scholar
• S. Lin, and Y. Kao. (1989). Solid particulates of drug–β-cyclodextrin inclusion complexes directly prepared by a spray-drying technique. Int. J. Pharm. 56:249–259.
   Google Scholar
• T. Loftsson, and H. Fridriksdóttir. (1998). The effect of water-soluble polymers on the aqueous solubility and complexing abilities of β-cyclodextrin. Int. J. Pharm. 163:115–121.
   Web of Science ®Google Scholar
• T. Loftsson, H. Fridriksdóttir, and T. K. Gudmundsdóttir. (1996). The effect of water-soluble polymers on aqueous solubility of drugs. Int. J. Pharm. 127:293–296.
   Web of Science ®Google Scholar
• T. Loftsson, D. Hreinsdottir, and M. Masson. (2005). Evaluation of cyclodextrin solubilization of drugs. Int. J. Pharm. 302:18–28.
   PubMed Web of Science ®Google Scholar
• L. Longxiao, and Z. Suyan. (2006). Preparation and characterization of inclusion complexes of prazosin hydrochloride with β-cyclodextrin and hydroxypropyl-β-cyclodextrin. J. Pharm. Biomed. Anal. 40:122–127.
   PubMed Web of Science ®Google Scholar
• J. Moyano, M. Arias-Blanco, J. Ginés, and F. Giordano. (1997). Solid-state characterization and dissolution characteristics of gliclazide-β-cyclo-dextrin inclusion complexes. Int. J. Pharm. 148:211–217.
   Web of Science ®Google Scholar
• N. Mulinacci, F. Melani, G. Mazzi, and F. Vincieri. (1993). Molecular modelling and NMR NOE experiments: Complementary tools for the investigation of complex ibuproxam-β-cyclodextrin topology. Int. J. Pharm. 90:35–41.
   Web of Science ®Google Scholar
• P. Mura, G. P. Bettinetti, M. Cirri, F. Maestrelli, M. Sorrenti, and L. Catenacci. (2005). Solid-state characterization and dissolution properties of naproxen–arginine–hydroxypropyl-β-cyclodextrin ternary system. Eur. J. Pharm. Biopharm. 59:99–106.
   PubMed Web of Science ®Google Scholar
• P. Mura, G. P. Bettinetti, A. Manderioli, M. T. Faucci, G. Bramanti, and M. Sorrenti. (1998). Interactions of ketoprofen and ibuprofen with β-cyclodextrins in solution and in the solid state. Int. J. Pharm. 166:189–203.
   Web of Science ®Google Scholar
• P. Mura, M. T. Faucci, and G. P. Bettinettib. (2001a). The influence of polyvinylpyrrolidone on naproxen complexation with hydroxypropyl-β-cyclodextrin. Eur. J. Pharm. Sci. 13:187–194.
   PubMed Web of Science ®Google Scholar
• P. Mura, M. T. Faucci, A. Manderioli, and G. Bramanti. (2001b). Multicomponent systems of econazole with hydroxyacids and cyclodextrins. J. Incl. Phenom. 39:131–138.
   Web of Science ®Google Scholar
• T. Nakajima, M. Sunagawa, T. Hirohashi, and K. Fujioka. (1984). Studies of cyclodextrin inclusion complexes. I. Complex between cyclodextrin and bencyclane in aqueous solution. Chem. Pharm. Bull. (Tokyo) 32:400–483.
   Google Scholar
• J. Nishijo, Y. Ushiroda, H. Ohbori, M. Sugiura, and N. Fujii. (1997). The interaction of 1-naphthalene sulfonate with/β-cyclodextrin: Studies by calorimetry and proton nuclear magnetic resonance spectroscopy. Chem. Pharm. Bull. 45:899–903.
   Web of Science ®Google Scholar
• E. Redenti, L. Szente, and J. Szejtli. (2000). Drug/cyclodextrin/hydroxy acid multicomponent systems. Properties and pharmaceutical applications. J. Pharm. Sci. 89:1–8.
   PubMed Web of Science ®Google Scholar
• M. V. Rekharsky, R. N. Goldberg, F. Z. Schwarz, Y. B. Tewari, P. D. Ross, Y. Yamashoji, and Y. Inoue. (1995). Thermodynamic and nuclear magnetic resonance study of the interactions of α- and β-cyclodextrin with model substances, phenethylamine, ephedrines, and related substances. J. Am. Chem. Soc. 117:8830–8840.
   Web of Science ®Google Scholar
• L. Ribeiro, T. Loftsson, D. Ferreira, and F. Veiga. (2003). Investigation and physicochemical characterization of vinpocetine-sulfobutyl ether β-cyclodextrin binary and ternary complexes. Chem. Pharm. Bull. 51:914–922.
   PubMed Web of Science ®Google Scholar
• A. D. Rodrigues, R. A. Halpin, and L. A. Geer. (2003). Absorption, metabolism, and excretion of etoricoxib, a potent and selective cyclooxygenase-2 inhibitor, in healthy male volunteers. Drug Metab. Dispos. 31:224–232.
   PubMed Web of Science ®Google Scholar
• J. A. Ryan. (1986). Compressed pellet X-ray diffraction monitoring for optimisation of crystallinity in lyophilised solids: Imipenem: Cilastatin sodium case. J. Pharm. Sci. 75:805–807.
   PubMed Web of Science ®Google Scholar
• H. J. Schneider, F. Hacket, V. Rudiger, and H. Ikeda. (1998). NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98:1755–1786.
   PubMed Web of Science ®Google Scholar
• L. Szente, and J. Szejtli. (1999). Highly soluble cyclodextrin derivatives: Chemistry, properties, and trends in development. Adv. Drug Deliv. Rev. 36:17–28.
   PubMed Web of Science ®Google Scholar
• D. O. Thompson. (1997). Cyclodextrins-enabling excipients: Their present and future use in pharmaceuticals. In D. O. Thompson (Ed.), Critical reviews in therapeutic drug carrier systems ( pp. 1–104). CT, USA: Begell House.
   Google Scholar
• K. Uekama, F. Hirayama, and T. Irie. (1998). Cyclodextrin drug carrier systems. Chem. Rev. 98:2045–2076.
   PubMed Web of Science ®Google Scholar
• F. Usui, K. Maeda, A. Kusai, K. Nishimura, and K. Yamamoto. (1997). Inhibitory effects of water-soluble polymers on precipitation of RS-8359. Int. J. Pharm. 154:59–66.
   Web of Science ®Google Scholar
• M. Valero, B. I. Perez-Revuelta, and L. J. Rodriguez. (2003). Effect of PVP K-25 on the formation of the naproxen: β-cyclodextrin complex. Int. J. Pharm. 253:97–110.
   PubMed Web of Science ®Google Scholar
• F. J. B. Veiga, L. S. S. Ribeiro, and D. C. Ferreira. (2003). Physicochemical investigation of the effects of water-soluble polymers on vinpocetine complexation with β-cyclodextrin and its sulfobutyl ether derivative in solution and solid state. Eur. J. Pharm. Sci. 20:253–266.
   PubMed Web of Science ®Google Scholar
• F. J. B. Veiga, J. J. C. Teixeira-Dias, F. Kedzierewicz, A. Sousa, and P. Maincent. (1996). Inclusion complexation of tolbutamide with β-cyclodextrin and hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 129:63–71.
   Web of Science ®Google Scholar
• M. Vikmon, J. Szeman, J. Szejtli, M. Pasini, E. Redenti, and P. Ventura (1994). In T. Osa (Ed.), Terfenadine/hydroxy acid/cyclodextrin complexes. Proceedings of Seventh International Symposium on Cyclodextrin ( pp. 480–483). Tokyo: Academic Society of Japan.
   Google Scholar