Structural evaluation of crystalline ternary γ-cyclodextrin complex

Journal of Pharmaceutical Sciences

Volumn 100, Issue 1, 2011, Pages 325-333

  Higashi, Kenjirou ^a   Ideura, Saori ^a   Waraya, Haruka ^a   Moribe, Kunikazu ^a   Yamamoto, Keiji ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Complexation; Crystal structure; Cyclodextrins; FTIR; Inclusion compounds; Sealed heating; Solid state NMR; Stoichiometry; Water sorption; X ray powder diffractometry

Indexed keywords

FLURBIPROFEN; GAMMA CYCLODEXTRIN; SALICYLIC ACID;

ADSORPTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPLEX FORMATION; CRYSTAL STRUCTURE; DESORPTION; HEATING; PRECIPITATION; PROTEIN QUATERNARY STRUCTURE; SOLID STATE; STOICHIOMETRY; WATER VAPOR; X RAY DIFFRACTION;

EID: 78650047055     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22273     Document Type: Article

References (31)

1. Uekama K, Hirayama F, Irie T. 1998. Cyclodextrin drug carrier systems. Chem Rev 98: 2045-2076.
2. Carrier RL, Miller LA, Ahmed I. 2007. The utility of cyclodextrins for enhancing oral bioavailability. J Control Release 123: 78-99.
3. Szejtli J. 2004. Past, present, and future of cyclodextrin research. Pure Appl Chem 76: 1825-1845.
4. Brewster ME, Loftsson T. 2007. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 59: 645-666.
5. Davis ME, Brewster ME. 2004. Cyclodextrin-based pharmaceutics: Past, present and future. Nat Rev Drug Discov 3: 1023-1035.
6. Munro IC, Newberne PM, Young VR, Bär A. 2004. Safety assessment of γ-cyclodextrin. Regul Toxicol Pharmacol 39: S3-S13.
7. Ikeda Y, Hirayama F, Arima H, Uekama K, Yoshitake Y, Harano K. 2004. NMR spectroscopic characterization of metoprolol/cyclodextrin complexes in aqueous solution: Cavity size dependency. J Pharm Sci 93: 1659-1671.
8. Williams RO III, Liu J. 1999. Influence of formulation technique for hydroxypropyl-β-cyclodextrin on the stability of aspirin in HFA 134a. Eur J Pharm Biopharm 47: 145-152.
9. Fernandes CM, Vieira MT, Veiga FJB. 2002. Physicochemical characterization and in vitro dissolution behavior of nicardipine-cyclodextrins inclusion compounds. Eur J Pharm Sci 15: 79-88.
10. Toropainen T, Heikkilä T, Leppänen J, Matilainen L, Velaga S, Jarho P, Carlfors J, Lehto VP, Järvinen T, Järvinen K. 2007. Crystal structure changes of γ-cyclodextrin after the SEDS process in supercritical carbon dioxide affect the dissolution rate of complexed budesonide. Pharm Res 24: 1058-1066.
11. Rusa CC, Bullions TA, Fox J, Porbeni FE, Wang X, Tonelli AE. 2002. Inclusion compound formation with a new columnar cyclodextrin host. Langmuir 18: 10016-10023.
12. Hunt MA, Rusa CC, Tonelli AE, Balik CM. 2005. Structure and stability of columnar cyclomaltooctaose (γ-cyclodextrin) hydrate. Carbohydr Res 340: 1631-1637.
13. Harata K. 1998. Structural aspects of stereodifferentiation in the solid state. Chem Rev 98: 1803-1828.
14. Kawasaki J, Satou D, Takagaki T, Nemoto T, Kawaguchi A. 2007. Structural features of inclusion complexes of γ-cyclodextrin with various polymers. Polymer 48: 1127-1138.
15. Higashi K, Tozuka Y, Moribe K, Yamamoto K. 2010. Salicylic acid/γ-cyclodextrin 2/1 and 4/1 complex formation by sealed-heating method. J Pharm Sci in press (#09-588).
16. Higashi K, Ideura S, Waraya H, Moribe K, Yamamoto K. 2009. Incorporation of salicylic acid molecules into the intermolecular spaces of γ-cyclodextrin-polypseudorotaxane. Cryst Growth Des 9: 4243-4245.
17. Higashi K, Ideura S, Waraya H, Limwikrant W, Moribe K, Yamamoto K. 2010. Simultaneous dissolution of naproxen and flurbiprofen from a novel ternary γ-cyclodextrin complex. Chem Pharm Bull 58: 769-772.
18. Arco M, Gutiérrez S, Martín C, Rives V, Rocha J. 2004. Synthesis and characterization of layered double hydroxides (LDH) intercalated with non-steroidal anti-inflammatory drugs (NSAID). J Solid State Chem 177: 3954-3962.
19. Yates JR, Dobbins SE, Pickard CJ, Mauri F, Ghi PY, Harris RK. 2005. A combined first principles computational and solid-state NMR study of a molecular crystal: Flurbiprofen. Phys Chem Chem Phys 7: 1402-1407.
20. Mollica G, Geppi M, Pignatello R, Veracini CA. 2006. Molecular properties of flurbiprofen and its solid dispersions with Eudragit RL100 studied by high- and low-resolution solid-state nuclear magnetic resonance. Pharm Res 23: 2129-2140.
21. Miller LA, Carrier RL, Ahmed I. 2007. Practical considerations in development of solid dosage forms that contain cyclodextrin. J Pharm Sci 96: 1691-1707.
22. Uyar T, Hunt MA, Gracz HS, Tonelli AE. 2006. Crystalline cyclodextrin inclusion compounds formed with aromatic guests: Guest-dependent stoichiometries and hydration-sensitive crystal structures. Cryst Growth Des 5: 1113-1119.
23. 12 with Z'=3/4: Crystal structure of the complex γ-cyclodextrin-methanol-n-hydrate. Acta Cryst B54: 450-455.
24. Grzesiak AL, Matzger AJ. 2007. New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer-induced heteronucleation. J Pharm Sci 96: 2978-2986.
25. Cirri M, Rangoni C, Maestrelli F, Corti G, Mura P. 2005. Development of fast-dissolving tablets of flurbiprofen-cyclodextrin complexes. Drug Dev Ind Pharm 31: 697-707.
26. 2, the organic additives 1-propanol, 2-propanol, and the surfactant sodium dodecyl sulfate. J Phys Chem B 106: 4763-4774.
27. Nakai Y, Nakajima S, Yamamoto K, Terada K, Konno T. 1980. Effects of grinding on the physical and chemical properties of crystalline medicinals with microcrystalline cellulose. IV. Comparison of the IR spectra of medicinals in the solid state and in solution. Chem Pharm Bull 28: 652-656.
28. Tozuka Y, Oguchi T, Yamamoto K. 2003. Adsorption and entrapment of salicylamide molecules into the mesoporous structure of folded sheets mesoporous material (FSM-16). Pharm Res 20: 926-930.
29. Saenger W, Jacob J, Gessler K, Steiner T, Hoffmann D, Sanbe H, Koizumi K, Smith SM, Takaha T. 1998. Structure of the common cyclodextrins and their larger analogues-Beyond the doughnut. Chem Rev 98: 1787-1802.
30. Chen W, Chang CE, Gilson MK. 2004. Calculation of cyclodextrin binding affinities: Energy, entropy, and implications for drug design. Biophys J 87: 3035-3049.
31. 3. Acta Cryst C41: 280-282.