Use of cyclodextrins to form inclusion complexes of pharmaceutical interest;Utilização de ciclodextrinas na formação de complexos de inclusão de interesse farmacêutico

Revista de Ciencias Farmaceuticas Basica e Aplicada

Volumn 28, Issue 1, 2007, Pages 1-9

  Da Cunha Filho, Marcílio Sérgio Soares ^a   Sa Barreto L C L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Bioavailability; Cyclodextrin; Inclusion complex; Pharmaceutical excipient

Indexed keywords

BENEXATE; CEFDITOREN PIVOXIL; CEFOTIAM HEXETIL; CETIRIZINE; CHLORAMPHENICOL; CHLORDIAZEPOXIDE; CISAPRIDE; CYCLODEXTRIN DERIVATIVE; DEXAMETHASONE; DEXTROMETHORPHAN; DICLOFENAC; ESTRADIOL; EXCIPIENT; GARLIC EXTRACT; GLYCERYL TRINITRATE; INDOMETACIN; IODINE; ITRACONAZOLE; MITOMYCIN; NICOTINE; NICOTINE GUM; NIMESULIDE; OMEPRAZOLE; PIROXICAM; PIROXICAM BETA CYCLODEXTRIN; PROSTAGLANDIN E2; TEBOROXIME TC 99M; TIAPROFENIC ACID; VORICONAZOLE; ZIPRASIDONE;

DRUG BIOAVAILABILITY; DRUG DOSAGE FORM; DRUG FORMULATION; DRUG QUALITY; DRUG STABILITY; REVIEW;

EID: 39549098143     PISSN: 18084532     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (48)

1. Al-Marzouqi AH, Jobe B, Dowaidar A, Maestrelli F, Mura P. Evaluation of supercritical fluid technology as preparative technique of benzocaine- cyclodextrin complexes - Comparison with conventional methods. J Pharm Biomed Anal 2007; 43(2):566-74.
2. th International Cyclodextrin Symposium; 2004 May 16-19; Montpellier. 2004:193-5.
3. th.ed. London: Pharmaceutical Press; 2006. 918p.
4. Biwer A, Antranikian G, Heinzle E. Enzymatic production of cyclodextrins. Appl Microbiol Biotechnol 2002; 59:609-17.
5. Cabrai Marques HM, Hadgraft J, Kellaway IW. Studies of cyclodextrin inclusion complexes. I. The salbutamol-cyclodextrin complex as studied by phase solubility and DSC. Int J Pharm 1990; 63(3):259-66.
6. Cameron KS, Fielding L. NMR diffusion spectroscopy as a measure of host-guest complex association constants and as a probe of complex size. J Org Chem 2001; 66(21):6891-5.
7. Cao F, Guo J, Ping Q. The physicochemical characteristics of freeze-dried scutellarin-cyclodextrin tetracomponent complexes. Drug Dev Ind Pharm 2005; 31(8):747-56.
8. Cirri M, Maestrelli F, Orlandini S, Furlanetto S, Pinzauti S, Mura P. Determination of stability constant values of flurbiprofen-cyclodextrin complexes using different techniques. J Pharm Biomed Anal 2005a; 37:995-1002.
9. Cirri M, Rangoni C, Maestrelli F, Corti G, Mura P. Development of fast-dissolving tablets of flurbiprofen-cyclodextrin complexes. Drug Dev Ind Pharm 2005b; 31(7):697-707.
10. Cobas JC, Martin-Pastor M. A homodecoupled diffusion experiment for the analysis of complex mixtures by NMR. J Magn Reson 2004; 171(1):20-4.
11. Cunha-Filho MSS, Landín M, Martínez-Pacheco R, Dacunha-Marinho B. beta-Lapachone. Acta Crystallogr C. 2006; 62(Pt 8):o473-5.
12. Cunha-Filho MSS, Dacunha-Marinho B, Torres-Labandeira JJ, Martínez-Pacheco R, Landín M. Characterization of β-Lapachone and Methylated β-Cyclodextrin Solid-state Systems. AAPS PharmSciTech [periódico on-line] 2007 8(3). Disponível em URL: http://www.aapspharmscitech.org [01 ago 2007]
13. Davis ME, Brewster ME. Cyclodextrin-based pharmaceutics: past, present and future. Nat Rev Drug Discov 2004; 3(12):1023-35.
14. Fernandes CM, Veiga FJB. Effect of the hydrophobic nature of triacetyl-b-cyclodextrin on the complexation with nicardipine hydrochloride: physicochemical and dissolution properties of the kneaded and spray-dried complexes. Chem Pharm Bull 2002; 50(12):1597-602.
15. Fielding L. Determination of Association Constant (Ka) from Solution NMR Data. Tetrahedron 2000; 56:6151-70.
16. Fromming K, Szejtli, J. Cyclodextrin in pharmacy. Dordrecht: Kluwer Academic; 1994. 219p.
17. Gargallo L, Vargas D, Leiva A, Radic D. Surface properties of inclusion complexes between a-cyclodextrin and poly (ethylene oxide). J Colloid Interface Sci 2006; 301(2):607-11.
18. Hedges AR. Industrial applications of cyclodextrins. Chem Rev 1998; 98(5):2035-44.
19. Higuchi T, Connors KA. Phase solubility techniques. Adv Anal Chem Instrum 1965; 4:117-212.
20. Iliescu T, Baia M, Miclaus V. A Raman spectroscopic study of the diclofenac sodium-b-cyclodextrin interaction. Eur J Pharm Sci 2004; 22(5):487-95.
21. Junco S, Casimiro T, Ribeiro N, Da Ponte MN, Marques HC. A comparative study of naproxen - beta cyclodextrin complexes prepared by conventional methods and using supercritical carbon dioxide. J Incl Phenom Mol Recognit Chem 2002; 44(1-4):117-21.
22. Lipkowitz KB. Applications of computational chemistry to the study of cyclodextrins. Chem Rev 1998; 98(5):1829-73.
23. Loftsson T, Brewster ME. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 1996; 85(10):1017-25.
24. Loftsson T, Masson M, Brewster ME. Self-association of cyclodextrins and cyclodextrin complexes. J Pharm Sci 2004; 93(5):1091-9.
25. Loftsson T, Duchene D. Cyclodextrins and their pharmaceutical applications. Int J Pharm 2007; 329(1-2):1-11.
26. Manzoori JL, Abdolmohammad-Zadeh H, Amjadi M. Study on the inclusion complex between b-cyclodextrin and celecoxib by spectrofluorimetry and its analytical application. Farmaco 2005; 60(6-7):575-81.
27. th.ed. London: Pharmaceutical Press; 2005. 2756p.
28. Miro A, Quaglia F, Sorrentino R, d'Emmanuele di Villa Bianca,R., Varricchio G, La Rotonda MI. Enhancement of gliquidone aqueous solubility by cyclodextrins for the optimization of its pharmacological profile. Proceedings of the International Symposium on Controlled Release of Bioactive Materials; 2000 July 11-13; Paris: Controlled Release Society, 2000:1270-1.
29. Mura P, Furlanetto S, Cirri M, Maestrelli F, Corti G, Pinzauti S. Interaction of naproxen with ionic cyclodextrins in aqueous solution and in the solid state. J Pharm Biomed Anal 2005; 37(5):987-94.
30. Palakodaty S, York P. Phase behavioral effects on particle formation processes using supercritical fluids. Pharm Res 1999; 16(7):976-85.
31. Pitha J, Hoshino T, Torres-Labandeira J, Irie T. Preparation of drug-hydroxypropyl cyclodextrin complexes by a method using ethanol or aqueous ammonium hydroxide as cosolubilizers. Int J Pharm 1992; 80(2-3):253-8.
32. Pose-Vilarnovo B, Perdomo-Lopez I, Echezarreta-Lopez M, Schroth-Pardo P, Estrada E, Torres-Labandeira JJ. Improvement of water solubility of sulfamethizole through its complexation with b- and hydroxypropyl-b- cyclodextrin. Characterization of the interaction in solution and in solid state. Eur J Pharm Sci 2001; 13(3):325-31.
33. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J Pharm Sci 1996; 85(11):1142-69.
34. RFE. Real Farmacopea Española, 3.ed., Madri: Imprenta Nacional del Boletín oficial del Estado, 2005.
35. Rodriguez-Perez AI, Rodriguez-Tenreiro C, Alvarez-Lorenzo C, Concheiro A, Torres-Labandeira JJ. Drug solubilization and delivery from cyclodextrin-pluronic aggregates. J Nanosci Nanotechnol 2006; 6(9/10):3179-86.
36. Schneider H, Hacket F, Ruediger V, Ikeda H. NMR Studies of cyclodextrins and cyclodextrin complexes. Chem Rev 1998; 98(5):1755-85.
37. Suzuki Y, Ogura T, Takagishi Y. Bitterness-suppressive formulation of benexate hydrochloride-Betadex prepared by melt granulation. Pharm Tech Japan 1993; 9(9):999-1008.
38. Szejtli J. Cyclodextrin and general overview of cyclodextrin chemistry. Chem Rev 1998; 98:1743-53.
39. Szejtli J. Past, present, and future of cyclodextrin. Pure Appl Chem 2004; 76 (10):1825-45.
40. Szejtli J. Cyclodextrin complexed generic drugs are generally not bio-equivalent with the reference products: therefore the increase in number of marketed drug/cyclodextrin formulations is so slow. J Incl Phenom Macroc Chem 2005; 52(1-2):1-11.
41. Taneri F, Gueneri T, Zoltan Z, Kata M. Influence of cyclodextrin complexation on the physicochemical and biopharmaceutical properties of ketoconazole. J Incl Phenom Macroc Chem 2003; 47(1-2):15-23.
42. Uekama K. Design and evaluation of cyclodextrin-based drug formulation. Chem Pharm Bull 2004; 52(8):900-15.
43. th.ed., Rock Ville, United States Pharamacopoeial Convention, 2006.
44. Veiga MD, Diaz PJ, Ahsan F. Interactions of griseofulvin with cyclodextrins in solid binary systems. J Pharm Sci 1998; 87(7):891-900.
45. Ventura CA, Giannone I, Paolino D, Pistara V, Corsaro A, Puglisi G. Preparation of celecoxib-dimethyl-beta-cyclodextrin inclusion complex: characterization and in vitro permeation study. Eur J Med Chem 2005; 40(7):624-31.
46. Vozone CM, Marques HMC. Complexation of budesonide in cyclodextrins and particle aerodynamic characterization of the complex solid form for dry powder inhalation. J Incl Phenom Macroc Chem 2003; 44(1-4):111-5.
47. Zema L, et al. Powder pelletization of a b-cyclodextrin / microcrystalline cellulose mixture in a fluid bed rotor granulator: Sequential statistical optimization of the process. Acta Tech Leg Med 2001;12(1):1-14.
48. Zia V, Rajewski RA, Stella VJ. Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of sulfobutyl ether-b-cyclodextrin to hydroxypropyl b-cyclodextrin. Pharm Res 2001; 18(5):667-73.