Cyclodextrins and chitosan derivatives in sublingual delivery of low solubility peptides: A study using cyclosporin A, α-cyclodextrin and quaternary chitosan N-betainate

International Journal of Pharmaceutics

Volumn 381, Issue 1, 2009, Pages 19-24

  Mannila, Janne ^a   Järvinen, Kristiina ^a   Holappa, Jukka ^a   Matilainen, Laura ^a   Auriola, Seppo ^a   Jarho, Pekka ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

Absorption enhancer; Bioavailability; Buccal; Cyclodextrins; Peptide delivery; Transmucosal drug delivery

Indexed keywords

ALPHA CYCLODEXTRIN; CHITOSAN DERIVATIVE; CHITOSAN N BETAINATE; CYCLOSPORIN A; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; AREA UNDER THE CURVE; ARTICLE; COMPLEX FORMATION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG FORMULATION; DRUG SOLUBILITY; HEAT SENSITIVITY; MALE; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; RABBIT;

ADMINISTRATION, SUBLINGUAL; ALGORITHMS; ALPHA-CYCLODEXTRINS; ANIMALS; AREA UNDER CURVE; BETAINE; BIOLOGICAL AVAILABILITY; CHITOSAN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLD TEMPERATURE; CYCLODEXTRINS; CYCLOSPORINE; DRUG DELIVERY SYSTEMS; DRUG STABILITY; HALF-LIFE; MALE; PEPTIDES; RABBITS; SOLUBILITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 70349208449     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2009.07.012     Document Type: Article

References (29)

1. Cui C.Y., Lu W.L., Xiao L., Zhang S.Q., Huang Y.B., Li S.L., Zhang R.J., Wang G.L., Zhang X., and Zhang Q. Sublingual delivery of insulin: effects of enhancers on the mucosal lipid fluidity and protein conformation, transport and in vivo hypoglycemic activity. Biol. Pharm. Bull. 28 (2005) 2279-2288
2. De Campos A.M., Sanchez A., and Alonso M.J. Chitosan nanoparticles: a new vehicle for the improvement of the delivery of drugs to the ocular surface. Application to cyclosporin A. Int. J. Pharm. 224 (2001) 159-168
3. Di Colo G., Zambito Y., and Zaino C. Polymeric enhancers of mucosal epithelia permeability: synthesis, transepithelial penetration-enhancing properties, mechanism of action, safety issues. J. Pharm. Sci. 97 (2008) 1652-1680
4. El-Shabouri M.H. Positively charged nanoparticles for improving the oral bioavailability of cyclosporin-A. Int. J. Pharm. 249 (2002) 101-108
5. Fukaya H., Iimura A., Hoshiko K., Fuyumuro T., Noji S., and Nabeshima T. A cyclosporin A/maltosyl-alpha-cyclodextrin complex for inhalation therapy of asthma. Eur. Respir. J. 22 (2003) 213-219
6. Harris D., and Robinson J.R. Drug delivery via the mucous membranes of the oral cavity. J. Pharm. Sci. 81 (1992) 1-10
7. Higuchi T., and Connors K.A. Phase-solubility techniques. In: Reilley C.N. (Ed). Advances in Analytical Chemistry and Instrumentation (1965), Interscience Publisher/John Wiley&Sons, New York 117-212
8. Holappa J., Hjalmarsdottir M., Masson M., Runarsson O., Asplund T., Luttikhedde T., Soininen P., Nevalainen T., and Jarvinen T. Antimicrobial activity of chitosan N-betainates. Carbohydr. Polym. 56 (2006) 114-118
9. Holappa J., Nevalainen T., Savolainen J., Soininen P., Elomaa M., Safin R., Suvanto S., Pakkanen T., Masson M., Loftsson T., and Jarvinen T. Synthesis and characterization of chitosan N-betainates having various degrees of substitution. Macromolecules 37 (2004) 2784-2789
10. Illum L. Chitosan and its use as a pharmaceutical excipient. Pharm. Res. 15 (1998) 1326-1331
11. Irie T., and Uekama K. Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J. Pharm. Sci. 86 (1997) 147-162
12. Ismailos G., Reppas C., Dressman J.B., and Macheras P. Unusual solubility behaviour of cyclosporin A in aqueous media. J. Pharm. Pharmacol. 43 (1991) 287-289
13. Kanai A., Alba R.M., Takano T., Kobayashi C., Nakajima A., Kurihara K., Yokoyama T., and Fukami M. The effect on the cornea of alpha cyclodextrin vehicle for cyclosporin eye drops. Transplant. Proc. 21 (1989) 3150-3152
14. Langoth N., Kahlbacher H., Schoffmann G., Schmerold I., Schuh M., Franz S., Kurka P., and Bernkop-Schnurch A. Thiolated chitosans: design and in vivo evaluation of a mucoadhesive buccal peptide drug delivery system. Pharm. Res. 23 (2006) 573-579
15. Lee V.H.L., and Yamamoto A. Penetration and enzymatic barriers to peptide and protein absorption. Adv. Drug Deliv. Rev. 4 (1990) 171-207
16. Loftsson T., Vogensen S.B., Brewster M.E., and Konradsdottir F. Effects of cyclodextrins on drug delivery through biological membranes. J. Pharm. Sci. 96 (2007) 2532-2546
17. Mannila J., Jarvinen T., Jarvinen K., and Jarho P. Precipitation complexation method produces cannabidiol/beta-cyclodextrin inclusion complex suitable for sublingual administration of cannabidiol. J. Pharm. Sci. 96 (2007) 312-319
18. Mannila J., Jarvinen T., Jarvinen K., Tervonen J., and Jarho P. Sublingual administration of Delta9-tetrahydrocannabinol/beta-cyclodextrin complex increases the bioavailability of Delta9-tetrahydrocannabinol in rabbits. Life Sci. 78 (2006) 1911-1914
19. Miyake K., Hirayama F., and Uekama K. Solubility and mass and nuclear magnetic resonance spectroscopic studies on interaction of cyclosporin A with dimethyl-alpha- and -beta-cyclodextrins in aqueous solution. J. Pharm. Sci. 88 (1999) 39-45
20. Molander L., and Lunell E. Pharmacokinetic investigation of a nicotine sublingual tablet. Eur. J. Clin. Pharmacol. 56 (2001) 813-819
21. Nakate T., Yoshida H., Ohike A., Tokunaga Y., Ibuki R., and Kawashima Y. Improvement of pulmonary absorption of cyclopeptide FK224 in rats by co-formulating with beta-cyclodextrin. Eur. J. Pharm. Biopharm. 55 (2003) 147-154
22. Odou P., Barthelemy C., Chatelier D., Luyckx M., Brunet C., Dine T., Gressier B., Cazin M., Cazin J.C., and Robert H. Pharmacokinetics of midazolam: comparison of sublingual and intravenous routes in rabbit. Eur. J. Drug Metab. Pharmacokinet. 24 (1999) 1-7
23. Okada Y., Matsuda K., Hara K., Hamayasu K., Hashimoto H., and Koizumi K. Properties and the inclusion behavior of 6-O-alpha-d-galactosyl- and 6-O-alpha-d-mannosyl-cyclodextrins. Chem. Pharm. Bull. (Tokyo) 47 (1999) 1564-1568
24. Rathbone M.J., Ponchel G., and Ghazali F.A. Systemic oral mucosal drug delivery and delivery systems. In: Rathbone M.J. (Ed). Oral Mucosal Drug Delivery (1996), Marcel Dekker, Hamilton
25. Salehian B., Wang C., Alexander G., Davidson T., McDonald V., Berman N., Dudley R.E., Ziel F., and Swerdloff R.S. Pharmacokinetics, bioefficacy, and safety of sublingual testosterone cyclodextrin in hypogonadal men: comparison to testosterone enanthate-a clinical research center study. J. Clin. Endocrinol. Metab. 80 (1995) 3567-3575
26. Sasamoto Y., Hirose S., Ohno S., Onoe K., and Matsuda H. Topical application of ciclosporin ophthalmic solution containing alpha-cyclodextrin in experimental uveitis. Ophthalmologica 203 (1991) 118-125
27. Senel S., Kremer M.J., Kas S., Wertz P.W., Hincal A.A., and Squier C.A. Enhancing effect of chitosan on peptide drug delivery across buccal mucosa. Biomaterials 21 (2000) 2067-2071
28. Shojaei A.H. Buccal mucosa as a route for systemic drug delivery: a review. J. Pharm. Pharm. Sci. 1 (1998) 15-30
29. Veuillez F., Kalia Y.N., Jacques Y., Deshusses J., and Buri P. Factors and strategies for improving buccal absorption of peptides. Eur. J. Pharm. Biopharm. 51 (2001) 93-109