Study of the Influence of Both Cyclodextrins and L-Lysine on the Aqueous Solubility of Nimesulide; Isolation and Characterization of Nimesulide-L-Lysine-Cyclodextrin Complexes
[en] Nimesulide is a nonsteroidal antiinflammatory drug that exhibits a very poor water solubility (0.01 mg.mL-1). A nimesulide-beta-cyclodextrin complex prepared according to patent application WO 94/ 02177 has an aqueous solubility of approximately 16 mg.mL-1 of nimesulide. A nimesulide-L-lysine salt has also been prepared and increases the aqueous solubility of nimesulide to approximately 5.0-7.5 mg.mL-1. The purpose of the present study was to investigate the interaction of both cyclodextrins and L-lysine on the aqueous solubility of nimesulide. Nimesulide-L-lysine-beta- or gamma-cyclodextrin complexes were prepared by spray-drying. The inclusion of the nimesulide-L-lysine salt into the cyclodextrin cavity was confirmed by differential scanning calorimetry and proton nuclear magnetic resonance spectroscopy. These complexes offered remarkable aqueous solubility. The incorporation of nimesulide in a nimesulide-L-lysine-beta-cyclodextrin complex increased its water solubility by a factor of 10 at pH 1.5 (0.050 mg.mL-1 for the complex versus 0.005 mg.mL-1 for nimesulide), 160 at pH 6.8 (2.373 mg.mL-1 for the complex versus 0.015 mg.mL-1 for nimesulide), and 3600 in purified water (36.400 mg.mL-1 for the complex versus 0.01 mg.mL-1 for nimesulide).
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Piel, Géraldine ; Université de Liège - ULiège > Département de pharmacie > Pharmacie galénique et magistrale
Pirotte, Bernard ; Université de Liège - ULiège > Chimie pharmaceutique
Delneuville, Isabelle
Neven, Philippe
Llabres, Gabriel ; Université de Liège - ULiège > Département de physique > Département de physique
Delarge, Jacques
Delattre, Luc ; Université de Liège - ULiège > Département de pharmacie > Département de pharmacie
Language :
English
Title :
Study of the Influence of Both Cyclodextrins and L-Lysine on the Aqueous Solubility of Nimesulide; Isolation and Characterization of Nimesulide-L-Lysine-Cyclodextrin Complexes
scite shows how a scientific paper has been cited by providing the context of the citation, a classification describing whether it supports, mentions, or contrasts the cited claim, and a label indicating in which section the citation was made.
Bibliography
Biscarini, L.; Patoia, L.; Del Favero A. Drugs Today 1988, 24, 23-27.
Aslanian, R.; Carruthers, N. I.; Kaminski, J. J. Exp. Opin. Invest. Drugs 1994, 3, 1323-1325.
Jensen, N. P. Med. Chem. Res. 1995, 5, 319-324.
Bevilacqua, M.; Vago, T.; Baldi, G.; et al. Eur. J. Pharmacol. 1994, 268, 415-423.
Kurozumi, M.; Nambu, N.; Nagai, T. Chem. Pharm. Bull. 1975, 23 (12), 3062-3068.
Chow, D.; Karara, A. H. Int. J. Pharm. 1986, 28, 95-101.
Otagiri, M.; Imai, T.; Matsuo, N.; Uekama, K. Acta Pharm. Sue. 1983a, 20, 1-11.
Otagiri, M.; Imai, T.; Hirayama, F.; Uekama, K. Acta Pharm. Sue. 1983b, 20, 11-20.
Otero Espinar, J.; Anguiano-Igea, S.; Garcia-Gonzalez, N.; Vila Jato, J. L.; Blanco-Mendez J. Int. J. Pharm. 1992, 79, 149-157.
Mafione, G. Method of preparation of inclusion compounds of nimesulide with cyclodextrins PCT/EP93/01560 WO94/02177, 1993.
Pirotte, B.; Piel, G.; Neven, P.; Delneuville, I. Sel de nimésulide hydrosoluble et leurs utilisations pour le traitement des affections inflammatoires PCT/BE95/00055 WO 95/34533, 1995.
Higuchi, T.; Connors, K. A. Adv. Anal. Chem. Instrum. 1965, 4, 117-212.
Djedaïni, F.; Perly, B. In New trends in cyclodextrins and derivatives; Duchêne, D., Ed.; de Santé: Paris, 1991.
This website uses cookies to improve user experience. Read more
Save & Close
Accept all
Decline all
Show detailsHide details
Cookie declaration
About cookies
Strictly necessary
Performance
Strictly necessary cookies allow core website functionality such as user login and account management. The website cannot be used properly without strictly necessary cookies.
This cookie is used by Cookie-Script.com service to remember visitor cookie consent preferences. It is necessary for Cookie-Script.com cookie banner to work properly.
Performance cookies are used to see how visitors use the website, eg. analytics cookies. Those cookies cannot be used to directly identify a certain visitor.
Used to store the attribution information, the referrer initially used to visit the website
Cookies are small text files that are placed on your computer by websites that you visit. Websites use cookies to help users navigate efficiently and perform certain functions. Cookies that are required for the website to operate properly are allowed to be set without your permission. All other cookies need to be approved before they can be set in the browser.
You can change your consent to cookie usage at any time on our Privacy Policy page.