Colon-specific drug delivery based on a cyclodextrin prodrug: Release behavior of biphenylylacetic acid from its cyclodextrin conjugates in rat intestinal tracts after oral administration

Journal of Pharmaceutical Sciences

Volumn 87, Issue 6, 1998, Pages 715-720

  Minami, Kunihiro ^a   Hirayama, Fumitoshi ^a   Uekama, Kaneto ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; CYCLODEXTRIN; FELBINAC;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; DRUG CONJUGATION; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SOLUBILITY; INTESTINE ABSORPTION; NONHUMAN; ORAL DRUG ADMINISTRATION; PH; PREFORMULATION; RAT;

EID: 0031807470     PISSN: 00223549     EISSN: None     Source Type: Journal    
DOI: 10.1021/js9704339     Document Type: Article

References (29)

1. Friend, D. R., Ed. Oral Colon-Specific Drug Delivery; CRC Press: Boca Raton, FL, 1992.
2. Rubinstein, A. Approaches and opportunities in colon-specific drug delivery. CRC Crit. Rev. Ther. Drug Carrier Syst. 1995, 12, 101-149.
3. Peeters, R.; Kinget, R. Film-forming polymers for colonic drug delivery: I. synthesis and physical and chemical properties of methyl derivatives of eudragit S. Int. J. Pharm. 1993, 94, 125-134.
4. Takaya, T.; Ikeda, C.; Imagawa, N.; Niwa, K.; Takada, K. Development of a colon delivery capsule and the pharmacological activity of recombinant human granulocyte colony-stimulating factor (rhG-CSF) in beagle dogs. J. Pharm. Pharmacol. 1995, 47, 474-478.
5. Gazzaniga, A.; Busetti, C.; Moro, L.; Sangalli, M. E.; Giordano, F. Time-dependent oral delivery systems for colon targeting. S.T.P. Pharma Sci. 1995, 5, 83-88.
6. Saffran, M.; Kumar, G. S.; Savariar, C.; Burnham, J. C.; Williams, F.; Neckers, D. C. A new approach to the oral administration of insulin and other peptide drugs. Science 1986, 233, 1081-1084.
7. Larsen, C.; Harboe, E.; Johansen, M.; Olesen, H. P. Macromolecular prodrugs. XVI. Colon-targeted delivery-comparison of the rate of release of naproxen from dextran ester prodrugs in homogenates of various segments of the pig gastrointestinal (GI) tract. Pharm. Res. 1989, 6, 995-999.
8. Kopeček, J.; Kopečková, P. N-(2-Hydroxypropyl)methacrylamide copolymers for colon-specific drug delivery. In Oral Colon-Specific Drug Delivery; Friend, D. R., Ed.; CRC Press: Boca Raton, 1992; pp 189-211.
9. Friend, D. R. Glycosides in colonic drug delivery. In Oral Colon-Specific Drug Delivery; Friend, D. R., Ed.; CRC Press: Boca Raton, 1992; pp 153-187.
10. Duchêne, D., Ed.; New Trend in Cyclodextrins and Their Derivatives; Editions de Santé: Paris, 1991.
11. Loftsson, T.; Brewster, M. E.; Derendorf, H.; Bodor, N. 2-Hydroxypropyl-β-cyclodextrin: properties and usage in pharmaceutical formulations. Pharm. Ztg. Wiss. 1991, 4, 5-10.
12. Uekama, K.; Hirayama, F.; Irie, T. Pharmaceutical uses of cyclodextrin derivatives. In High Performance Biomaterials; Szycher, M., Ed.; Technomic Publishing: Lancaster, 1991; pp 789-806.
13. Szejtli, J.; Szente, L., Ed. Proceedings of the Eighth International Symposium on Cyclodextrins; Kluwer: Dordrecht, 1996.
14. Stella, V. J.; Rajewski, R. A. Cyclodextrins: their future in drug formulation and delivery. Pharm. Res. 1997, 14, 556-567.
15. Andersen, G. H.; Robbins, F. M.; Domingues, F. J.; Moores, R. G.; Long, C. L. The utilization of schardinger dextrins by the rat. Toxicol. Appl. Pharmacol. 1983, 5, 257-266.
16. Antenucci, R.; Palmer, J. K. Enzymatic degradation of α- and β-cyclodextrins by bacteroids of the human colon. J. Agric. Food Chem. 1984, 32, 1316-1321.
17. 14C-β-cyclodextrin in rat. Arzneim. Forsch. / Drug Res. 1985, 35, 1042-1047.
18. Flourié, B.; Molis, C.; Achour, L.; Dupas, H.; Hatat, C.; Rambaud, J. C. Fate of β-cyclodextrin in the human intestine. J. Nutr. 1993, 123, 676-680.
19. Hirayama, F.; Minami, K.; Uekama, K. In vitro evalution of biphenylyl acetic acid-β-cyclodextrin conjugates as colon-targeting prodrug: drug release behaviour in rat biological media. J. Pham. Pharmacol. 1996, 48, 27-31.
20. A-[[(4-biphenylyl)acetyl]amino]-α-, -β- and -γ-cyclodextrins: potential prodrugs for colon-specific delivery. J. Med. Chem. 1997, 40, 2755-2761.
21. Arima, H.; Adachi, H.; Irie, T.; Uekama, K.; Pitha, J. Enhancement of the antiinflammatory effect of ethyl 4-biphenylylacetate in ointment by β-cyclodextrin derivatives: increased absorption and localized activation of the prodrugs in rats. Pharm. Res. 1990, 11, 1152-1156.
22. Ohnishi, A.; Fujuwara, H.; Kitamura, M.; Sasaki. T. Study of pharmcokinetics and safety of felbinac patch. Jpn. Pharmcol. Ter. 1992, 20, 115-138.
23. Chiccarelli, F. S.; Eisner, H. J.; Van Lear, G. E. Disposition and metabolism of fenbufen in several laboratory animals. Arzneim. Forsch. / Drug Res. 1980, 30, 707-715.
24. Nakamura, H.; Yokoyama, Y.; Motoyoshi, S.; Seto, Y.; Kadokawa, T.; Shimizu, T. Antiinflammatony activity of a nonsteroidal anti-inflammatony agent, zomepirac sodium, in experimental animals. Folia Pharmacol. Jpn. 1982, 79, 509-527.
25. Winter, C. A.; Risley, E. A.; Nuss, G. W. Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatony drugs. Proc. Soc. Exp. Bio. Med. 1962, 111, 544-547.
26. Simpkins, J. W.; Smulkowski, M.; Dixon, R.; Tuttle, R. Evidence for the delivery of narcotic antagonists to the colon as their glucuronide conjugates. J. Pharmcol. Exp. Ther. 1988, 244, 195-205.
27. McLeod. A. D.; Tozer, T. N. Kinetic perspectives in colonic drug delivery. In Oral Colon-Specific Drug Delivery; Friend, D. R., Ed.; CRC Press: Boca Raton, 1992; pp 85-114.
28. Matsuoka, O.; Muramatsu, E. Introduction to Comparative Animal Science: Extrapolation from Experimental Animal to Human (in Japanese); Science Soft: Tokyo, 1980; p 248.
29. Hirayama, F.; Kurihara, M.; Utsuki, T.; Uekama, K. Inhibitory effect of guest molecules on acid-catalyzed ring-opining of β-cyclodextrin. J. Chem. Soc., Chem. Commun. 1993, 1578-1580.