Synthesis and in vitro properties of prednisolone 21-sulfate sodium as a colon-specific prodrug of prednisolone

Archives of Pharmacal Research

Volumn 26, Issue 4, 2003, Pages 258-263

  Min, Ju Doh ^a   Yun, Jin Jung ^a   In, Ho Kim ^a   Hye, Sik Kong ^a   Young, Mi Kim ^a  

^a Pusan National University   (South Korea)

Author keywords

Colon specific prodrugs of glucocorticoid; Prednisolone; Sulfatase

Indexed keywords

DRUG DERIVATIVE; PREDNISOLONE; PRODRUG;

ANIMAL; ANTIBODY SPECIFICITY; ARTICLE; CHEMISTRY; COLON; DRUG DELIVERY SYSTEM; DRUG EFFECT; INTESTINE ABSORPTION; MALE; ORAL DRUG ADMINISTRATION; PATHOPHYSIOLOGY; PHARMACEUTICS; RAT; SPRAGUE DAWLEY RAT; SYNTHESIS;

ADMINISTRATION, ORAL; ANIMALS; BIOPHARMACEUTICS; CHEMISTRY, PHARMACEUTICAL; COLON; DRUG DELIVERY SYSTEMS; INTESTINAL ABSORPTION; MALE; ORGAN SPECIFICITY; PREDNISOLONE; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 0642312376     PISSN: 02536269     EISSN: 02536269     Source Type: Journal    
DOI: 10.1007/bf02976952     Document Type: Article

References (23)

1. Brown, J. P., McGarraugh, G. V., Parkinson, T. M., Wingard, R. E., and Onderdonk, A. B., A polymeric drug for treatment of inflammatory bowel disease. J. Med. Chem., 26, 1300-1307 (1983).
2. Crotty, B. and Jewel, J. P., Drug therapy of ulcerative colitis. Br. J. Clin. Pharmaco., 34, 189-198 (1992).
3. Faigle, J. W., Drug metabolism in the colon wall and lumen. In: Bieck P. R. (ed), Colonic drug absorption and metabolism. New York, NY: Marcel Dekker Inc. pp 29-54 (1993).
4. rd, Jewell, L. D., and Friend, D. R., Colonic delivery of dexamethasone from a prodrug accelerates healing of colitis in rats without adrenal suppression. Gastroenterology., 108, 1688-1699 (1995).
5. Friedman, S. and Blumberg, R. S., Inflammatory bowel disease. In: Harrisons principles of internal medicine, 15th edn. CDROM, New York: McGraw-Hill (2001).
6. Friend, D. R. and Chang, G. W., A colon-specific drug-delivery system based on drug glycosides and the glycosidases of colonic bacteria. J. Med. Chem., 27, 261-266 (1984).
7. Friend, D. R. and Chang, G. W., Drug glycosides: Potential prodrugs for colon-specific drug delivery. J. Med. Chem., 28, 51-57 (1985).
8. Huijghebaert, S., Sim, S. M., Back, D. J., and Eyssen, H. J., Distribution of estrone sulfatase activity in the intestine of germ-free and conventional rats. Steroid Biochem., 20, 1175-1179 (1984).
9. Istran, C., Gabor, S., and Ferene, S., Glycosides of 5-aminosalicylic acid. Magy. Kem. FOLY., 97, 143-147 (1991).
10. Jung, Y. J., Lee, J. S., and Kim Y. M., Synthesis and in vitro/in vivo evaluation of 5-aminosalicyl-glycine as a colon-specific prodrug of 5-aminosalicylic acid. J. Pharm. Sci., 89, 594-602 (2000).
11. Jung, Y. J., Lee, J. S., and Kim, Y. M., Colon-specific prodrug of 5-aminosalicylic acid: Synthesis and in vitro/ in vivo properties of acidic amino acid derivatives of 5-aminosalicylic acid. J. Pharm. Sci., 90, 1767-1775 (2001).
12. Kopeckova, P. and Kopecek, J., Release of 5-aminosalicylic acid from bioadhesive N-(2-hydroxypropyl) methacrylamide copolymers by azoreductases in vitro. Makromol. Chem., 191, 2037-2045 (1990).
13. Larsen, C. and Johansen, M., Dextrans as carriers for drug compounds-realized and potential applications. Arch. Pharm. Chemi., 92, 809-830 (1985).
14. Mallett, A. K., Rowland, I. R., and Bearne, C. A., Influence of wheat bran on some reductive and hydrolytic activity of rat cecal flora. Nutrition and Cancer, 8, 125-131 (1986).
15. McLeod, A. D., Friend, D. R., and Tozer, T. N., Glucocorticoid-dextran conjugate as potential prodrugs for colon-specific delivery: Hydrolysis in rat gastrointestinal tract contents. J. Pharm. Sci., 83, 1284-1288 (1994).
16. McLeod, A. D., Friend, D. R., and Tozer, T. N., Synthesis and chemical stability of glucocorticoid-dextran ester: potential prodrugs for colon-specific delivery. Int. J. Pharm., 92, 105-114 (1993).
17. Nakamura, J., Haraguchi, Y., Sasaki, H., and Shibasaki, J., Effect of fasting on the hydrolysis of salicyluric acid in rabbit intestinal microorganisms. J. Pharmacobiodyn., 12, 602-607 (1989).
18. Rubinstein, A., Microbially controlled drug delivery to the colon. Biopharm & Drug Disposition, 11, 465-475 (1990).
19. Ryde, E. M., Low-molecular-weight azo compounds. In: Friend D. R. (Ed), Oral colon specific drug delivery. CRC press, Boca Raton, FL. Pp. 143-152, (1992).
20. Schimmer, B. P. and Parker, K. L., Adrenocorticotropic Hormone; Adrenocortical steroids and their synthetic analogs; Inhibitors of the synthesis and actions of adrenocortical hormones. In: Hardman, J. G., Limbird, L. E., (Editors-in-chief) Goodman and Gilman's The pharmacological basis of therapeutics, 10th Ed. McGrow-Hill, New York, N.Y. pp. 1649-1677 (2001).
21. Schwenk, M., Frank, B., Bolt, H. M., and Winne, D., Intestinal first-pass effects of estrone sulfate and estrone in the rat. Arzneimittelforschung., 31, 1254-1257 (1982).
22. Shiau, S. Y. and Chang, G., Effect of dietary fiber on fecal mucinase and beta-glucuronidase activity in rats. J. Nutrition., 13, 138-144 (1983).
23. Van Eldere, J., Robben, J., De Pauw, G., Merckx, R., and Eyssen, H., Isolation and identification of intestinal steroiddesulfating bacteria from rats and humans. Appl. Evirn. Microbiol., 54, 2112-2117 (1994).