Synthesis and properties of N-nicotinoyl-2-(5-fluorouracil-1-yl)-d,l-glycine ester as a prodrug of 5-fluorouracil for rectal administration

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 66, Issue 2, 2007, Pages 260-267

  Yang, Young Wook ^a   Lee, Jeoung Soo ^b   Kim, Inho ^a   Jung, Yun Jin ^a   Kim, Young Mi ^a  

^a Pusan National University   (South Korea)

^b Clemson University   (United States)

Author keywords

5 Fluorouracil; 5 Fluorouracil prodrug; N Nicotinoyl 2 (5 fluorouracil 1 yl) d,l glycine esters; Rectal absorption; Rectal administration

Indexed keywords

BUFFER; FLUOROURACIL; N NICOTINOYL 2 (5 FLUOROURACIL 1 YL)DEXTRO,LEVO GLYCINE ESTER; N NICOTINOYL 2 (5 FLUOROURACIL 1 YL)DEXTRO,LEVO GLYCINE ETHYL; N NICOTINOYL 2 (5 FLUOROURACIL 1 YL)DEXTRO,LEVO GLYCINE ISOPROPYL; N NICOTINOYL 2 (5 FLUOROURACIL 1 YL)DEXTRO,LEVO GLYCINE METHYL; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; INCUBATION TIME; PHYSICAL CHEMISTRY;

ADMINISTRATION, RECTAL; ANIMALS; ANTIMETABOLITES, ANTINEOPLASTIC; BIOLOGICAL AVAILABILITY; BUFFERS; CHEMISTRY, PHARMACEUTICAL; DRUG STABILITY; ENEMA; FLUOROURACIL; GLYCINE; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; MALE; MOLECULAR STRUCTURE; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY; SOLUBILITY; TECHNOLOGY, PHARMACEUTICAL;

EID: 34247518173     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2006.11.002     Document Type: Article

References (19)

1. Schmoll H.J., Buchele T., Grothey A., and Dempke W. Where do we stand with 5-fluorouracil?. Semin. Oncol. 26 (1999) 589-605
2. Abbruzzese J.L., and Levin B. Treatment of advanced colorectal cancer. Hematol./Oncol. Clin. North America 3 (1989) 135-153
3. Sayed Y.M.L., and Sadee W. The fluoropyrimidines. In: Ames M.M., Powis G., and Kovach J.S. (Eds). Pharmacokinetics of Anticancer Agents in Humans (1983), Elsevier, Amsterdam 209-227
4. Queener S.F., Morris H.P., and Weber G. Dihydrouracil dehydrogenase activity in normal, differentiating and regenerating liver and in hepatomas. Cancer Res. 31 (1971) 1004-1009
5. Phillips T.A., Howell A., Grieve R.J., and Welling P.G. Pharmacokinetics of oral and intravenous 5-fluorouracil in humans. J. Pharm. Sci. 69 (1980) 1428-1431
6. Fraile R.J., Baker L.N., Buroker T.R., Horwitz J., and Vaitkevicius V.K. Pharmacokinetics of 5-fluorouracil administered orally by rapid intravenous and by slow infusion. Cancer Res. 40 (1980) 2223-2228
7. Buur A., and Bundgarrd H. Prodrugs of 5-fluorouracil V. 1-Alkoxycarbonyl derivatives as potential prodrug forms for improved rectal or oral delivery of 5-fluorouracil. J. Pharm. Sci. 75 (1986) 522-527
8. Buur A., and Bundgarrd H. Prodrugs of 5-fluorouracil VIII. Improved rectal and oral delivery of 5-fluorouracil via various prodrugs; Structure-rectal absorption relationships. Int. J. Pharm. 36 (1987) 41-49
9. Wang W., Bundgarrd H., and Buur A. Corneal penetration of 5-fuorouracil and its improvement by prodrug derivatization in the albino rabbit: implication in glaucoma filtration surgery. Curr. Eye Res. 10 1 (1991) 87-97
10. Taylor H.E., and Sloan K.B. 1-Alkylcarbonyloxymethyl prodrugs of 5-fluorouracil (5-FU): synthesis, physicochemical properties, and topical delivery of 5-FU. J. Pharm. Sci. 87 1 (1998) 15-20
11. Shimma N., Umeda I., Arasaki M., Murasaki K., Kohchi Y., Miwa M., Ura M., Sawada N., Tahara H., Kuruma I., Horii I., and Ishitsuka H. The design and synthesis of a new tumor-selective fluoropyrimidine carbamate. Capecitabine Bioorg. Med. Chem. 8 7 (2000) 1697-1706
12. Kelly T.R., Schmidt T.E., and Haggerty J.G. A convenient preparation of methyl and ethyl glyoxalate. Synthesis (1972) 544-545
13. Nichifor M., and Schacht E.H. Synthesis of peptide derivatives of 5-fluorouracil. Tetrahedron 50 12 (1994) 3747-3760
14. Lee J.S., Jung Y.J., and Kim Y.M. Synthesis and evaluation of N-acyl-2-(5-fluorouracil-1-yl)-d,l-glycine as a colon-specific prodrug of 5-fluorouracil. J. Pharm. Sci. 90 (2001) 1787-1794
15. Buur A., and Bundgarrd H. Prodrugs of 5-fuorouracil I. Hydrolysis kinetics and physicochemical properties of various N-acyl derivatives of 5-fluorouracil. Int. J. Pharm. 21 (1984) 349-364
16. Suda Y., Schimidzu K., Sumi M., Oku N., and Kusumoto S. The synthesis and in vitro and in vivo stability of 5-fluorouracil prodrugs which possess serum albumin binding potency. Biol. Pharm. Bull. 16 9 (1993) 876-878
17. de Blaey C.J., and Polderman J. Rationale in the design of rectal and vaginal delivery form of drugs. In: Ariens E.J. (Ed). Drug Design IX (1980), Academic Press, London 237-266
18. Bundgarrd H., Falch E., Pedersen S.B., and Nielsen G.H. Allopurinol prodrugs IV. Improved rectal and pareteral delivery of allopurinol using the prodrug approach as evaluated in rabbits. Int. J. Pharm. 27 (1985) 71-80
19. Stevens H.P., Ostlere L.S., Begent R.H., Dooley J.S., and Rustin M.H. Pellagra secondary to 5-fluorouracil. Br. J. Dermatol. 128 5 (1993) 578-580