Anhydride prodrugs for nonsteroidal anti-inflammatory drugs

Pharmaceutical Research

Volumn 20, Issue 2, 2003, Pages 205-211

  Shaaya, Osnat ^a   Magora, Amir ^b   Sheskin, Tzviel ^a,c   Kumar, Neeraj ^a   Domb, Abraham J ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b Israel Police   (Israel)

^c Taro Pharmaceutical Industries Ltd   (Israel)

Author keywords

Ibuprofen; Mixed anhydride; NSAID; Prodrugs; Prolong action

Indexed keywords

ACETIC ANHYDRIDE; CARBOXYLIC ACID; DRUG RECEPTOR; FATTY ACID; IBUPROFEN; NONSTEROID ANTIINFLAMMATORY AGENT;

ANALGESIA; ANIMAL EXPERIMENT; ANIMAL MODEL; AQUEOUS SOLUTION; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; DEGRADATION; DRUG EFFECT; DRUG HYDROLYSIS; DRUG PURIFICATION; DRUG RELEASE; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; PAW EDEMA; PRIORITY JOURNAL; RAT; TEMPERATURE;

ANHYDRIDES; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; EDEMA; FEMALE; PRODRUGS; RATS; RATS, SPRAGUE-DAWLEY;

EID: 0037331840     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1022214919481     Document Type: Article

References (17)

1. H. Bundgaard. Design of Prodrugs, Elsevier, Amsterdam, 1985.
2. I. T. Harrison, B. Lawis, P. Nelson, and W. Rooks. Nonsteroidal antiinflammatory agents. I. 6-substituted 2-naphthylacetic acids. J. Med. Chem. 13:203-205 (1970).
3. R. G. Child, A. C. Osterberg, A. E. Sloboda, and A. S. Tomcufcik. Fenbufen, a new anti-inflammatory analgesic: synthesis and structure-activity relationships of analogs. J. Pharm. Sci. 66:466-476 (1977).
4. L. B. Hansen, L. L. Christrup, and H. Bundgaard. Ketobemidone prodrugs for buccal delivery. Acta Pharm. Nord. 3:77-82 (1991).
5. D. G. Waller and C. F. George. Prodrugs. Br. J. Clin. Pharmacol. 28:497-507 (1989).
6. R. M. Goetz and J. Holtz. Enhanced angiotensin-converting enzyme activity and impaired endothelium-dependent vasodilation in aortae from hypertensive rats: evidence for a causal link. Clin. Sci. 97:165-174 (1999).
7. F. Higashikawa, T. Murakami, T. Kaneda, A. Kato, and M. Takano. Dose-dependent intestinal and hepatic first-pass metabolism of midazolam, a cytochrome P450 3A substrate with differently modulated enzyme activity in rats. J. Pharm. Pharmacol. 51:67-72 (1999).
8. N. Kumar, A.-C. Albertsson, U. Edlund, D. Teomim, A. Rasiel, and A. J. Domb. Polyanhydrides. In A. Steinbuchel and Y. Doi (eds.), Biopolymers: Polyesters (Part-B), Chap. 7, Wiley-VCH Germany, 2002 pp. 203-234.
9. A. J. Domb, Z. H. Israel, O. Elmalak, D. Teomim, and A. Bentolila. Preparation and characterization of carmustine loaded polyanhydride wafers for treating brain tumors. Pharm. Res. 16:762-765 (1999).
10. J. Tamada and R. Langer. The development of polyanhydrides for drug delivery applications. J. Biomater. Sci. Polym. Ed. 3:315-353 (1992).
11. M. A. Zahran, L. Kovacs, I. el-Sakka, E. B. Pedersen, and C. Nielsen. The potential of aspirin in prodrug synthesis: a new potential delivery system of AZT and FLT. Arch. Pharm. (Weinheim) 329:417-420 (1996).
12. R. J. Capetola, D. A. Shriver, and M. E. Rosenthale. Suprofen, a new peripheral analgesic. J. Pharmacol. Exp. Ther. 214:16-23 (1980).
13. A. J. Domb. Quantitative analysis of mixed anhydrides. J. Chromatogr. 673:31-35 (1994).
14. A. J. Domb and R. Nudelman. In vivo and in vitro elimination of aliphatic polyanhydrides. Biomaterials 16:319-323 (1995).
15. W. K. Fife and Z.-d. Zhang. Phase managed organic synthesis 3. Symmetrical anhydrides from carboxylic acids via polymer assisted reaction. Tetrahedron Lett. 27:4937-4940 (1986).
16. S. Patai. The Chemistry of Acid Derivatives-Part 1, John Wiley & Sons, New York, 1979.
17. C. A. Buehler and D. E. Pearson. Organic Synthesis (Vol. 2), John Wiley & Sons, New York, 1974.