A facile enzymatic process for the preparation of (s)-Naproxen ester prodrug in organic solvents

Enzyme and Microbial Technology

Volumn 20, Issue 8, 1997, Pages 635-639

  Chang, Chun Sheng ^a   Tsai, Shau Wei ^a  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

(s) naproxen ester; Esterification; Lipase; Prodrug

Indexed keywords

ALCOHOLS; BIOCATALYSTS; BIOSYNTHESIS; DRUG PRODUCTS; ESTERIFICATION; ESTERS; ORGANIC SOLVENTS;

FACILE ENZYMATIC PROCESS; LIPASE; NAPROXEN ESTER; PRODRUG;

ENZYME KINETICS;

ALCOHOL; CYCLOHEXANE; NAPROXEN; ORGANIC SOLVENT; PRODRUG; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYST; COMPETITIVE INHIBITION; CONTROLLED STUDY; DRUG SYNTHESIS; ENANTIOMER; ENZYME KINETICS;

EID: 0031172576     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(96)00222-0     Document Type: Article

References (17)

1. Todd, P. A. and Clissold, S. P. Naproxen: A reappraisal of its pharmacology, and therapeutic use in rheumatic diseases and pain states. Drugs 1990, 40, 91-137
2. Shanbhag, V. R., Crider, A. M., Gokhale, R., Harpalani, A., and Dick, R. M. Ester and amide prodrugs of Ibuprofen and Naproxen: Synthesis, anti-inflammatory activity, and gastrointestinal toxicity. J. Pharm. Sci. 1992, 81, 149-154
3. Nielsen, N. M. and Bundgaard, H. Glycolamide esters as biolabile prodrugs of carboxylic acid agents: Synthesis, stability, bioconversion, and physicochemical properties. J. Pharm. Sci. 1988, 77, 285-298
4. Ranucci, E., Sartore, L., Peroni, I., Latini, R., Bernasconi, R., and Ferruti, P. Pharmacokinetic results on Naproxen prodrugs based on poly(ethyleneglycol)s. J. Biomater. Sci. Polymer Edn. 1994, 6, 141-147
5. Harboe, E., Larsen, C., Johansen, M., and Olesen, H. P. Macromolecular prodrugs. XIV. Absorption characteristics of Naproxen after oral administration of a dextran T-70-Naproxen ester prodrug in pigs. Int. J. Pharm. 1989, 53, 157-165
6. Harboe, E., Larsen, C., Johansen, M., and Olesen, H. P. Macromolecular prodrugs. XV. Colon-targeted delivery-bioavailability of Naproxen from orally administered dextran-Naproxen ester prodrugs varying in molecular size in the pig. Pharm. Res. 1989, 6, 919-923
7. Larsen, C., Harboe, E., Johansen, M., and Olesen, H. P. Macromolecular prodrugs. XVI. 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. Venuti, M. C., Young, J. M., Maloney, P. J., Johnson, D., and Mcgreevy, K. Synthesis and biological evaluation of Ω-(N,N,N,-trialkylammonium) alkyl ester and thioesters of carboxylic acid non-steroidal anti-inflammatory agents. Pharm. Res. 1989, 6, 867-873
9. Bundgaard, H. and Nielsen, N. M. Glycoamide ester as a novel biolabile prodrug type for nonsteroidal anti-inflammatory carboxylic acid drugs. Int. J. Pharm. 1988, 43, 101-110
10. Tammara, V. K., Narurkar, M. M., Crider, A. M. and Khan, M. A. Synthesis and evaluation of morpholinoalkyl ester prodrugs of indomethacin and Naproxen. Pharm. Res. 1993, 10, 1191-1199
11. Chen, C. S. and Sih, C. J. General aspects and optimization of enantioselective biocatalysis in organic solvents: The use of lipase. Angew. Chem. Int. Engl. 1989, 28, 695-707
12. Tsai, S. W. and Wei, H. J. Kinetics of enantioselective esterification of Naproxen by Lipase in organic solvents. Biocatalysis 1994, 11, 33-45
13. Parida, S. and Dordick, J. S. Substrate structure and solvent hydrophobicity control lipase catalysis and enantioselectivity in organic media. J. Am. Chem. Soc. 1991, 113, 2253-2259
14. Tsai, S.W. and Wei, H. J. Self-normalized analysis of lipase-catalyzed conversion of Naproxen enantiomers. J. Liq. Chromatogr. 1993, 16, 2993-3001
15. Tsai, S. W. and Wei, H. J. Enantioselective esterification of racemic Naproxen by lipases in organic solvent. Enzyme Microb. Technol. 1994, 16, 328-333
16. Tsai, S. W., Lin, J. J., Chang, C. S., and Chen, J. P. Enzymatic synthesis of (s)-Ibuprofen ester prodrug from racemic Ibuprofen by lipase in organic solvents. Biotechnol. Progress (in press)
17. Holmberg, E. and Hult, K. Application induced reversal of enantioselectivity in a lipase catalyzed resolution of 2-chloropropionic acid. Biocatalysis 1992, 5, 289-296