Kinetics of base catalyzed racemization of ibuprofen enantiomers

International Journal of Pharmaceutics

Volumn 196, Issue 1, 2000, Pages 21-26

  Yuchun, Xie ^a   Huizhou, Liu ^a   Jiayong, Chen ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

Base catalysis; Ibuprofen enantiomer; Racemization kinetics; Resolution

Indexed keywords

DIMETHYL SULFOXIDE; IBUPROFEN;

ARTICLE; CALCULATION; CATALYSIS; CATALYST; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; PRIORITY JOURNAL; RACEMIC MIXTURE;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CATALYSIS; DIMETHYL SULFOXIDE; HYDROGEN-ION CONCENTRATION; IBUPROFEN; KINETICS; MODELS, CHEMICAL; PREDICTIVE VALUE OF TESTS; SODIUM HYDROXIDE; STEREOISOMERISM; WATER;

EID: 0033962969     PISSN: 03785173     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-5173(99)00438-X     Document Type: Article

References (12)

1. Chiang Y., Kresge A.J., Santaballa J.A., Wirz J. Ketonization of acetophenone enol in aqueous buffer solutions: rate-equilibrium relations and mechnism of the 'uncatalyzed' reaction. J. Am. Chem. Soc. 110:1988;5506-5510.
2. Geroffen, 1990, 3824353.
3. Hutt A.J., Caldwell J. The importance of stereochemistry in the clinical pharmacokinetics of the 2-arylpropionic acid non stereoidal anti-inflammatory drugs. Clin. Pharmacokin. 9:1984;371-373.
4. Kresge A.J. Simple enols. Chemtech. 16:1986;250-254.
5. March J. Advanced Organic Chemistry. 1992;Wiley, New York.
6. Mills S.G., Beak P. Solvent effects on keto-enol equilibria: tests of quantitative models. J. Org. Chem. 50:1985;1216-1224.
7. Roure F., Ducret A., Trani M., Lortie R. Enantioselective esterification of racemic ibuprofen in solvent media under reduced pressure. J. Chem. Tech. Biotechnol. 69:1997;266-270.
8. Sonawane R.H., Bellur N.S., Ahuja J.R. Recent developments in the synthesis of optically active 2-arylpropionic acids: an important class of non steroidal anti-inflammatory agents. Tetrahed. Asym. 3:1992;163-192.
9. Stinson S.C. Chiral drugs. Chem. Eng. News. 73(25):1995;44-74.
10. Tsai S.W., Lin J.J., Chang C.S., Chen J.P. Enzymatic synthesis of S-ibuprofen ester prodrug from racemic ibuprofen by lipase in organic solvents. Biotechnol. Prog. 13:1997;82-88.
11. Xie Y.C., Liu H.Z., Chen J.Y. Candida rugosa lipase catalyzed esterification of racemic ibuprofen with butanol: racemization of R-ibuprofen and chemical hydrolysis of S-ester formed. Biotechnol. Lett. 20:1998a;455-458.
12. Xie Y.C., Liu H.Z., Chen J.Y. Effect of water content on enzyme activity and enantioselectivity of lipase catalyzed esterification of racemic ibuprofen in organic solvents. Ann. N.Y. Acad. Sci. 864:1998b;570-575.