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Preparative resolution of etodolac enantiomers by preferential crystallization method

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Abstract

Pure enantiomers are of large interest for several industries. This study was aimed to establish a method for separation of etodolac enantiomers by preferential crystallization after a conglomerate formation of its derivatives. S-(+)-etodolac and R-(−)-etodolac enantiomers were both prepared by classical resolution via crystallization of diastereoisomeric salt with (−)-brucine and (−)-cinchonidine. Enantiomeric purity of etodolac was determined by HPLC method using Chiralcel OD-H column. The pure diastereomeric salt collected from repeated recrystallization was further fractionated by liquid-liquid extraction to pure enantiomers. Etodolac enantiomers were recovered with overall yield more than 20% and the purities were over 99.9%.

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References

  • Ali, I. and Aboul-Enein, H. Y., Enantioseparation of some clinically used drugs by HPLC using cellulose Tris (3,5-dichlorophenylcarbamate) chiral stationary phase. Biomed. Chromatogr., 17, 113–117 (2003).

    Article  CAS  PubMed  Google Scholar 

  • Brocks, D. R., Jamali, F., Russell, A. S., and Skeith, D. J., The stereoselective pharmacokinetics of etodolac in young and elderly subjects, and after cholecystectomy. Clin. Pharmacol., 32, 982–989 (1992).

    CAS  Google Scholar 

  • Brocks, D. R., and Jamali, F., Etodolac clinical pharmacokinetics. Clin. Pharmacokinet., 26, 259–274 (1994).

    Article  CAS  PubMed  Google Scholar 

  • Beckerscharfenkamp, U., and Blaschke, G. J., Evaluation of the steroselective metabolism of the chiral analgesic drug etodolac by High-Performance Liquid Chromatography. J. Chromatogr. B., 621, 199–207 (1993).

    Article  CAS  Google Scholar 

  • Brenna, E., Fuganti, C., Fuganti, D., Grasselli, P., Luciana Malpezzi, L., and Giuseppe, P. G., New enzymatic and chemical approaches to enantiopure etodolac. Tetrahedron, 53, 17769–17780 (1997).

    Article  CAS  Google Scholar 

  • Challener, C. A., Preferential crystallization: Chiral Drugs. Ashgate, Aldershot (2002).

  • Chou, S., Tseng, C., and Chang, L., Exploration of an efficient method for optical resolution of etodolac., J. Chin. Chem. Soc., 48, 229–234 (2001).

    CAS  Google Scholar 

  • Fanali, S., Identification of chiral drug isomers by capillary electrophoresis. J. Chromatogr. A., 735, 77–121 (1996).

    Article  CAS  PubMed  Google Scholar 

  • Mignot, I., Presle, N., Lapicque, F., Monot, C., Dropsy, R., and Netter, P., Albumin binding sites for etodolac enantiomers. Chirality, 8, 271–280 (1996).

    Article  CAS  PubMed  Google Scholar 

  • Nishi, H. and Terabe, S., Optical resolution of drugs by capillary electrophoretic techniques. J. Chromatogr, A., 694, 245–276 (1995).

    Article  CAS  Google Scholar 

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Correspondence to Kyeong Ho Kim.

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Dung, P.T., Trung, T.Q. & Kim, K.H. Preparative resolution of etodolac enantiomers by preferential crystallization method. Arch. Pharm. Res. 32, 1425–1431 (2009). https://doi.org/10.1007/s12272-009-2012-5

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  • DOI: https://doi.org/10.1007/s12272-009-2012-5

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