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Solubility and hydrolytic stability of indomethacin in aqueous micellar solutions

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Abstract

The solubility of the indomethacin drug in aqueous micellar solutions of a series of dicationic surfactants was characterized by spectrophotometry. The use of these surfactants can significantly increase the indomethacin content in aqueous solutions without destruction of the drug. The increase in the solubility can be explained by the multifactorial mechanism of the influence of micelles involving the solubilization of the drug and its binding with surfactants due to electrostatic and specific interactions. The use of dicationic surfactants in alkaline solutions was shown to markedly accelerate the hydrolytic cleavage of indomethacin. The highest catalytic effect is observed for N,N´-(hexane-1,6-diyl)bis(2-hydroxyethyl)(methyl)(cetyl)ammonium dibromide: a 1200-fold increase in the reaction rate of alkaline hydrolysis of the drug.

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Authors and Affiliations

  1. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, 8 ul. Arbuzova, 420088, Kazan, Russian Federation

    E. I. Yackevich, A. B. Mirgorodskaya, L. Ya. Zakharova & O. G. Sinyashin

  2. Kazan National Research Technological University, 68 ul. K. Marksa, 420111, Kazan, Russian Federation

    L. Ya. Zakharova & O. G. Sinyashin

Authors
  1. E. I. Yackevich
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  2. A. B. Mirgorodskaya
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  3. L. Ya. Zakharova
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  4. O. G. Sinyashin
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Corresponding author

Correspondence to A. B. Mirgorodskaya.

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Dedicated to Academician of the Russian Academy of Sciences N. S. Zefirov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2232–2237, September, 2015.

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Yackevich, E.I., Mirgorodskaya, A.B., Zakharova, L.Y. et al. Solubility and hydrolytic stability of indomethacin in aqueous micellar solutions. Russ Chem Bull 64, 2232–2237 (2015). https://doi.org/10.1007/s11172-015-1143-8

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  • DOI: https://doi.org/10.1007/s11172-015-1143-8

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