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Influence of various cyclodextrins on the stability of hydrocortisone 17-butyrate in aqueous solution

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Abstract

The stabilizing effects of α-, β-, γ- and dimethyl-β-cyclodextrins (α-, β-, γ-and DM-β-CyDs) on the degradation of hydrocortisone 17-butyrate (HC-17B) in aqueous solution was investigated. HC-17B underwent a facile hydroxide ion-catalyzed rearrangement to the less active 21-butyrate ester by the apparent first-order kinetics, and maximum stability of HC-17B was obtained at around, pH 4.0. The stability of HC-17B was increased by inclusion complexation with α-, γ- and DM-β-CyD in the pH range of 2.0–8.0 examined, whereas β-CyD accelerated the degradation of HC-17B at the pH higher than 5.0. The effects of ionic strength, solvent, temperature and CyD concentration were also investigated. Stability constants and apparent degradation rate constants of HC-17B-γ-CyD and HC-17B-DM-β-CyD complexes were determined kinetically on the basis of 1∶1 complexation. The results suggested that the inclusion complexation with γ-CyD or DM-β-CyD was most useful means to enhance the stability of the steroid.

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Authors and Affiliations

  1. Department of Pharmaceutics, College of Pharmacy, Dongduck Women's University, 136-714, Seoul, Korea

    In Koo Chun & Bo Young Kim

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  1. In Koo Chun
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  2. Bo Young Kim
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Chun, I.K., Kim, B.Y. Influence of various cyclodextrins on the stability of hydrocortisone 17-butyrate in aqueous solution. Arch. Pharm. Res. 15, 176–183 (1992). https://doi.org/10.1007/BF02974095

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