Crystallographic and Energetic Insights into Reduced Dissolution and Physical Stability of a Drug-Surfactant Salt: The Case of Norfloxacin Lauryl Sulfate

Yiwang Guo, Manish Kumar Mishra, Chenguang Wang, Changquan Calvin Sun

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

A commonly used pharmaceutical surfactant, sodium lauryl sulfate (SLS), has been reported to reduce the dissolution rate of drugs due to the formation of a less soluble drug-lauryl sulfate salt. In this study, we provide direct crystallographic evidence of the formation of salt between SLS and norfloxacin (NOR), [NORH+][LS-]·1.5 H2O. The available crystal structure also enables the use of the energy framework to gain an understanding of the structure-property relationship. Results show that the hydrophobic methyl groups in SLS dominate the surfaces of the [NORH+][LS-]·1.5 H2O crystals, resulting in the increased hydrophobicity and reduced wettability by aqueous media. Moreover, an analysis of molecular environments and energy calculations of water molecules provides insight into the stability of [NORH+][LS-]·1.5 H2O with variations in the relative humidity and temperature. In summary, important pharmaceutical properties, such as solubility, dissolution, and thermal stability, of the drug-surfactant salt [NORH+][LS-]·1.5 H2O have been characterized and understood based on crystallographic and energetic analyses of the crystal structure.

Original languageEnglish (US)
Pages (from-to)579-587
Number of pages9
JournalMolecular Pharmaceutics
Volume17
Issue number2
DOIs
StatePublished - Feb 3 2020

Bibliographical note

Funding Information:
We thank the Minnesota Supercomputing Institute (MSI) at the University of Minnesota for providing resources that contributed to the research results reported in this paper. We also thank the Chinese Scholarship Council for partial financial support to Y.G.

Publisher Copyright:
Copyright © 2019 American Chemical Society.

Keywords

  • crystal energy framework
  • crystallography
  • dissolution
  • hydrate
  • norfloxacin
  • physical stability
  • sodium lauryl sulfate

PubMed: MeSH publication types

  • Journal Article
  • Research Support, Non-U.S. Gov't

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