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 journalArticle

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)
JournalMolecular Pharmaceutics
DOIs
StateAccepted/In press - Jan 1 2020

Fingerprint

Drug Stability
Norfloxacin
Surface-Active Agents
Sodium Dodecyl Sulfate
Salts
Pharmaceutical Preparations
Wettability
Humidity
Hydrophobic and Hydrophilic Interactions
Solubility
Hot Temperature
Temperature
Water
dodecyl sulfate

Keywords

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

PubMed: MeSH publication types

  • Journal Article

Cite this

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title = "Crystallographic and Energetic Insights into Reduced Dissolution and Physical Stability of a Drug-Surfactant Salt: The Case of Norfloxacin Lauryl Sulfate",
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.",
keywords = "crystal energy framework, crystallography, dissolution, hydrate, norfloxacin, physical stability, sodium lauryl sulfate",
author = "Yiwang Guo and Mishra, {Manish Kumar} and Chenguang Wang and Sun, {Changquan Calvin}",
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AU - Mishra, Manish Kumar

AU - Wang, Chenguang

AU - Sun, Changquan Calvin

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AB - 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.

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