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Related Experiment Videos

Enoxacin trihydrate.

Masood Parvez1, Saeed Arayne, Najma Sultana

  • 1Department of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4. parvez@ucalgary.ca

Acta Crystallographica. Section C, Crystal Structure Communications
|April 9, 2004
PubMed
Summary
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This study details the crystal structure of enoxacin trihydrate, revealing zwitterions forming parallel sheets stabilized by water molecule hydrogen bonds. The naphthyridine ring is planar, with distinct orientations of the carboxylate and ethyl groups.

Area of Science:

  • Crystallography
  • Medicinal Chemistry
  • Structural Biology

Background:

  • Enoxacin is a fluoroquinolone antibiotic.
  • Understanding the solid-state structure of pharmaceuticals is crucial for formulation and stability.

Purpose of the Study:

  • To elucidate the crystal structure of 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-4-ium-1-yl)-1,8-naphthyridine-3-carboxylate trihydrate (enoxacin trihydrate).
  • To analyze the intermolecular interactions and conformational aspects of the molecule in the solid state.

Main Methods:

  • Single-crystal X-ray diffraction analysis was employed to determine the crystal structure.
  • Hydrogen bonding networks and molecular conformations were analyzed.

Main Results:

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  • The asymmetric unit contains a zwitterion of enoxacin and three water molecules.
  • Zwitterions form parallel sheets stabilized by head-to-tail hydrogen bonds involving water molecules.
  • The naphthyridine ring system is planar; the carboxylate group is at 26.13 degrees out of plane.
  • The piperazinium ring adopts a chair conformation.

    • Conclusions:

    • The crystal structure provides detailed insights into the solid-state behavior of enoxacin.
    • Hydrogen bonding interactions significantly contribute to the crystal lattice stability.
    • The observed conformation and structural features are important for understanding enoxacin's physicochemical properties.