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Structural Aspects and Intermolecular Energy for Some Short Testosterone Esters.

Alexandru Turza1, Violeta Popescu2, Liviu Mare2

  • 1Mass Spectrometry, Chromatography and Applied Physics Department, National Institute for R&D of Isotopic and Molecular Technologies, 67-103 Donat, 400293 Cluj-Napoca, Romania.

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This study determined the crystal structures of short-esterified testosterone forms, analyzing their structural features and solubility. Longer ester chains correlated with decreased solubility, impacting pharmaceutical applications of anabolic-androgenic steroids.

Keywords:
17β-hydroxyandrost-4-en-3-onecrystal structureesterlattice energysolubilitytestosterone

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Area of Science:

  • Crystallography
  • Pharmaceutical Chemistry
  • Biochemistry

Background:

  • Testosterone is the primary anabolic-androgenic steroid.
  • Esterification modifies steroid properties for pharmaceutical use.

Purpose of the Study:

  • To determine the crystal structures of short-esterified testosterone forms.
  • To evaluate structural features, crystal energies, and Hirshfeld surfaces.
  • To assess the solubility of these compounds and correlate it with ester chain length.

Main Methods:

  • Single-crystal X-ray diffraction for crystal structure determination.
  • Powder X-ray diffraction for sample investigation.
  • Evaluation of crystal energies and Hirshfeld surfaces.
  • Solubility testing and correlation with ester length.

Main Results:

  • Crystal structures of testosterone propionate, phenylpropionate, and isocaproate were determined.
  • Structural features were analyzed and compared to testosterone and its acetate ester.
  • Solubility decreased with increasing ester chain length.

Conclusions:

  • Ester chain length significantly influences the solubility of testosterone esters.
  • Understanding these structure-property relationships is crucial for developing effective testosterone-based pharmaceuticals.
  • The findings provide insights into the solid-state properties and pharmaceutical potential of anabolic-androgenic steroids.