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Tautomeric polymorphism in omeprazole.

Prashant M Bhatt1, Gautam R Desiraju

  • 1School of Chemistry, University of Hyderabad, Hyderabad 500 046, India.

Chemical Communications (Cambridge, England)
|August 24, 2007
PubMed
Summary
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Crystalline omeprazole forms solid solutions of two tautomers across a composition range. This challenges the traditional definition of polymorphs in solid-state chemistry.

Area of Science:

  • Solid-state chemistry
  • Pharmaceutical science
  • Crystallography

Background:

  • Omeprazole is a widely used proton pump inhibitor.
  • The solid-state properties of active pharmaceutical ingredients (APIs) significantly impact their efficacy and stability.
  • Understanding crystalline forms is crucial for drug development.

Purpose of the Study:

  • To investigate the crystalline nature of omeprazole.
  • To determine if omeprazole exists as distinct polymorphs or a continuous solid solution.
  • To re-evaluate the definition of "polymorph" in light of experimental findings.

Main Methods:

  • X-ray powder diffraction (XRPD) analysis.
  • Differential scanning calorimetry (DSC) measurements.
  • Spectroscopic techniques (e.g., FTIR, Raman) for tautomer identification.

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Main Results:

  • Crystalline omeprazole was found to exist as a continuous solid solution of its two tautomers.
  • No discrete polymorphic forms were identified within the studied composition range.
  • The solid solution behavior suggests a non-classical crystallization phenomenon.

Conclusions:

  • The crystalline form of omeprazole does not conform to the classical definition of polymorphs.
  • The findings necessitate a broader understanding of solid-state forms, including solid solutions, in pharmaceutical contexts.
  • This research impacts the classification and characterization of crystalline APIs.