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Meloxicam hydro-chloride.

Fermin Flores Manuel1, Martha Sosa Rivadeneyra1, Sylvain Bernès2

  • 1Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, 72570 Puebla, Pue., Mexico.

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|May 14, 2023
PubMed
Summary
This summary is machine-generated.

The hydrochloride salt of meloxicam, a non-steroidal anti-inflammatory drug, exhibits a distinct crystal structure due to conformational changes in the thiazolium ring. This structural difference may explain the polymorphism observed in meloxicam.

Keywords:
benzo­thia­zinecrystal structuremeloxicampolymorphismthia­zole

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Area of Science:

  • Crystallography
  • Medicinal Chemistry
  • Pharmacology

Background:

  • Meloxicam is a widely used non-steroidal anti-inflammatory drug (NSAID) for treating pain and inflammation in rheumatic disorders and osteoarthritis.
  • The hydrochloride salt of meloxicam (C14H14N3O4S2+·Cl−) is a derivative with potential therapeutic applications.
  • Understanding the solid-state properties of drug derivatives is crucial for pharmaceutical development.

Purpose of the Study:

  • To characterize the crystal structure of the meloxicam hydrochloride salt.
  • To compare the crystal structure and conformation of the hydrochloride salt with its hydro-bromide analogue and parent meloxicam.
  • To investigate the structural basis for potential polymorphism in meloxicam.

Main Methods:

  • Single-crystal X-ray diffraction analysis was performed on the meloxicam hydrochloride salt.
  • Conformational analysis was conducted by comparing the dihedral angles of the thiazolium ring and the 1,2-benzothiazine core.
  • Structural comparisons were made with previously reported data for meloxicam hydro-bromide and meloxicam.

Main Results:

  • The meloxicam hydrochloride salt and its hydro-bromide analogue are not isomorphous, indicating different crystal packing arrangements.
  • A conformational difference was observed, specifically a twist of the thiazolium ring by 10.96° in the hydrochloride salt and -16.70° in the hydro-bromide salt, relative to the parent meloxicam.
  • The 1,2-benzothiazine core of the molecule was found to be conformationally rigid in both salts.

Conclusions:

  • The observed conformational flexibility of the thiazolium ring in meloxicam derivatives contributes to their distinct crystal structures.
  • These structural variations, particularly the rotational freedom of the thiazolium ring, likely play a role in the observed polymorphism of meloxicam.
  • The findings provide insights into the structure-property relationships of meloxicam and its salts, relevant for drug formulation and stability.