Pressure-temperature phase diagram of the dimorphism of the anti-inflammatory drug nimesulide

Int J Pharm. 2017 Jun 15;525(1):54-59. doi: 10.1016/j.ijpharm.2017.04.016. Epub 2017 Apr 12.

Abstract

Understanding the phase behavior of active pharmaceutical ingredients is important for formulations of dosage forms and regulatory reasons. Nimesulide is an anti-inflammatory drug that is known to exhibit dimorphism; however up to now its stability behavior was not clear, as few thermodynamic data were available. Therefore, calorimetric melting data have been obtained, which were found to be TI-L=422.4±1.0K, ΔI→LH=117.5±5.2Jg-1,TII-L=419.8±1.0K and ΔII→LH=108.6±3.3Jg-1. In addition, vapor-pressure data, high-pressure melting data, and specific volumes have been obtained. It is demonstrated that form II is intrinsically monotropic in relation to form I and the latter would thus be the best polymorph to use for drug formulations. This result has been obtained by experimental means, involving high-pressure measurements. Furthermore, it has been shown that with very limited experimental and statistical data, the same conclusion can be obtained, demonstrating that in first instance topological pressure-temperature phase diagrams can be obtained without necessarily measuring any high-pressure data. It provides a quick method to verify the phase behavior of the known phases of an active pharmaceutical ingredient under different pressure and temperature conditions.

Keywords: Calorimetry; Crystallography; Phase behavior; Polymorphism; Preformulation; Pressure-temperature phase diagram; Thermodynamics.

MeSH terms

  • Crystallization
  • Drug Stability
  • Sulfonamides / chemistry*
  • Temperature*
  • Thermodynamics

Substances

  • Sulfonamides
  • nimesulide