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Solid-state investigation of piroxicam benzoate
Biserka Cetina-Cizmek1, Marijan Tudja, Ernest Mestrović
1Faculty of Pharmacy and Biochemistry, University of Zagreb, Zagreb, Croatia. biserka.cetina-cizmek@pliva.hr
Acta Pharmaceutica (Zagreb, Croatia)
|February 11, 2004
Summary
Piroxicam benzoate, a piroxicam prodrug, exhibits two solid-state pseudopolymorphic forms (A and B) dependent on crystallization conditions. Understanding these forms is crucial for drug formulation and stability.
Area of Science:
- Pharmaceutical Sciences
- Solid-State Chemistry
- Materials Science
Background:
- Piroxicam benzoate is an ester prodrug of piroxicam, designed to improve drug delivery.
- Investigating the solid-state properties of drug candidates is essential for formulation development and ensuring therapeutic efficacy.
- Polymorphism and pseudopolymorphism significantly impact drug solubility, stability, and bioavailability.
Purpose of the Study:
- To investigate the solid-state properties of piroxicam benzoate.
- To identify and characterize different pseudopolymorphic forms of piroxicam benzoate.
- To understand the influence of crystallization solvents and conditions on pseudopolymorph formation.
Main Methods:
- Recrystallization of piroxicam benzoate from various organic solvents (toluene, ethanol, methanol, ethyl acetate, acetone).
- Characterization using Fourier-Transform Infrared Spectroscopy (FTIR), Differential Scanning Calorimetry (DSC), Thermogravimetric Analysis (TGA), Scanning Electron Microscopy (SEM), and X-ray Powder Diffraction (XRPD).
Main Results:
- Piroxicam benzoate was confirmed to crystallize in two distinct pseudopolymorphic forms, designated A and B.
- Form A was obtained under specific cooling conditions (slow or rapid) from ethanol, methanol, and toluene.
- Form B was exclusively obtained from toluene under slow cooling conditions at room temperature.
Conclusions:
- Piroxicam benzoate exhibits pseudopolymorphism, forming two distinct crystalline structures (A and B).
- The crystallization solvent and cooling rate critically influence the formation of these pseudopolymorphic forms.
- This study provides foundational knowledge for controlling the solid-state characteristics of piroxicam benzoate in pharmaceutical development.