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Related Experiment Videos

Solid-state study of mepivacaine hydrochloride.

V Giannellini1, M Bambagiotti-Alberti, G Bartolucci

  • 1Dipartimento di Scienze Farmaceutiche, Università di Firenze, Via U. Schiff 6, I-50019 Sesto Fiorentino, Firenze, Italia. valerio.giannellini@unifi.it

Journal of Pharmaceutical and Biomedical Analysis
|June 14, 2005
PubMed
Summary

Mepivacaine hydrochloride exhibits distinct crystalline forms, including anhydrous polymorphs and solvates, identified using spectroscopy and diffraction. These polymorphic forms are important for drug master files but do not impact clinical use in aqueous solutions.

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Area of Science:

  • Solid-state chemistry
  • Pharmaceutical sciences
  • Crystallography

Background:

  • Mepivacaine hydrochloride (MH) is a widely used local anesthetic.
  • Understanding its solid-state properties, including polymorphism, is crucial for pharmaceutical development and manufacturing.
  • Conventional thermal analysis methods like DSC may not fully reveal MH's crystalline diversity.

Purpose of the Study:

  • To identify and characterize different crystalline forms of mepivacaine hydrochloride (MH).
  • To investigate the relationships between these forms, particularly the commercial form and its precursors or degradation products.
  • To assess the relevance of observed polymorphism to the clinical application of MH.

Main Methods:

  • Fourier transform infrared spectroscopy (FT-IR) for initial detection of crystalline forms.

Related Experiment Videos

  • X-ray powder diffraction (XRPD) and thermal analysis for characterization of anhydrous polymorphs.
  • Single crystal X-ray diffraction for structure determination of solvates.
  • Recrystallization and desolvation experiments to interconvert forms.

    • Main Results:

    • Two anhydrous polymorphic forms of MH were identified: a commercial metastable Form II and a more stable Form I.
    • Two pseudopolymorphs (solvates) were characterized: Form III (ethanol solvate) and Form IV (methanol solvate).
    • Form II, the commercial form, is generated via desolvation of Form III, often encountered in industrial ethanol crystallization processes.

    Conclusions:

    • The study revealed significant polymorphism in mepivacaine hydrochloride, with implications for its manufacturing and quality control.
    • Polymorphic forms, especially solvates like Form III, should be documented in drug master files.
    • Despite the observed polymorphism, MH's high water solubility renders these solid-state variations clinically irrelevant for its use in aqueous solutions.