Pharmaceutical Research

, Volume 23, Issue 10, pp 2375–2380

Additive-Induced Metastable Single Crystal of Mefenamic Acid

  • Eun Hee Lee
  • Stephen R. Byrn
  • M. Teresa Carvajal
Research Paper

DOI: 10.1007/s11095-006-9045-y

Cite this article as:
Lee, E.H., Byrn, S.R. & Carvajal, M.T. Pharm Res (2006) 23: 2375. doi:10.1007/s11095-006-9045-y


To utilize additives to develop a strategy and a method to grow single crystals that allow structure determination of a metastable form of a drug.

Materials and Methods

The metastable form of mefenamic acid (MFA) was grown in the presence of various amounts of the structurally similar additive flufenamic acid (FFA) in ethanol. Single crystal X-ray analysis was performed on the single crystals of MFA II that were formed. The solubility of MFA in the presence of FFA was measured to elucidate the mechanism of MFA II formation.


A supersaturated solution of MFA in ethanol produced the metastable form using FFA as an additive. Ethanol–water mixtures and toluene were also used to investigate the relationships between form produced and solvent since these two solvent systems do not produce MFA II.


Additives can be used to obtain the metastable form of pharmaceutical compounds, and the relationships between molecules and solvent as well as between host and guest molecules are critical to obtaining the desired form.

Key words

flufenamic acid mefenamic acid polymorph selection single crystal XRPD 

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Eun Hee Lee
    • 1
  • Stephen R. Byrn
    • 1
  • M. Teresa Carvajal
    • 1
  1. 1.Department of Industrial and Physical PharmacyPurdue UniversityWest LafayetteUSA

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