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Initial salt screening procedures for manufacturing ibuprofen.

Tu Lee1, Yeh Wen Wang

  • 1Department of Chemical and Materials Engineering, National Central University, Jhong-Li City, Taiwan, Republic of China. tulee@cc.ncu.edu.tw

Drug Development and Industrial Pharmacy
|November 14, 2008
PubMed
Summary
This summary is machine-generated.

Researchers developed new salt forms of ibuprofen, including a novel amine salt. This new ibuprofen salt exhibits improved stability, hydrophobicity, and dissolution properties, suggesting potential for sustained-release drug formulations.

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Area of Science:

  • Pharmaceutical Chemistry
  • Materials Science
  • Drug Development

Background:

  • Ibuprofen is a widely used nonsteroidal anti-inflammatory drug (NSAID).
  • Optimizing ibuprofen's salt form is crucial for enhancing its physicochemical properties and therapeutic efficacy.
  • Existing salt forms may have limitations in stability, solubility, or manufacturability.

Purpose of the Study:

  • To design and implement initial salt screening procedures for manufacturing ibuprofen.
  • To identify novel, "developable" salt forms of racemic ibuprofen with improved characteristics.
  • To evaluate the synthetic routes and properties of newly discovered ibuprofen salts.

Main Methods:

  • Screening of seven different bases (including L-arginine, L-histidine, L-lysine, diethanolamine, and tris(hydroxymethyl)aminomethane (THAM)) with racemic (R,S)-(+/-)-ibuprofen.
  • Utilized nine organic solvents (e.g., methanol, ethanol, dimethyl sulfoxide) in the presence of water for salt synthesis.
  • Characterization of synthesized salts included determination of molecular weight, melting point, solubility product (K'sp), crystal structure (space group, lattice parameters), and aspect ratio.

Main Results:

  • Successfully synthesized racemic (R,S)-(+/-)-sodium ibuprofen dihydrate and a novel racemic (R,S)-(+/-)-THAM ibuprofen salt.
  • The new THAM ibuprofen salt is monoclinic (space group P2(1)/c) with specific lattice parameters and an aspect ratio of approximately 1.0, indicating superior flowability compared to the sodium salt.
  • The THAM ibuprofen salt demonstrated enhanced stability in moist/dried atmospheres, increased hydrophobicity, and slower dissolution, suggesting reduced bitterness and suitability for sustained-release applications.

Conclusions:

  • The developed salt screening procedures are effective for identifying promising ibuprofen salt forms.
  • The novel THAM ibuprofen salt offers significant advantages over the sodium salt in terms of stability, flowability, and dissolution profile.
  • Future research will focus on exploring polymorphs of the THAM ibuprofen salt and extending screening methods to co-crystal formation.