Abstract

The chiral drug (RS)-2-(4-(2-methylpropyl)phenyl) propanoic acid, known as ibuprofen, is an important non-steroidal anti-inflammatory drug, also notorious for its analgesic and antipyretic properties. This medicine is market in racemic form R-(-)-ibuprofen and S-(+)-ibuprofen, however, in some countries only the second enantiomer is applied. This paper refers to the study of the thermodynamic parameters relative for separation of the racemic mixture in analytical chiral chromatographic columns packed with cellulose tris (3,5-dimethylphenylcarbamate). In this analysis, the enthalpy (ΔH 0 ), entropy (ΔS 0 ), enthalpy difference (ΔΔH 0 ), entropy difference (ΔΔS 0 ), and isoenantioselective temperature (Tiso) was determined by van’t Hoff approach.

Highlights

  • Ibuprofen was commercially introduced as a non-steroidal anti-inflammatory drug (NSAID) in the United Kingdom in 1969, and in the United States in 1974

  • The results obtained for the separation of racemic ibuprofen in columns packed with cellulose tris (3,5-dimethylphenylcarbamate) demonstrated a phenomenon of endothermic physisorption

  • The R-(-)ibuprofen binds more energetically chiral stationary phase (CSP) and S-(+)-ibuprofen has a lower degree of freedom

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Summary

Introduction

Ibuprofen was commercially introduced as a non-steroidal anti-inflammatory drug (NSAID) in the United Kingdom in 1969, and in the United States in 1974. This drug replaced others NSAIDs that caused gastrointestinal irritation and severe intolerance in the body (Palma et al, 2009). The S-(+)-ibuprofen is a prostaglandin and thromboxane inhibitor This enantiomer demonstrates better clinical efficiency, less variability in therapeutic effects and toxicity, if compared with this racemic form. R-(-)-ibuprofen structure does not display pharmacological action. It triggers a chiral inversion on human body causing toxicity by the formation of hybrid triglycerides (Yoon et al, 2008)

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