, Volume 17, Issue 2, pp 145–155 | Cite as

Characterization and metal affinity of Tirofiban, a pharmaceutical compound used in acute coronary syndromes

  • E. Ferrari
  • L. Menabue
  • M. Saladini


The crystal and molecular structure of Tirofiban [N-(n-butanesulfonyl)-O-(4-(4-piperidinyl)-butyl)-(S)-tyrosine] is here reported. In the solid state the carboxylic group is in the anionic form while the piperidine molecule appear in the protonated form. By H NMR spectroscopy and potentiometric study three pKa are found: pKaCOOH=3.1(1), pKaNHPIP=11.6(1) and pKaNHSO2=13.8(1). The complexing ability of Tirofiban towards various metal ions (Cu(II), Ni(II), Co(II), Cd(II), Pb(II), Zn(II) and Ca(II)) is also determined by means of potentiometric studies. The prevailing species are [M(TirH)2]2+ where the ligand coordinates the metal ion through carboxylic group, while the piperidine nitrogen is still protonated. The great stability of these complexes may be due to the presence of hydrogen bond interactions, as well as the formation of stacking interactions involving the phenyl ring of the tyrosine residue.

crystal structure metal-complexes Tirofiban 


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Copyright information

© Kluwer Academic Publishers 2004

Authors and Affiliations

  1. 1.Dipartimento di ChimicaUniversità degli Studi di Modena e Reggio EmiliaModena(Italy)

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