Monitoring of β-blockers ozone degradation via electrospray ionization mass spectrometry

Abstract

As estruturas dos produtos de degradação mediada por ozônio de diferentes compostos farmacêuticos foram estudadas. Uma completa degradação do nadolol foi observada nas condições empregadas após 100 min. Os produtos de degradação obtidos nas soluções aquosas foram caracterizados por espectrometria de massas com ionização por electrospray (ESI-MS e ESI-MS/MS). O mecanismo proposto para a degradação consiste inicialmente do ataque de ozônio ao grupo amino da anilina formando nitro compostos, seguida de uma série de processos oxidativos. Monitoramento por ESI-MS(/MS) mostrou que a degradação de atenolol (ATE) e acebutolol (ACE) por ozônio ocorrem via um mecanismo similar ao do nadolol.The structures of intermediate products of ozone degradation of different pharmaceutical compounds have been studied. Under the conditions employed, complete ozone degradation of nadolol was achieved after 100 min. The degradation products obtained in aqueous solution were characterized by electrospray ionization mass (and tandem mass) spectrometry (ESI-MS and ESI-MS/MS). The proposed mechanism for degradation, ozone attacks at the aniline amino group giving rise to nitro compounds and further degradation occurs via a series of oxidative processes. Continuous online monitoring by ESI-MS(/MS) with high accuracy mass measurements showed that ozone degradation of atenolol (ATE) and acebutolol (ACE) occurs via mechanisms similar to that of nadolol.

Ozonation of acebutolol in aqueous solution: Ozonation by-products and degradation pathway

“…A1n) [16,17]. This ozonation by-product also has been reported by Quispe et al [13] in the ozonation of acebutolol.…”

“…Ozonation has been proven to be an efficient method for the removal of different b-blockers such as acebutolol, atenolol, metoprolol and propranolol according to kinetic studies [3]. Based on our literature review, the ozonation by-products of atenolol [13,16], metoprolol [4,17] and propanolol [5] have been reported. Although a few common ozonation breakdown products of bblockers have been reported by Quispe et al [13] in the ozonation of acebutolol, however the ozonation by-products of acebutolol have not been fully explored.…”

“…Based on our literature review, the ozonation by-products of atenolol [13,16], metoprolol [4,17] and propanolol [5] have been reported. Although a few common ozonation breakdown products of bblockers have been reported by Quispe et al [13] in the ozonation of acebutolol, however the ozonation by-products of acebutolol have not been fully explored. The main objectives of this study were (i) to identify the water soluble ozonation by-products of acebutolol and (ii) to elaborate the transformation mechanisms of acebutolol during ozonation.…”

Evaluation of advanced oxidation processes for β-blockers degradation: a review

“…It is relatively easy to eliminate β-blockers by O 3 treatment (Benner et al 2008;Quispe et al 2011;Wilde et al 2014). Ozone may react with the target molecules in direct (O 3 ) and indirect ( • OH) reactions.…”