The rate constants of the reactions of O(3) with some typical wastewater pollutants (tributyltin, the macrolide antibiotic clarithromycin, the beta blocker metoprolol and the analgesic diclofenac) were determined and some mechanistic aspects were elucidated. Except for tributyltin compounds that react only slowly with O(3) (k=4-7 M(-1) s(-1)), the compounds react fast (k>10(4) M(-1) s(-1)) and can be eliminated at low O(3) doses. Clarithromycin reacts at its dimethylamino group and yields the corresponding N-oxide that is no longer biologically active. The nitrogen is also the major site of O(3) attack in diclofenac and in metoprolol. This gives rise to *OH radicals and these are the precursors of hydroxylated products and markedly contribute to chloride release in diclofenac.