The Relationship between Structure and Activity of Taurolin

Abstract

Taurolin [Bis(1,1‐dioxo‐perhydro‐1,2,4 thiadiazinyl‐4)methane] is an antimicrobial compound formed by the condensation of two molecules of taurine with three of formaldehyde. It has been suggested that it releases formaldehyde in contact with bacteria. Evidence from TLC, HPLC and NMR spectroscopy indicates that taurolin is mostly hydrolysed in aqueous solution to release one molecule of formaldehyde and two monomeric molecules (1,1‐dioxo‐perhydro‐1,2,4‐thiadiazine and its carbinolamine derivative). A stable equilibrium is established. Antibacterial activity is not entirely due to adsorption of free formaldehyde but also to reaction with a masked (or latent) formaldehyde, as the activity of taurolin is greater than formaldehyde. The monomer is only slightly active by comparison.