Abstract:
:Chlorprothixene (CPTX, Taractan) is a low potency antipsychotic mainly used for the treatment of psychotic disorders (e.g. schizophrenia) and acute mania occurring as part of bipolar disorders. As in the case of other numerous drugs used in the treatment of psychiatric disorders, CPTX presents geometric isomerism. Therefore, in vitro irradiation induces a rapid Z/E isomerization, which can affect its pharmacokinetic properties. This photoisomerization is not dependent on the oxygen concentration. The Z/E quantum yields determined for zCPTX in acetonitrile are 0.22 and 0.21 in anaerobic and aerobic environments, respectively. In the presence of water, both isomers decompose to produce 2-chlorothioxanthone (CTX) after prolonged irradiation. This process strongly depends on the water concentration and the irradiation time, i.e. it is autocatalyzed by the CTX through a triplet-energy transfer mechanism. The protonation state of the terminal amino group, on the other hand, has no effect on the isomerization process, but inhibits the formation of CTX. These results indicate that the phototoxicity of zCPTX is somehow affected by the formation of CTX.
journal_name
Photochem Photobioljournal_title
Photochemistry and photobiologyauthors
Piñero LE,García C,Lhiaubet-Vallet V,Oyola R,Miranda MAdoi
10.1111/j.1751-1097.2009.00584.xsubject
Has Abstractpub_date
2009-07-01 00:00:00pages
895-900issue
4eissn
0031-8655issn
1751-1097journal_volume
85pub_type
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