This invited paper is part of a Symposium-in-Print on Pharmaceutical Photochemistry.
Photophysics and Photochemistry of z-Chlorprothixene in Acetonitrile†
Article first published online: 22 JUN 2009
© 2009 The Authors. Journal Compilation. The American Society of Photobiology
Photochemistry and Photobiology
Volume 85, Issue 4, pages 895–900, July/August 2009
How to Cite
Piñero, L. E., García, C., Lhiaubet-Vallet, V., Oyola, R. and Miranda, M. A. (2009), Photophysics and Photochemistry of z-Chlorprothixene in Acetonitrile. Photochemistry and Photobiology, 85: 895–900. doi: 10.1111/j.1751-1097.2009.00584.x
- Issue published online: 22 JUN 2009
- Article first published online: 22 JUN 2009
- Received 2 January 2009, accepted 7 April 2009
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.