Issue 8, 2010
From the journal:

Photochemical & Photobiological Sciences

Investigation on the phototransformation of tadalafil in aqueous media. 6-Epimerization vs.solvent trapping reaction

Fabio Temussi,*a   Giovanni Bassolino,a   Flavio Cermola,a   Marina DellaGreca,a   Maria Rosaria Iesce,a   Sara Montanaro,a   Lucio Previtera*a  and  Maria Rubinoa  

* Corresponding authors

a ‘IC-REACH’ Dipartimento di Chimica Organica e Biochimica, Università Federico II, Complesso Universitario Monte S. Angelo, Via Cinthia 4, Napoli, Italy
E-mail: ftemussi@unina.it, previter@unina.it
Fax: +39 081674393
Tel: +39 081674333

Abstract

Irradiation of tadalafil at λ > 290 nm in aqueous solutions leads to 6-epimer and/or water adducts depending on concentration and pH. A rationalization of the results involves the heterolytic cleavage of C6–N5 bond via a well-stabilized zwitterionic intermediate. The drug is stable in the dark except under strongly basic conditions where it undergoes C12a-epimerization.

Graphical abstract: Investigation on the phototransformation of tadalafil in aqueous media. 6-Epimerization vs. solvent trapping reaction

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Article information

DOI
https://doi.org/10.1039/C0PP00019A
Article type
Paper
Submitted
09 Feb 2010
Accepted
04 Jun 2010
First published
23 Jun 2010

Photochem. Photobiol. Sci., 2010,9, 1139-1144

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Investigation on the phototransformation of tadalafil in aqueous media. 6-Epimerization vs. solvent trapping reaction

F. Temussi, G. Bassolino, F. Cermola, M. DellaGreca, M. R. Iesce, S. Montanaro, L. Previtera and M. Rubino, Photochem. Photobiol. Sci., 2010, 9, 1139 DOI: 10.1039/C0PP00019A

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