Jv. Castell et al., A GENERAL PROCEDURE FOR ISOTOPIC (DEUTERIUM) LABELING OF NONSTEROIDALANTIINFLAMMATORY 2-ARYLPROPIONIC ACIDS, Journal of labelled compounds & radiopharmaceuticals, 34(1), 1994, pp. 93-100
Alkaline treatment of nonsteroidal antiinflammatory 2-arylpropionic ac
ids in deuterium oxide led in all cases to isotopic exchange of the pr
oton located at the alpha-position of the side chain. Monodeuteration
was observed in the case of carprofen, ibuprofen, ketoprofen, fenoprof
en, flurbiprofen and naproxen. Additional exchange of one or two proto
ns of the heterocyclic ring occurred in indoprofen, suprofen and tiapr
ofenic acid. The isotopic labelling survived under the conditions requ
ired to perform in vitro photoallergic studies (photolysis in non-deut
erated aqueous media).