1991
DOI: 10.1016/0140-6736(91)92382-c
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Chirality in antirheumatic drugs

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Cited by 103 publications
(48 citation statements)
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“…As noted, the molecule found in the solid state is chiral and we have previously described problems that can be caused by the use of racemic mixtures of enantiomers in the treatment of patients (11)(12)(13). This is unlikely to be a problem with azapropazone because of the rapid inversion between the two enantiomers.…”
Section: Resultsmentioning
confidence: 99%
“…As noted, the molecule found in the solid state is chiral and we have previously described problems that can be caused by the use of racemic mixtures of enantiomers in the treatment of patients (11)(12)(13). This is unlikely to be a problem with azapropazone because of the rapid inversion between the two enantiomers.…”
Section: Resultsmentioning
confidence: 99%
“…This may result in a supraproportional bioavailability of S(+)-ibuprofen from the racemate in vivo (Romero et al, 1991) as well as a reduced risk of formation of potentially toxic metabolites from the R(-)-isomer (Kean et al, 1991), although it is not entirely clear whether this is really a stereoselective reaction (Freneaux et al, 1990). However, in our study there was no evidence for any interconversion of R(-)-ibuprofen into the S(+)-form in vitro, confirming the data of others (Knihinicki et al, 1989).…”
Section: Discussionmentioning
confidence: 99%
“…Inhibition of cyclooxygenase by these compounds resides almost exclusively in the S(+)-enantiomer (Adams et al, 1976;Kean et al, 1991). Since ibuprofen, like most of the other agents in this group, is used as a racemate, the question arises whether both stereoisomers contribute to the analgetic and antiinflammatory efficacy.…”
Section: Introductionmentioning
confidence: 99%
“…It has been used in the treatment of rheumatoid arthritis and hepatitis and for the prevention of infant retina disease (Phelps et al, 2001). L-penicillamine has been found to have considerable toxicity (Kean et al, 1991). Copper chelation of D-PenA has been shown to generate reactive oxygen species that are cytotoxic to human leukemia and breast cancer cells (Gupte and Mumper, 2007).…”
Section: Introductionmentioning
confidence: 99%