Suprofen enantiomers

Y Shinohara, H Magara, S Baba. Stereoselective pharmacokinetics and inversion of suprofen enantiomers in humans. J Pharm Sci 80 1075, 1991. 

An analgesic with greater antiinflammatory and antipyretic activity than Naproxen is a-methyl-4-(2-thienylcarbonyl)benzeneacetic acid, Suprofen.63 This compound has been tested only as a racemic mixture, and any difference in the activity of the enantiomers is not known. Hydroformylation of 4-(2-thienylcarbonyl)styrene (entry 3, Table 4) to the 2-aiylpropanal was achieved in 78% ee for the branched aldehyde [(-t-)-enantiomer in excess], which can be converted to Suprofen by oxidation. 

Clinically this bioinversion process does not occur appreciably with tiaprofenic acid, indoprofen, carprofen, or flurbiprofen, but it does occur substantially for fenoprofen and ibuprofen, for which 100% and 60% of the R-enantiomer is inverted, respectively [32-34]. Bioinversion also occurs for benoxaprofen, an NSAID withdrawn from the market, and it may also occurs for loxoprofen, suprofen, and CS-670, all 2-APA NSAIDs primarily utilized clinically throughout Asia [34-37]. 

A number of enantiomers (aminoglutethimide, chlorpheniramine, chlorthalidone, fluoxetine, ibuprofen, ketoprofen, methylphenidate, metoprolol, phensuximide, propranolol, suprofen and mephenytoin) were separated on a -cyclodextrin column using 40/60 to 20/80 acetonitrile/water (0.1% triethylammonium acetate pH 4.1 or 7.1) mobile phase (analyte dependent) [1550]. 

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