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Clinical Pharmacokinetics of Tiaprofenic Acid and its Enantiomers

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Summary

Tiaprofenic acid is a chiral nonsteroidal anti-inflammatory drug (NSAID) of the 2-arylpropionic acid (2-APA) class. A common structural feature of 2-APA NSAIDs is a sp3-hybridised tetrahedral chiral carbon heteroatom within the propionic acid side chain moiety, with the S-enantiomer possessing most of the beneficial anti-inflammatory activity. However, all tiaprofenic acid preparations to date are marketed as the racemate. Tiaprofenic acid has been suggested to exhibit limited pharmacokinetic stereoselectivity.

The synovium is the proposed site of action of NSAIDs when used for musculoskeletal disorders, and substantial concentrations of tiaprofenic acid are attained in synovial fluid. Recent data suggest the possibility of stereoselective distribution of tiaprofenic acid into synovium and cartilage. Hence, data generated using non-stereospecific assays may not always be extrapolated to explain the disposition of the individual enantiomers.

Tiaprofenic acid is rapidly and almost completely absorbed when given orally. The area under the plasma concentration-time curve (AUC) of tiaprofenic acid is proportional to the oral dose administered.

A sustained release dosage form is available, which may be beneficial due to the short terminal phase half-life of tiaprofenic acid (3 to 6 hours). The bioavailability is the same as that with conventional rapid release preparations, although the peak plasma drug concentration is reduced and time to peak is prolonged.

Tiaprofenic acid binds extensively to plasma albumin. There is negligible R to S inversion upon oral administration. Tiaprofenic acid is eliminated following extensive biotransformation to glucuronide-conjugated metabolites. Approximately 60% is eliminated as conjugates excreted in urine, and little drug is eliminated unchanged. The rate of excretion of tiaprofenic acid and its conjugates may be related to renal function; accumulation of conjugates occurs in end-stage renal disease, but not in young individuals or elderly patients.

Potentially clinically important drug interactions with tiaprofenic acid have been demonstrated for some anticoagulants and probenecid. Relationships between tiaprofenic acid concentrations in biological matrices and therapeutic or toxic effects have not yet been elucidated for this drug.

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    Neal M. Davies

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Davies, N.M. Clinical Pharmacokinetics of Tiaprofenic Acid and its Enantiomers. Clin-Pharmacokinet 31, 331–347 (1996). https://doi.org/10.2165/00003088-199631050-00002

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