Direct high-performance liquid chromatographic resolution of the enantiomers of tiaprofenic acid using immobilized human serum albumin

Muller, Noëlle; Lapicque, Françoise; Drelon, E.; Gillet, Pierre; Monot, C.; Poletto, B.; Netter, Patrick

doi:10.1016/0378-4347(93)80394-j

Cited by 15 publications

(9 citation statements)

References 30 publications

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“…13 In a study in which racemic TIA was administered subcutaneously to rats, the S -enantiomer plasma concentrations were significantly greater than the plasma concentrations of the Renantiomer from 1 hr. 15 A similar difference between enantiomer concentrations was also observed in humans. However, these findings, together with our data, are not consistent with those of other authors.…”

Section: Disposition Of S-and R-tiaprofenic Acidsupporting

confidence: 62%

“…Like other groups 15 we used TIA enantiomers with a significant content of the optical antipode because enantiomers of greater purity were not available. However, dose- …”

Section: Discussionmentioning

confidence: 99%

“…In order to avoid racemisation, we determined enantiomer concentrations using a chiral column with ␣1-acid glycoprotein as stationary phase. An analogous HPLC approach was chosen by Muller et al, 15 who used a chiral column with immobilized albumin. Under these conditions there is no racemisation during analysis or sample preparation.…”

Section: Disposition Of S-and R-tiaprofenic Acidmentioning

confidence: 99%

“…14 In a recent study of TIA in rats, S -enantiomer plasma concentrations significantly exceeded those of the Renantiomer from 1 hr after subcutaneous administration of R,S -TIA and similar data have been reported in humans. 15 This could be caused by different clearances of the enantiomers and/or by chiral metabolic inversion of TIA enantiomers. Therefore, we investigated the pharmacokinetics and metabolic inversion of TIA enantiomers in rats.…”

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confidence: 99%

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Stereoselective disposition of tiaprofenic acid enantiomers in rats

et al. 1999

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Section: Disposition Of S-and R-tiaprofenic Acidsupporting

confidence: 62%

“…Like other groups 15 we used TIA enantiomers with a significant content of the optical antipode because enantiomers of greater purity were not available. However, dose- …”

Section: Discussionmentioning

confidence: 99%

Section: Disposition Of S-and R-tiaprofenic Acidmentioning

confidence: 99%

mentioning

confidence: 99%

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Stereoselective disposition of tiaprofenic acid enantiomers in rats

et al. 1999

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“…[28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] More recently, analysis has been accomplished using micellar electrokinetic capillary chromatography and capillary zone electrophoresis, but with higher observed detection limits than HPLC application to pharmacokinetic studies remains limited.l 46 ,47] The earlier assays of tiaprofenic acid overlooked the fact that it is administered as the racemate. However, since 1986, validated GC and HPLC techniques [16][17][18]21,27] have been available which allow for the separation and quantification of the 2 enantiomers. These methods either involve the formation of amide diastereomeric derivatives through the use of an optically pure derivatising reagent and separate chromatographic quantification on an achiraJlI6,27] or chiral N,N'-dinitrobenzoyl derivative of IR,2R-diaminocyclohexane, [40] or experimental tris(4-methylbenzoate) cellulose stationary phase.…”

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confidence: 99%

Clinical Pharmacokinetics of Tiaprofenic Acid and its Enantiomers

Davies

1996

Clinical Pharmacokinetics

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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 suggested that 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 peak is prolonged. Tiaprofenic acid binds extensively to plasma albumin. These 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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Enantiospecific analysis: Applications in bioanalysis and metabolism

Hutt

Hadley

Tan

1994

Eur. J. Drug Metab. Pharmacokinet.

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Enantiospecific analysis has a significant role in modern drug development from discovery-chemistry to the clinical evaluation of novel compounds. Chromatographic techniques, involving the use of either chiral derivatizing agents or chiral stationary phases, represent the most commonly used approaches to enantiospecific analysis. The advantages and limitations of these two techniques are examined using the analysis of the enantiomers of the 2-arylpropionic acids (tiaprofenic acid and ibuprofen) and the chiral N-oxides of N-ethyl-N-methylaniline and pargyline, as representative examples for each approach. The potential of biosensors in enantiospecific analysis is addressed and some preliminary results on the development of an enantioselective biosensor for the analysis of (S)-warfarin are presented.

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Direct high-performance liquid chromatographic resolution of the enantiomers of tiaprofenic acid using immobilized human serum albumin

Cited by 15 publications

References 30 publications

Stereoselective disposition of tiaprofenic acid enantiomers in rats

Stereoselective disposition of tiaprofenic acid enantiomers in rats

Clinical Pharmacokinetics of Tiaprofenic Acid and its Enantiomers

Enantiospecific analysis: Applications in bioanalysis and metabolism

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