Determination of the (+)- and (−)-enantiomers of pirprofen in human plasma by high-performance liquid chromatography

Sioufi, A.; Colussi, D.; Marfil, F.; Dubois, J.P.

doi:10.1016/0378-4347(87)80031-2

Cited by 24 publications

(4 citation statements)

References 10 publications

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“…These results are due to the loss of the R enantiomer, both by glucuronidation and/or excretion and by inversion to the S antipode (Fournel & Caldwell 1986). This inversion, observed for ibuprofen (Geisslinger et al 1990;Lee et al 1985) and suggested for pirprofen (Jamali 1988;Sioufi et al 1987), can explain the apparent discrepancy between pharmacokinetics parameters and protein binding.…”

Section: Pharmacokinetic Implicationsmentioning

confidence: 68%

“…Its proportion in the total concentration varies with the ratio between the enantiomers, for example, S<R S<R Jamali et al (1988b) Knadler et al (1989 S=R S>R Jamali et al (1988a); Young et al (1991) Hansen et al (1985; S>R S>R Lee et al (1985) Evans et al (1989) S=R S>R Geisslinger et al (1990) Siebler & Kinawi Tamassia et al (1984) (1989) Hayball et al (1991) S<R S=R Foster et al (1988a) Dubois et al (1993 S=R S=R Foster et al (1988b); Sallustio et al (1988 S > RC S > RC Fournel & Caldwell (1986); Melfin et al Otagiri et al (1989) S>R S>R Sioufi et al (1987) Oravcova et al (1991 Abbreviations: ty, = elimination half-life; AUC = area under the plasma concentration-time curve; UF = ultrafiltration; GF = gel filtration; ED = equilibrium dialysis; HPLC = high performance liquid chromatography; HSA = human serum albumin; NO = not determined.…”

Section: Pharmacological Considerationsmentioning

confidence: 96%

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Protein Binding and Stereoselectivity of Nonsteroidal Anti-Inflammatory Drugs

Lapicque¹,

Muller²,

Payan³

et al. 1993

Clinical Pharmacokinetics

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Stereoselective binding of nonsteroidal anti-inflammatory drugs (NSAIDs) can be studied using various techniques. Thus the results obtained by different investigators may be poorly consistent and even contradictory. NSAIDs are bound stereoselectively to serum albumin to different degrees depending on the drug investigated (ibuprofen, indoprofen, carprofen, etodolac, ketoprofen and flurbiprofen). For other drugs, both enantiomers are bound to a similar extent (pirprofen, fenoprofen). This stereoselectivity could vary with experimental conditions, in particular with protein concentration (ketoprofen, etodolac), leading to individual differences. Finally, the stereoselectivity of protein binding and of pharmacokinetics can be compared: differences in binding between enantiomers can explain their differences in pharmacokinetics, once metabolic properties such as inversion have been taken into account.

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Section: Pharmacokinetic Implicationsmentioning

confidence: 68%

Section: Pharmacological Considerationsmentioning

confidence: 96%

Protein Binding and Stereoselectivity of Nonsteroidal Anti-Inflammatory Drugs

Lapicque¹,

Muller²,

Payan³

et al. 1993

Clinical Pharmacokinetics

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“…In contrast, the high efficiencies typically achievable with CE facilitate the baseline resolution of enantiomers with very low separation factors e.g., 1.01, which would be either impossible, or extremely difficult using conventional HPLC or GC [6,16]. In addition, while the enantioselectivity of a CSP may be satisfactory, the chemical selectivity may be inadequate, such that structurally similar metabolites coelute with the parent drug peak [23,24]. The separation efficiency of CE, however, can enable the simultaneous separation and resolution of structurally similar metabolites [25].…”

Section: Enantiomeric Resolution By Cementioning

confidence: 99%

Enantiospecific analysis by capillary electrophoresis: Applications in drug metabolism and pharmacokinetics

2000

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Enantiospecific analysis has an important role in drug metabolism and pharmacokinetic investigations and its now no longer acceptable to determine total drug, or metabolite, concentrations following the administration of a racemate. Inspite of the fact that capillary electrophoresis (CE) has become an essential technique in pharmaceutical and enantiospecific analysis, the chromatographic methodologies remain the most commonly used approach for the determination of the enantiomeric composition of drugs in biological fluids. The application of CE to bioanalysis has been slow, which is in part associated with the complexity of biological matrices together with the relatively poor concentration limits of detection achievable. However, as a result of its versatility, high separation efficiency, minimal sample requirements, speed of analysis and low consumable expense CE is likely to play an increasingly significant role in the area. This review present an overview of enantiospecific CE in bioanalysis in which the approaches to enantiomeric resolution and the problems associated with biological matrices are briefly discussed. The application of enantiospecific CE to samples of biological origin is illustrated using examples where the methodology has either solved an analytical problem, or provided a useful alternative to the currently available chromatographic methods. Such improvements in methodology are associated with either the high separation efficiency and/or microanalytical capabilities of the technique. Enantiospecific CE will not replace the chromatographic methodologies but does provide the bioanalyst with a useful addition to his armamentarium.

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“…Thus, significant inversion, 50-80%, occurs for ibuprofen (52,68) (Fig. 2), benoxaprofen (73), fenoprofen (74), and loxaprofen (75), and possibly occurs for pirprofen (76), cicloprofen (77), and for one enantiomer within one species but not necessarily for all species. Thus, for deamination and dealkylation, there is stereoselectivity for the (+)-enantiomers in man but for the (-)-enantiomer for deamination in rabbit and dealkylation in rat and dog.…”

Section: Substrate Selectivitymentioning

confidence: 99%

Stereoselectivity in clinical pharmacokinetics and drug development

Campbell

1990

Eur. J. Drug Metab. Pharmacokinet.

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Determination of the (+)- and (−)-enantiomers of pirprofen in human plasma by high-performance liquid chromatography

Cited by 24 publications

References 10 publications

Protein Binding and Stereoselectivity of Nonsteroidal Anti-Inflammatory Drugs

Protein Binding and Stereoselectivity of Nonsteroidal Anti-Inflammatory Drugs

Enantiospecific analysis by capillary electrophoresis: Applications in drug metabolism and pharmacokinetics

Stereoselectivity in clinical pharmacokinetics and drug development

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