Resolution of the enantiomers of ibuprofen; comparison study of diastereomeric method and chiral stationary phase method

Ahn, Hyun-Sik; Shiu, Gerald K.; Trafton, Walter F.; Doyle, Thomas D.

doi:10.1016/0378-4347(93)e0425-p

Cited by 28 publications

(19 citation statements)

References 11 publications

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“…The measured enantiomeric compositions were in good agreement with the expected values and the variation involved was within acceptable limits at all three "total" concentrations examined. These results indicate that racemization had not occurred during the extraction and derivatization process as has been reported for some derivatization procedures [23,45], and that increasing concentrations of ibuprofen do not appear to affect the measured enantiomeric compositions.…”

Section: Enantiospecific Analysis Of Lbuprofen In Serummentioning

confidence: 51%

Enantiospecific analysis of ibuprofen by high performance liquid chromatography: Determination of free and total drug enantiomer concentrations in serum and urine

et al. 1997

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SummaryA reversed-phase high-performance liquid chromatographic (HPLC) assay, based on the indirect approach to enantiomeric analysis, for the determination of ibuprofen in human serum and urine has been developed. Following the addition of (R,S)-flurbiprofen, as internal standard, the enantiomers of ibuprofen were isolated from plasma and urine samples by liquid-liquid extraction at acidic pH. The enantiomers of flurbiprofen and ibuprofen were derivatized with (R)-l-(naphthen-1-yl)ethylamine, using 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 1-hydroxybenzotriazole as coupling reagents, to yield the corresponding diastereoisomeric amides. Chromatographic resolution of the derivatives was achieved using a C18 column (Waters Resolve C18; 5 gin, 150 x 3.9 mm) using a mobile phase of phosphate buffer (pH 3.5, 0.01 M): acetonitrile (50:50 v/v) at a flow rate of 1.5 mL min -1 at ambient temperature. Quantification was carried out using a spectrofluorometer with excitation and emission wavelengths of 290 and 330 nm respectively. The use of a semimicrobore column (150 x 2.1 mm) containing the same stationary phase facilitated the analysis of the free drug enantiomer concentrations following equilibrium dialysis. The derivatization procedure was carried out as described above but with a reduction in the quantities of the reagents used in order to reduce the background noise in the chromatographic analysis. The HPLC methodology for the determination of free drug enantiomer concentrations was validated against a previously reported method employing the radiolabelled drug.

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Section: Enantiospecific Analysis Of Lbuprofen In Serummentioning

confidence: 51%

Enantiospecific analysis of ibuprofen by high performance liquid chromatography: Determination of free and total drug enantiomer concentrations in serum and urine

et al. 1997

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“…Construction of a chiral stationary phase or prederivatization of the individual enantiomers to produce the diastereisomeric pair are the two important techniques employed. Though these techniques vary from normal to reverse phase and utilize a variety of detector systems, the separations achieved thus far are similar (Ahn et al, 1994).…”

Section: Chromatographic Separation Methodsmentioning

confidence: 97%

Review- Alternatives for the separation of drug enantiomers: ibuprofen as a model compound

Carvalho

Cass

Calafatti

et al. 2006

Braz. J. Chem. Eng.

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-Given the inherent dangers associated with racemic pharmaceuticals, exhaustive studies of techniques designed to separate enantiomers have been conducted. This paper reports a brief review of the different physical, chemical, and enzymatic methods used for the enantiomeric separation of rac-ibuprofen. The possible contribution of each technique to the preparation of enantiomerically pure drugs is reviewed in the context of competitive approaches that depend on the scale of application, with special emphasis on the recent progress achieved in this particular area.

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“…Moreover, the amidation reaction with 1-PEA was found not to be stereospecific to any significant extent [24], and the stereochemical conversion of profens [18,31,32] could be minimized by using excess amount (≥17 mM) of ECF [18]. Polar acetonitrile as the reaction solvent was found to induce more racemization than toluene [32]. Therefore, the rapid ECF/1-PEA procedure required to be optimized prior to GC analysis.…”

Section: Introductionmentioning

confidence: 95%

“…Among the chiral resolving reagents used for chiral amidation such as l-leucinamide [16,18,19], amphetamine [28], (R)-(+)-1-phenylethylamine (1-PEA) or its antipode [24][25][26][27]29,30], 1-PEA with ethyl chloroformate (ECF) activation provides more volatile diastereomeric amides suitable for GC analysis at room temperature within a few min. Moreover, the amidation reaction with 1-PEA was found not to be stereospecific to any significant extent [24], and the stereochemical conversion of profens [18,31,32] could be minimized by using excess amount (≥17 mM) of ECF [18]. Polar acetonitrile as the reaction solvent was found to induce more racemization than toluene [32].…”

Section: Introductionmentioning

confidence: 95%

Chiral discrimination of multiple profens as diastereomeric (R)-(+)-1-phenylethylamides by achiral dual-column gas chromatography

Paik

Lee

Goto

et al. 2004

Journal of Chromatography B

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Resolution of the enantiomers of ibuprofen; comparison study of diastereomeric method and chiral stationary phase method

Cited by 28 publications

References 11 publications

Enantiospecific analysis of ibuprofen by high performance liquid chromatography: Determination of free and total drug enantiomer concentrations in serum and urine

Enantiospecific analysis of ibuprofen by high performance liquid chromatography: Determination of free and total drug enantiomer concentrations in serum and urine

Review- Alternatives for the separation of drug enantiomers: ibuprofen as a model compound

Chiral discrimination of multiple profens as diastereomeric (R)-(+)-1-phenylethylamides by achiral dual-column gas chromatography

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