Investigation of isomerization of dexibuprofen in a ball mill using chiral capillary electrophoresis
Please always quote using this URN: urn:nbn:de:bvb:20-opus-225852
- Besides the racemate, the S‐enantiomer of ibuprofen (Ibu) is used for the treatment of inflammation and pain. Since the configurational stability of S‐Ibu in solid state is of interest, it was studied by means of ball milling experiments. For the evaluation of the enantiomeric composition, a chiral CE method was developed and validated according to the ICH guideline Q2(R1). The addition of Mg\(^{2+}\), Ca\(^{2+}\), or Zn\(^{2+}\) ions to the background electrolyte (BGE) was found to improve Ibu enantioresolution. Chiral separation of IbuBesides the racemate, the S‐enantiomer of ibuprofen (Ibu) is used for the treatment of inflammation and pain. Since the configurational stability of S‐Ibu in solid state is of interest, it was studied by means of ball milling experiments. For the evaluation of the enantiomeric composition, a chiral CE method was developed and validated according to the ICH guideline Q2(R1). The addition of Mg\(^{2+}\), Ca\(^{2+}\), or Zn\(^{2+}\) ions to the background electrolyte (BGE) was found to improve Ibu enantioresolution. Chiral separation of Ibu enantiomers was achieved on a 60.2 cm (50.0 cm effective length) x 75 μm fused‐silica capillary using a background electrolyte (BGE) composed of 50 mM sodium acetate, 10 mM magnesium acetate tetrahydrate, and 35 mM heptakis‐(2,3,6‐tri‐O‐methyl)‐β‐cyclodextrin (TM‐β‐CD) as chiral selector. The quantification of R‐Ibu in the mixture was performed using the normalization procedure. Linearity was evaluated in the range of 0.68–5.49% R‐Ibu (R\(^{2}\) = 0.999), recovery was found to range between 97 and 103%, the RSD of intra‐ and interday precision below 2.5%, and the limit of quantification for R‐ in S‐Ibu was calculated to be 0.21% (extrapolated) and 0.15% (dilution of racemic ibuprofen), respectively. Isomerization of S‐Ibu was observed under basic conditions by applying long milling times and high milling frequencies.…
Author: | Jonas Urlaub, Reinhard P. Kaiser, Oliver Scherf‐Clavel, Carsten Bolm, Ulrike Holzgrabe |
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URN: | urn:nbn:de:bvb:20-opus-225852 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Pharmazie und Lebensmittelchemie |
Language: | English |
Parent Title (English): | Electrophoresis |
Year of Completion: | 2021 |
Volume: | 42 |
Issue: | 17-18 |
First Page: | 1790 |
Last Page: | 1799 |
Source: | Electrophoresis 2021, 42(17-18):1790–1799. DOI: 10.1002/elps.202000307 |
DOI: | https://doi.org/10.1002/elps.202000307 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
Tag: | Ibuprofen; capillary electrophoresis; chiral separation; isomerization; validation |
Release Date: | 2021/10/15 |
Licence (German): | CC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International |