Release of S(+) enantiomers in breath samples after anaesthesia with isoflurane racemate

Haeberle, Helene A.; Wahl, Hans Günther; Aigner, G.; Unertl, K.; Dieterich, Hans-Jürgen

doi:10.1017/s026502150400211x

Cited by 3 publications

(4 citation statements)

References 23 publications

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“…Isoflurane could be detected in breath even 23 days after surgery [88]. The percentage of isoflurane enantiomers in human breath, although the anesthetic is administered as a racemate, varied significantly with the time of exhalation [91,92]. Breath samples were collected using a 1-L-tedlar bag and were then transferred onto a freshly conditioned thermodesorption tube filled with Tenax ® .…”

Section: Amounts Of (+)-(S)-isoflurane and (-)-(R)-isoflurane [%] (+)mentioning

confidence: 99%

“…The temperature of the CIS was held at À150 C to cryo-focus the components efficiently and then heated to 250 C at a rate of 12 C/s. Isoflurane enantiomers in breath were quantified up to 19 days after surgery [91,92]. During the early postoperative phase, (+)-(S)-isoflurane was slightly enriched (50.5% at day 3) whereas up to 5 days after surgery a noticeable excess of (-)-(R)-isoflurane (51.8% at day 19) was observed [91].…”

Section: Amounts Of (+)-(S)-isoflurane and (-)-(R)-isoflurane [%] (+)mentioning

confidence: 99%

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Salient Features of Enantioselective Gas Chromatography: The Enantiomeric Differentiation of Chiral Inhalation Anesthetics as a Representative Methodological Case in Point

Schurig

2013

Topics in Current Chemistry

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The enantiomeric differentiation of the volatile chiral inhalation anesthetics enflurane, isoflurane, and desflurane by analytical and preparative gas chromatography on various modified cyclodextrins is described. Very large enantioseparation factors α are obtained on the chiral selector octakis(3-O-butanoyl-2,6-di-O-pentyl)-γ-cyclodextrin (Lipodex E). The gas-chromatographically observed enantioselectivities are corroborated by NMR-spectroscopy using Lipodex E as chiral solvating agent and by various sensor devices using Lipodex E as sensitive chiral coating layer. The assignment of the absolute configuration of desflurane is clarified. Methods are described for the determination of the enantiomeric distribution of chiral inhalation anesthetics during narcosis in clinical trials. The quantitation of enantiomers in a sample by the method of enantiomeric labeling is outlined. Reliable thermodynamic parameters of enantioselectivity are determined by using the retention-increment R' approach for the enantiomeric differentiation of various chiral halocarbon selectands on diluted cyclodextrin selectors.

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Section: Amounts Of (+)-(S)-isoflurane and (-)-(R)-isoflurane [%] (+)mentioning

confidence: 99%

Section: Amounts Of (+)-(S)-isoflurane and (-)-(R)-isoflurane [%] (+)mentioning

confidence: 99%

Salient Features of Enantioselective Gas Chromatography: The Enantiomeric Differentiation of Chiral Inhalation Anesthetics as a Representative Methodological Case in Point

Schurig

2013

Topics in Current Chemistry

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“…Differences in action of single enantiomers of the fluorinated anesthetics were examined in many studies. Research conducted on animals [4][5][6][7][8][9][10] and humans [11][12][13] indicated that the S-enantiomer of both isoflurane and desflurane is more effective as an anesthetic and is faster eliminated from the body. Yet, more tests with pure substances should be done to clarify the action of the enantiomers.…”

Section: Introductionmentioning

confidence: 99%

Gas Chromatographic Enantioseparation of Fluorinated Anesthetics: Single‐Column Performance and Scale‐up Estimation

et al. 2018

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Results of a study devoted to provide the pure enantiomers of isoflurane and desflurane from racemic mixtures using gas chromatography are presented. For that purpose, a cyclodextrin‐based selector described in earlier work was immobilized on porous glass beads. The adsorption isotherms were determined and applied to predict operating parameters which provide the highest possible productivity of the separation. The analysis included evaluation of the performance of larger columns applying simplifying scale‐up considerations. Using repetitive batches, the method can provide per day with a laboratory scale column approximately 1 g pure enantiomer. Selected model predictions were validated experimentally.

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“…Isofluran und Desfluran sind chiral und werden als Racemate eingesetzt. Die unterschiedlichen biologischen und chemischen Eigenschaften der Enantiomere wurden bisher nicht berücksichtigt, wodurch der spezifische und pharmakologische Wirkungsmechanismus noch nicht eindeutig geklärt werden konnte 2. Des Weiteren wurde ein unterschiedlicher Abbau der einzelnen Enantiomere festgestellt.…”

Section: Introductionunclassified

Synthese von porösen Voll‐ und Core‐Shell‐Glaskugeln zur Trennung von chiralen Anästhetika

Münzner¹,

Dornberg²,

Küster³

et al. 2016

Chemie Ingenieur Technik

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Zur Trennung chiraler Anästhetika werden für die Selektoren maßgeschneiderte kugelförmige Trägermaterialien benötigt. Dabei zeigen poröse Gläser besondere Eignung, da deren Textureigenschaften gezielt einstellbar sind. Durch die Nutzung einer speziellen Wirbelschichtapparatur sowie das Verfahren der ionotropen Gelierung konnten poröse Glaskugeln mit Durchmessern von 40 – 400 µm bzw. 2 – 4 mm synthetisiert werden. Zur Erzeugung von Core‐Shell‐Kugeln wurden erstmals die Prozesse des Ionenaustausches und der Phasenseparation in Alkaliborosilikatgläsern kombiniert, wodurch eine kontrollierbare mesoporöse Schicht an der Oberfläche unporöser Alkaliborosilikatglaskugeln erhalten wurde.

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Release of S(+) enantiomers in breath samples after anaesthesia with isoflurane racemate

Abstract: During the first days after application of isoflurane racemate, the percentage of S(+) enantiomers are higher in breath and blood samples of patients. We suggest that resorption and/or redistribution of enantiomers are responsible for the different kinetics of isoflurane enantiomers.

Cited by 3 publications

References 23 publications

Salient Features of Enantioselective Gas Chromatography: The Enantiomeric Differentiation of Chiral Inhalation Anesthetics as a Representative Methodological Case in Point

Salient Features of Enantioselective Gas Chromatography: The Enantiomeric Differentiation of Chiral Inhalation Anesthetics as a Representative Methodological Case in Point

Gas Chromatographic Enantioseparation of Fluorinated Anesthetics: Single‐Column Performance and Scale‐up Estimation

Synthese von porösen Voll‐ und Core‐Shell‐Glaskugeln zur Trennung von chiralen Anästhetika

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