Sensitive RP-HPLC Enantioseparation of (RS)-Ketamine via Chiral Derivatization Based on (S)-Levofloxacin

作者: Vinod Kumar Vashistha , Jürgen Martens , Ravi Bhushan

DOI: 10.1007/S10337-017-3367-2

关键词:

摘要: Enantioseparation of (RS)-ketamine has been achieved in the form its diastereomeric hydrazones. A new chiral reagent was synthesized from enantiomerically pure (S)-levofloxacin by converting carboxyl group into a hydrazide derivative: provided reaction site for ketonic present (RS)-ketamine. Because structural feature formation hydrazones successful without protection amino group. The were separated on reversed-phase C18 column with mobile phase consisting MeCN and 0.1% TFA under gradient elution 35 to 65% MeCN. limit detection found be 3.2 3.4 nmol first second eluting hydrazones, respectively. separation mechanism order proposed supported developing geometry optimized ‘lowest energy’ structures two using DFT-based Gaussian software.

参考文章(21)
Angster R, Doenicke A, Hoffmann P, Kugler J, Mayer M, [Ketamine racemate or S-(+)-ketamine and midazolam. The effect on vigilance, efficacy and subjective findings]. Anaesthesist. ,vol. 41, pp. 610- 618 ,(1992)
Xuebao Wang, Xianqin Wang, Ming Zeng, Wei Li, Lufeng Hu, Jianshe Ma, Determination of ketamine in rabbit plasma by gradient elution liquid chromatography/electrospray mass spectrometry Latin American Journal of Pharmacy. ,(2011)
Anne Rousseau, Florian Gillotin, Patrice Chiap, Ede Bodoki, Jacques Crommen, Marianne Fillet, Anne-Catherine Servais, Generic systems for the enantioseparation of basic drugs in NACE using single-isomer anionic CDs Journal of Pharmaceutical and Biomedical Analysis. ,vol. 54, pp. 154- 159 ,(2011) , 10.1016/J.JPBA.2010.08.004
Regula Theurillat, Monika Knobloch, Andrea Schmitz, Paul-Gerhard Lassahn, Meike Mevissen, Wolfgang Thormann, Enantioselective analysis of ketamine and its metabolites in equine plasma and urine by CE with multiple isomer sulfated β‐CD Electrophoresis. ,vol. 28, pp. 2748- 2757 ,(2007) , 10.1002/ELPS.200600820
Arthur D. Hirschfelder, THE UNITED STATES PHARMACOPEIAL CONVENTION JAMA. ,vol. 95, pp. 220- 220 ,(1930) , 10.1001/JAMA.1930.02720030050030
Youssef Hijazi, Roselyne Boulieu, Contribution of CYP3A4, CYP2B6, and CYP2C9 isoforms to N-demethylation of ketamine in human liver microsomes. Drug Metabolism and Disposition. ,vol. 30, pp. 853- 858 ,(2002) , 10.1124/DMD.30.7.853
James D. Adams, Thomas F. Woolf, Anthony J. Trevor, Lyall R. Williams, Neal Castagnoli, Derivatization of Chiral Amines with (S,S)-N-Trifluoroacetylproline Anhydride for GC Estimation of Enantiomeric Composition Journal of Pharmaceutical Sciences. ,vol. 71, pp. 658- 661 ,(1982) , 10.1002/JPS.2600710613