Chiral Separation of Duloxetine and Its R-Enantiomer by LC

Yang, Jing; Lu, Xiumei; Bi, Yujin; Qin, Feng; Li, Famei

doi:10.1365/s10337-007-0337-0

Cited by 20 publications

(15 citation statements)

References 30 publications

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“…13 It was subsequently discovered that the (+)/(S) enantiomer, LY248686, was a more potent inhibitor of serotonin reuptake, 14,15 and further animal studies suggested the potential of duloxetine as a therapeutic agent for depression. 16 Clinical trials were initiated and eventually, approval was granted by the FDA in 2004 for the treatment of depression, as noted above.…”

Section: Discussionmentioning

confidence: 99%

Adverse events, toxicity and post-mortem data on duloxetine: Case reports and literature survey

Vey¹,

Kovelman

2010

Journal of Forensic and Legal Medicine

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Section: Discussionmentioning

confidence: 99%

Adverse events, toxicity and post-mortem data on duloxetine: Case reports and literature survey

Vey¹,

Kovelman

2010

Journal of Forensic and Legal Medicine

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“…However, in both methods, the enantiomeric impurity, R ‐DLX, was the second to elute, making it hard to be detected in the presence of high amounts of S ‐DLX. The LOD for R ‐DLX was 0.06 μg mL −1 (Yang, Lu, Bi, Qin, & Li, 2007).…”

Section: Introductionmentioning

confidence: 99%

Achiral and chiral analysis of duloxetine by chromatographic and electrophoretic methods, a review on the separation methodologies

Lupu

Hancu

2020

Biomedical Chromatography

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Duloxetine (DLX) is a widely used antidepressant drug belonging to the class of selective serotonin and norepinephrine reuptake inhibitors (SNRIs); its efficacy has been demonstrated in the treatment of not only major depressive disorders but also diabetic neuropathic pain, generalized anxiety disorder, fibromyalgia or stress urinary incontinence. It is a chiral substance and is used in therapy in the form of the enantiopure S-DLX, which is twice as active as R-DLX. Several methods have been published for the achiral and chiral determination of DLX in pharmaceuticals, biological materials and environmental samples, the majority using liquid chromatography and capillary electrophoresis coupled with different detection techniques (UV detection, fluorescence, mass spectrometry). The aim of the current review is to provide a systematic survey of the analytical techniques used for the determination of DLX from different matrices.

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“…Duloxetine enantiomers were firstly separated using CE by Rickard et al who reported a method with (2‐hydroxypropyl)‐β‐CD (HP‐β‐CD) as chiral selector enabling duloxetine impurity to migrate in first place. Yang et al developed a method by HPLC employing also HP‐β‐CD as additive in the mobile phase, involving high consumption of the chiral selector. In this case, the observed EMO was reversed: duloxetine impurity was the last enantiomer to elute, in opposition to what was observed by CE employing the same chiral selector.…”

Section: Introductionmentioning

confidence: 99%

“…In this case, the observed EMO was reversed: duloxetine impurity was the last enantiomer to elute, in opposition to what was observed by CE employing the same chiral selector. There are other works employing chiral stationary phases in HPLC and different chiral selectors in CE showing duloxetine enantioseparation besides some other drugs . However, none of the aforementioned works investigated the molecular mechanisms of the chiral recognition of duloxetine with any chiral selector and either justified the obtained EMO using the same CD and different analytical techniques.…”

Section: Introductionmentioning

confidence: 99%

Investigation on the enantioseparation of duloxetine by capillary electrophoresis, NMR, and mass spectrometry

et al. 2014

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The enantiomeric separation of the antidepressant drug duloxetine was investigated by CE using 15 neutral CDs as chiral selectors. Among them, (2-hydroxypropyl)-β-CD and methyl-γ-CD gave rise to the highest enantioresolution. The enantiomer migration order for duloxetine was found to be reversed depending on the CD employed: R-duloxetine was the first-migrating enantiomer for (2-hydroxypropyl)-β-CD while it was the second-migrating enantiomer for methyl-γ-CD. NMR and MS experiments were performed in order to justify this behavior. Although the elucidation of the structure of the enantiomer-CD complexes was not possible, their averaged stoichiometry was studied and their apparent and averaged equilibrium constants were calculated. The results obtained showed that the chiral separation of duloxetine by CE depends not only on the thermodynamic stability of the enantiomer-chiral selector complexes but also on their electrophoretic mobility.

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Chiral Separation of Duloxetine and Its R-Enantiomer by LC

Cited by 20 publications

References 30 publications

Adverse events, toxicity and post-mortem data on duloxetine: Case reports and literature survey

Adverse events, toxicity and post-mortem data on duloxetine: Case reports and literature survey

Achiral and chiral analysis of duloxetine by chromatographic and electrophoretic methods, a review on the separation methodologies

Investigation on the enantioseparation of duloxetine by capillary electrophoresis, NMR, and mass spectrometry

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