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Determination of the Enantiomeric Purity of Solriamfetol by High-Performance Liquid Chromatography in Polar Organic Mode Using Polysaccharide-Type Chiral Stationary Phases

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Abstract

Solriamfetol is a novel FDA approved enantiopure drug used for the treatment of excessive sleepiness associated with narcolepsy or obstructive sleep apnea. Only the active R-enantiomer is marketed, therefore, a method to determine the chiral purity is essential. Chiral separation of solriamfetol was performed by HPLC using polysaccharide-type chiral stationary phases in polar organic mode and described for the first time. Seven different polysaccharide-based chiral columns (Lux Amylose-1, Lux i-Amylose-1, Lux Amylose-2, Lux Cellulose-1, Lux Cellulose-2, Lux Cellulose-3 and Lux Cellulose-4) were employed for the separation of enantiomers using polar organic mode, with mobile phases consisting of 0.15% diethylamine in methanol (MeOH), 2-propanol (IPA) or acetonitrile (ACN). During the screening phase, the best results (Rs> 5, in less than 10 min) was obtained on a Lux Amylose-1 column with 0.15% diethylamine in methanol with an ideal elution order (the distomer eluted before the R-enantiomer). The effects of binary mobile phases on the resolutions and retention factors were also investigated containing different percentages of MeOH:ACN and MeOH:IPA. Using optimized parameters (Lux Amylose-1 column with 0.05% diethylamine in MeOH with 0.6 mL/min flow rate at 20 °C) high enantioresolution (Rs = 5.3) was achieved within 6 min. Thermodynamic analysis was performed and revealed an enthalpy-driven enantioseparation. The developed, isocratic HPLC method was validated according to current ICH guidelines and proved to be reliable, linear, precise and accurate for the determination of 0.1% S-enantiomer as a chiral impurity in R-solriamfetol.

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Acknowledgements

This work was supported by the Transylvanian Museum Society and the Faculty of Pharmacy of Semmelweis University (Z.-I. Szabó, G. Tóth) and by the János Bolyai Research Scholarship of the Hungarian Academy of Sciences (I. Boldizsár and G. Tóth). The financial support from Semmelweis Innovation Found (STIA‐M‐17 and STIA‐18‐KF) and from Bolyai + New National Excellence Program (grant number: UNKP‐19‐4‐SE‐28) of the Ministry for Innovation and Technology is highly appreciated (G. Tóth). This research was supported by the National Research, Development and Innovation Office, Hungary (NKFIH KH-130401, VEKOP-2.3.3-15-2017-00020), the ELTE Institutional Excellence Program (1783-3/2018/FEKUTSRAT) of the Hungarian Ministry of Human Capacities.

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Correspondence to Zoltán-István Szabó.

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Köteles, I., Foroughbakhshfasaei, M., Dobó, M. et al. Determination of the Enantiomeric Purity of Solriamfetol by High-Performance Liquid Chromatography in Polar Organic Mode Using Polysaccharide-Type Chiral Stationary Phases. Chromatographia 83, 909–913 (2020). https://doi.org/10.1007/s10337-020-03911-1

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