Solriamfetol impurities: Synthesis, characterization, and analytical method (UPLC-UV) validation

Nafisah Al-Rifai; Anas Alshishani; Fouad Darras; Ola Taha; Shereen Abu-Jalloud; Lena Shaghlil; Yousef Al-Ebini

doi:10.1016/j.jpha.2023.02.012

Volume 13 Issue 4

Apr. 2023

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Article Navigation > Journal of Pharmaceutical Analysis > 2023 > 13(4): 403-411

Nafisah Al-Rifai, Anas Alshishani, Fouad Darras, Ola Taha, Shereen Abu-Jalloud, Lena Shaghlil, Yousef Al-Ebini. Solriamfetol impurities: Synthesis, characterization, and analytical method (UPLC-UV) validation[J]. Journal of Pharmaceutical Analysis, 2023, 13(4): 403-411. doi: 10.1016/j.jpha.2023.02.012

Citation:

Nafisah Al-Rifai, Anas Alshishani, Fouad Darras, Ola Taha, Shereen Abu-Jalloud, Lena Shaghlil, Yousef Al-Ebini. Solriamfetol impurities: Synthesis, characterization, and analytical method (UPLC-UV) validation[J]. Journal of Pharmaceutical Analysis, 2023, 13(4): 403-411. doi: 10.1016/j.jpha.2023.02.012

Citation:

Nafisah Al-Rifai, Anas Alshishani, Fouad Darras, Ola Taha, Shereen Abu-Jalloud, Lena Shaghlil, Yousef Al-Ebini. Solriamfetol impurities: Synthesis, characterization, and analytical method (UPLC-UV) validation[J]. Journal of Pharmaceutical Analysis, 2023, 13(4): 403-411. doi: 10.1016/j.jpha.2023.02.012

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Solriamfetol impurities: Synthesis, characterization, and analytical method (UPLC-UV) validation

doi: 10.1016/j.jpha.2023.02.012

a. Pharmaceutical and Chemical Engineering Department, School of Medical Sciences, German Jordanian University, Amman, Jordan;
b. Faculty of Pharmacy, Zarqa University, Zarqa, Jordan;
c. Research and Development Department, Resonance Research Lab, Amman, Jordan;
d. Department of Pharmaceutics, College of Pharmacy, King Khalid University, Abha, Saudi Arabia

Funds:

This research was funded by the Deanship of Scientific Research at the German-Jordanian University and the Deanship of Scientific Research at Zarqa University. The graphical abstract was created with BioRender software.

Received Date: Nov. 12, 2022
Accepted Date: Feb. 23, 2023
Rev Recd Date: Feb. 17, 2023
Publish Date: Mar. 01, 2023

Abstract

Abstract

Given that impurities may affect the quality and safety of drug products, impurity identification and profiling is an integral part of drug quality control and is particularly important for newly developed medications such as solriamfetol, which is used to treat excessive daytime sleepiness. Although the high-performance liquid chromatography analysis of commercial solriamfetol has revealed the presence of several impurities, their synthesis, structure elucidation, and chromatographic determination have not been reported yet. To bridge this gap, we herein identified, synthesized, and isolated eight process-related solriamfetol impurities, characterized them using spectroscopic and chromatographic techniques, and proposed plausible mechanisms of their formation. Moreover, we developed and validated a prompt impurity analysis method based on ultrahigh-performance liquid chromatography with UV detection, revealing that its selectivity, linearity, accuracy, precision, and quantitation limit meet the acceptance criteria of method validation stipulated by the International Council for Harmonization of Technical Requirements for Pharmaceuticals for Human Use. Thus, the developed method was concluded to be suitable for the routine analysis of solriamfetol substances.
- Solriamfetol,
- Impurity analysis,
- Impurity synthesis,
- UPLC,
- Method validation

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References(22)

References

S. Yuan, B. Yu, H. Liu, New drug approvals for 2019: Synthesis and clinical applications, Eur. J. Med. Chem. 205 (2020), 112667.

A. Markham, Solriamfetol: First global approval, Drugs 79 (2019) 785-790.

M.J. Thorpy, C. Shapiro, G. Mayer et al., A randomized study of solriamfetol for excessive sleepiness in narcolepsy, Ann. Neurol. 85 (2019) 359-370.

T. Takahashi, S. Noriaki, M. Matsumura, et al., Advances in pharmaceutical treatment options for narcolepsy, Expert Opin. Orphan Drugs 6 (2018) 597-610.

J. Powell, C. Piszczatoski, S. Garland, Solriamfetol for excessive sleepiness in narcolepsy and obstructive sleep apnea, Ann. Pharmacother. 54 (2020) 1016-1020.

Y.M. Choi, J.K. Byun, Inventors; Phenylalkylaminoalcohol carbamates and process for preparing the same, United States patent US05955499A, 21 September 1999.

Y.M. Choi, M.W. Kim, Inventors; Process of preparing o-carbamoyl compounds in the presence of active amine group, PCT patent application WO2005033064 A1, 14 April 2005.

S.B. Bhirud, S. Naik, S.K. Mishra, et al, Inventors; Process for the preparation of solriamfetol and salt thereof, PCT patent application WO2020035769 A1, 20 February 2020.

P. Poojashree, T. Pramila, S. Manoj Kumar, et al., A review on pharmaceutical impurities and its importance in pharmacy, Am. J. Pharmtech Res. 9 (2019) 76-87.

International Conference on Harmonization, ICH Guidelines, Impurities in new drug substances, Q3A, 2006, (p. R2).

E. Bellur Atici, B. Karliga, Identification, synthesis and characterization of process related desfluoro impurity of ezetimibe and HPLC method validations, J. Pharm. Anal. 5 (2015) 356-370.

A.K. Awasthi, L. Kumar, P. Tripathi, et al., Prospects to the formation and control of potential dimer impurity E of pantoprazole sodium sesquihydrate, J. Pharm. Anal. 9 (2019) 170-177.

N. Kumar, S.R. Devineni, P.R. Gajjala, et al., Synthesis, isolation, identification and characterization of new process-related impurity in isoproterenol hydrochloride by HPLC, LC/ESI-MS and NMR, J. Pharm. Anal. 7 (2017) 394-400.

A.K. Awasthi, B. Kumar, M.A. Aga, et al., An efficient, facile synthesis of etoricoxib substantially free from impurities: Isolation, characterization and synthesis of novel impurity, ChemistrySelect 2 (2017) 9722-9725.

S. Thomas, S.K. Paul, S.C. Joshi, et al., Identification, synthesis and characterization of an unknown process related impurity in eslicarbazepine acetate active pharmaceutical ingredient by LC/ESI-IT/MS, 1H, 13C and 1H-1H COSY NMR, J. Pharm. Anal. 4 (2014) 339-344.

I. Koteles, M. Foroughbakhshfasaei, M. Dobo, 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 (2020) 909-913.

I. Fejős, G. Toth, B. Varnai, et al., Enantioseparation of solriamfetol and its major impurity phenylalaninol by capillary electrophoresis using sulfated gamma cyclodextrin, Electrophoresis 42 (2021) 1818-1825.

F. Chiesa, L. Vahdati, M. Scotti, et al, Inventors, A process for the purification of (R)-2-amino-3-phenylpropyl carbamate, PCT patent application WO2021250067 A2, 2021.

M. Suzuki, T. Yamazaki, H. Ohta, et al., N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction, Synlett 2000 (2000) 189-192.

J. Paz, C. Perez-Balado, B. Iglesias, et al., Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: Scope and limitations, J. Org. Chem. 75 (2010) 3037-3046.

S.Q. Tang, Y.Y. Lee, D.S. Packiaraj, et al., Systematic evaluation of the metabolism and toxicity of thiazolidinone and imidazolidinone heterocycles, Chem. Res. Toxicol. 28 (2015) 2019-2033.

International Conference on Harmonization, ICH Guidelines, Validation of analytical procedures, Q2, 2005, (p. R1).

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