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Identification, isolation, and structural characterization of novel forced degradation products of Ertugliflozin using advanced analytical techniques.

ABSTRACT: The research elucidates the stress degradation behavior of Ertugliflozin, which is used for the treatment of type-2 diabetics. The degradation was conducted as per ICH guidelines and Ertugliflozin is relatively stable in thermal, photolytic, neutral, and alkaline hydrolysis conditions; however, considerable degradation was detected in acid hydrolysis and oxidative hydrolysis. Degradation products were identified by ultra-high-performance liquid chromatography-mass spectrometry, isolated by semi-preparative high-performance liquid chromatography, and structural characterization using high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy. Total four degradation products were identified and isolated in acid degradation, which are degradation products 1, 2, 3, and 4. Whereas in oxidative conditions, degradation product 5 was identified. All the five degradation products formed are novel, which was not reported earlier. This is the first time documented complete structural characterization of all five degradation products by using a hyphenated analytical technique. High-resolution mass, and nuclear magnetic resonance spectroscopy were used in the present study to get concrete confirmation of degradation products structures. The current method is also used to identify degradation products with shorter runtime in the future.

SUBMITTER: Salakolusu S

PROVIDER: S-EPMC10257675 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Identification, isolation, and structural characterization of novel forced degradation products of Ertugliflozin using advanced analytical techniques.

Salakolusu Suresh S Katari Naresh Kumar NK Sharma Ganapavarapu Veera Raghava GVR Kaliyaperumal Muralidharan M Puppala Umamaheshwar U Ranga Mahesh M Jonnalagadda Sreekantha Babu SB

Scientific reports 20230610 1

The research elucidates the stress degradation behavior of Ertugliflozin, which is used for the treatment of type-2 diabetics. The degradation was conducted as per ICH guidelines and Ertugliflozin is relatively stable in thermal, photolytic, neutral, and alkaline hydrolysis conditions; however, considerable degradation was detected in acid hydrolysis and oxidative hydrolysis. Degradation products were identified by ultra-high-performance liquid chromatography-mass spectrometry, isolated by semi- ...[more]

PMID: 37301855

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Project description:Since the stability of the pharmaceuticals plays a crucial role in efficacy and safety while using them in the treatment of disorders, the evaluation of purity and impurity profiling of pharmaceuticals is of utmost importance using efficient analytical techniques. The present study explains the identification, isolation, and characterization of stress degradation products of the anti-human immunovirus drug Darunavir. The degradation study was performed to evaluate the stability profile of Darunavir in different stress conditions like hydrolytic, oxidative, thermal, and photolytic conditions as per the ICH guidelines. Degradation products were identified using ultra-performance liquid chromatography coupled with mass spectrometry, isolated using semi-preparative high-performance liquid chromatography, and structural characterization by HRMS and 1H, 13C NMR (1D, 2D). Darunavir is relatively stable in oxidative, thermal, and photolytic conditions; however, considerable degradation was observed in acid and base hydrolysis. A total of five degradation products were identified and isolated in acid and base degradation. DP-1, DP -2, & DP-3 were observed in acid conditions, whereas in base conditions, along with DP-2, two more DPs, i.e., DP-4 & DP-5, were identified. Among the five DPs, two degradation products, namely DP-1: N-(4-(N-(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylsulfamoyl) phenyl) acetimidamide. & DP-3: hexahydrofuro[2,3-b]furan-3-yl(4-((4-acetimidamido-N-isobutylphenyl)sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate, are novel, remaining degradation products DP-2: 4-amino-N-(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide, DP-4: 4-amino-N-(((5S)-4-benzyl-2-oxooxazolidin-5-yl) methyl) -N-isobutyl benzenesulfonamide and DP-5: methyl ((3S)-4-((4-amino-N-isobutylphenyl) sulfonamido)-3-hydroxy-1-phenylbutan-2-yl) carbamate are already reported tentatively using a single analytical technique coupled with mass analysis without any evidence from NMR and IR data. Hence, the present study focused on using High-Resolution Mass, 1D, and 2D 1H, 13C NMR data for concrete confirmation of structures for degradation products.Supplementary informationThe online version contains supplementary material available at 10.1007/s10337-022-04226-z.

Dataset Information

Identification, isolation, and structural characterization of novel forced degradation products of Ertugliflozin using advanced analytical techniques.

Publications

Identification, isolation, and structural characterization of novel forced degradation products of Ertugliflozin using advanced analytical techniques.

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