Identification of the acid-induced degradation products of omeprazole and 5-hydroxyomeprazole by high resolution mass spectrometry

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Abstract

Rationale
Omeprazole is used to treat gastric disorders and is one of the most commonly consumed drugs in the western world. It forms several metabolites but is mostly excreted unchanged and as 5-hydroxyomeprazole. Since omeprazole is widely prescribed, its excretion from the body has a potential environmental effect. After excretion it will enter the wastewater system and if not adequately removed during wastewater treatment will be discharged into rivers in the wastewater effluent. It is important to consider not only the parent drug but also the main metabolite (5-hydroxyomeprazole) and their degradation products to fully understand the fate of this drug during wastewater treatment. In order to do this potential degradation products need to be determined.

Methods
Acid was used to artificially accelerate the degradation of omeprazole and 5-hydroxyomeprazole. A Q-Exactive Orbitrap mass spectrometer with an electrospray ion source was used to determine precursor and product ion data for the degradation products.

Results
Both starting materials quickly degrade under acidic conditions and the main degradation product formed in each case was a re-arranged monomer. Other species identified were doubly and singly charged dimers with varying numbers of sulphur atoms in the dimer bridge. Careful interpretation of the accurate mass, isotope pattern, isotope abundance and product ion spectra was used to interpret the data.

Conclusion
The resultant degradants from omeprazole and 5-hydroxyomeprazole were analogous to each other, differing only by an oxygen atom. This investigation determined the degradation products of omeprazole and 5-hydroxyomeprazole and proposed structures based on the accurate mass and isotope information. The product ions from the degradation products are also reported.
Original languageEnglish
JournalRapid Communications in Mass Spectrometry
Early online date23 Mar 2018
DOIs
Publication statusPublished - Jun 2018

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Omeprazole
Mass spectrometry
Degradation
Acids
Isotopes
Ions
Metabolites
Wastewater treatment
Dimers
Wastewater
Pharmaceutical Preparations
Atoms
Mass spectrometers
Ion sources
5-hydroxymethylomeprazole
Sulfur
Environmental impact
Effluents
Monomers
Rivers

Keywords

  • omeprazole
  • wastewater treatment
  • degradation products

Cite this

@article{e444ba4ab8394c5d9defa7d74719d8a3,
title = "Identification of the acid-induced degradation products of omeprazole and 5-hydroxyomeprazole by high resolution mass spectrometry",
abstract = "RationaleOmeprazole is used to treat gastric disorders and is one of the most commonly consumed drugs in the western world. It forms several metabolites but is mostly excreted unchanged and as 5-hydroxyomeprazole. Since omeprazole is widely prescribed, its excretion from the body has a potential environmental effect. After excretion it will enter the wastewater system and if not adequately removed during wastewater treatment will be discharged into rivers in the wastewater effluent. It is important to consider not only the parent drug but also the main metabolite (5-hydroxyomeprazole) and their degradation products to fully understand the fate of this drug during wastewater treatment. In order to do this potential degradation products need to be determined.MethodsAcid was used to artificially accelerate the degradation of omeprazole and 5-hydroxyomeprazole. A Q-Exactive Orbitrap mass spectrometer with an electrospray ion source was used to determine precursor and product ion data for the degradation products.ResultsBoth starting materials quickly degrade under acidic conditions and the main degradation product formed in each case was a re-arranged monomer. Other species identified were doubly and singly charged dimers with varying numbers of sulphur atoms in the dimer bridge. Careful interpretation of the accurate mass, isotope pattern, isotope abundance and product ion spectra was used to interpret the data.ConclusionThe resultant degradants from omeprazole and 5-hydroxyomeprazole were analogous to each other, differing only by an oxygen atom. This investigation determined the degradation products of omeprazole and 5-hydroxyomeprazole and proposed structures based on the accurate mass and isotope information. The product ions from the degradation products are also reported.",
keywords = "omeprazole, wastewater treatment , degradation products",
author = "J. Roberts and M. McNaughtan and J. MacLachlan and C. Hunter and O. Pahl",
note = "Acceptance in SAN AAM: 12m embargo",
year = "2018",
month = "6",
doi = "10.1002/rcm.8120",
language = "English",
journal = "Rapid Communications in Mass Spectrometry",
issn = "0951-4198",
publisher = "John Wiley & Sons",

}

TY - JOUR

T1 - Identification of the acid-induced degradation products of omeprazole and 5-hydroxyomeprazole by high resolution mass spectrometry

AU - Roberts, J.

AU - McNaughtan, M.

AU - MacLachlan, J.

AU - Hunter, C.

AU - Pahl, O.

N1 - Acceptance in SAN AAM: 12m embargo

PY - 2018/6

Y1 - 2018/6

N2 - RationaleOmeprazole is used to treat gastric disorders and is one of the most commonly consumed drugs in the western world. It forms several metabolites but is mostly excreted unchanged and as 5-hydroxyomeprazole. Since omeprazole is widely prescribed, its excretion from the body has a potential environmental effect. After excretion it will enter the wastewater system and if not adequately removed during wastewater treatment will be discharged into rivers in the wastewater effluent. It is important to consider not only the parent drug but also the main metabolite (5-hydroxyomeprazole) and their degradation products to fully understand the fate of this drug during wastewater treatment. In order to do this potential degradation products need to be determined.MethodsAcid was used to artificially accelerate the degradation of omeprazole and 5-hydroxyomeprazole. A Q-Exactive Orbitrap mass spectrometer with an electrospray ion source was used to determine precursor and product ion data for the degradation products.ResultsBoth starting materials quickly degrade under acidic conditions and the main degradation product formed in each case was a re-arranged monomer. Other species identified were doubly and singly charged dimers with varying numbers of sulphur atoms in the dimer bridge. Careful interpretation of the accurate mass, isotope pattern, isotope abundance and product ion spectra was used to interpret the data.ConclusionThe resultant degradants from omeprazole and 5-hydroxyomeprazole were analogous to each other, differing only by an oxygen atom. This investigation determined the degradation products of omeprazole and 5-hydroxyomeprazole and proposed structures based on the accurate mass and isotope information. The product ions from the degradation products are also reported.

AB - RationaleOmeprazole is used to treat gastric disorders and is one of the most commonly consumed drugs in the western world. It forms several metabolites but is mostly excreted unchanged and as 5-hydroxyomeprazole. Since omeprazole is widely prescribed, its excretion from the body has a potential environmental effect. After excretion it will enter the wastewater system and if not adequately removed during wastewater treatment will be discharged into rivers in the wastewater effluent. It is important to consider not only the parent drug but also the main metabolite (5-hydroxyomeprazole) and their degradation products to fully understand the fate of this drug during wastewater treatment. In order to do this potential degradation products need to be determined.MethodsAcid was used to artificially accelerate the degradation of omeprazole and 5-hydroxyomeprazole. A Q-Exactive Orbitrap mass spectrometer with an electrospray ion source was used to determine precursor and product ion data for the degradation products.ResultsBoth starting materials quickly degrade under acidic conditions and the main degradation product formed in each case was a re-arranged monomer. Other species identified were doubly and singly charged dimers with varying numbers of sulphur atoms in the dimer bridge. Careful interpretation of the accurate mass, isotope pattern, isotope abundance and product ion spectra was used to interpret the data.ConclusionThe resultant degradants from omeprazole and 5-hydroxyomeprazole were analogous to each other, differing only by an oxygen atom. This investigation determined the degradation products of omeprazole and 5-hydroxyomeprazole and proposed structures based on the accurate mass and isotope information. The product ions from the degradation products are also reported.

KW - omeprazole

KW - wastewater treatment

KW - degradation products

U2 - 10.1002/rcm.8120

DO - 10.1002/rcm.8120

M3 - Article

JO - Rapid Communications in Mass Spectrometry

JF - Rapid Communications in Mass Spectrometry

SN - 0951-4198

ER -