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Omeprazole sulfone

PubChem CID
145900
Structure
Omeprazole sulfone_small.png
Omeprazole sulfone_3D_Structure.png
Molecular Formula
Synonyms
  • Omeprazole sulfone
  • 88546-55-8
  • Omeprazole metabolite Omeprazole sulfone
  • 5-Methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfonyl)-1H-benzo[d]imidazole
  • Omeprazole sulphone
Molecular Weight
361.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-25
Description
Omeprazole sulfone is a sulfoxide and a member of benzimidazoles.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Omeprazole sulfone.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfonyl]-1H-benzimidazole
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C17H19N3O4S/c1-10-8-18-15(11(2)16(10)24-4)9-25(21,22)17-19-13-6-5-12(23-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

IXEQEYRTSRFZEO-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=CN=C(C(=C1OC)C)CS(=O)(=O)C2=NC3=C(N2)C=C(C=C3)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C17H19N3O4S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 PharmGKB ID

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • omeprazole sulfone
  • omeprazole sulphone

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
361.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
2.2
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
361.10962727 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
361.10962727 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
103 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
25
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
553
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

Pharmaceuticals -> Metabolite of Esomeprazole, Omeprazole
S113 | SWISSPHARMA24 | 2024 Swiss Pharmaceutical List with Metabolites | DOI:10.5281/zenodo.10501043

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 Other MS

Authors
Tara J. Bowen, University of Birmingham
Instrument
Dionex Ultimate 3000 UHPLC Thermo Scientific; Q Exactive Focus Orbitrap MS Thermo Scientific
Instrument Type
LC-ESI-FT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
25,60,100% (stepped)
Fragmentation Mode
HCD
Column Name
Accucore 150 Amide, 2.6um, 2.1x100mm, Thermo Scientific
Retention Time
0.008 min
Precursor m/z
362.1169
Precursor Adduct
[M+H]+
Top 5 Peaks

168.1019 999

149.071 515

120.0809 322

362.1171 289

195.0223 224

Thumbnail
Thumbnail
License
CC BY
Reference
Bowen, T.J.; Southam, A.D.; Hall, A.R.; Weber, R.J.M.; Lloyd, G.R.; Macdonald, R.; Wilson, A.; Pointon, A.; Viant, M.R. Simultaneously discovering the fate and biochemical effects of xenobiotics through untargeted metabolomics. Nat. Commun. (under review)

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Metabolism / Metabolites

Omeprazole sulfone is a known human metabolite of omeprazole and esomeprazole.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

7.2 Human Metabolite Information

7.2.1 Tissue Locations

  • Kidney
  • Liver

7.2.2 Cellular Locations

Extracellular

7.3 Biochemical Reactions

7.4 Transformations

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (90.7%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (90.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (90.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 43 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

8.1.2 Hazard Classes and Categories

Skin Irrit. 2 (90.7%)

Eye Irrit. 2 (90.7%)

STOT SE 3 (90.7%)

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Thieme References

9.5 Chemical Co-Occurrences in Literature

9.6 Chemical-Gene Co-Occurrences in Literature

9.7 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Pathways

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 ChemIDplus

13.4 ChEMBL Target Tree

13.5 UN GHS Classification

13.6 NORMAN Suspect List Exchange Classification

13.7 EPA DSSTox Classification

13.8 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfonyl]-1H-benzimidazole
    https://echa.europa.eu/substance-information/-/substanceinfo/100.169.157
    6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfonyl]-1H-benzimidazole (EC: 641-364-6)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/174043
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  7. ChEBI
  8. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  9. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Omeprazole-sulfone
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  10. Japan Chemical Substance Dictionary (Nikkaji)
  11. MassBank Europe
  12. Metabolomics Workbench
  13. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  14. Springer Nature
  15. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  16. Wikidata
  17. PubChem
  18. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  19. GHS Classification (UNECE)
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS