Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-10-16 12:36:47 UTC |
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Update Date | 2022-03-07 02:49:25 UTC |
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HMDB ID | HMDB0005009 |
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Secondary Accession Numbers | - HMDB0014874
- HMDB05009
- HMDB14874
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Metabolite Identification |
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Common Name | Esomeprazole |
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Description | Esomeprazole (brand names Nexium; Lucen; Esopral and Axagon in Italy) is a proton pump inhibitor which reduces gastric acid secretion through the inhibition of H+/K+-ATPase in gastric parietal cells. By inhibiting the functioning of this enzyme, the drug prevents the formation of gastric acid. Esomeprazole is used in the treatment of dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD), and Zollinger-Ellison syndrome. Esomeprazole is the S-enantiomer of omeprazole (marketed as Losec/Prilosec), and AstraZeneca claims improved efficacy of this single enantiomer product over the racemic mixture of omeprazole. |
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Structure | COC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1 InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1 |
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Synonyms | Value | Source |
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(-)-Omeprazole | ChEBI | (S)-(-)-Omeprazole | ChEBI | (S)-Omeprazole | ChEBI | Alenia | ChEBI | Escz | ChEBI | Esofag | ChEBI | Esomeprazol | ChEBI | Esomeprazolum | ChEBI | Inexium paranova | ChEBI | (S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole | HMDB | (S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole | HMDB | Esomeprazole strontium anhydrous | HMDB | Strontium, esomeprazole | HMDB | Esomeprazole sodium | HMDB | Esomeprazole strontium | HMDB | Nexium | HMDB | AstraZeneca brand OF esomeprazole magnesium | HMDB | Esomeprazole magnesium | HMDB | Esomeprazole potassium | HMDB |
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Chemical Formula | C17H19N3O3S |
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Average Molecular Weight | 345.416 |
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Monoisotopic Molecular Weight | 345.114712179 |
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IUPAC Name | 5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole |
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Traditional Name | 5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole |
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CAS Registry Number | 119141-88-7 |
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SMILES | COC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1 |
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InChI Identifier | InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1 |
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InChI Key | SUBDBMMJDZJVOS-DEOSSOPVSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Benzimidazoles |
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Sub Class | Sulfinylbenzimidazoles |
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Direct Parent | Sulfinylbenzimidazoles |
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Alternative Parents | |
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Substituents | - Sulfinylbenzimidazole
- Anisole
- Alkyl aryl ether
- Methylpyridine
- Pyridine
- Benzenoid
- Azole
- Imidazole
- Heteroaromatic compound
- Sulfoxide
- Azacycle
- Ether
- Sulfinyl compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | - 5-methoxy-2-\{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl\}-1H-benzimidazole (CHEBI:50275 )
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Ontology |
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Physiological effect | |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Esomeprazole,1TMS,isomer #1 | COC1=CC=C2C(=C1)N=C([S@@](=O)CC1=NC=C(C)C(OC)=C1C)N2[Si](C)(C)C | 3141.4 | Semi standard non polar | 33892256 | Esomeprazole,1TMS,isomer #1 | COC1=CC=C2C(=C1)N=C([S@@](=O)CC1=NC=C(C)C(OC)=C1C)N2[Si](C)(C)C | 2957.0 | Standard non polar | 33892256 | Esomeprazole,1TMS,isomer #1 | COC1=CC=C2C(=C1)N=C([S@@](=O)CC1=NC=C(C)C(OC)=C1C)N2[Si](C)(C)C | 4039.9 | Standard polar | 33892256 | Esomeprazole,1TBDMS,isomer #1 | COC1=CC=C2C(=C1)N=C([S@@](=O)CC1=NC=C(C)C(OC)=C1C)N2[Si](C)(C)C(C)(C)C | 3269.7 | Semi standard non polar | 33892256 | Esomeprazole,1TBDMS,isomer #1 | COC1=CC=C2C(=C1)N=C([S@@](=O)CC1=NC=C(C)C(OC)=C1C)N2[Si](C)(C)C(C)(C)C | 3183.5 | Standard non polar | 33892256 | Esomeprazole,1TBDMS,isomer #1 | COC1=CC=C2C(=C1)N=C([S@@](=O)CC1=NC=C(C)C(OC)=C1C)N2[Si](C)(C)C(C)(C)C | 4010.9 | Standard polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Esomeprazole GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udj-0902000000-d7c360235f936b712320 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Esomeprazole GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Esomeprazole 35V, Positive-QTOF | splash10-0f7t-0900000000-f43785dbdafca5df5996 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Esomeprazole 35V, Negative-QTOF | splash10-0006-0900000000-e0837329e37e32c98da2 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 10V, Positive-QTOF | splash10-0002-0509000000-a35086072388d122723e | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 20V, Positive-QTOF | splash10-0002-0902000000-cf6c80499c6b8e76c5d5 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 40V, Positive-QTOF | splash10-0ul9-3900000000-2356754b2ae17bd3bc19 | 2016-08-02 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 10V, Negative-QTOF | splash10-0007-0709000000-1b29375937cfcb406414 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 20V, Negative-QTOF | splash10-002b-0900000000-3383df9e4bfd7979d5e5 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 40V, Negative-QTOF | splash10-004i-0900000000-4fb7ec8321857498646d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 10V, Negative-QTOF | splash10-0007-0809000000-40107975e9855389175a | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 20V, Negative-QTOF | splash10-004i-0900000000-ce24ac86003c1fd0c915 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 40V, Negative-QTOF | splash10-004i-0900000000-7094bcd15e524be40740 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 10V, Positive-QTOF | splash10-0002-0907000000-7d804584599dc64c2e69 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 20V, Positive-QTOF | splash10-0f6t-0900000000-cd37c0cf17dabe7285d1 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Esomeprazole 40V, Positive-QTOF | splash10-00m0-0900000000-c05d93e4947b35f8cede | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00736 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB023582 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 7843323 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Esomeprazole |
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METLIN ID | Not Available |
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PubChem Compound | 9568614 |
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PDB ID | Not Available |
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ChEBI ID | 50275 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Kohl, Bernhard; Senn-Bilfinger, Joerg. Enantiomerically pure (pyridylmethylsulfinyl)benzimidazoles useful as drugs, and their preparation from racemates. Ger. Offen. (1992), 8 pp. CODEN: GWXXBX DE 4035455 A1 19920514 CAN 117:90285 AN 1992:490285 |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7. [PubMed:10886041 ]
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