Esomeprazole (CED0003125)

Record Information
Version1.0
Creation Date2009-07-21 20:27:31 UTC
Update Date2026-05-14 16:47:28 UTC
Accession NumberCHEM002260
Identification
Common NameEsomeprazole
ClassSmall Molecule
Description
Esomeprazole is an exogenous organic compound with the formula C17H19N3O3S and an average molecular weight of 345.42 g/mol. It exists as a solid at room temperature. Esomeprazole belongs to the sulfinylbenzimidazoles, a subclass of benzimidazoles within the organic compounds. As a proton pump inhibitor, esomeprazole suppresses gastric acid secretion through the specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, it blocks the final step in acid production, which reduces gastric acidity. The compound has seven recorded protein targets, including the potassium-transporting ATPase alpha chain 1 (ATP4A), the sodium/potassium-transporting ATPase subunit alpha-1 (ATP1A1), the potassium-transporting ATPase subunit beta (ATP4B), the ATP-dependent translocase ABCB1, cytochrome P450 3A4 (CYP3A4), cytochrome P450 2C9 (CYP2C9), and one other protein. Esomeprazole is found in or released from 13 recorded sources. These include healthcare, pharmaceuticals, and veterinary products such as antiinflammatory and antirheumatic products and drugs for acid related disorders. It is also associated with drinking water and water supply, household cleaning and consumer products including pipe accessories and other smoking requisites, building and construction materials such as ladders, floors, tents or canopies, and electrical and electronic equipment including amplifiers, antennas, magnets, relays, and video games. Recorded exposure routes for the compound include oral, intravenous, and topical administration.
Contaminant Type
  • Anti-Ulcer Agent
  • Drug
  • Enzyme Inhibitor
  • Ether
  • Histamine Antagonist
  • Metabolite
  • Organic Compound
  • Proton Pump Inhibitor
  • Synthetic Compound
Chemical Structure
Synonyms
ValueSource
(-)-OmeprazoleChEBI
(S)-(-)-OmeprazoleChEBI
(S)-OmeprazoleChEBI
AleniaChEBI
EsczChEBI
EsofagChEBI
EsomeprazolChEBI
EsomeprazolumChEBI
Inexium paranovaChEBI
(S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazoleHMDB
(S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazoleHMDB
Esomeprazole strontium anhydrousHMDB
Strontium, esomeprazoleHMDB
Esomeprazole sodiumHMDB
Esomeprazole strontiumHMDB
NexiumHMDB
AstraZeneca brand OF esomeprazole magnesiumHMDB
Esomeprazole magnesiumHMDB
Esomeprazole potassiumHMDB
Chemical FormulaC17H19N3O3S
Average Molecular Mass345.416 g/mol
Monoisotopic Mass345.115 g/mol
CAS Registry Number161796-78-7
IUPAC Name5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
Traditional Name5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
SMILESCOC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1
InChI IdentifierInChI=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
InChI KeySUBDBMMJDZJVOS-DEOSSOPVSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassSulfinylbenzimidazoles
Direct ParentSulfinylbenzimidazoles
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • 5-methoxy-2-\{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl\}-1H-benzimidazole (CHEBI:50275 )
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point155°C
Boiling PointNot Available
Solubility3.53e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP1.66ALOGPS
logP2.43ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)4.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.1 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.66 m³·mol⁻¹ChemAxon
Polarizability35.81 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0udj-0902000000-d7c360235f936b712320Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f7t-0900000000-f43785dbdafca5df5996Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-e0837329e37e32c98da2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0509000000-a35086072388d122723eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0902000000-cf6c80499c6b8e76c5d5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ul9-3900000000-2356754b2ae17bd3bc19Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-0709000000-1b29375937cfcb406414Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002b-0900000000-3383df9e4bfd7979d5e5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-4fb7ec8321857498646dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0007-0809000000-40107975e9855389175aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-ce24ac86003c1fd0c915Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0900000000-7094bcd15e524be40740Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0907000000-7d804584599dc64c2e69Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6t-0900000000-cd37c0cf17dabe7285d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00m0-0900000000-c05d93e4947b35f8cedeNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityEsomeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, Esomeprazole blocks the final step in acid production, thus reducing gastric acidity.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsBlurred vision, confusion, drowsiness, dry mouthflushingheadache, nausea, rapid heartbeat, sweating.
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2186.0Log mg/kg[1200:3900]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
242Drugs for acid related disordersHealthcare, pharmaceuticals & veterinary productsNot Available
363Antiinflammatory and antirheumatic productsHealthcare, pharmaceuticals & veterinary productsNot Available
497FloorsBuilding & ConstructionNot Available
498LaddersBuilding & ConstructionNot Available
503Tents Or CanopiesBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
527MagnetsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
562Pipe AccessoriesHousehold cleaning & consumer productsNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
658Touch FastenersTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)51.6919
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)111.636
Cytochrome P450 2C8 structureClick to view 3D structureCytochrome P450 2C8P10632HumansPredicted (SEA)35.0322
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)227.32
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)680.013
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)595.78
Cytochrome P450 2B6 structureClick to view 3D structureCytochrome P450 2B6P20813HumansPredicted (SEA)23.744
Fatty acid synthase structureClick to view 3D structureFatty acid synthaseP49327HumansPredicted (SEA)21.0971
Induced myeloid leukemia cell differentiation protein Mcl-1 structureClick to view 3D structureInduced myeloid leukemia cell differentiation protein Mcl-1Q07820HumansPredicted (SEA)220.78
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)557.945
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)640.232
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)463.436
5-hydroxytryptamine receptor 5A structureClick to view 3D structure5-hydroxytryptamine receptor 5AP47898HumansPredicted (SEA)280.179
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)845.754
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)1261.86
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)694.649
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)959.414
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)747.119
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)1968.42
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)1462.32
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)2138.52
Cyclin-dependent kinase 9 structureClick to view 3D structureCyclin-dependent kinase 9P50750HumansPredicted (SEA)1240.68
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP08909RatPredicted (SEA)487.258
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)2178.61
5-hydroxytryptamine receptor 3A structureClick to view 3D structure5-hydroxytryptamine receptor 3AP46098HumansPredicted (SEA)445.531
Sodium/potassium-transporting ATPase subunit alpha-1 structureClick to view 3D structureSodium/potassium-transporting ATPase subunit alpha-1P05023HumansKnownEsomeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, Esomeprazole blocks the final step in acid production, thus reducing gastric acidity.
Click to view 3D structurePotassium-transporting ATPase subunit betaP51164HumansKnownNot Available
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansKnownNot Available
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansKnownNot Available
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansKnownNot Available
Click to view 3D structurePotassium-transporting ATPase alpha chain 1P20648HumansKnownEsomeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, Esomeprazole blocks the final step in acid production, thus reducing gastric acidity.
Concentrations
Not Available
External Links
DrugBank IDDB00736
HMDB IDHMDB0005009
FooDB IDFDB023582
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEsomeprazole
Chemspider ID7843323
ChEBI ID50275
PubChem Compound ID9568614
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Manne Reddy, “Amorphous hydrates of esomeprazole magnesium and process for the preparation thereof.” U.S. Patent US20040167173, issued August 26, 2004.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10983736
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15080761
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18407713
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18472988
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23677700
6. 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
7. 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.