Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H19N3O3S |
Molecular Weight | 345.416 |
Optical Activity | ( - ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(NC(=N2)[S@@+]([O-])CC3=C(C)C(OC)=C(C)C=N3)C=C1
InChI
InChIKey=SUBDBMMJDZJVOS-DEOSSOPVSA-N
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
Molecular Formula | C17H19N3O3S |
Molecular Weight | 345.416 |
Charge | 0 |
Count |
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Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Esomeprazole strontium is a proton pump inhibitor. It suppresses gastric acid secretion by specific inhibition H+/K+ ATPase in the gastric parietal cell. The S- and R-isomers of omeprazole are protonated and converted in the acidic compartment of the parietal cell forming the active inhibitor, the achiral sulphenamide. By acting specifically on the proton pump, esomeprazole blocks the final step in acid production, thus reducing gastric acidity. The drug is indicated for the treatment of gastroesophageal reflux disease, reduction the risk of NSAID-associated gastric ulcer, eradication of H.pylori, and pathological hypersecretory conditions.
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
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7.5 μM |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.2 μM × h |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.4 h |
40 mg 1 times / day multiple, intravenous dose: 40 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: |
ESOMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
strong [IC50 3.7 uM] | yes (co-administration study) Comment: Esomeprazole administration resulted in a significant increase (1.67‐fold) in the AUC0–∞ of proguanil and a significant decrease (0.522‐fold) in that of cycloguanil |
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weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
weak [IC50 >40 uM] | ||||
yes [IC50 1.2 uM] | likely (co-administration study) Comment: The frequency of delayed MTX elimination in patients administered esomeprazole was 71.4% Sources: https://pubmed.ncbi.nlm.nih.gov/28801980/ |
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yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | yes (co-administration study) Comment: Drugs which induce CYP2C19 or CYP3A4 (such as St. John’s Wort or rifampin) can substantially decrease esomeprazole concentrations |
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yes | yes (pharmacogenomic study) Comment: Drugs which induce CYP2C19 or CYP3A4 (such as St. John’s Wort or rifampin) can substantially decrease esomeprazole concentrations; The CYP2C19 isoenzyme exhibits polymorphism in the metabolism of esomeprazole, since some 3% of Caucasians and 15–20% of Asians lack CYP2C19 and are termed poor metabolizers. At steady state, the ratio of AUC in poor metabolizers to AUC in the rest of the population (normal metabolizers) is approximately 2 |
PubMed
Title | Date | PubMed |
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[Losec was probably the cause of interstitial nephritis]. | 1999 Apr 7 |
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Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites. | 2000 Apr |
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Reversible renal failure after treatment with omeprazole. | 2000 Aug |
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Omeprazole-induced delirium. | 2000 Jan |
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Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction. | 2000 Jul |
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Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine. | 2000 Mar |
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Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance. | 2001 Apr |
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Effect of the treatment of Helicobacter pylori infection on gastric emptying and its influence on the glycaemic control in type 1 diabetes mellitus. | 2001 Apr |
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Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis. | 2001 Feb |
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Improved high performance liquid chromatographic analysis of omeprazole in human plasma. | 2001 Feb |
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Gastroesophageal reflux disease and Barrett's esophagus. | 2001 Feb |
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A randomized, pharmacokinetic and pharmacodynamic, cross-over study of duodenal or jejunal administration compared to nasogastric administration of omeprazole suspension in patients at risk for stress ulcers. | 2001 Feb |
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Do some patients with Helicobacter pylori infection benefit from an extension to 2 weeks of a proton pump inhibitor-based triple eradication therapy? | 2001 Feb |
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Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy. | 2001 Feb |
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Comparison of the efficacy and safety of different formulations of omeprazole-based triple therapies in the treatment of Helicobacter pylori-positive peptic ulcer. | 2001 Feb |
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Aggressive acid control: minimizing progression of Barrett's esophagus. | 2001 Feb |
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[Recent guidelines for the management of Helicobacter pylori infection]. | 2001 Feb |
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Analysis of gastrin receptor gene expression in proliferating cells in the neck zone of gastric fundic glands using laser capture microdissection. | 2001 Feb 2 |
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Management of GERD: medical versus surgical. | 2001 Jan |
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Randomized study of two "rescue" therapies for Helicobacter pylori-infected patients after failure of standard triple therapies. | 2001 Jan |
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Long-term follow-up and serologic assessment after triple therapy with omeprazole or lansoprazole of Helicobacter-associated duodenal ulcer. | 2001 Jan |
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Helicobacter pylori effects on gastritis, gastrin and enterochromaffin-like cells in Zollinger-Ellison syndrome and non-Zollinger-Ellison syndrome acid hypersecretors treated long-term with lansoprazole. | 2001 Jan |
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Accuracy of the stool antigen test in the diagnosis of Helicobacter pylori infection before treatment and in patients on omeprazole therapy. | 2001 Jan |
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[Ulcer therapy with a new proton pump inhibitor. One week of treatment is enough]. | 2001 Jan 11 |
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Propylene glycol toxicosis in a llama. | 2001 Jan 15 |
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Clinical onset of the Crohn's disease after eradication therapy of Helicobacter pylori infection. Does Helicobacter pylori infection interact with natural history of inflammatory bowel diseases? | 2001 Jan-Feb |
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The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication. | 2001 Mar |
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Effect of genotypic differences in CYP2C19 on cure rates for Helicobacter pylori infection by triple therapy with a proton pump inhibitor, amoxicillin, and clarithromycin. | 2001 Mar |
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A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication. | 2001 Mar |
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Five-day proton pump inhibitor-based quadruple therapy regimen is more effective than 7-day triple therapy regimen for Helicobacter pylori infection. | 2001 Mar |
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One-week ranitidine bismuth citrate-based triple therapy for the eradication of Helicobacter pylori in Hong Kong with high prevalence of metronidazole resistance. | 2001 Mar |
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Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen. | 2001 Mar 29 |
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Omeprazole therapy and salivary flow rate in duodenal ulcer patients. | 2001 Mar-Apr |
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Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication. | 2001 Mar-Apr |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:47:59 GMT 2023
by
admin
on
Sat Dec 16 17:47:59 GMT 2023
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Record UNII |
N3PA6559FT
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QB01AC56
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WHO-ATC |
B01AC56
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WHO-ATC |
A02BC05
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NDF-RT |
N0000175525
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WHO-VATC |
QM01AE52
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WHO-ATC |
A02BD06
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LIVERTOX |
370
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WHO-ATC |
M01AE52
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NDF-RT |
N0000000147
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WHO-VATC |
QA02BC05
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NCI_THESAURUS |
C29723
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FDA ORPHAN DRUG |
684119
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WHO-VATC |
QA02BD06
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EMA ASSESSMENT REPORTS | NEXIUM CONTROL (AUTHOIRIZED: GASTROESOPHAGEAL REFLUX) |
Code System | Code | Type | Description | ||
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m8209
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PRIMARY | Merck Index | ||
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5488
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PRIMARY | |||
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8158
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PRIMARY | |||
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1055
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PRIMARY | |||
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N0000182140
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PRIMARY | Cytochrome P450 2C19 Inhibitors [MoA] | ||
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N3PA6559FT
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CHEMBL1201320
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PRIMARY | |||
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9568614
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PRIMARY | |||
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283742
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PRIMARY | RxNorm | ||
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DB00736
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PRIMARY | |||
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100000087252
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PRIMARY | |||
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ESOMEPRAZOLE
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PRIMARY | |||
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SUB01960MIG
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PRIMARY | |||
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DTXSID4044292
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PRIMARY | |||
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Esomeprazole
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7766
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50275
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PRIMARY | |||
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C65538
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119141-88-7
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N3PA6559FT
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D064098
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TARGET -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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METABOLITE INACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
MAJOR
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METABOLITE INACTIVE -> PARENT |
Metabolism of esomeprazole occurs via the hepatic CYP isoforms CYP2C19 and CYP3A4, which produce the 2 main pharmacologically inactive hydroxy and sulphone metabolites, respectively
MAJOR
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METABOLITE ACTIVE -> PRODRUG |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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PEDIATRICS PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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CHILDREN |
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ORAL BIOAVAILABILITY | PHARMACOKINETIC |
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