Details
Stereochemistry | ABSOLUTE |
Molecular Formula | 2C17H18N3O3S.Mg.3H2O |
Molecular Weight | 767.167 |
Optical Activity | ( - ) |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.[Mg++].COC1=CC2=C([N-]C(=N2)[S@@+]([O-])CC3=C(C)C(OC)=C(C)C=N3)C=C1.COC4=CC5=C([N-]C(=N5)[S@@+]([O-])CC6=C(C)C(OC)=C(C)C=N6)C=C4
InChI
InChIKey=VEVZQDGATGBLIC-OXLUMUBXSA-N
InChI=1S/2C17H18N3O3S.Mg.3H2O/c2*1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17;;;;/h2*5-8H,9H2,1-4H3;;3*1H2/q2*-1;+2;;;/t2*24-;;;;/m00..../s1
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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Clarithromycin-induced acute psychoses in peptic ulcer disease. | 1999 Jan |
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Omeprazole-induced acute interstitial nephritis. | 1999 Nov |
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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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The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents. | 2001 |
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Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole? | 2001 Apr |
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Antireflux surgery in children suffering from reflux-associated respiratory disease? | 2001 Apr |
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Maximal acid reflux control for Barrett's oesophagus: feasible and effective. | 2001 Apr |
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Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance. | 2001 Apr |
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A new cause of Zollinger-Ellison syndrome: non-small cell lung cancer. | 2001 Apr |
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Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection. | 2001 Apr 1 |
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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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[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages]. | 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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[Selection of antibiotics and planning of eradication for H. pylori infection]. | 2001 Feb |
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CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam. | 2001 Feb |
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Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase. | 2001 Feb |
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Eradication of Helicobacter pylori prevents ulcer development in patients with ulcer-like functional dyspepsia. | 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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Approach to the patient with unexplained chest pain. | 2001 Jan |
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Esomeprazole once daily for 6 months is effective therapy for maintaining healed erosive esophagitis and for controlling gastroesophageal reflux disease symptoms: a randomized, double-blind, placebo-controlled study of efficacy and safety. | 2001 Jan |
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Changes in pulmonary hyperinflation and bronchial hyperresponsiveness following treatment with lansoprazole in children with cystic fibrosis. | 2001 Jan |
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Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome? | 2001 Jan |
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A multicentre study on eradication of Helicobacter pylori using four 1-week triple therapies in China. | 2001 Jan |
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Helicobacter pylori and nonsteroidal anti-inflammatory drugs: interaction with proton pump inhibitor therapy for prevention of nonsteroidal anti-inflammatory drug ulcers and ulcer complications--future research needs. | 2001 Jan 8 |
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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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Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs. | 2001 Mar |
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Bioequivalence evaluation of lansoprazole 30-mg capsules (Lanfast and Lanzor) in healthy volunteers. | 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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[Heartburn. Only a harmless symptom?]. | 2001 Mar 8 |
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New OTC drugs and devices 2000: a selective review. | 2001 Mar-Apr |
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Omeprazole therapy and salivary flow rate in duodenal ulcer patients. | 2001 Mar-Apr |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29723
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EMA ASSESSMENT REPORTS |
NEXIUM CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
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R6DXU4WAY9
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SUB16427MIG
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LL-98
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21121303
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283562
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217087-09-7
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R6DXU4WAY9
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CHEMBL1201320
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SUB126849
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C29032
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DTXSID30904663
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100000153033
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1249789
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D064098
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DBSALT001222
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SUBSTANCE RECORD