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 |
|||
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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Pharmacokinetic study of esomeprazole in the elderly. | 2001 |
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Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole. | 2001 |
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Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole? | 2001 Apr |
|
Antireflux surgery in children suffering from reflux-associated respiratory disease? | 2001 Apr |
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Pantoprazole and cyclosporine or tacrolimus. | 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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Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue. | 2001 Apr |
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A new cause of Zollinger-Ellison syndrome: non-small cell lung cancer. | 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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[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages]. | 2001 Feb |
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Re: Ammonia cannot explain the effect of H. pylori on omeprazole-induced acid suppression. | 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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Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication. | 2001 Feb |
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Aggressive acid control: minimizing progression of Barrett's esophagus. | 2001 Feb |
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Continued (5-year) followup of a randomized clinical study comparing antireflux surgery and omeprazole in gastroesophageal reflux disease. | 2001 Feb |
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[A strategy for second-line anti-Helicobacter pylori therapy in patients with previously failed treatment]. | 2001 Feb |
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[Usefulness of new triple therapy containing PPI]. | 2001 Feb |
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[Selection of antibiotics and planning of eradication for H. pylori infection]. | 2001 Feb |
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[Recent guidelines for the management of Helicobacter pylori infection]. | 2001 Feb |
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Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats. | 2001 Feb |
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[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege]. | 2001 Jan |
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Upper gastrointestinal bleeding as a metastatic manifestation of breast cancer: a case report and review of the literature. | 2001 Jan |
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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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Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis. | 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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Level of malondialdehyde after short-time omeprazole administration. | 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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Pharmacodynamic modeling of lansoprazole using an indirect irreversible response model. | 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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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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Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin. | 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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Bioequivalence evaluation of lansoprazole 30-mg capsules (Lanfast and Lanzor) in healthy volunteers. | 2001 Mar |
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Clarithromycin vs. furazolidone in quadruple therapy regimens for the treatment of Helicobacter pylori in a population with a high metronidazole resistance rate. | 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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Esomeprazole 20 mg maintains symptom control in endoscopy-negative gastro-oesophageal reflux disease: a controlled trial of 'on-demand' therapy for 6 months. | 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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Improvement in atrophic gastritis and intestinal metaplasia in patients in whom Helicobacter pylori was eradicated. | 2001 Mar 6 |
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[Heartburn. Only a harmless symptom?]. | 2001 Mar 8 |
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Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice. | 2001 Mar 9 |
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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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Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication. | 2001 Mar-Apr |
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c-myc gene mutation in gastric mucosa-associated lymphoid tissue (MALT) lymphoma and diffuse large B-cell lymphoma. | 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