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
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 |
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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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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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Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study. | 2001 |
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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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A new cause of Zollinger-Ellison syndrome: non-small cell lung cancer. | 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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Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection. | 2001 Apr 1 |
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From the Food and Drug Administration. | 2001 Apr 4 |
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Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats. | 2001 Feb |
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Improved high performance liquid chromatographic analysis of omeprazole in human plasma. | 2001 Feb |
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[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages]. | 2001 Feb |
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Recurrent ulcer bleeding: is intravenous omeprazole the solution? | 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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Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication. | 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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Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats. | 2001 Feb |
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Relaxation induced by omeprazole does not change in diabetic rabbit corpus cavernosum. | 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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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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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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Gastroesophageal reflux disease: extraesophageal manifestations and therapy. | 2001 Jan |
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Management of GERD: medical versus surgical. | 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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[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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Current approaches to reducing gastrointestinal toxicity of low-dose aspirin. | 2001 Jan 8 |
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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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Effect of polaprezinc on impaired healing of chronic gastric ulcers in adjuvant-induced arthritic rats--role of insulin-like growth factors (IGF)-1. | 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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Efficacy and safety of esomeprazole compared with omeprazole in GERD patients with erosive esophagitis: a randomized controlled trial. | 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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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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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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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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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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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
Created by
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NDF-RT |
N0000000147
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WHO-VATC |
QA02BC05
Created by
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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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PRIMARY | |||
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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
Created by
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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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PRIMARY | |||
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7766
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PRIMARY | |||
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50275
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PRIMARY | |||
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C65538
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PRIMARY | |||
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119141-88-7
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PRIMARY | |||
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N3PA6559FT
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PRIMARY | |||
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D064098
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PRIMARY |
METABOLITE ACTIVE (PRODRUG)
METABOLITE INACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
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SUBSTANCE RECORD