Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H18N3O2S |
| Molecular Weight | 328.409 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 1 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1)N3SCC4=C(C)C(OC)=C(C)C=[N+]4C3=N2
InChI
InChIKey=ULDYIZLGTORGDF-UHFFFAOYSA-N
InChI=1S/C17H18N3O2S/c1-10-8-19-15(11(2)16(10)22-4)9-23-20-14-6-5-12(21-3)7-13(14)18-17(19)20/h5-8H,9H2,1-4H3/q+1
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 |
|---|---|---|---|---|
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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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 |
|||
| 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% |
|||
| 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 |
|---|---|---|
| Pharmacokinetic study of esomeprazole in the elderly. | 2001 |
|
| Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole. | 2001 |
|
| 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 |
|
| Pantoprazole and cyclosporine or tacrolimus. | 2001 Apr |
|
| Maximal acid reflux control for Barrett's oesophagus: feasible and effective. | 2001 Apr |
|
| Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance. | 2001 Apr |
|
| Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue. | 2001 Apr |
|
| A new cause of Zollinger-Ellison syndrome: non-small cell lung cancer. | 2001 Apr |
|
| Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection. | 2001 Apr 1 |
|
| From the Food and Drug Administration. | 2001 Apr 4 |
|
| Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis. | 2001 Feb |
|
| Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats. | 2001 Feb |
|
| Improved high performance liquid chromatographic analysis of omeprazole in human plasma. | 2001 Feb |
|
| Gastroesophageal reflux disease and Barrett's esophagus. | 2001 Feb |
|
| [Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages]. | 2001 Feb |
|
| Re: Ammonia cannot explain the effect of H. pylori on omeprazole-induced acid suppression. | 2001 Feb |
|
| Recurrent ulcer bleeding: is intravenous omeprazole the solution? | 2001 Feb |
|
| 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 |
|
| 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 |
|
| Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy. | 2001 Feb |
|
| 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 |
|
| Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication. | 2001 Feb |
|
| Aggressive acid control: minimizing progression of Barrett's esophagus. | 2001 Feb |
|
| Continued (5-year) followup of a randomized clinical study comparing antireflux surgery and omeprazole in gastroesophageal reflux disease. | 2001 Feb |
|
| [A strategy for second-line anti-Helicobacter pylori therapy in patients with previously failed treatment]. | 2001 Feb |
|
| [Usefulness of new triple therapy containing PPI]. | 2001 Feb |
|
| [Selection of antibiotics and planning of eradication for H. pylori infection]. | 2001 Feb |
|
| [Recent guidelines for the management of Helicobacter pylori infection]. | 2001 Feb |
|
| [Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege]. | 2001 Jan |
|
| Upper gastrointestinal bleeding as a metastatic manifestation of breast cancer: a case report and review of the literature. | 2001 Jan |
|
| Approach to the patient with unexplained chest pain. | 2001 Jan |
|
| Gastroesophageal reflux disease: extraesophageal manifestations and therapy. | 2001 Jan |
|
| Management of GERD: medical versus surgical. | 2001 Jan |
|
| [Ulcer therapy with a new proton pump inhibitor. One week of treatment is enough]. | 2001 Jan 11 |
|
| The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication. | 2001 Mar |
|
| Electrochemical studies and differential pulse polarographic analysis of lansoprazole in pharmaceuticals. | 2001 Mar |
|
| Efficacy and safety of esomeprazole compared with omeprazole in GERD patients with erosive esophagitis: a randomized controlled trial. | 2001 Mar |
|
| Pharmacodynamic modeling of lansoprazole using an indirect irreversible response model. | 2001 Mar |
|
| Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs. | 2001 Mar |
|
| 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 |
|
| Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin. | 2001 Mar |
|
| A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication. | 2001 Mar |
|
| Bioequivalence evaluation of lansoprazole 30-mg capsules (Lanfast and Lanzor) in healthy volunteers. | 2001 Mar |
|
| Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen. | 2001 Mar 29 |
|
| Improvement in atrophic gastritis and intestinal metaplasia in patients in whom Helicobacter pylori was eradicated. | 2001 Mar 6 |
|
| [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 |
|
| New OTC drugs and devices 2000: a selective review. | 2001 Mar-Apr |
|
| Omeprazole therapy and salivary flow rate in duodenal ulcer patients. | 2001 Mar-Apr |
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ZVL67L3RDK
Created by
admin on Sat Dec 16 18:18:13 GMT 2023 , Edited by admin on Sat Dec 16 18:18:13 GMT 2023
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PRIMARY | |||
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13553714
Created by
admin on Sat Dec 16 18:18:13 GMT 2023 , Edited by admin on Sat Dec 16 18:18:13 GMT 2023
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PRIMARY |
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
