Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H19N3O3S |
Molecular Weight | 345.4178 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cc1cnc(C[S@](=O)c2nc3ccc(cc3[nH]2)OC)c(C)c1OC
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 | 345.4178 |
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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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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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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Pharmacokinetic study of esomeprazole in the elderly. | 2001 |
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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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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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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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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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[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages]. | 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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[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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[Recent guidelines for the management of Helicobacter pylori infection]. | 2001 Feb |
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Relaxation induced by omeprazole does not change in diabetic rabbit corpus cavernosum. | 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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The effect of oral administration of Lactobacillus GG on antibiotic-associated gastrointestinal side-effects during Helicobacter pylori eradication therapy. | 2001 Feb |
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Leishmania plasma membrane Mg2+-ATPase is a H+/K+-antiporter involved in glucose symport. Studies with sealed ghosts and vesicles of opposite polarity. | 2001 Feb 23 |
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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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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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Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome? | 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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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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Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-. | 2001 Jan 5 |
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Biochemical properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-. | 2001 Jan 5 |
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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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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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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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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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Predictive factors for regression of gastric MALT lymphoma after anti-Helicobacter pylori treatment. | 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 |
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 03:03:53 UTC 2021
by
admin
on
Sat Jun 26 03:03:53 UTC 2021
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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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Common Name | English | ||
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QB01AC56
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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WHO-ATC |
B01AC56
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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WHO-ATC |
A02BC05
Created by
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NDF-RT |
N0000175525
Created by
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WHO-VATC |
QM01AE52
Created by
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WHO-ATC |
A02BD06
Created by
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LIVERTOX |
370
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WHO-ATC |
M01AE52
Created by
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NDF-RT |
N0000000147
Created by
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WHO-VATC |
QA02BC05
Created by
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NCI_THESAURUS |
C29723
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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FDA ORPHAN DRUG |
684119
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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WHO-VATC |
QA02BD06
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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EMA ASSESSMENT REPORTS | NEXIUM CONTROL (AUTHOIRIZED: GASTROESOPHAGEAL REFLUX) |
Code System | Code | Type | Description | ||
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M8209
Created by
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PRIMARY | Merck Index | ||
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5488
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PRIMARY | |||
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8158
Created by
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PRIMARY | |||
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1055
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PRIMARY | |||
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N0000182140
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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PRIMARY | Cytochrome P450 2C19 Inhibitors [MoA] | ||
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CHEMBL1201320
Created by
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PRIMARY | |||
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9568614
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PRIMARY | |||
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283742
Created by
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PRIMARY | RxNorm | ||
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DB00736
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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PRIMARY | |||
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ESOMEPRAZOLE
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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PRIMARY | |||
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SUB01960MIG
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admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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PRIMARY | |||
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119141-88-7
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Esomeprazole
Created by
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7766
Created by
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PRIMARY | |||
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C65538
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PRIMARY | |||
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119141-88-7
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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PRIMARY | |||
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N3PA6559FT
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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PRIMARY | |||
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D064098
Created by
admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
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PRIMARY |
Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR | |||
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TARGET -> SUBSTRATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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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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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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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