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=NC=C(C)C(OC)=C3C)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
Molecular Formula | C17H19N3O3S |
Molecular Weight | 345.416 |
Charge | 0 |
Count |
|
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11999751
Curator's Comment: Known to be CNS penetrant in mouse. Human data not available
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095173 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10411559 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | NEXIUM 24HR Approved Usetreats frequent heartburn (occurs 2 or more days a week) Launch Date2014 |
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Primary | PRILOSEC Approved UsePRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date2008 |
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Primary | PRILOSEC Approved UsePRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date2008 |
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Primary | PRILOSEC Approved UsePRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date1989 |
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Primary | PRILOSEC Approved UsePRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults. Launch Date2008 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
668 ng/mL |
1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
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 |
---|---|---|---|---|
1200 nM*h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01361217 |
20 mg single, oral dose: 20 mg route of administration: oral experiment type: single co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: healthy age: adults sex: food status: |
|
1220 ng × h/mL |
1 mg/kg single, oral dose: 1 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1179 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2350532 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
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 |
---|---|---|---|---|
0.58 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2350532 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OMEPRAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
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 |
Doses
Dose | Population | Adverse events |
---|---|---|
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, 45.2 |
Other AEs: Nausea, Diarrhoea... |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Headache, Abdominal pain... Other AEs: Headache (6.9%) Sources: Abdominal pain (5.2%) Nausea (4%) Diarrhea (3.7%) Vomiting (3.2%) Flatulence (2.7%) Esophageal acid reflux (1.9%) Upper respiratory infection (1.9%) Constipation (1.5%) Dizziness (1.5%) Rash (1.5%) Asthenia (1.3%) Back pain (1.1%) Cough (1.1%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Headache | 3% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, 45.2 |
Diarrhoea | 6% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, 45.2 |
Nausea | 7% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, 45.2 |
Back pain | 1.1% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Cough | 1.1% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Asthenia | 1.3% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Constipation | 1.5% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Dizziness | 1.5% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Rash | 1.5% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Esophageal acid reflux | 1.9% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Upper respiratory infection | 1.9% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Flatulence | 2.7% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Vomiting | 3.2% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Diarrhea | 3.7% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Nausea | 4% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Abdominal pain | 5.2% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Headache | 6.9% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
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] | ||||
weak [Ki 150 uM] | weak (co-administration study) Comment: Omeprazole exerts a concentration-dependent inhibition of CYP1A2 activity in man. However, even after single oral doses up to 80 mg, this effect is weak and without clinical relevance |
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weak [Ki 367.5 uM] | ||||
weak [Ki 745.1 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 [IC50 15.7 uM] | ||||
yes [IC50 17.6 uM] | ||||
yes [IC50 17.7 uM] | ||||
yes [IC50 22 uM] | ||||
yes [IC50 4.32 uM] | ||||
yes [IC50 6.7 uM] | ||||
yes [IC50 6.8 uM] | ||||
yes [IC50 84.3 uM] | unlikely (co-administration study) Comment: Coaministration with simvastatin acid unlikely results in DDIs Sources: https://pubmed.ncbi.nlm.nih.gov/25975815/ |
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yes [Ki 7.1 uM] | yes (co-administration study) Comment: Omeprazole increased Cmax and AUC of cilostazol by 18% and 26% respectively |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/10445394/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12623754/ |
yes | |||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/12538803/ |
yes | yes (expression study) Comment: livers of patients treated with omeprazole showed higher MRP3 protein expression Sources: https://pubmed.ncbi.nlm.nih.gov/12538803/ |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | yes (co-administration study) Comment: When voriconazole was given with omeprazole to healthy subjects, it significantly increased the steady-state Cmax and AUC0-24 of omeprazole, an average of 2 times and 4 times, respectively |
|||
major | yes (co-administration study) Comment: Drugs known to induce CYP2C19 or CYP3A4 (such as rifampin) may lead to decreased omeprazole serum levels. In a cross-over study in 12 healthy male subjects, St John’s wort, an inducer of CYP3A4, decreased the systemic exposure of omeprazole in CYP2C19 poor metabolisers (Cmax and AUC decreased by 37.5% and 37.9%, respectively) and extensive metabolisers (Cmax and AUC decreased by 49.6% and 43.9%, respectively) |
|||
minor | ||||
minor | ||||
minor | ||||
no | ||||
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 |
---|---|---|
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies. | 2000 Oct |
|
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis. | 2001 Feb |
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Recurrent ulcer bleeding: is intravenous omeprazole the solution? | 2001 Feb |
|
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam. | 2001 Feb |
|
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 |
|
Upper gastrointestinal bleeding as a metastatic manifestation of breast cancer: a case report and review of the literature. | 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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The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication. | 2001 Mar |
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Electrochemical studies and differential pulse polarographic analysis of lansoprazole in pharmaceuticals. | 2001 Mar |
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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 |
Patents
Sample Use Guides
Active Duodenal Ulcer: 20 mg Once daily for 4 weeks. Some patients may require an addition 4 weeks.
Gastric Ulcer: oral dose is 40 mg once daily for 4-8 weeks.
Gastroesophageal Reflux Disease: The recommended adult oral dose for the treatment of patients with symptomatic GERD and no esophageal lesions is 20 mg daily for up to 4 weeks. The recommended adult oral dose for the treatment of patients with erosive esophagitis and accompanying symptoms due to GERD is 20 mg daily for 4 to 8 weeks.
Route of Administration:
Oral
Pretreatment of omeprazole (10-6 - 10-4M) dose-dependently inhibits neutrophil adherence and respiratory burst induced by H. pylori. These evidences imply that omeprazole may exhibit a beneficial effect on H. pylori-associated gastric mucosal damage caused by activated neutrophils.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:33:02 GMT 2025
by
admin
on
Wed Apr 02 09:33:02 GMT 2025
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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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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
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NDF-RT |
N0000000147
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WHO-VATC |
QA02BC05
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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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1055
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N0000182140
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PRIMARY | Cytochrome P450 2C19 Inhibitors [MoA] | ||
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N3PA6559FT
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CHEMBL1201320
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9568614
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283742
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PRIMARY | RxNorm | ||
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DB00736
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100000087252
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ESOMEPRAZOLE
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SUB01960MIG
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DTXSID4044292
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Esomeprazole
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7766
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50275
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C65538
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119141-88-7
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N3PA6559FT
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D064098
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG |
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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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METABOLITE ACTIVE -> PRODRUG |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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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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