U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ESOMEPRAZOLE

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

HIDE SMILES / InChI

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NEXIUM 24HR

Approved Use

treats frequent heartburn (occurs 2 or more days a week)

Launch Date

1.3958784E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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

Drug as victim

TargetModalityActivityMetaboliteClinical 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

PubMed

TitleDatePubMed
Pharmacokinetic study of esomeprazole in the elderly.
2001
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents.
2001
Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study.
2001
Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole?
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
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
Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection.
2001 Apr 1
Improved high performance liquid chromatographic analysis of omeprazole in human plasma.
2001 Feb
Gastroesophageal reflux disease and Barrett's esophagus.
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
Gastroesophageal reflux disease: extraesophageal manifestations and therapy.
2001 Jan
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
Changes in pulmonary hyperinflation and bronchial hyperresponsiveness following treatment with lansoprazole in children with cystic fibrosis.
2001 Jan
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.
2001 Jan 15
Propylene glycol toxicosis in a llama.
2001 Jan 15
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
Level of malondialdehyde after short-time omeprazole administration.
2001 Jan-Feb
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
Electrochemical studies and differential pulse polarographic analysis of lansoprazole in pharmaceuticals.
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
Five-day proton pump inhibitor-based quadruple therapy regimen is more effective than 7-day triple therapy regimen for Helicobacter pylori infection.
2001 Mar
Clarithromycin vs. furazolidone in quadruple therapy regimens for the treatment of Helicobacter pylori in a population with a high metronidazole resistance rate.
2001 Mar
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
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
Omeprazole therapy and salivary flow rate in duodenal ulcer patients.
2001 Mar-Apr
Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication.
2001 Mar-Apr
c-myc gene mutation in gastric mucosa-associated lymphoid tissue (MALT) lymphoma and diffuse large B-cell lymphoma.
2001 Mar-Apr
Patents

Sample Use Guides

In Vivo Use Guide
The drug is administered orally, once daily. The dose depends on the condition treated.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:47:59 UTC 2023
Edited
by admin
on Sat Dec 16 17:47:59 UTC 2023
Record UNII
N3PA6559FT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESOMEPRAZOLE
INN   MART.   VANDF   WHO-DD  
INN  
Official Name English
H199/18
Common Name English
A02BC05
Code English
OMEPRAZOLE S-FORM [MI]
Common Name English
ESOMEPRAZOLE [VANDF]
Common Name English
1H-BENZIMIDAZOLE, 5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-
Systematic Name English
Esomeprazole [WHO-DD]
Common Name English
esomeprazole [INN]
Common Name English
INEXIUM PARANOVA
Brand Name English
5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYL)SULFINYL)BENZIMIDAZOLE
Systematic Name English
ESOMEPRAZOLE [MART.]
Common Name English
OMEPRAZOLE S-FORM
MI  
Common Name English
OMEPRAZOLE, (S)-
Common Name English
Classification Tree Code System Code
WHO-VATC QB01AC56
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
WHO-ATC B01AC56
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
WHO-ATC A02BC05
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
NDF-RT N0000175525
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
WHO-VATC QM01AE52
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
WHO-ATC A02BD06
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
LIVERTOX 370
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
WHO-ATC M01AE52
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
NDF-RT N0000000147
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
WHO-VATC QA02BC05
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
NCI_THESAURUS C29723
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
FDA ORPHAN DRUG 684119
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
WHO-VATC QA02BD06
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
EMA ASSESSMENT REPORTS NEXIUM CONTROL (AUTHOIRIZED: GASTROESOPHAGEAL REFLUX)
Code System Code Type Description
MERCK INDEX
m8209
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY Merck Index
IUPHAR
5488
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
HSDB
8158
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
DRUG CENTRAL
1055
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
NDF-RT
N0000182140
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY Cytochrome P450 2C19 Inhibitors [MoA]
DAILYMED
N3PA6559FT
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201320
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
PUBCHEM
9568614
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
RXCUI
283742
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB00736
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
SMS_ID
100000087252
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
WIKIPEDIA
ESOMEPRAZOLE
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
EVMPD
SUB01960MIG
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID4044292
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
LACTMED
Esomeprazole
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
INN
7766
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
CHEBI
50275
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
NCI_THESAURUS
C65538
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
CAS
119141-88-7
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
FDA UNII
N3PA6559FT
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
MESH
D064098
Created by admin on Sat Dec 16 17:48:01 UTC 2023 , Edited by admin on Sat Dec 16 17:48:01 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TARGET -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
METABOLITE INACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
MAJOR
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
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC PEDIATRICS
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC CHILDREN

ORAL BIOAVAILABILITY PHARMACOKINETIC