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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C17H18N3O3S.Mg.3H2O
Molecular Weight 767.167
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESOMEPRAZOLE MAGNESIUM

SMILES

O.O.O.[Mg++].COC1=CC2=C([N-]C(=N2)[S@@+]([O-])CC3=C(C)C(OC)=C(C)C=N3)C=C1.COC4=CC5=C([N-]C(=N5)[S@@+]([O-])CC6=C(C)C(OC)=C(C)C=N6)C=C4

InChI

InChIKey=VEVZQDGATGBLIC-OXLUMUBXSA-N
InChI=1S/2C17H18N3O3S.Mg.3H2O/c2*1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17;;;;/h2*5-8H,9H2,1-4H3;;3*1H2/q2*-1;+2;;;/t2*24-;;;;/m00..../s1

HIDE SMILES / InChI
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

2014
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
[Losec was probably the cause of interstitial nephritis].
1999 Apr 7
Clarithromycin-induced acute psychoses in peptic ulcer disease.
1999 Jan
Omeprazole-induced acute interstitial nephritis.
1999 Nov
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites.
2000 Apr
Reversible renal failure after treatment with omeprazole.
2000 Aug
Omeprazole-induced delirium.
2000 Jan
Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction.
2000 Jul
Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.
2000 Mar
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents.
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
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
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
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.
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
Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy.
2001 Feb
[Selection of antibiotics and planning of eradication for H. pylori infection].
2001 Feb
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.
2001 Feb
Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase.
2001 Feb
Eradication of Helicobacter pylori prevents ulcer development in patients with ulcer-like functional dyspepsia.
2001 Feb
Analysis of gastrin receptor gene expression in proliferating cells in the neck zone of gastric fundic glands using laser capture microdissection.
2001 Feb 2
Approach to the patient with unexplained chest pain.
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
Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome?
2001 Jan
A multicentre study on eradication of Helicobacter pylori using four 1-week triple therapies in China.
2001 Jan
Helicobacter pylori and nonsteroidal anti-inflammatory drugs: interaction with proton pump inhibitor therapy for prevention of nonsteroidal anti-inflammatory drug ulcers and ulcer complications--future research needs.
2001 Jan 8
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.
2001 Mar
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs.
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
[Heartburn. Only a harmless symptom?].
2001 Mar 8
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
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
Name Type Language
ESOMEPRAZOLE MAGNESIUM
MART.   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
H199/18 MAGNESIUM TRIHYDRATE
Code English
ESOMEPRAZOLE MAGNESIUM COMPONENT OF VIMOVO
Common Name English
Esomeprazole magnesium trihydrate [WHO-DD]
Common Name English
ESOMEPRAZOLE MAGNESIUM [MART.]
Common Name English
1H-BENZIMIDAZOLE, 5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-, MAGNESIUM SALT, TRIHYDRATE
Common Name English
ESOMEPRAZOLE MAGNESIUM [USAN]
Common Name English
ESOMEPRAZOLE MAGNESIUM HYDRATE
JAN  
Common Name English
ESOMEPRAZOLE MAGNESIUM TRIHYDRATE
EP  
Common Name English
ESOMEPRAZOLE MAGNESIUM TRIHYDRATE [EP MONOGRAPH]
Common Name English
ESOMEPRAZOLE MAGNESIUM [USP-RS]
Common Name English
ESOMEPRAZOLE (AS MAGNESIUM TRIHYDRATE)
Common Name English
ESOMEPRAZOLE MAGNESIUM [ORANGE BOOK]
Common Name English
ESOMEPRAZOLE MAGNESIUM [USP MONOGRAPH]
Common Name English
VIMOVO COMPONENT ESOMEPRAZOLE MAGNESIUM
Common Name English
PN400 COMPONENT ESOMEPRAZOLE MAGNESIUM
Common Name English
ESOMEPRAZOLE MAGNESIUM HYDRATE [JAN]
Common Name English
Esomeprazole magnesium [WHO-DD]
Common Name English
NEXIUM CONTROL
Brand Name English
ESOMEPRAZOLE MAGNESIUM [VANDF]
Common Name English
NEXIUM
Brand Name English
ESOMEPRAZOLE (AS MAGNESIUM)
Common Name English
5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYL)SULFINYL)BENZIMIDAZOLE, MAGNESIUM SALT (2:1), TRIHYDRATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29723
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
EMA ASSESSMENT REPORTS NEXIUM CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
Code System Code Type Description
DAILYMED
R6DXU4WAY9
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
EVMPD
SUB16427MIG
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
USAN
LL-98
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
PUBCHEM
21121303
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
RXCUI
283562
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY RxNorm
CAS
217087-09-7
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
FDA UNII
R6DXU4WAY9
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201320
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
EVMPD
SUB126849
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
NCI_THESAURUS
C29032
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID30904663
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
SMS_ID
100000153033
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
RS_ITEM_NUM
1249789
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
MESH
D064098
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY
DRUG BANK
DBSALT001222
Created by admin on Fri Dec 15 15:31:31 GMT 2023 , Edited by admin on Fri Dec 15 15:31:31 GMT 2023
PRIMARY