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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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Molecular Formula Mg
Molecular Weight 24.305
Charge 2
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
[Losec was probably the cause of interstitial nephritis].
1999 Apr 7
Omeprazole-induced delirium.
2000 Jan
Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.
2000 Mar
Hypercalcaemia and acute interstitial nephritis associated with omeprazole therapy.
2000 Sep
Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole.
2001
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
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.
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
[Usefulness of new triple therapy containing PPI].
2001 Feb
Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats.
2001 Feb
Upper gastrointestinal bleeding as a metastatic manifestation of breast cancer: a case report and review of the literature.
2001 Jan
Randomized study of two "rescue" therapies for Helicobacter pylori-infected patients after failure of standard triple therapies.
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
Duration of effect of lansoprazole on gastric pH and acid secretion in normal male volunteers.
2001 Jan
A multicentre study on eradication of Helicobacter pylori using four 1-week triple therapies in China.
2001 Jan
[Ulcer therapy with a new proton pump inhibitor. One week of treatment is enough].
2001 Jan 11
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.
2001 Jan 15
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.
2001 Jan 5
Current approaches to reducing gastrointestinal toxicity of low-dose aspirin.
2001 Jan 8
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 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
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
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 Fri Dec 15 15:31:31 UTC 2023
Edited
by admin
on Fri Dec 15 15:31:31 UTC 2023
Record UNII
R6DXU4WAY9
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
EMA ASSESSMENT REPORTS NEXIUM CONTROL (AUTHORIZED: GASTROESOPHAGEAL REFLUX)
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
Code System Code Type Description
DAILYMED
R6DXU4WAY9
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
EVMPD
SUB16427MIG
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
USAN
LL-98
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
PUBCHEM
21121303
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
RXCUI
283562
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY RxNorm
CAS
217087-09-7
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
FDA UNII
R6DXU4WAY9
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201320
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
EVMPD
SUB126849
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
NCI_THESAURUS
C29032
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
EPA CompTox
DTXSID30904663
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
SMS_ID
100000153033
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
RS_ITEM_NUM
1249789
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
MESH
D064098
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
DRUG BANK
DBSALT001222
Created by admin on Fri Dec 15 15:31:31 UTC 2023 , Edited by admin on Fri Dec 15 15:31:31 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE