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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C17H18N3O3S.Mg
Molecular Weight 713.121
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESOMEPRAZOLE MAGNESIUM ANHYDROUS

SMILES

[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=KWORUUGOSLYAGD-YPPDDXJESA-N
InChI=1S/2C17H18N3O3S.Mg/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;/q2*-1;+2/t2*24-;/m00./s1

HIDE SMILES / InChI

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

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
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies.
2000 Oct
Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole.
2001
Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole?
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
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.
2001 Feb
Gastroesophageal reflux disease and Barrett's esophagus.
2001 Feb
[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages].
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
Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats.
2001 Feb
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.
2001 Feb
Eradication of Helicobacter pylori prevents ulcer development in patients with ulcer-like functional dyspepsia.
2001 Feb
The effect of oral administration of Lactobacillus GG on antibiotic-associated gastrointestinal side-effects during Helicobacter pylori eradication therapy.
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
Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome?
2001 Jan
Allergic contact dermatitis due to lansoprazole, a proton pump inhibitor.
2001 Jan
Duration of effect of lansoprazole on gastric pH and acid secretion in normal male volunteers.
2001 Jan
Helicobacter pylori effects on gastritis, gastrin and enterochromaffin-like cells in Zollinger-Ellison syndrome and non-Zollinger-Ellison syndrome acid hypersecretors treated long-term with lansoprazole.
2001 Jan
Propylene glycol toxicosis in a llama.
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
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
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.
2001 Mar
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
Bioequivalence evaluation of lansoprazole 30-mg capsules (Lanfast and Lanzor) in healthy volunteers.
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
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
Improvement in atrophic gastritis and intestinal metaplasia in patients in whom Helicobacter pylori was eradicated.
2001 Mar 6
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
Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication.
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 Thu Jul 06 10:50:04 UTC 2023
Edited
by admin
on Thu Jul 06 10:50:04 UTC 2023
Record UNII
925R0D7W1O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESOMEPRAZOLE MAGNESIUM ANHYDROUS
Common Name English
MAGNESIUM, BIS(6-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL-.KAPPA.O)-1H-BENZIMIDAZOLATO-.KAPPA.N3)-, (T-4)-
Common Name English
1H-BENZIMIDAZOLE, 5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-, MAGNESIUM SALT
Common Name English
OMEPRAZOLE S-FORM MANGESIUM SALT [MI]
Common Name English
5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYL)SULFINYL)BENZIMIDAZOLE, MAGNESIUM SALT (2:1)
Common Name English
OMEPRAZOLE S-FORM MANGESIUM SALT
MI  
Common Name English
Code System Code Type Description
PUBCHEM
9568613
Created by admin on Thu Jul 06 10:50:04 UTC 2023 , Edited by admin on Thu Jul 06 10:50:04 UTC 2023
PRIMARY
FDA UNII
925R0D7W1O
Created by admin on Thu Jul 06 10:50:04 UTC 2023 , Edited by admin on Thu Jul 06 10:50:04 UTC 2023
PRIMARY
CAS
161973-10-0
Created by admin on Thu Jul 06 10:50:04 UTC 2023 , Edited by admin on Thu Jul 06 10:50:04 UTC 2023
PRIMARY
SMS_ID
100000085059
Created by admin on Thu Jul 06 10:50:04 UTC 2023 , Edited by admin on Thu Jul 06 10:50:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID5044231
Created by admin on Thu Jul 06 10:50:04 UTC 2023 , Edited by admin on Thu Jul 06 10:50:04 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS