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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C17H18N3O3S.Sr
Molecular Weight 776.44
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESOMEPRAZOLE STRONTIUM ANHYDROUS

SMILES

[Sr++].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=FEVPVZSYBDUVGY-YPPDDXJESA-N
InChI=1S/2C17H18N3O3S.Sr/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 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 Sr
Molecular Weight 87.62
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
The rates of common adverse events reported during treatment with proton pump inhibitors used in general practice in England: cohort studies.
2000 Oct
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
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
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.
2001 Apr
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.
2001 Feb
Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats.
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
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
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
Relaxation induced by omeprazole does not change in diabetic rabbit corpus cavernosum.
2001 Feb
Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase.
2001 Feb
The prescribing of acid suppressants prior to the endoscopic diagnosis of Barrett's oesophagus and oesophagitis.
2001 Feb
The effect of oral administration of Lactobacillus GG on antibiotic-associated gastrointestinal side-effects during Helicobacter pylori eradication therapy.
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
[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
Approach to the patient with unexplained chest pain.
2001 Jan
Gastroesophageal reflux disease: extraesophageal manifestations and therapy.
2001 Jan
Management of GERD: medical versus surgical.
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
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
Long-term follow-up and serologic assessment after triple therapy with omeprazole or lansoprazole of Helicobacter-associated duodenal ulcer.
2001 Jan
Duration of effect of lansoprazole on gastric pH and acid secretion in normal male volunteers.
2001 Jan
Accuracy of the stool antigen test in the diagnosis of Helicobacter pylori infection before treatment and in patients on omeprazole therapy.
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
Current approaches to reducing gastrointestinal toxicity of low-dose aspirin.
2001 Jan 8
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
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
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.
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
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication.
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
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.
2001 Mar 9
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
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 Thu Jul 06 03:35:48 UTC 2023
Edited
by admin
on Thu Jul 06 03:35:48 UTC 2023
Record UNII
SCC2RK476A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESOMEPRAZOLE STRONTIUM ANHYDROUS
Common Name English
1H-BENZIMIDAZOLE, 5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-, STRONTIUM SALT
Common Name English
(-)-5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYLPYRIDIN-2-YL)METHYL)SULFINYL)-1H- BENZIMIDAZOLE STRONTIUM SALT
Common Name English
1H-BENZIMIDAZOLE, 6-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-, STRONTIUM SALT (2:1)
Common Name English
FM0F67 ANHYDROUS
Code English
Code System Code Type Description
CAS
914613-86-8
Created by admin on Thu Jul 06 03:35:48 UTC 2023 , Edited by admin on Thu Jul 06 03:35:48 UTC 2023
PRIMARY
FDA UNII
SCC2RK476A
Created by admin on Thu Jul 06 03:35:48 UTC 2023 , Edited by admin on Thu Jul 06 03:35:48 UTC 2023
PRIMARY
EPA CompTox
DTXSID30238576
Created by admin on Thu Jul 06 03:35:48 UTC 2023 , Edited by admin on Thu Jul 06 03:35:48 UTC 2023
PRIMARY
PUBCHEM
11954521
Created by admin on Thu Jul 06 03:35:48 UTC 2023 , Edited by admin on Thu Jul 06 03:35:48 UTC 2023
PRIMARY
SMS_ID
100000138852
Created by admin on Thu Jul 06 03:35:48 UTC 2023 , Edited by admin on Thu Jul 06 03:35:48 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS