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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H18N3O3S.K
Molecular Weight 383.506
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESOMEPRAZOLE POTASSIUM

SMILES

[K+].COC1=CC2=C([N-]C(=N2)[S@@+]([O-])CC3=C(C)C(OC)=C(C)C=N3)C=C1

InChI

InChIKey=FOFFPEFVSRGLOZ-JIDHJSLPSA-N
InChI=1S/C17H18N3O3S.K/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;/q-1;+1/t24-;/m0./s1

HIDE SMILES / InChI

Molecular Formula K
Molecular Weight 39.0983
Charge 1
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

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
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
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
Antireflux surgery in children suffering from reflux-associated respiratory disease?
2001 Apr
Pantoprazole and cyclosporine or tacrolimus.
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
From the Food and Drug Administration.
2001 Apr 4
Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats.
2001 Feb
[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages].
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
Aggressive acid control: minimizing progression of Barrett's esophagus.
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
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study.
2001 Feb
Relaxation induced by omeprazole does not change in diabetic rabbit corpus cavernosum.
2001 Feb
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.
2001 Feb
Meta-analysis of randomized controlled trials comparing standard clinical doses of omeprazole and lansoprazole in erosive oesophagitis.
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
Analysis of gastrin receptor gene expression in proliferating cells in the neck zone of gastric fundic glands using laser capture microdissection.
2001 Feb 2
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
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
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
A multicentre study on eradication of Helicobacter pylori using four 1-week triple therapies in China.
2001 Jan
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.
2001 Jan 15
Biochemical 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
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
Efficacy and safety of esomeprazole compared with omeprazole in GERD patients with erosive esophagitis: a randomized controlled trial.
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
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
Clarithromycin vs. furazolidone in quadruple therapy regimens for the treatment of Helicobacter pylori in a population with a high metronidazole resistance rate.
2001 Mar
One-week ranitidine bismuth citrate-based triple therapy for the eradication of Helicobacter pylori in Hong Kong with high prevalence of metronidazole resistance.
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
[Heartburn. Only a harmless symptom?].
2001 Mar 8
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
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 16:33:50 GMT 2023
Edited
by admin
on Fri Dec 15 16:33:50 GMT 2023
Record UNII
F37S7G37O2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESOMEPRAZOLE POTASSIUM
MART.   USAN   WHO-DD  
USAN  
Official Name English
NSC-759647
Code English
Esomeprazole potassium [WHO-DD]
Common Name English
1H-BENZIMIDAZOLE, 6-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2- PYRIDINYL)METHYL)SULFINYL)-, POTASSIUM SALT (1:1)
Common Name English
ESOMEPRAZOLE POTASSIUM [USAN]
Common Name English
ESOMEPRAZOLE POTASSIUM [MART.]
Common Name English
(-)-5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYLPYRIDIN-2-YL)METHYL)SULFINYL)-1H- BENZIMIDAZOLE POTASSIUM SALT
Common Name English
Code System Code Type Description
USAN
UU-66
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
FDA UNII
F37S7G37O2
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID20167240
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
EVMPD
SUB79200
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
PUBCHEM
23672364
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
SMS_ID
100000138850
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
NCI_THESAURUS
C169962
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
CAS
161796-84-5
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
NSC
759647
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201320
Created by admin on Fri Dec 15 16:33:50 GMT 2023 , Edited by admin on Fri Dec 15 16:33:50 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE