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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H18N3O3S.Na
Molecular Weight 367.398
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Esomeprazole Sodium

SMILES

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

InChI

InChIKey=RYXPMWYHEBGTRV-JIDHJSLPSA-N
InChI=1S/C17H18N3O3S.Na/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 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 Na
Molecular Weight 22.9898
Charge 1
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
Pharmacokinetic study of esomeprazole in the elderly.
2001
Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole.
2001
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents.
2001
Effect of Lactobacillus GG supplementation on antibiotic-associated gastrointestinal side effects during Helicobacter pylori eradication therapy: a pilot study.
2001
Antireflux surgery in children suffering from reflux-associated respiratory disease?
2001 Apr
Pantoprazole and cyclosporine or tacrolimus.
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
Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats.
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
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
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
Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase.
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
Approach to the patient with unexplained chest pain.
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
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
Switching between intravenous and oral pantoprazole.
2001 Jan
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.
2001 Jan 15
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
Level of malondialdehyde after short-time omeprazole administration.
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
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
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
Predictive factors for regression of gastric MALT lymphoma after anti-Helicobacter pylori treatment.
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
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 Wed Jul 05 23:24:38 UTC 2023
Edited
by admin
on Wed Jul 05 23:24:38 UTC 2023
Record UNII
L2C9GWQ43H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Esomeprazole Sodium
MART.   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
1H-Benzimidazole, 5-methoxy-2-[(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-, sodium salt
Systematic Name English
H199/18 SODIUM
Code English
ESOMEPRAZOLE SODIUM [EP MONOGRAPH]
Common Name English
Esomeprazole sodium [WHO-DD]
Common Name English
NEXIUM IV
Brand Name English
ESOMEPRAZOLE (AS SODIUM)
Common Name English
ESOMEPRAZOLE SODIUM [ORANGE BOOK]
Common Name English
ESOMEPRAZOLE SODIUM [VANDF]
Common Name English
1H-Benzimidazole, 6-methoxy-2-[(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-, sodium salt (1:1)
Systematic Name English
ESOMEPRAZOLE SODIUM [MART.]
Common Name English
5-Methoxy-2-[(S)-[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole, sodium salt
Common Name English
ESOMEPRAZOLE SODIUM [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29723
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
Code System Code Type Description
FDA UNII
L2C9GWQ43H
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
RS_ITEM_NUM
1249790
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
PUBCHEM
23674541
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
DRUG BANK
DB00736
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
NCI_THESAURUS
C65539
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
CAS
161796-78-7
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID90904644
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201320
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
MESH
D064098
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
RXCUI
1294569
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY RxNorm
DAILYMED
L2C9GWQ43H
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
USAN
PP-34
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
EVMPD
SUB20377
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
SMS_ID
100000089784
Created by admin on Wed Jul 05 23:24:38 UTC 2023 , Edited by admin on Wed Jul 05 23:24:38 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
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ACTIVE MOIETY