U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19N3O3S
Molecular Weight 345.4178
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESOMEPRAZOLE

SMILES

Cc1cnc(C[S@](=O)c2nc3ccc(cc3[nH]2)OC)c(C)c1OC

InChI

InChIKey=SUBDBMMJDZJVOS-DEOSSOPVSA-N
InChI=1S/C17H19N3O3S/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,(H,19,20)/t24-/m0/s1

HIDE SMILES / InChI

Molecular Formula C17H19N3O3S
Molecular Weight 345.4178
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
[Losec was probably the cause of interstitial nephritis].
1999 Apr 7
Clarithromycin-induced acute psychoses in peptic ulcer disease.
1999 Jan
Omeprazole-induced acute interstitial nephritis.
1999 Nov
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites.
2000 Apr
Omeprazole-induced delirium.
2000 Jan
Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction.
2000 Jul
Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.
2000 Mar
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
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
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
Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection.
2001 Apr 1
From the Food and Drug Administration.
2001 Apr 4
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.
2001 Feb
Improved high performance liquid chromatographic analysis of omeprazole in human plasma.
2001 Feb
[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages].
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
[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
[Recent guidelines for the management of Helicobacter pylori infection].
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
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
Leishmania plasma membrane Mg2+-ATPase is a H+/K+-antiporter involved in glucose symport. Studies with sealed ghosts and vesicles of opposite polarity.
2001 Feb 23
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
Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome?
2001 Jan
Long-term follow-up and serologic assessment after triple therapy with omeprazole or lansoprazole of Helicobacter-associated duodenal ulcer.
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
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.
2001 Jan 5
Biochemical properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.
2001 Jan 5
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
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication.
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
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
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
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 Sat Jun 26 03:03:53 UTC 2021
Edited
by admin
on Sat Jun 26 03:03:53 UTC 2021
Record UNII
N3PA6559FT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESOMEPRAZOLE
INN   MART.   VANDF   WHO-DD  
INN  
Official Name English
H199/18
Common Name English
A02BC05
Code English
OMEPRAZOLE S-FORM [MI]
Common Name English
ESOMEPRAZOLE [VANDF]
Common Name English
1H-BENZIMIDAZOLE, 5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-
Systematic Name English
ESOMEPRAZOLE [INN]
Common Name English
ESOMEPRAZOLE [WHO-DD]
Common Name English
INEXIUM PARANOVA
Brand Name English
5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYL)SULFINYL)BENZIMIDAZOLE
Systematic Name English
ESOMEPRAZOLE [MART.]
Common Name English
OMEPRAZOLE S-FORM
MI  
Common Name English
OMEPRAZOLE, (S)-
Common Name English
Classification Tree Code System Code
WHO-VATC QB01AC56
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
WHO-ATC B01AC56
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
WHO-ATC A02BC05
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
NDF-RT N0000175525
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
WHO-VATC QM01AE52
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
WHO-ATC A02BD06
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
LIVERTOX 370
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
WHO-ATC M01AE52
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
NDF-RT N0000000147
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
WHO-VATC QA02BC05
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
NCI_THESAURUS C29723
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
FDA ORPHAN DRUG 684119
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
WHO-VATC QA02BD06
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
EMA ASSESSMENT REPORTS NEXIUM CONTROL (AUTHOIRIZED: GASTROESOPHAGEAL REFLUX)
Code System Code Type Description
MERCK INDEX
M8209
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY Merck Index
IUPHAR
5488
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
HSDB
8158
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
DRUG CENTRAL
1055
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
NDF-RT
N0000182140
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY Cytochrome P450 2C19 Inhibitors [MoA]
ChEMBL
CHEMBL1201320
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
PUBCHEM
9568614
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
RXCUI
283742
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00736
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
WIKIPEDIA
ESOMEPRAZOLE
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
EVMPD
SUB01960MIG
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
EPA CompTox
119141-88-7
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
LACTMED
Esomeprazole
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
INN
7766
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
NCI_THESAURUS
C65538
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
CAS
119141-88-7
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
FDA UNII
N3PA6559FT
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
MESH
D064098
Created by admin on Sat Jun 26 03:03:53 UTC 2021 , Edited by admin on Sat Jun 26 03:03:53 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
TARGET -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE INACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
MAJOR
METABOLITE INACTIVE -> PARENT
Metabolism of esomeprazole occurs via the hepatic CYP isoforms CYP2C19 and CYP3A4, which produce the 2 main pharmacologically inactive hydroxy and sulphone metabolites, respectively
MAJOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC PEDIATRICS
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC CHILDREN

ORAL BIOAVAILABILITY PHARMACOKINETIC