Esomeprazole Sodium

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/202342s002lbl.pdf

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

Condition	Modality	Targets	Highest Phase	Product
Heartburn 24 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=477cfda2-44cf-4d0e-bdc4-e30bf16bfea9	Primary		Approved 8429	NEXIUM 24HR Approved Use treats frequent heartburn (occurs 2 or more days a week) Launch Date 2014

C_max

Value	Dose	Co-administered	Analyte	Population
7.5 μM EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021689Orig1s034lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
16.2 μM × h EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021689Orig1s034lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.4 h EXPERIMENT https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021689Orig1s034lbl.pdf	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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 substrate 1737	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT3 642 CYP2C19 1478 CYP2B6 810 CYP2C8 911 CYP1A2 1524	CYP2C19 991

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/ \| https://pubmed.ncbi.nlm.nih.gov/30845361/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf	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 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/ \| https://pubmed.ncbi.nlm.nih.gov/30845361/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/28801980/	yes [IC50 1.2 uM]	likely (co-administration study) Comment: The frequency of delayed MTX elimination in patients administered esomeprazole was 71.4% Sources: https://pubmed.ncbi.nlm.nih.gov/28801980/
MRP1 172	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/30349304/	yes
P-gp 1650	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/33049093/ \| https://pubmed.ncbi.nlm.nih.gov/30349304/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf	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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf
CYP2C19 991	substrate 3367 Sources: https://www.ncbi.nlm.nih.gov/books/NBK100896/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf	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 Sources: https://www.ncbi.nlm.nih.gov/books/NBK100896/ \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/022101s014021957s017021153s050lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:50275	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50275
MolPort	MolPort-023-330-012	https://www.molport.com/shop/molecule-link/MolPort-023-330-012
ZINC	ZINC000004693574	http://zinc15.docking.org/substances/ZINC000004693574

PubMed

Title	Date	PubMed
Study of the electrospray ionization mass spectrometry of the proton pump inhibiting drug Omeprazole.	2001	11223960
Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole?	2001 Apr	11300989
Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance.	2001 Apr	11284780
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.	2001 Apr	11266411
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	11182211
Complete remission of primary high-grade B-cell gastric lymphoma after cure of Helicobacter pylori infection.	2001 Apr 1	11283137
From the Food and Drug Administration.	2001 Apr 4	11277810
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.	2001 Feb	11293500
Improved high performance liquid chromatographic analysis of omeprazole in human plasma.	2001 Feb	11272330
[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages].	2001 Feb	11260880
Re: Ammonia cannot explain the effect of H. pylori on omeprazole-induced acid suppression.	2001 Feb	11232721
Recurrent ulcer bleeding: is intravenous omeprazole the solution?	2001 Feb	11232716
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	11232677
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	11232676
Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy.	2001 Feb	11232672
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	11227677
Early stage gastric MALT lymphoma with high-grade component cured by Helicobacter pylori eradication.	2001 Feb	11227668
Aggressive acid control: minimizing progression of Barrett's esophagus.	2001 Feb	11225348
Continued (5-year) followup of a randomized clinical study comparing antireflux surgery and omeprazole in gastroesophageal reflux disease.	2001 Feb	11220717
[A strategy for second-line anti-Helicobacter pylori therapy in patients with previously failed treatment].	2001 Feb	11218406
[Usefulness of new triple therapy containing PPI].	2001 Feb	11218404
[Selection of antibiotics and planning of eradication for H. pylori infection].	2001 Feb	11218403
Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats.	2001 Feb	11210394
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study.	2001 Feb	11172654
Relaxation induced by omeprazole does not change in diabetic rabbit corpus cavernosum.	2001 Feb	11167654
CYP3A4 is the major CYP isoform mediating the in vitro hydroxylation and demethylation of flunitrazepam.	2001 Feb	11159802
Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase.	2001 Feb	11156634
Analysis of gastrin receptor gene expression in proliferating cells in the neck zone of gastric fundic glands using laser capture microdissection.	2001 Feb 2	11165251
[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege].	2001 Jan	11256133
Gastroesophageal reflux disease: extraesophageal manifestations and therapy.	2001 Jan	11215855
Randomized study of two "rescue" therapies for Helicobacter pylori-infected patients after failure of standard triple therapies.	2001 Jan	11197288
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	11197282
Changes in pulmonary hyperinflation and bronchial hyperresponsiveness following treatment with lansoprazole in children with cystic fibrosis.	2001 Jan	11180676
Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome?	2001 Jan	11157153
Allergic contact dermatitis due to lansoprazole, a proton pump inhibitor.	2001 Jan	11156022
Long-term follow-up and serologic assessment after triple therapy with omeprazole or lansoprazole of Helicobacter-associated duodenal ulcer.	2001 Jan	11154169
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.	2001 Jan 15	11212260
Propylene glycol toxicosis in a llama.	2001 Jan 15	11195832
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.	2001 Mar	11303370
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	11240980
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication.	2001 Mar	11231401
Bioequivalence evaluation of lansoprazole 30-mg capsules (Lanfast and Lanzor) in healthy volunteers.	2001 Mar	11226823
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	11207516
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	11207509
Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen.	2001 Mar 29	11274623
[Heartburn. Only a harmless symptom?].	2001 Mar 8	11277116
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.	2001 Mar 9	11292068
New OTC drugs and devices 2000: a selective review.	2001 Mar-Apr	11297337
Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication.	2001 Mar-Apr	11182043
c-myc gene mutation in gastric mucosa-associated lymphoid tissue (MALT) lymphoma and diffuse large B-cell lymphoma.	2001 Mar-Apr	11182042

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

Name

Type

Language

Esomeprazole Sodium

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