ESOMEPRAZOLE

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 Search

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

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 20 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=477cfda2-44cf-4d0e-bdc4-e30bf16bfea9	Primary		Approved 8043	NEXIUM 24HR Approved Use treats frequent heartburn (occurs 2 or more days a week) Launch Date 1.3958784E12

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 1467 substrate 1601	inhibitor 1604	inhibitor 1702

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT3 588 CYP2C19 1325 CYP2B6 717 CYP2C8 818 CYP1A2 1383	CYP2C19 910

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C19 1392	inhibitor 3045 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 1532	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2B6 884	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2C8 865	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2C9 1648	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP2D6 1738	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
CYP3A4 1772	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/22648560/	weak [IC50 >40 uM]
OAT3 590	inhibitor 3045 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 166	supressor 140 Sources: https://pubmed.ncbi.nlm.nih.gov/30349304/	yes
P-gp 1514	supressor 140 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 1601	substrate 3113 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 910	substrate 3113 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
[Losec was probably the cause of interstitial nephritis].	1999 Apr 7	10222687
Clarithromycin-induced acute psychoses in peptic ulcer disease.	1999 Jan	10192720
Omeprazole-induced acute interstitial nephritis.	1999 Nov	10566755
Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites.	2000 Apr	10783826
Omeprazole-induced delirium.	2000 Jan	10701899
Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction.	2000 Jul	10859152
Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.	2000 Mar	10750652
Pharmacokinetic study of esomeprazole in the elderly.	2001	11286324
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents.	2001	11178116
Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole?	2001 Apr	11300989
Antireflux surgery in children suffering from reflux-associated respiratory disease?	2001 Apr	11288221
Effects of lansoprazole, clarithromycin and pH gradient on uptake of [14C]amoxycillin into rat gastric tissue.	2001 Apr	11266411
A new cause of Zollinger-Ellison syndrome: non-small cell lung cancer.	2001 Apr	11266390
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
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
[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
[Recent guidelines for the management of Helicobacter pylori infection].	2001 Feb	11218393
Relaxation induced by omeprazole does not change in diabetic rabbit corpus cavernosum.	2001 Feb	11167654
Helicobacter pylori augments the acid inhibitory effect of omeprazole on parietal cells and gastric H(+)/K(+)-ATPase.	2001 Feb	11156634
Eradication of Helicobacter pylori prevents ulcer development in patients with ulcer-like functional dyspepsia.	2001 Feb	11148437
The effect of oral administration of Lactobacillus GG on antibiotic-associated gastrointestinal side-effects during Helicobacter pylori eradication therapy.	2001 Feb	11148433
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	11087746
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
Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome?	2001 Jan	11157153
Long-term follow-up and serologic assessment after triple therapy with omeprazole or lansoprazole of Helicobacter-associated duodenal ulcer.	2001 Jan	11154169
Accuracy of the stool antigen test in the diagnosis of Helicobacter pylori infection before treatment and in patients on omeprazole therapy.	2001 Jan	11136280
Pharmacological properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.	2001 Jan 5	11137875
Biochemical properties of a newly synthesized H(+)/K(+) ATPase inhibitor, 1-(2-methyl-4-methoxyphenyl)-4-.	2001 Jan 5	11137874
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.	2001 Mar	11303370
Efficacy and safety of esomeprazole compared with omeprazole in GERD patients with erosive esophagitis: a randomized controlled trial.	2001 Mar	11280530
Pharmacodynamic modeling of lansoprazole using an indirect irreversible response model.	2001 Mar	11269565
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs.	2001 Mar	11256484
A case of gastric plasmacytoma associated with Helicobacter pylori infection: improvement of abnormal endoscopic and EUS findings after H. pylori eradication.	2001 Mar	11231401
Five-day proton pump inhibitor-based quadruple therapy regimen is more effective than 7-day triple therapy regimen for Helicobacter pylori infection.	2001 Mar	11207518
Clarithromycin vs. furazolidone in quadruple therapy regimens for the treatment of Helicobacter pylori in a population with a high metronidazole resistance rate.	2001 Mar	11207517
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
Predictive factors for regression of gastric MALT lymphoma after anti-Helicobacter pylori treatment.	2001 Mar	11171816
Preventing recurrent upper gastrointestinal bleeding in patients with Helicobacter pylori infection who are taking low-dose aspirin or naproxen.	2001 Mar 29	11274623
Improvement in atrophic gastritis and intestinal metaplasia in patients in whom Helicobacter pylori was eradicated.	2001 Mar 6	11242498
[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
Omeprazole therapy and salivary flow rate in duodenal ulcer patients.	2001 Mar-Apr	11257735

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

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Name

Type

Language

ESOMEPRAZOLE

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

Common Name

English

OMEPRAZOLE, (S)-

Common Name

English

Classification Tree Code System Code

WHO-VATC

QB01AC56