ESOMEPRAZOLE MAGNESIUM DIHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C17H18N3O3S.Mg.2H2O
Molecular Weight	749.152
Optical Activity	( - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ESOMEPRAZOLE MAGNESIUM DIHYDRATE

Structure Search

SMILES

O.O.[Mg++].COC1=CC2=C([N-]C(=N2)[S@@+]([O-])CC3=C(C)C(OC)=C(C)C=N3)C=C1.COC4=CC5=C([N-]C(=N5)[S@@+]([O-])CC6=C(C)C(OC)=C(C)C=N6)C=C4

InChI

InChIKey=DBOUSUONOXEWHU-VCKZSRROSA-N

InChI=1S/2C17H18N3O3S.Mg.2H2O/c2*1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17;;;/h2*5-8H,9H2,1-4H3;;2*1H2/q2*-1;+2;;/t2*24-;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula	Mg
Molecular Weight	24.305
Charge	2
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

Molecular Formula	HO
Molecular Weight	17.0073
Charge	-1
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 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 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 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
Pharmacokinetic study of esomeprazole in the elderly.	2001	11286324
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
Antireflux surgery in children suffering from reflux-associated respiratory disease?	2001 Apr	11288221
Pantoprazole and cyclosporine or tacrolimus.	2001 Apr	11284790
Maximal acid reflux control for Barrett's oesophagus: feasible and effective.	2001 Apr	11284781
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
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
Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats.	2001 Feb	11281181
Improved high performance liquid chromatographic analysis of omeprazole in human plasma.	2001 Feb	11272330
Gastroesophageal reflux disease and Barrett's esophagus.	2001 Feb	11272213
[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
[Recent guidelines for the management of Helicobacter pylori infection].	2001 Feb	11218393
[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege].	2001 Jan	11256133
Upper gastrointestinal bleeding as a metastatic manifestation of breast cancer: a case report and review of the literature.	2001 Jan	11248910
Approach to the patient with unexplained chest pain.	2001 Jan	11216468
Gastroesophageal reflux disease: extraesophageal manifestations and therapy.	2001 Jan	11215855
Management of GERD: medical versus surgical.	2001 Jan	11215853
[Ulcer therapy with a new proton pump inhibitor. One week of treatment is enough].	2001 Jan 11	11216011
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.	2001 Mar	11303370
Electrochemical studies and differential pulse polarographic analysis of lansoprazole in pharmaceuticals.	2001 Mar	11284340
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
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
Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin.	2001 Mar	11240974
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
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 `Fri Dec 15 19:39:14 UTC 2023` Edited by `admin` on `Fri Dec 15 19:39:14 UTC 2023`
Record UNII	36H71644EQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESOMEPRAZOLE MAGNESIUM DIHYDRATE

Common Name

English

(S)-OMEPRAZOLE MAGNESIUM DIHYDRATE

Common Name

English

MAGNESIUM, BIS(6-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL-.KAPPA.O)-1H-BENZIMIDAZOLATO-.KAPPA.N3)-, HYDRATE (1:2), (T-4)-

Common Name

English

ESOMEPRAZOLE (AS MAGNESIUM DIHYDRATE)

Common Name

English

Esomeprazole magnesium dihydrate [WHO-DD]

Common Name

English

ESOMEPRAZOLE MAGNESIUM DIHYDRATE [EP MONOGRAPH]

Common Name

English

MAGNESIUM, BIS(6-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL-.KAPPA.O)-1H-BENZIMIDAZOLATO-.KAPPA.N3)-, DIHYDRATE, (T-4)-

Common Name

English

Code System Code Type Description

RXCUI

1601995