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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

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 HO
Molecular Weight 17.0073
Charge -1
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 Mg
Molecular Weight 24.305
Charge 2
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
Reversible renal failure after treatment with omeprazole.
2000 Aug
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
Which patients with ulcer- or reflux-like dyspepsia will respond favorably to omeprazole?
2001 Apr
Protective effect of famotidine, omeprazole, and melatonin against acetylsalicylic acid-induced gastric damage in rats.
2001 Feb
Gastroesophageal reflux disease and Barrett's esophagus.
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
[A strategy for second-line anti-Helicobacter pylori therapy in patients with previously failed treatment].
2001 Feb
[Selection of antibiotics and planning of eradication for H. pylori infection].
2001 Feb
[Recent guidelines for the management of Helicobacter pylori infection].
2001 Feb
Pharmacodynamic modeling of pantoprazole's irreversible effect on gastric acid secretion in humans and rats.
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
Meta-analysis of randomized controlled trials comparing standard clinical doses of omeprazole and lansoprazole in erosive oesophagitis.
2001 Feb
The prescribing of acid suppressants prior to the endoscopic diagnosis of Barrett's oesophagus and oesophagitis.
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
[Prevalence and treatment of Helicobacter pylori in gastro-duodenal ulcers. An experience in Liege].
2001 Jan
Upper gastrointestinal bleeding as a metastatic manifestation of breast cancer: a case report and review of the literature.
2001 Jan
Randomized study of two "rescue" therapies for Helicobacter pylori-infected patients after failure of standard triple therapies.
2001 Jan
Does pantoprazole alleviate mouth dryness in patients with Sjögren's syndrome?
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
Duration of effect of lansoprazole on gastric pH and acid secretion in normal male volunteers.
2001 Jan
Helicobacter pylori effects on gastritis, gastrin and enterochromaffin-like cells in Zollinger-Ellison syndrome and non-Zollinger-Ellison syndrome acid hypersecretors treated long-term with lansoprazole.
2001 Jan
A multicentre study on eradication of Helicobacter pylori using four 1-week triple therapies in China.
2001 Jan
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.
2001 Jan 15
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
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
Pharmacokinetic differences between lansoprazole enantiomers and contribution of cytochrome P450 isoforms to enantioselective metabolism of lansoprazole in dogs.
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
New OTC drugs and devices 2000: a selective review.
2001 Mar-Apr
c-myc gene mutation in gastric mucosa-associated lymphoid tissue (MALT) lymphoma and diffuse large B-cell lymphoma.
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 Thu Jul 06 02:42:31 UTC 2023
Edited
by admin
on Thu Jul 06 02:42:31 UTC 2023
Record UNII
36H71644EQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESOMEPRAZOLE MAGNESIUM DIHYDRATE
WHO-DD  
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
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID90944323
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY
PUBCHEM
17747012
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY
DAILYMED
36H71644EQ
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY
FDA UNII
36H71644EQ
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY
DRUG BANK
DBSALT001223
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY
CAS
217087-10-0
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY
SMS_ID
100000128480
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY
EVMPD
SUB35549
Created by admin on Thu Jul 06 02:42:31 UTC 2023 , Edited by admin on Thu Jul 06 02:42:31 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE