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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C17H18N3O3S.Mg
Molecular Weight 713.121
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESOMEPRAZOLE MAGNESIUM ANHYDROUS

SMILES

[Mg++].COC1=CC2=C([N-]C(=N2)[S@@+]([O-])CC3=NC=C(C)C(OC)=C3C)C=C1.COC4=CC5=C([N-]C(=N5)[S@@+]([O-])CC6=NC=C(C)C(OC)=C6C)C=C4

InChI

InChIKey=KWORUUGOSLYAGD-YPPDDXJESA-N
InChI=1S/2C17H18N3O3S.Mg/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;/q2*-1;+2/t2*24-;/m00./s1

HIDE SMILES / InChI

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.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NEXIUM 24HR

Approved Use

treats frequent heartburn (occurs 2 or more days a week)

Launch Date

2014
Primary
PRILOSEC

Approved Use

PRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults.

Launch Date

2008
Primary
PRILOSEC

Approved Use

PRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults.

Launch Date

2008
Primary
PRILOSEC

Approved Use

PRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults.

Launch Date

1989
Primary
PRILOSEC

Approved Use

PRILOSEC is a proton pump inhibitor indicated for: treatment of duodenal ulcer in adults, treatment of gastric ulcer in adults. Treatment of Gastroesophageal Reflux Disease. Maintenance of healing of erosive esophagitis in pediatric patients and adults. Treatment of pathological hypersecretory conditions in adults.

Launch Date

2008
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
668 ng/mL
1 mg/kg single, oral
dose: 1 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMEPRAZOLE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
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
1200 nM*h
20 mg single, oral
dose: 20 mg
route of administration: oral
experiment type: single
co-administered:
OMEPRAZOLE plasma
Homo sapiens
population: healthy
age: adults
sex:
food status:
1220 ng × h/mL
1 mg/kg single, oral
dose: 1 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
OMEPRAZOLE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1179 nM × h
20 mg 1 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
OMEPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
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
0.58 h
20 mg 1 times / day multiple, oral
dose: 20 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
OMEPRAZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
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
Doses

Doses

DosePopulationAdverse events​
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 45.2
Health Status: unhealthy
Age Group: 45.2
Sex: M+F
Sources:
Other AEs: Nausea, Diarrhoea...
Other AEs:
Nausea (7%)
Diarrhoea (6%)
Headache (3%)
Sources:
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Other AEs: Headache, Abdominal pain...
Other AEs:
Headache (6.9%)
Abdominal pain (5.2%)
Nausea (4%)
Diarrhea (3.7%)
Vomiting (3.2%)
Flatulence (2.7%)
Esophageal acid reflux (1.9%)
Upper respiratory infection (1.9%)
Constipation (1.5%)
Dizziness (1.5%)
Rash (1.5%)
Asthenia (1.3%)
Back pain (1.1%)
Cough (1.1%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Headache 3%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 45.2
Health Status: unhealthy
Age Group: 45.2
Sex: M+F
Sources:
Diarrhoea 6%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 45.2
Health Status: unhealthy
Age Group: 45.2
Sex: M+F
Sources:
Nausea 7%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy, 45.2
Health Status: unhealthy
Age Group: 45.2
Sex: M+F
Sources:
Back pain 1.1%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Cough 1.1%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Asthenia 1.3%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Constipation 1.5%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Dizziness 1.5%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Rash 1.5%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Esophageal acid reflux 1.9%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Upper respiratory infection 1.9%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Flatulence 2.7%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Vomiting 3.2%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Diarrhea 3.7%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Nausea 4%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Abdominal pain 5.2%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
Headache 6.9%
20 mg 1 times / day multiple, oral
Recommended
Dose: 20 mg, 1 times / day
Route: oral
Route: multiple
Dose: 20 mg, 1 times / day
Sources:
unhealthy
OverviewDrug 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]
weak [Ki 150 uM]
weak (co-administration study)
Comment: Omeprazole exerts a concentration-dependent inhibition of CYP1A2 activity in man. However, even after single oral doses up to 80 mg, this effect is weak and without clinical relevance
weak [Ki 367.5 uM]
weak [Ki 745.1 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 [IC50 15.7 uM]
yes [IC50 17.6 uM]
yes [IC50 17.7 uM]
yes [IC50 22 uM]
yes [IC50 4.32 uM]
yes [IC50 6.7 uM]
yes [IC50 6.8 uM]
yes [IC50 84.3 uM]
unlikely (co-administration study)
Comment: Coaministration with simvastatin acid unlikely results in DDIs
yes [Ki 7.1 uM]
yes (co-administration study)
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes (expression study)
Comment: livers of patients treated with omeprazole showed higher MRP3 protein expression
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major
yes (co-administration study)
Comment: When voriconazole was given with omeprazole to healthy subjects, it significantly increased the steady-state Cmax and AUC0-24 of omeprazole, an average of 2 times and 4 times, respectively
major
yes (co-administration study)
Comment: Drugs known to induce CYP2C19 or CYP3A4 (such as rifampin) may lead to decreased omeprazole serum levels. In a cross-over study in 12 healthy male subjects, St John’s wort, an inducer of CYP3A4, decreased the systemic exposure of omeprazole in CYP2C19 poor metabolisers (Cmax and AUC decreased by 37.5% and 37.9%, respectively) and extensive metabolisers (Cmax and AUC decreased by 49.6% and 43.9%, respectively)
minor
minor
minor
no
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
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
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
Antireflux surgery in children suffering from reflux-associated respiratory disease?
2001 Apr
Pantoprazole and cyclosporine or tacrolimus.
2001 Apr
Maximal acid reflux control for Barrett's oesophagus: feasible and effective.
2001 Apr
Nitrofurantoin quadruple therapy for Helicobacter pylori infection: effect of metronidazole resistance.
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
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
Differentiation between reinfection and recrudescence of helicobacter pylori strains using PCR-based restriction fragment length polymorphism analysis.
2001 Feb
Gastroesophageal reflux disease and Barrett's esophagus.
2001 Feb
[Suppressive effect of lansoprazole on anti-Candida activity of murine macrophages].
2001 Feb
Re: Ammonia cannot explain the effect of H. pylori on omeprazole-induced acid suppression.
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
Increased acid and bile reflux in Barrett's esophagus compared to reflux esophagitis, and effect of proton pump inhibitor therapy.
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
Antibiotic-resistance patterns of Helicobacter pylori in Croatia: cohort study.
2001 Feb
The prescribing of acid suppressants prior to the endoscopic diagnosis of Barrett's oesophagus and oesophagitis.
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
Gastroesophageal reflux disease: extraesophageal manifestations and therapy.
2001 Jan
Management of GERD: medical versus surgical.
2001 Jan
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
Changes in pulmonary hyperinflation and bronchial hyperresponsiveness following treatment with lansoprazole in children with cystic fibrosis.
2001 Jan
Hypergastrinemia promotes adenoma progression in the APC(Min-/+) mouse model of familial adenomatous polyposis.
2001 Jan 15
Propylene glycol toxicosis in a llama.
2001 Jan 15
Effect of polaprezinc on impaired healing of chronic gastric ulcers in adjuvant-induced arthritic rats--role of insulin-like growth factors (IGF)-1.
2001 Jan-Feb
The effect of culture results for Helicobacter pylori on the choice of treatment following failure of initial eradication.
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
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
Stereoselective pharmacokinetics of pantoprazole, a proton pump inhibitor, in extensive and poor metabolizers of S-mephenytoin.
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
Bioequivalence evaluation of lansoprazole 30-mg capsules (Lanfast and Lanzor) in healthy volunteers.
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
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
Microsatellite instability at D18S61 is associated with no regression of gastric mucosa-associated lymphoid tissue lymphoma after Helicobacter pylori eradication.
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

Active Duodenal Ulcer: 20 mg Once daily for 4 weeks. Some patients may require an addition 4 weeks. Gastric Ulcer: oral dose is 40 mg once daily for 4-8 weeks. Gastroesophageal Reflux Disease: The recommended adult oral dose for the treatment of patients with symptomatic GERD and no esophageal lesions is 20 mg daily for up to 4 weeks. The recommended adult oral dose for the treatment of patients with erosive esophagitis and accompanying symptoms due to GERD is 20 mg daily for 4 to 8 weeks.
Route of Administration: Oral
Pretreatment of omeprazole (10-6 - 10-4M) dose-dependently inhibits neutrophil adherence and respiratory burst induced by H. pylori. These evidences imply that omeprazole may exhibit a beneficial effect on H. pylori-associated gastric mucosal damage caused by activated neutrophils.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:25:54 GMT 2025
Edited
by admin
on Mon Mar 31 21:25:54 GMT 2025
Record UNII
925R0D7W1O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESOMEPRAZOLE MAGNESIUM ANHYDROUS
Common Name English
OMEPRAZOLE S-FORM MANGESIUM SALT
MI  
Preferred Name English
MAGNESIUM, BIS(6-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL-.KAPPA.O)-1H-BENZIMIDAZOLATO-.KAPPA.N3)-, (T-4)-
Common Name English
1H-BENZIMIDAZOLE, 5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL)SULFINYL)-, MAGNESIUM SALT
Common Name English
OMEPRAZOLE S-FORM MANGESIUM SALT [MI]
Common Name English
5-METHOXY-2-((S)-((4-METHOXY-3,5-DIMETHYL-2-PYRIDYL)METHYL)SULFINYL)BENZIMIDAZOLE, MAGNESIUM SALT (2:1)
Common Name English
Code System Code Type Description
PUBCHEM
9568613
Created by admin on Mon Mar 31 21:25:54 GMT 2025 , Edited by admin on Mon Mar 31 21:25:54 GMT 2025
PRIMARY
FDA UNII
925R0D7W1O
Created by admin on Mon Mar 31 21:25:54 GMT 2025 , Edited by admin on Mon Mar 31 21:25:54 GMT 2025
PRIMARY
CAS
161973-10-0
Created by admin on Mon Mar 31 21:25:54 GMT 2025 , Edited by admin on Mon Mar 31 21:25:54 GMT 2025
PRIMARY
SMS_ID
100000085059
Created by admin on Mon Mar 31 21:25:54 GMT 2025 , Edited by admin on Mon Mar 31 21:25:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID5044231
Created by admin on Mon Mar 31 21:25:54 GMT 2025 , Edited by admin on Mon Mar 31 21:25:54 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS