Identification

Name
Esomeprazole
Accession Number
DB00736  (APRD00363)
Type
Small Molecule
Groups
Approved, Investigational
Description

A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and zollinger-ellison syndrome. The drug inhibits the H(+)-K(+)-ATPase (H(+)-K(+)-exchanging ATPase) in the proton pump of gastric parietal cells. [PubChem]

Structure
Thumb
Synonyms
  • (−)-omeprazole
  • (S)-(−)-omeprazole
  • (S)-omeprazole
  • Esomeprazol
  • Ésoméprazole
  • Esomeprazolum
  • Omeprazole S-form
  • Perprazole
External IDs
A02BC05 / H 199/18
Product Ingredients
IngredientUNIICASInChI Key
Esomeprazole magnesium925R0D7W1O161973-10-0KWORUUGOSLYAGD-YPPDDXJESA-N
Esomeprazole magnesium dihydrate36H71644EQ217087-10-0DBOUSUONOXEWHU-VCKZSRROSA-N
Esomeprazole magnesium trihydrateR6DXU4WAY9217087-09-7VEVZQDGATGBLIC-UHFFFAOYSA-N
Esomeprazole sodiumL2C9GWQ43H161796-78-7RYXPMWYHEBGTRV-JIDHJSLPSA-N
Esomeprazole strontiumSCC2RK476A914613-86-8FEVPVZSYBDUVGY-YPPDDXJESA-N
Esomeprazole strontium hydrateC5N25H3803934714-36-0NCGHIAKEJNQSMS-QLGOZJDFSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act EsomeprazoleTablet, delayed release20 mgOralTeva2015-11-09Not applicableCanada
Act EsomeprazoleTablet, delayed release40 mgOralTeva2015-11-09Not applicableCanada
EsomeprazoleTablet, delayed release20 mgOralPro Doc Limitee2013-06-06Not applicableCanada
EsomeprazoleTablet, delayed release40 mgOralRanbaxy Inc.Not applicableNot applicableCanada
EsomeprazoleTablet, delayed release40 mgOralTevaNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release40 mgOralSanis Health Inc2014-09-22Not applicableCanada
EsomeprazoleTablet, delayed release40 mgOralEthypharmNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release20 mgOralRanbaxy Inc.Not applicableNot applicableCanada
EsomeprazoleTablet, delayed release40 mgOralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
EsomeprazoleTablet, delayed release20 mgOralTevaNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-esomeprazoleTablet, delayed release20 mgOralApotex Corporation2012-03-02Not applicableCanada
Apo-esomeprazoleTablet, delayed release40 mgOralApotex Corporation2011-03-07Not applicableCanada
Esomeprazole magnesiumCapsule, delayed release40 mg/1OralAscend Laboratories, LLC2017-10-20Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1Oralbryant ranch prepack2016-04-21Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralNucare Pharmaceuticals,inc.2016-04-21Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 mg/1OralNucare Pharmaceuticals,inc.2016-04-21Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralNucare Pharmaceuticals,inc.2016-04-21Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 mg/1Oralbryant ranch prepack2015-12-10Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 mg/1OralTorrent Pharmaceuticals Limited2015-10-19Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 mg/1OralDr Reddy's Laboratories2015-09-25Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Basic Care Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralL. Perrigo Company2018-01-09Not applicableUs
Berkley and Jensen Heartburn TreatmentCapsule, delayed release20 mg/1OralBJWC2017-09-25Not applicableUs
Careone Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralAmerican Sales Company2017-09-26Not applicableUs
DG Health Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralDolgencorp2017-09-22Not applicableUs
Equaline Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralSUPERVALU INC2017-09-25Not applicableUs
Equate Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralWalmart Stores2017-10-05Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralMeijer Distribution Inc2017-09-22Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralWalgreen2017-09-22Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralWalmart Stores2017-10-16Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralChain Drug Consortium2017-10-16Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Anodyne IleEsomeprazole magnesium trihydrate (40 mg/1) + Ibuprofen (100 mg/5mL) + Lidocaine (4 g/100g) + Menthol (1 g/100g)KitFortus Pharma, Llc2017-10-162018-08-27Us
Mylan-naproxen/esomeprazole MrEsomeprazole (20 mg) + Naproxen (375 mg)Tablet, delayed releaseOralMylan Pharmaceuticals2017-02-27Not applicableCanada
Mylan-naproxen/esomeprazole MrEsomeprazole (20 mg) + Naproxen (500 mg)Tablet, delayed releaseOralMylan Pharmaceuticals2017-02-10Not applicableCanada
VimovoEsomeprazole (20 mg) + Naproxen (375 mg)Tablet, delayed releaseOralAstra Zeneca2011-02-04Not applicableCanada
VimovoEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralHorizon Pharma, Inc.2014-01-01Not applicableUs
VimovoEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)Tablet, delayed releaseOralAstra Zeneca Lp2010-07-062017-03-31Us00186 0520 60 nlmimage10 c41de20f
VimovoEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralStat Rx USA2011-07-01Not applicableUs
VimovoEsomeprazole (20 mg) + Naproxen (500 mg)Tablet, delayed releaseOralAstra Zeneca2011-02-04Not applicableCanada
VimovoEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)Tablet, delayed releaseOralHorizon Pharma, Inc.2014-01-01Not applicableUs
VimovoEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralAstra Zeneca Lp2010-07-062017-03-31Us
International/Other Brands
Alenia (Delta) / Awa-Block (Usawa) / Axagon (Simesa) / Cor (Prater) / Cronopep (Biotoscana) / Emanera (Krka) / Emep (Aristopharma) / Emozul (HYGIA) / ES-OD (Piramal Healthcare) / Esmep (HYGIA) / Eso (Asiatic Lab) / Esofag (Micro Labs) / Esogastrosedol (Nova Argentia) / Esolok (Ibn Sina) / Esomarfan (Marfan) / Esomenta (RAK) / Esomep (ACI) / Esomeprazol Genfar (Genfar S.A) / Esopral (Maquifarma) / Esorest (Centaur) / Inexium paranova / Lucen (Malesci) / Nexiam (AstraZeneca)
Categories
UNII
N3PA6559FT
CAS number
119141-88-7
Weight
Average: 345.416
Monoisotopic: 345.114712179
Chemical Formula
C17H19N3O3S
InChI Key
SUBDBMMJDZJVOS-DEOSSOPVSA-N
InChI
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
IUPAC Name
5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
SMILES
COC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1

Pharmacology

Indication

For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.

Associated Conditions
Pharmacodynamics

Esomeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Esomeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase at the secretory surface of the gastric parietal cell. By doing so, it inhibits acid secretion into the gsatric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.

Mechanism of action

Esomeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, Esomeprazole blocks the final step in acid production, thus reducing gastric acidity.

TargetActionsOrganism
APotassium-transporting ATPase alpha chain 1
inhibitor
Human
Absorption

90%

Volume of distribution
  • 16 L [healthy volunteers]
Protein binding

97%

Metabolism

Mainly hepatic. Esomeprazole is completely metabolized by the cytochrome P450 system via CYP2C19 and CYP3A4. Metabolism produces inactive hydroxy and desmethyl metabolites, which have no effect on gastric acid secretion. Less than 1% of the parent drug is excreted in urine.

Route of elimination

Approximately 80% of the administered dose of esomeprazole is excreted as metabolites in urine and the remaining 20% is excreted in feces.

Half life

1-1.5 hours

Clearance
Not Available
Toxicity

Blurred vision, confusion, drowsiness, dry mouth, flushing headache, nausea, rapid heartbeat, sweating

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Esomeprazole Action PathwayDrug action
Esomeprazole Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYP2C19*2(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of esomeprazole.Details
Cytochrome P450 2C19CYP2C19*3(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of esomeprazole.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Esomeprazole.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Esomeprazole.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Esomeprazole.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Esomeprazole.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Esomeprazole.
6-Deoxyerythronolide BThe metabolism of Esomeprazole can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Esomeprazole.
AbacavirEsomeprazole may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Esomeprazole.
AbirateroneThe metabolism of Esomeprazole can be decreased when combined with Abiraterone.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

Manne Reddy, "Amorphous hydrates of esomeprazole magnesium and process for the preparation thereof." U.S. Patent US20040167173, issued August 26, 2004.

US20040167173
General References
  1. Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7. [PubMed:10886041]
  2. Klotz U: Clinical impact of CYP2C19 polymorphism on the action of proton pump inhibitors: a review of a special problem. Int J Clin Pharmacol Ther. 2006 Jul;44(7):297-302. [PubMed:16961157]
External Links
Human Metabolome Database
HMDB0005009
KEGG Drug
D07917
PubChem Compound
9568614
PubChem Substance
46504894
ChemSpider
7843323
ChEBI
50275
ChEMBL
CHEMBL1201320
Therapeutic Targets Database
DCL000524
PharmGKB
PA10075
IUPHAR
4279
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Esomeprazole
ATC Codes
M01AE52 — Naproxen and esomeprazoleA02BC05 — EsomeprazoleA02BD06 — Esomeprazole, amoxicillin and clarithromycin
AHFS Codes
  • 56:28.36 — Proton-pump Inhibitors
FDA label
Download (104 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableBone and Bones / Homeostasis1
1CompletedNot AvailableEndoscopically-Proven GERD / Reflux1
1CompletedNot AvailableHealthy Volunteers3
1CompletedNot AvailableHealthy Volunteers / Ilaprazole / Pharmacodynamics / Pharmacokinetics1
1CompletedNot AvailableUlcers / Upper GI Symptoms1
1CompletedBasic ScienceArthritis1
1CompletedBasic ScienceBioequivalence Study2
1CompletedBasic ScienceBioequivalence / Healthy Volunteers1
1CompletedBasic ScienceGastro-esophageal Reflux Disease (GERD)1
1CompletedBasic ScienceHealthy Volunteers10
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of Isavuconazole1
1CompletedBasic ScienceJuvenile Idiopathic Arthritis (JIA)1
1CompletedOtherHealthy Participants1
1CompletedPreventionPeptic Ulcers1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentDose Finding Study1
1CompletedTreatmentGastro-esophageal Reflux Disease (GERD)3
1CompletedTreatmentHealthy Volunteers5
1CompletedTreatmentMalignant Lymphomas / Tumors, Solid1
1CompletedTreatmentPharmacokinetics1
1CompletedTreatmentPulmonary Arterial Hypertension (PAH) / Pulmonary Hypertension (PH)1
1Enrolling by InvitationTreatmentHealthy Volunteers1
1Not Yet RecruitingBasic ScienceHealthy Volunteers1
1Not Yet RecruitingOtherNeoplasms, Advanced Solid1
1RecruitingBasic ScienceHealthy Male Volunteers / Pharmacodynamics / Pharmacokinetics1
1TerminatedNot AvailablePeptic Ulcer Disease1
1TerminatedTreatmentExercise Triggered Asthma / Reflux, Gastroesophageal1
1TerminatedTreatmentPancreatitis, Chronic1
1Unknown StatusTreatmentEsophagitis / Esophagus, Barrett / Reflux1
1, 2CompletedDiagnosticTooth Erosion1
1, 2CompletedTreatmentHealthy Volunteers With Ileostomy1
1, 2Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD) / Heartburn / Indigestion1
2CompletedDiagnosticGastro-esophageal Reflux Disease (GERD) / Reflux, Gastroesophageal1
2CompletedPreventionEsophageal Cancers / Esophagus, Barrett1
2CompletedPreventionPeptic Ulcers1
2CompletedTreatmentAsthma Bronchial1
2CompletedTreatmentAsthma Bronchial / Gastro-esophageal Reflux Disease (GERD)1
2CompletedTreatmentCancer, Breast / Neoplasms Metastasis1
2CompletedTreatmentErosive Esophagitis(EE) / Gastro-esophageal Reflux Disease (GERD)1
2CompletedTreatmentErosive Gastroesophageal Reflux Disease1
2CompletedTreatmentEsophagitis1
2CompletedTreatmentGram-Negative Bacterial Infections / Helicobacter Infections / Indigestion1
2CompletedTreatmentIndigestion2
2CompletedTreatmentNon-erosive Reflux Disease (NERD)1
2CompletedTreatmentReflux Esophagitis (RE)1
2CompletedTreatmentReflux, Gastroesophageal2
2Not Yet RecruitingTreatmentAcid Dyspepsia / Gastritis1
2Not Yet RecruitingTreatmentKnee Replacement Surgery / Manipulation1
2RecruitingPreventionPain, Neuropathic1
2RecruitingTreatmentAutism Spectrum Conditions/Disorders1
2RecruitingTreatmentGastrointestinal Erosions and/or Ulcers1
2TerminatedTreatmentCystic Fibrosis (CF)1
2TerminatedTreatmentGastro-esophageal Reflux Disease (GERD)1
2TerminatedTreatmentHemorrhage, Gastrointestinal1
2Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
2, 3CompletedTreatmentEE / Gastro-esophageal Reflux Disease (GERD) / Oesophagitis, Eosinophilic1
2, 3RecruitingTreatmentHepatic Encephalopathy1
2, 3RecruitingTreatmentPreeclampsia1
2, 3Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
3Active Not RecruitingPreventionEsophageal Cancers / Precancerous Conditions1
3CompletedNot AvailableAirway Responsiveness1
3CompletedPreventionBack Pain Lower Back / Duodenal Ulcer / Gastric Ulcer (GU) / Osteoarthritis (OA) / Rheumatoid Arthritis2
3CompletedPreventionDuodenal Ulcer / Gastric Ulcer (GU)1
3CompletedPreventionERCP / Haemorrhage1
3CompletedPreventionHemorrhage, Gastrointestinal1
3CompletedPreventionNSAID Associated Gastric Ulcers2
3CompletedPreventionPeptic ulcer haemorrhage1
3CompletedPreventionPrevention1
3CompletedPreventionReflux, Gastroesophageal1
3CompletedPreventionStress Ulcer Prophylaxis1
3CompletedTreatmentArthritis / Bleeding Ulcers1
3CompletedTreatmentAsthma Bronchial1
3CompletedTreatmentAsthma Bronchial / Chronic Lung Diseases / Lung Diseases, Obstructive1
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
3CompletedTreatmentDyslipidemia (Fredrickson Type Ⅱa)1
3CompletedTreatmentErosive Esophagitis(EE)2
3CompletedTreatmentGastric Ulcer (GU)4
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD)9
3CompletedTreatmentGastrointestinal Diseases / Indigestion / Signs and Symptoms, Digestive2
3CompletedTreatmentHaemorrhage / Peptic Ulcers1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentHeartburn2
3CompletedTreatmentHeartburn / Indigestion / Reflux, Gastroesophageal1
3CompletedTreatmentHemorrhage, Gastrointestinal1
3CompletedTreatmentNSAID Associated Gastric Ulcers2
3CompletedTreatmentNSAIDs / Upper GI Symptoms2
3CompletedTreatmentOsteoarthritis (OA)2
3CompletedTreatmentReflux Esophagitis (RE)2
3CompletedTreatmentReflux, Gastroesophageal2
3CompletedTreatmentReflux, Gastroesophageal / Thoracic Pain1
3CompletedTreatmentSymptomatic Gastroesophageal Reflux Disease (sGERD)1
3CompletedTreatmentType 2 Diabetes Mellitus1
3CompletedTreatmentZollinger-Ellison Syndrome1
3Not Yet RecruitingPreventionProphylaxis of preeclampsia1
3Not Yet RecruitingTreatmentSepsis / Shock, Septic1
3RecruitingPreventionDuodenal Ulcer / Gastric Ulcer (GU) / Reflux Esophagitis (RE)1
3RecruitingTreatmentAcute and Chronic Inflammation / Indigestion1
3RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
3RecruitingTreatmentDry Eye Syndrome (DES) / Ophthalmopathy, Thyroid-Associated1
3RecruitingTreatmentErosive Esophagitis (EE)1
3RecruitingTreatmentIndigestion1
3TerminatedTreatmentGastric Ulcer (GU)1
3TerminatedTreatmentNausea1
3Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastritis Chronic1
3Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
3Unknown StatusTreatmentLymphocytic Gastritis1
3WithdrawnTreatmentGastro-esophageal Reflux Disease (GERD)1
3WithdrawnTreatmentLarynx Disease1
4Active Not RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4Active Not RecruitingTreatmentReflux, Gastroesophageal1
4CompletedNot AvailableErosive Esophagitis(EE) / Gastro-esophageal Reflux Disease (GERD) / Reflux Esophagitis (RE)1
4CompletedNot AvailableHealthy Volunteers2
4CompletedBasic ScienceHeartburn1
4CompletedDiagnosticBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4CompletedDiagnosticGastro-esophageal Reflux Disease (GERD)1
4CompletedDiagnosticReflux, Gastroesophageal1
4CompletedPreventionAbdominal Pain (AP) / Nausea / Vomiting1
4CompletedPreventionPostoperative Bariatric Surgery1
4CompletedPreventionUlcers1
4CompletedSupportive CareImpacted Third Molar Tooth / Other Surgical Procedures / Pain NOS1
4CompletedTreatmentAcid Regurgitation / Heartburn / Nausea / Upper Abdominal Pain1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)5
4CompletedTreatmentChronic Posterior Laryngitis (CPL)1
4CompletedTreatmentColorectal Cancers1
4CompletedTreatmentCoughing / Gastro-esophageal Reflux Disease (GERD)1
4CompletedTreatmentCritically Ill Patients / Indication for Stress Ulcer Prophylaxis1
4CompletedTreatmentErosive Esophagitis(EE)3
4CompletedTreatmentErosive Esophagitis(EE) / Gastro-esophageal Reflux Disease (GERD) / Non-erosive Esophagitis1
4CompletedTreatmentEsophagus, Barrett3
4CompletedTreatmentFunctional Dyspepsia / Helicobacter Pylori / Peptic Ulcers1
4CompletedTreatmentGastric Ulcer (GU)1
4CompletedTreatmentGastritis Chronic / Non Erosive Reflux Disease1
4CompletedTreatmentGastritis / Indigestion / Peptic Ulcers1
4CompletedTreatmentGastro-Oesophageal Reflux1
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD)15
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD) / Heartburn1
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD) / Reflux Esophagitis (RE)1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHeartburn2
4CompletedTreatmentHeartburn / Reflux, Gastroesophageal1
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentHelicobacter Infections1
4CompletedTreatmentIndigestion2
4CompletedTreatmentJuvenile Idiopathic Arthritis (JIA)1
4CompletedTreatmentNSAID Induced Gastropathy1
4CompletedTreatmentOsteoporosis1
4CompletedTreatmentPeptic Ulcer Bleeding1
4CompletedTreatmentReflux, Gastroesophageal2
4CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
4CompletedTreatmentSchizophrenic Disorders1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Not Yet RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4Not Yet RecruitingTreatmentPsoriasis1
4RecruitingDiagnosticIndigestion / Reflux, Gastroesophageal1
4RecruitingPreventionAcid-related Symptoms / Stomach Diseases1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)10
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastric Ulcer (GU) / Gastritis / Gastritis Chronic / Malignant Neoplasm of Stomach1
4RecruitingTreatmentIndigestion1
4RecruitingTreatmentOsteoarthritis (OA)1
4TerminatedTreatmentIndigestion1
4Unknown StatusScreening30 Healthy People1
4Unknown StatusTreatmentAspirin / Indigestion1
4Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD) / Heartburn / Sleep Disturbances1
4Unknown StatusTreatmentGastroesophageal Refluxdisease / Indigestion / Ulcers1
4Unknown StatusTreatmentHealthy Volunteers1
4Unknown StatusTreatmentNonulcer Dyspepsia1
4Unknown StatusTreatmentPeptic Ulcers1
4Unknown StatusTreatmentUpper Gastrointestinal Hemorrhage2
4WithdrawnPreventionAnastomotic Stricture / Obesity, Morbid1
4WithdrawnTreatmentLaryngopharyngeal Reflux1
4WithdrawnTreatmentPeptic Ulcers1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableGastro-esophageal Reflux Disease (GERD) / Quality of Life1
Not AvailableCompletedNot AvailablePharmacokinetics / Voriconazole1
Not AvailableCompletedBasic ScienceReflux, Gastroesophageal1
Not AvailableCompletedDiagnosticGastro-esophageal Reflux Disease (GERD)2
Not AvailableCompletedHealth Services ResearchGastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedPreventionStomach Neoplasms1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
Not AvailableCompletedTreatmentGastritis1
Not AvailableCompletedTreatmentLaryngopharyngeal Reflux / Oesophageal pH-impedance1
Not AvailableCompletedTreatmentOesophagitis, Eosinophilic1
Not AvailableCompletedTreatmentReflux, Gastroesophageal1
Not AvailableCompletedTreatmentTreatment of Helicobacter Pylori1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentVasomotor Rhinitis1
Not AvailableNot Yet RecruitingNot AvailableGastro-esophageal Reflux Disease (GERD)1
Not AvailableNot Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableNot Yet RecruitingTreatmentGastro-esophageal Reflux Disease (GERD)1
Not AvailableNot Yet RecruitingTreatmentPreeclampsia1
Not AvailableNot Yet RecruitingTreatmentProphylaxis of preeclampsia1
Not AvailableRecruitingNot AvailableReflux, Gastroesophageal1
Not AvailableRecruitingDiagnosticNon-erosive Reflux Disease (NERD)1
Not AvailableRecruitingDiagnosticNon-erosive Reflux Disease (NERD) / Reflux, Gastroesophageal1
Not AvailableRecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableRecruitingTreatmentGastric Peroral Endoscopic Pyloromyotomy (G-POEM)1
Not AvailableRecruitingTreatmentHelicobacter Infection1
Not AvailableTerminatedDiagnosticAchalasia / GORD1
Not AvailableTerminatedPreventionEsophagus, Barrett1
Not AvailableTerminatedTreatmentDuodenal Ulcer Induced by Anti-platelet Agent / Gastric Ulcer Induced by Anti-platelet Agent / OGD1
Not AvailableTerminatedTreatmentGastro-Esophageal Reflux1
Not AvailableUnknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableUnknown StatusTreatmentHemostasis / Hexacapron / Rebleeding / The Mortality Rate / Upper Gastrointestinal Hemorrhage1

Pharmacoeconomics

Manufacturers
  • Astrazeneca lp
Packagers
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Cardinal Health
  • Direct Pharmaceuticals Inc.
  • Diversified Healthcare Services Inc.
  • Innoviant Pharmacy Inc.
  • Lake Erie Medical and Surgical Supply
  • Merck & Co.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Rebel Distributors Corp.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
Dosage forms
FormRouteStrength
Kit
Capsule, delayed releaseOral20 1/1
Capsule, delayed releaseOral40 1/1
Capsule, delayed release pelletsOral20 mg/1
Capsule, delayed release pelletsOral40 mg/1
Injection, powder, lyophilized, for solutionIntravenous20 mg/1
Injection, powder, lyophilized, for solutionIntravenous20 mg/5mL
Injection, powder, lyophilized, for solutionIntravenous40 mg/1
Injection, powder, lyophilized, for solutionIntravenous40 mg/5mL
Capsule, delayed releaseOral24.65 mg/1
Capsule, delayed releaseOral49.3 mg/1
Capsule, delayed releaseOral20 mg/1
Capsule, delayed releaseOral40 mg/1
Granule, delayed releaseOral10 mg/1
Granule, delayed releaseOral10 mg
Granule, delayed releaseOral2.5 mg/1
Granule, delayed releaseOral20 mg/1
Granule, delayed releaseOral40 mg/1
Granule, delayed releaseOral5 mg/1
Tablet, delayed releaseOral20 mg
Tablet, delayed releaseOral40 mg
TabletOral20 mg/1
InjectionIntravenous20 mg/5mL
InjectionIntravenous40 mg/5mL
Kit20 mg/1
Capsule, delayed releaseOral20 mg
Capsule, delayed releaseOral40 mg
Tablet, delayed releaseOral
Prices
Unit descriptionCostUnit
Nexium i.v. 20 mg vial33.91USD vial
Nexium i.v. 40 mg vial33.91USD vial
NexIUM 20 mg Delayed Release Capsule6.76USD capsule
NexIUM 40 mg Delayed Release Capsule6.76USD capsule
Nexium 10 mg packet6.5USD each
Nexium 20 mg capsule6.5USD capsule
Nexium 20 mg packet6.5USD each
Nexium 40 mg capsule6.5USD capsule
Nexium 40 mg packet6.5USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5877192No1994-05-272014-05-27Us
CA1338377No1996-06-112013-06-11Canada
CA2346988No2009-02-102019-11-03Canada
US6191148Yes1999-04-092019-04-09Us
US6147103Yes1999-04-092019-04-09Us
US6166213Yes1999-04-092019-04-09Us
US5900424Yes1996-11-042016-11-04Us
US6369085Yes1998-11-252018-11-25Us
US6428810Yes2000-05-032020-05-03Us
US7411070Yes1998-11-252018-11-25Us
US8466175Yes1998-11-252018-11-25Us
US8852636No2002-05-312022-05-31Us
US8858996No2002-05-312022-05-31Us
US6926907No2003-02-282023-02-28Us
US7745466No1998-10-132018-10-13Us
US9161920No2002-05-312022-05-31Us
US9198888No2002-05-312022-05-31Us
US8945621No2011-10-172031-10-17Us
US8557285No2002-05-312022-05-31Us
US9220698No2011-03-102031-03-10Us
US5714504Yes1995-08-032015-08-03Us
US9345695No2002-05-312022-05-31Us
US9393208No2009-09-032029-09-03Us
US9707181No2002-05-312022-05-31Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)155 °CNot Available
water solubilityVery slightly soluble in waterNot Available
logP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.353 mg/mLALOGPS
logP1.66ALOGPS
logP2.43ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
pKa (Strongest Basic)4.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.1 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.66 m3·mol-1ChemAxon
Polarizability35.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9968
Blood Brain Barrier-0.6326
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5573
P-glycoprotein inhibitor IInhibitor0.6622
P-glycoprotein inhibitor IINon-inhibitor0.968
Renal organic cation transporterNon-inhibitor0.542
CYP450 2C9 substrateNon-substrate0.7838
CYP450 2D6 substrateSubstrate0.6175
CYP450 3A4 substrateSubstrate0.6901
CYP450 1A2 substrateInhibitor0.7505
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7895
Ames testNon AMES toxic0.5692
CarcinogenicityNon-carcinogens0.8318
BiodegradationNot ready biodegradable0.9778
Rat acute toxicity2.2254 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.719
hERG inhibition (predictor II)Non-inhibitor0.8977
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Sulfinylbenzimidazoles
Direct Parent
Sulfinylbenzimidazoles
Alternative Parents
Anisoles / Methylpyridines / Alkyl aryl ethers / Imidazoles / Heteroaromatic compounds / Sulfoxides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 2 more
Substituents
Sulfinylbenzimidazole / Anisole / Alkyl aryl ether / Methylpyridine / Pyridine / Benzenoid / Azole / Imidazole / Heteroaromatic compound / Sulfoxide
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
5-methoxy-2-\{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl\}-1H-benzimidazole (CHEBI:50275)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sodium:potassium-exchanging atpase activity
Specific Function
Catalyzes the hydrolysis of ATP coupled with the exchange of H(+) and K(+) ions across the plasma membrane. Responsible for acid production in the stomach.
Gene Name
ATP4A
Uniprot ID
P20648
Uniprot Name
Potassium-transporting ATPase alpha chain 1
Molecular Weight
114117.74 Da
References
  1. Saccar CL: The pharmacology of esomeprazole and its role in gastric acid related diseases. Expert Opin Drug Metab Toxicol. 2009 Sep;5(9):1113-24. doi: 10.1517/17425250903124363. [PubMed:19606942]
  2. McKeage K, Blick SK, Croxtall JD, Lyseng-Williamson KA, Keating GM: Esomeprazole: a review of its use in the management of gastric acid-related diseases in adults. Drugs. 2008;68(11):1571-607. [PubMed:18627213]
  3. Vachhani R, Olds G, Velanovich V: Esomeprazole: a proton pump inhibitor. Expert Rev Gastroenterol Hepatol. 2009 Feb;3(1):15-27. doi: 10.1586/17474124.3.1.15. [PubMed:19210109]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Klotz U: Clinical impact of CYP2C19 polymorphism on the action of proton pump inhibitors: a review of a special problem. Int J Clin Pharmacol Ther. 2006 Jul;44(7):297-302. [PubMed:16961157]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da

Drug created on June 13, 2005 07:24 / Updated on November 14, 2018 13:02