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 release40 mgOralRanbaxy Inc.Not applicableNot applicableCanada
EsomeprazoleTablet, delayed release40 mgOralPro Doc Limitee2012-11-22Not applicableCanada
EsomeprazoleTablet, delayed release20 mgOralEthypharmNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release40 mgOralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
EsomeprazoleTablet, delayed release40 mgOralSanis Health Inc2014-09-22Not applicableCanada
EsomeprazoleTablet, delayed release40 mgOralEthypharmNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release20 mgOralTevaNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release20 mgOralPro Doc Limitee2013-06-06Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-esomeprazoleTablet, delayed release40 mgOralApotex Corporation2011-03-07Not applicableCanada
Apo-esomeprazoleTablet, delayed release20 mgOralApotex Corporation2012-03-02Not applicableCanada
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralCamber Pharmaceuticals2015-09-21Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 1/1OralLake Erie Medical Dba Quality Care Produts Llc2015-10-19Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 mg/1OralTeva2015-02-17Not applicableUs00093 6451 56 nlmimage10 54402a41
Esomeprazole MagnesiumCapsule, delayed release pellets40 mg/1OralMylan Institutional2016-05-31Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 mg/1OralAurobindo Pharma2016-04-21Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 mg/1OralA S Medication Solutions2015-12-102017-06-20Us
Esomeprazole MagnesiumCapsule, delayed release20 1/1OralTorrent Pharmaceuticals Limited2015-10-19Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release pellets20 mg/1OralMylan Institutional2016-06-01Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
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/1OralSupervalu2017-09-25Not applicableUs
Equate Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralWalmart Stores2017-10-05Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralChain Drug Consortium2017-10-16Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralWalmart Stores2017-10-16Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralRite Aid2017-09-22Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralWalgreen2017-09-22Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralMeijer Distribution2017-09-22Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Esomeprazole magnesiumCapsule, delayed release20 mg/1OralAscend Laboratories, LLC2017-10-20Not applicableUs
Esomeprazole magnesiumCapsule, delayed release40 mg/1OralAscend Laboratories, LLC2017-10-20Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralHarris Teeter2017-10-16Not applicableUs
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)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Mylan-naproxen/esomeprazole MrEsomeprazole (20 mg) + Naproxen (500 mg)Tablet, delayed releaseOralMylan Pharmaceuticals2017-02-10Not applicableCanada
Mylan-naproxen/esomeprazole MrEsomeprazole (20 mg) + Naproxen (375 mg)Tablet, delayed releaseOralMylan Pharmaceuticals2017-02-27Not applicableCanada
VimovoEsomeprazole (20 mg) + Naproxen (375 mg)Tablet, delayed releaseOralAstra Zeneca2011-02-04Not applicableCanada
VimovoEsomeprazole magnesium (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralStat Rx USA2011-07-01Not applicableUs
VimovoEsomeprazole magnesium (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralHorizon Pharma, Inc.2014-01-01Not applicableUs
VimovoEsomeprazole (20 mg) + Naproxen (500 mg)Tablet, delayed releaseOralAstra Zeneca2011-02-04Not applicableCanada
VimovoEsomeprazole magnesium (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralAstra Zeneca Lp2010-07-062017-03-31Us
VimovoEsomeprazole magnesium (20 mg/1) + Naproxen (500 mg/1)Tablet, delayed releaseOralHorizon Pharma, Inc.2014-01-01Not applicableUs
VimovoEsomeprazole magnesium (20 mg/1) + Naproxen (500 mg/1)Tablet, delayed releaseOralAstra Zeneca Lp2010-07-062017-03-31Us00186 0520 60 nlmimage10 c41de20f
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)[[email protected]@](=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.

Structured Indications
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
DrugInteractionDrug group
AbirateroneThe metabolism of Esomeprazole can be decreased when combined with Abiraterone.Approved
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Esomeprazole.Approved
AdinazolamThe metabolism of Adinazolam can be decreased when combined with Esomeprazole.Approved
Alendronic acidThe therapeutic efficacy of Alendronic acid can be decreased when used in combination with Esomeprazole.Approved
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Esomeprazole.Approved, Investigational
AmbrisentanThe metabolism of Ambrisentan can be decreased when combined with Esomeprazole.Approved, Investigational
AminophenazoneThe metabolism of Aminophenazone can be decreased when combined with Esomeprazole.Approved, Withdrawn
AmiodaroneThe metabolism of Esomeprazole can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Esomeprazole.Approved
AmoxicillinThe metabolism of Amoxicillin can be decreased when combined with Esomeprazole.Approved, Vet Approved
AmphetamineEsomeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Illicit
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Esomeprazole.Approved
ApixabanThe metabolism of Apixaban can be decreased when combined with Esomeprazole.Approved
AprepitantThe serum concentration of Esomeprazole can be increased when it is combined with Aprepitant.Approved, Investigational
ArformoterolThe metabolism of Arformoterol can be decreased when combined with Esomeprazole.Approved, Investigational
ArmodafinilThe metabolism of Esomeprazole can be decreased when combined with Armodafinil.Approved, Investigational
ArtemetherThe metabolism of Artemether can be decreased when combined with Esomeprazole.Approved
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Esomeprazole.Approved, Investigational
AtomoxetineThe metabolism of Esomeprazole can be decreased when combined with Atomoxetine.Approved
AxitinibThe metabolism of Axitinib can be decreased when combined with Esomeprazole.Approved, Investigational
AzelastineThe metabolism of Azelastine can be decreased when combined with Esomeprazole.Approved
BenzatropineThe metabolism of Benzatropine can be decreased when combined with Esomeprazole.Approved
BoceprevirThe metabolism of Esomeprazole can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Esomeprazole can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Esomeprazole can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Esomeprazole.Approved
BrivaracetamThe metabolism of Brivaracetam can be decreased when combined with Esomeprazole.Approved, Investigational
BromazepamThe metabolism of Bromazepam can be decreased when combined with Esomeprazole.Approved, Illicit
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Esomeprazole.Approved
BupivacaineThe metabolism of Bupivacaine can be decreased when combined with Esomeprazole.Approved, Investigational
CarbamazepineThe metabolism of Esomeprazole can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Esomeprazole.Approved
CarisoprodolThe metabolism of Carisoprodol can be decreased when combined with Esomeprazole.Approved
CefditorenThe serum concentration of Cefditoren can be decreased when it is combined with Esomeprazole.Approved
CeritinibThe serum concentration of Esomeprazole can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Esomeprazole can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChlorpropamideThe metabolism of Chlorpropamide can be decreased when combined with Esomeprazole.Approved
CholecalciferolThe metabolism of Esomeprazole can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Esomeprazole.Approved
CimetidineThe metabolism of Esomeprazole can be decreased when combined with Cimetidine.Approved
CisaprideThe metabolism of Cisapride can be decreased when combined with Esomeprazole.Approved, Investigational, Withdrawn
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Esomeprazole.Approved
ClarithromycinThe metabolism of Esomeprazole can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Esomeprazole can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Clobazam can be decreased when combined with Esomeprazole.Approved, Illicit
Clodronic AcidThe therapeutic efficacy of Clodronic Acid can be decreased when used in combination with Esomeprazole.Approved, Investigational, Vet Approved
clomethiazoleThe metabolism of clomethiazole can be decreased when combined with Esomeprazole.Investigational
ClomipramineThe metabolism of Clomipramine can be decreased when combined with Esomeprazole.Approved, Vet Approved
ClopidogrelEsomeprazole may decrease the antiplatelet activities of Clopidogrel.Approved, Nutraceutical
ClorindioneThe serum concentration of Clorindione can be increased when it is combined with Esomeprazole.Experimental
ClotiazepamThe metabolism of Clotiazepam can be decreased when combined with Esomeprazole.Approved, Illicit
ClotrimazoleThe metabolism of Esomeprazole can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Clozapine can be decreased when combined with Esomeprazole.Approved
CobicistatThe metabolism of Esomeprazole can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Esomeprazole can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Esomeprazole can be decreased when combined with Crizotinib.Approved
CyclophosphamideThe metabolism of Cyclophosphamide can be decreased when combined with Esomeprazole.Approved, Investigational
CyclosporineThe metabolism of Esomeprazole can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CysteamineThe therapeutic efficacy of Cysteamine can be decreased when used in combination with Esomeprazole.Approved, Investigational
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be reduced when Dabigatran etexilate is used in combination with Esomeprazole resulting in a loss in efficacy.Approved
DabrafenibThe serum concentration of Dabrafenib can be decreased when it is combined with Esomeprazole.Approved
DapsoneThe metabolism of Dapsone can be decreased when combined with Esomeprazole.Approved, Investigational
DarunavirThe metabolism of Esomeprazole can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Esomeprazole can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Esomeprazole can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Esomeprazole.Approved
DesipramineThe metabolism of Desipramine can be decreased when combined with Esomeprazole.Approved
DexlansoprazoleThe metabolism of Dexlansoprazole can be decreased when combined with Esomeprazole.Approved
DexmethylphenidateEsomeprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved
DextroamphetamineEsomeprazole can cause an increase in the absorption of Dextroamphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Illicit
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Esomeprazole.Approved
DiazepamThe metabolism of Diazepam can be decreased when combined with Esomeprazole.Approved, Illicit, Vet Approved
DiclofenacThe metabolism of Diclofenac can be decreased when combined with Esomeprazole.Approved, Vet Approved
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Esomeprazole.Approved
DihydroergotamineThe metabolism of Esomeprazole can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Esomeprazole can be decreased when combined with Diltiazem.Approved
DiphenadioneThe serum concentration of Diphenadione can be increased when it is combined with Esomeprazole.Experimental
DiphenhydramineThe metabolism of Diphenhydramine can be decreased when combined with Esomeprazole.Approved
DopamineThe metabolism of Dopamine can be decreased when combined with Esomeprazole.Approved
DoxazosinThe metabolism of Doxazosin can be decreased when combined with Esomeprazole.Approved
DoxepinThe metabolism of Doxepin can be decreased when combined with Esomeprazole.Approved
DoxycyclineThe metabolism of Esomeprazole can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronabinolThe metabolism of Dronabinol can be decreased when combined with Esomeprazole.Approved, Illicit
DronedaroneThe metabolism of Esomeprazole can be decreased when combined with Dronedarone.Approved
EfavirenzThe metabolism of Esomeprazole can be decreased when combined with Efavirenz.Approved, Investigational
EletriptanThe metabolism of Eletriptan can be decreased when combined with Esomeprazole.Approved, Investigational
EnasidenibThe metabolism of Enasidenib can be decreased when combined with Esomeprazole.Approved
EnfuvirtideThe metabolism of Enfuvirtide can be decreased when combined with Esomeprazole.Approved, Investigational
EnzalutamideThe serum concentration of Esomeprazole can be decreased when it is combined with Enzalutamide.Approved
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Esomeprazole.Approved, Investigational
ErythromycinThe metabolism of Esomeprazole can be decreased when combined with Erythromycin.Approved, Vet Approved
EscitalopramThe metabolism of Escitalopram can be decreased when combined with Esomeprazole.Approved, Investigational
Eslicarbazepine acetateThe metabolism of Esomeprazole can be decreased when combined with Eslicarbazepine acetate.Approved
EstradiolThe metabolism of Estradiol can be decreased when combined with Esomeprazole.Approved, Investigational, Vet Approved
Ethyl biscoumacetateThe serum concentration of Ethyl biscoumacetate can be increased when it is combined with Esomeprazole.Withdrawn
Etidronic acidThe therapeutic efficacy of Etidronic acid can be decreased when used in combination with Esomeprazole.Approved
EtizolamThe metabolism of Etizolam can be decreased when combined with Esomeprazole.Approved
EtravirineThe metabolism of Etravirine can be decreased when combined with Esomeprazole.Approved
FamotidineThe metabolism of Famotidine can be decreased when combined with Esomeprazole.Approved
Ferric CarboxymaltoseEsomeprazole can cause a decrease in the absorption of Ferric Carboxymaltose resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Ferric CitrateEsomeprazole can cause a decrease in the absorption of Ferric Citrate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Investigational
Ferric pyrophosphateEsomeprazole can cause a decrease in the absorption of Ferric pyrophosphate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
FluconazoleThe serum concentration of Esomeprazole can be increased when it is combined with Fluconazole.Approved
FluindioneThe serum concentration of Fluindione can be increased when it is combined with Esomeprazole.Investigational
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Esomeprazole.Approved, Illicit
FluoxetineThe metabolism of Fluoxetine can be decreased when combined with Esomeprazole.Approved, Vet Approved
FlutamideThe metabolism of Flutamide can be decreased when combined with Esomeprazole.Approved
FluvoxamineThe metabolism of Esomeprazole can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolThe metabolism of Formoterol can be decreased when combined with Esomeprazole.Approved, Investigational
FosamprenavirThe metabolism of Esomeprazole can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Esomeprazole can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Esomeprazole can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Esomeprazole can be increased when it is combined with Fusidic Acid.Approved
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Esomeprazole.Approved, Investigational
GemfibrozilThe metabolism of Esomeprazole can be decreased when combined with Gemfibrozil.Approved
GliclazideThe metabolism of Gliclazide can be decreased when combined with Esomeprazole.Approved
GlucosamineThe metabolism of Glucosamine can be decreased when combined with Esomeprazole.Approved
GlyburideThe metabolism of Glyburide can be decreased when combined with Esomeprazole.Approved
GuanfacineThe metabolism of Guanfacine can be decreased when combined with Esomeprazole.Approved, Investigational
HaloperidolThe metabolism of Haloperidol can be decreased when combined with Esomeprazole.Approved
HexobarbitalThe metabolism of Hexobarbital can be decreased when combined with Esomeprazole.Approved
IbandronateThe therapeutic efficacy of Ibandronate can be decreased when used in combination with Esomeprazole.Approved, Investigational
IbuprofenThe metabolism of Ibuprofen can be decreased when combined with Esomeprazole.Approved
IdelalisibThe serum concentration of Esomeprazole can be increased when it is combined with Idelalisib.Approved
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Esomeprazole.Approved
ImatinibThe metabolism of Esomeprazole can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Imipramine can be decreased when combined with Esomeprazole.Approved
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Esomeprazole.Approved
IndomethacinThe metabolism of Indomethacin can be decreased when combined with Esomeprazole.Approved, Investigational
IronEsomeprazole can cause a decrease in the absorption of Iron resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Iron DextranEsomeprazole can cause a decrease in the absorption of Iron Dextran resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
Iron saccharateEsomeprazole can cause a decrease in the absorption of Iron saccharate resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
IsavuconazoniumThe metabolism of Esomeprazole can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Esomeprazole can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Esomeprazole can be decreased when combined with Isradipine.Approved
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Esomeprazole.Approved, Investigational
IvacaftorThe serum concentration of Esomeprazole can be increased when it is combined with Ivacaftor.Approved
IxazomibThe metabolism of Ixazomib can be decreased when combined with Esomeprazole.Approved
KetobemidoneThe metabolism of Ketobemidone can be decreased when combined with Esomeprazole.Approved, Investigational
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Esomeprazole.Approved, Investigational
LansoprazoleThe metabolism of Lansoprazole can be decreased when combined with Esomeprazole.Approved, Investigational
LapatinibThe metabolism of Lapatinib can be decreased when combined with Esomeprazole.Approved, Investigational
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Esomeprazole.Approved
LevomilnacipranThe metabolism of Levomilnacipran can be decreased when combined with Esomeprazole.Approved
LobeglitazoneThe metabolism of Esomeprazole can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Esomeprazole can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Lorcaserin can be decreased when combined with Esomeprazole.Approved
LovastatinThe metabolism of Esomeprazole can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Esomeprazole can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Esomeprazole can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibThe metabolism of Lumiracoxib can be decreased when combined with Esomeprazole.Approved, Investigational
MacitentanThe metabolism of Macitentan can be decreased when combined with Esomeprazole.Approved
MelatoninThe metabolism of Melatonin can be decreased when combined with Esomeprazole.Approved, Nutraceutical, Vet Approved
MephenytoinThe metabolism of Mephenytoin can be decreased when combined with Esomeprazole.Investigational, Withdrawn
MeprobamateThe metabolism of Meprobamate can be decreased when combined with Esomeprazole.Approved, Illicit
MesalazineThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Esomeprazole.Approved
MethadoneThe metabolism of Methadone can be decreased when combined with Esomeprazole.Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Esomeprazole.Approved
MethsuximideThe metabolism of Methsuximide can be decreased when combined with Esomeprazole.Approved
MethylphenidateEsomeprazole can cause an increase in the absorption of Methylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.Approved, Investigational
MethylphenobarbitalThe metabolism of Methylphenobarbital can be decreased when combined with Esomeprazole.Approved
MetoprololThe metabolism of Metoprolol can be decreased when combined with Esomeprazole.Approved, Investigational
MifepristoneThe serum concentration of Esomeprazole can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Esomeprazole can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Moclobemide can be decreased when combined with Esomeprazole.Approved
ModafinilThe metabolism of Esomeprazole can be decreased when combined with Modafinil.Approved, Investigational
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Esomeprazole.Approved
NefazodoneThe metabolism of Esomeprazole can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of the active metabolites of Nelfinavir can be reduced when Nelfinavir is used in combination with Esomeprazole resulting in a loss in efficacy.Approved
NetupitantThe serum concentration of Esomeprazole can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Esomeprazole can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Esomeprazole can be decreased when combined with Nicardipine.Approved
NicotineThe metabolism of Nicotine can be decreased when combined with Esomeprazole.Approved
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Esomeprazole.Approved, Investigational
NilutamideThe metabolism of Nilutamide can be decreased when combined with Esomeprazole.Approved
NortriptylineThe metabolism of Nortriptyline can be decreased when combined with Esomeprazole.Approved
OlaparibThe metabolism of Esomeprazole can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Esomeprazole can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Esomeprazole can be increased when it is combined with Osimertinib.Approved
OspemifeneThe metabolism of Ospemifene can be decreased when combined with Esomeprazole.Approved
OxiconazoleThe metabolism of Oxiconazole can be decreased when combined with Esomeprazole.Approved
PalbociclibThe serum concentration of Esomeprazole can be increased when it is combined with Palbociclib.Approved
PamidronateThe therapeutic efficacy of Pamidronate can be decreased when used in combination with Esomeprazole.Approved
PantoprazoleThe metabolism of Esomeprazole can be decreased when combined with Pantoprazole.Approved
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Esomeprazole.Approved
PentamidineThe metabolism of Pentamidine can be decreased when combined with Esomeprazole.Approved
PentobarbitalThe metabolism of Esomeprazole can be increased when combined with Pentobarbital.Approved, Vet Approved
PerphenazineThe metabolism of Perphenazine can be decreased when combined with Esomeprazole.Approved
PethidineThe metabolism of Pethidine can be decreased when combined with Esomeprazole.Approved
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Esomeprazole.Withdrawn
PhenindioneThe serum concentration of Phenindione can be increased when it is combined with Esomeprazole.Approved, Investigational
PhenobarbitalThe metabolism of Esomeprazole can be increased when combined with Phenobarbital.Approved
PhenprocoumonThe serum concentration of Phenprocoumon can be increased when it is combined with Esomeprazole.Approved, Investigational
PhenytoinThe metabolism of Esomeprazole can be increased when combined with Phenytoin.Approved, Vet Approved
PipotiazineThe metabolism of Pipotiazine can be decreased when combined with Esomeprazole.Approved, Investigational
PodofiloxThe metabolism of Podofilox can be decreased when combined with Esomeprazole.Approved
PosaconazoleThe serum concentration of Posaconazole can be decreased when it is combined with Esomeprazole.Approved, Investigational, Vet Approved
PrasugrelThe metabolism of Prasugrel can be decreased when combined with Esomeprazole.Approved
PraziquantelThe metabolism of Praziquantel can be decreased when combined with Esomeprazole.Approved, Vet Approved
PrimidoneThe metabolism of Esomeprazole can be increased when combined with Primidone.Approved, Vet Approved
ProgesteroneThe metabolism of Progesterone can be decreased when combined with Esomeprazole.Approved, Vet Approved
ProguanilThe metabolism of Proguanil can be decreased when combined with Esomeprazole.Approved
PromazineThe metabolism of Promazine can be decreased when combined with Esomeprazole.Approved, Vet Approved
PropofolThe metabolism of Propofol can be decreased when combined with Esomeprazole.Approved, Investigational, Vet Approved
PropranololThe metabolism of Propranolol can be decreased when combined with Esomeprazole.Approved, Investigational
QuazepamThe metabolism of Quazepam can be decreased when combined with Esomeprazole.Approved, Illicit
QuetiapineThe metabolism of Quetiapine can be decreased when combined with Esomeprazole.Approved
QuinineThe metabolism of Quinine can be decreased when combined with Esomeprazole.Approved
RabeprazoleThe metabolism of Rabeprazole can be decreased when combined with Esomeprazole.Approved, Investigational
RaltegravirThe serum concentration of Raltegravir can be increased when it is combined with Esomeprazole.Approved
RamelteonThe metabolism of Ramelteon can be decreased when combined with Esomeprazole.Approved, Investigational
RanitidineThe metabolism of Ranitidine can be decreased when combined with Esomeprazole.Approved
RanolazineThe metabolism of Esomeprazole can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Esomeprazole can be increased when combined with Rifabutin.Approved
RifampicinThe serum concentration of Esomeprazole can be decreased when it is combined with Rifampicin.Approved
RifapentineThe metabolism of Esomeprazole can be increased when combined with Rifapentine.Approved
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Esomeprazole.Approved
RiociguatThe serum concentration of Riociguat can be decreased when it is combined with Esomeprazole.Approved
RisedronateThe therapeutic efficacy of Risedronate can be decreased when used in combination with Esomeprazole.Approved, Investigational
RitonavirThe metabolism of Esomeprazole can be decreased when combined with Ritonavir.Approved, Investigational
RomidepsinThe metabolism of Romidepsin can be decreased when combined with Esomeprazole.Approved, Investigational
RosuvastatinThe metabolism of Rosuvastatin can be decreased when combined with Esomeprazole.Approved
RupatadineThe metabolism of Rupatadine can be decreased when combined with Esomeprazole.Approved
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Esomeprazole.Approved, Investigational
SelegilineThe metabolism of Selegiline can be decreased when combined with Esomeprazole.Approved, Investigational, Vet Approved
SeratrodastThe metabolism of Seratrodast can be decreased when combined with Esomeprazole.Approved
SertralineThe metabolism of Sertraline can be decreased when combined with Esomeprazole.Approved
SildenafilThe metabolism of Esomeprazole can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Esomeprazole can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Esomeprazole can be increased when it is combined with Simeprevir.Approved
St. John's WortThe serum concentration of Esomeprazole can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Esomeprazole can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Esomeprazole can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Esomeprazole.Approved, Investigational
TamoxifenThe metabolism of Tamoxifen can be decreased when combined with Esomeprazole.Approved
TapentadolThe metabolism of Tapentadol can be decreased when combined with Esomeprazole.Approved
Technetium Tc-99m etidronateThe therapeutic efficacy of Technetium Tc-99m etidronate can be decreased when used in combination with Esomeprazole.Approved
Technetium Tc-99m medronateThe therapeutic efficacy of Technetium Tc-99m medronate can be decreased when used in combination with Esomeprazole.Approved
TelaprevirThe metabolism of Esomeprazole can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Esomeprazole can be decreased when combined with Telithromycin.Approved
TemazepamThe metabolism of Temazepam can be decreased when combined with Esomeprazole.Approved
TeniposideThe metabolism of Teniposide can be decreased when combined with Esomeprazole.Approved
TerbinafineThe metabolism of Terbinafine can be decreased when combined with Esomeprazole.Approved, Investigational, Vet Approved
TestosteroneThe metabolism of Testosterone can be decreased when combined with Esomeprazole.Approved, Investigational
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Esomeprazole.Approved, Investigational, Withdrawn
ThioridazineThe metabolism of Thioridazine can be decreased when combined with Esomeprazole.Approved, Withdrawn
TiclopidineThe metabolism of Esomeprazole can be decreased when combined with Ticlopidine.Approved
Tiludronic acidThe therapeutic efficacy of Tiludronic acid can be decreased when used in combination with Esomeprazole.Approved, Investigational, Vet Approved
TimololThe metabolism of Timolol can be decreased when combined with Esomeprazole.Approved
TioclomarolThe serum concentration of Tioclomarol can be increased when it is combined with Esomeprazole.Experimental
TipranavirThe serum concentration of Esomeprazole can be decreased when it is combined with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Esomeprazole can be decreased when it is combined with Tocilizumab.Approved
TofacitinibThe metabolism of Tofacitinib can be decreased when combined with Esomeprazole.Approved, Investigational
TolbutamideThe metabolism of Tolbutamide can be decreased when combined with Esomeprazole.Approved
TolterodineThe metabolism of Tolterodine can be decreased when combined with Esomeprazole.Approved, Investigational
TopiramateThe metabolism of Esomeprazole can be decreased when combined with Topiramate.Approved
TrabectedinThe metabolism of Trabectedin can be decreased when combined with Esomeprazole.Approved, Investigational
TranylcypromineThe metabolism of Esomeprazole can be decreased when combined with Tranylcypromine.Approved
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Esomeprazole.Approved
TrimipramineThe metabolism of Trimipramine can be decreased when combined with Esomeprazole.Approved
TroglitazoneThe metabolism of Troglitazone can be decreased when combined with Esomeprazole.Investigational, Withdrawn
Valproic AcidThe metabolism of Valproic Acid can be decreased when combined with Esomeprazole.Approved, Investigational
VenlafaxineThe metabolism of Esomeprazole can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Esomeprazole can be decreased when combined with Verapamil.Approved
VoriconazoleThe serum concentration of Esomeprazole can be increased when it is combined with Voriconazole.Approved, Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Esomeprazole.Approved
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Esomeprazole.Approved
ZidovudineThe metabolism of Zidovudine can be decreased when combined with Esomeprazole.Approved
ZiprasidoneThe metabolism of Esomeprazole can be decreased when combined with Ziprasidone.Approved
Zoledronic acidThe therapeutic efficacy of Zoledronic acid can be decreased when used in combination with Esomeprazole.Approved
ZolpidemThe metabolism of Zolpidem can be decreased when combined with Esomeprazole.Approved
ZucapsaicinThe metabolism of Esomeprazole can be decreased when combined with Zucapsaicin.Approved
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]
External Links
Human Metabolome Database
HMDB14874
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
1Active Not RecruitingTreatmentPharmacokinetics / Voriconazole1
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 ScienceGastroesophageal Reflux Disease1
1CompletedBasic ScienceHealthy Volunteers9
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of Isavuconazole1
1CompletedBasic ScienceJuvenile Idiopathic Arthritis (JIA)1
1CompletedOtherHealthy Participants1
1CompletedPreventionPeptic Ulcers1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentDose Finding Study1
1CompletedTreatmentHealthy Volunteers5
1CompletedTreatmentMalignant Lymphomas / Tumors, Solid1
1CompletedTreatmentPharmacokinetics1
1CompletedTreatmentPulmonary Arterial Hypertension (PAH) / Pulmonary Hypertension (PH)1
1Enrolling by InvitationTreatmentHealthy Volunteers1
1RecruitingTreatmentGERD1
1TerminatedNot AvailablePeptic Ulcer Disease1
1TerminatedTreatmentExercise Triggered Asthma / Reflux, Gastroesophageal1
1TerminatedTreatmentPancreatitis, Chronic1
1Unknown StatusBasic ScienceHealthy Volunteers1
1Unknown StatusTreatmentEsophagitis / Esophagus, Barrett / Reflux1
1, 2CompletedDiagnosticTooth Erosion1
1, 2CompletedTreatmentHealthy Volunteers With Ileostomy1
1, 2Unknown StatusTreatmentGastroesophageal Reflux Disease (GERD) / Heartburn / Indigestion1
2CompletedDiagnosticGastroesophageal Reflux Disease / Reflux, Gastroesophageal1
2CompletedPreventionEsophageal Cancers / Esophagus, Barrett1
2CompletedPreventionPeptic Ulcers1
2CompletedTreatmentAsthma Bronchial1
2CompletedTreatmentAsthma Bronchial / GERD1
2CompletedTreatmentCancer, Breast / Neoplasms Metastasis1
2CompletedTreatmentErosive Esophagitis(EE) / GERD1
2CompletedTreatmentEsophagitis1
2CompletedTreatmentGram-Negative Bacterial Infections / Helicobacter Infections / Indigestion1
2CompletedTreatmentIndigestion2
2CompletedTreatmentNon-erosive Reflux Disease (NERD)1
2CompletedTreatmentReflux Esophagitis (RE)1
2CompletedTreatmentReflux, Gastroesophageal1
2RecruitingPreventionPain, Neuropathic1
2RecruitingTreatmentErosive Gastroesophageal Reflux Disease1
2RecruitingTreatmentGastrointestinal Erosions and/or Ulcers1
2RecruitingTreatmentReflux, Gastroesophageal1
2TerminatedTreatmentCystic Fibrosis (CF)1
2TerminatedTreatmentGastroesophageal Reflux Disease1
2TerminatedTreatmentHemorrhage, Gastrointestinal1
2Unknown StatusTreatmentGastroesophageal Reflux Disease1
2, 3CompletedTreatmentEE / Gastroesophageal Reflux Disease / GERD / Oesophagitis, Eosinophilic1
2, 3Not Yet RecruitingTreatmentPreeclampsia1
2, 3RecruitingTreatmentHepatic Encephalopathy1
2, 3Unknown StatusTreatmentGastroesophageal Reflux Disease1
3Active Not RecruitingPreventionEsophageal Cancers / Precancerous Conditions1
3CompletedNot AvailableAirway Responsiveness1
3CompletedPreventionDuodenal Ulcer / Gastric Ulcer (GU)1
3CompletedPreventionDuodenal Ulcer / Gastric Ulcer (GU) / Low Back Pain (LBP) / Rheumatoid Arthritis / Synovitis of osteoarthritis2
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
3CompletedTreatmentErosive Esophagitis(EE)2
3CompletedTreatmentGERD3
3CompletedTreatmentGastric Ulcer (GU)4
3CompletedTreatmentGastroesophageal Reflux Disease2
3CompletedTreatmentGastroesophageal Reflux Disease (GERD)4
3CompletedTreatmentGastrointestinal Diseases / Indigestion / Signs and Symptoms, Digestive2
3CompletedTreatmentHaemorrhage / Peptic Ulcers1
3CompletedTreatmentHealthy Volunteers1
3CompletedTreatmentHeartburn2
3CompletedTreatmentHeartburn / Indigestion / Reflux, Gastroesophageal1
3CompletedTreatmentHemorrhage, Gastrointestinal1
3CompletedTreatmentHypercholesterolemia, Familial1
3CompletedTreatmentNSAID Associated Gastric Ulcers2
3CompletedTreatmentNSAIDs / Upper GI Symptoms2
3CompletedTreatmentReflux Esophagitis (RE)2
3CompletedTreatmentReflux, Gastroesophageal2
3CompletedTreatmentReflux, Gastroesophageal / Thoracic Pain1
3CompletedTreatmentSymptomatic Gastroesophageal Reflux Disease (sGERD)1
3CompletedTreatmentType 2 Diabetes Mellitus1
3CompletedTreatmentZollinger-Ellison Syndrome1
3CompletedTreatmentSynovitis of osteoarthritis2
3RecruitingTreatmentAcute and Chronic Inflammation / Indigestion1
3RecruitingTreatmentDry Eye Syndrome (DES) / Ophthalmopathy, Thyroid-Associated1
3RecruitingTreatmentH. Pylori Infection1
3RecruitingTreatmentIndigestion1
3TerminatedTreatmentGastric Ulcer (GU)1
3TerminatedTreatmentNausea1
3Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Chronic Gastritis1
3Unknown StatusTreatmentGastroesophageal Reflux Disease (GERD)1
3Unknown StatusTreatmentLymphocytic Gastritis1
3WithdrawnTreatmentGastroesophageal Reflux Disease1
3WithdrawnTreatmentLarynx Disease1
4Active Not RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4CompletedNot AvailableErosive Esophagitis(EE) / Gastroesophageal Reflux Disease / Reflux Esophagitis (RE)1
4CompletedNot AvailableHealthy Volunteers2
4CompletedBasic ScienceHeartburn1
4CompletedDiagnosticBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4CompletedDiagnosticGERD1
4CompletedDiagnosticReflux, Gastroesophageal1
4CompletedPreventionAbdominal Pain (AP) / Nausea / Vomiting1
4CompletedPreventionPostoperative Bariatric Surgery1
4CompletedPreventionUlcers1
4CompletedSupportive CareImpacted Third Molar Tooth / Other Surgical Procedures / Pain1
4CompletedTreatmentAcid Regurgitation / Heartburn / Nausea / Upper Abdominal Pain1
4CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
4CompletedTreatmentChronic Gastritis / Non Erosive Reflux Disease1
4CompletedTreatmentChronic Posterior Laryngitis (CPL)1
4CompletedTreatmentColorectal Cancers1
4CompletedTreatmentCoughing / GERD1
4CompletedTreatmentCritically Ill Patients / Indication for Stress Ulcer Prophylaxis1
4CompletedTreatmentErosive Esophagitis(EE)3
4CompletedTreatmentErosive Esophagitis(EE) / Gastroesophageal Reflux Disease (GERD) / Non-erosive Esophagitis1
4CompletedTreatmentEsophagus, Barrett3
4CompletedTreatmentFunctional Dyspepsia / Helicobacter Pylori / Peptic Ulcers1
4CompletedTreatmentGERD5
4CompletedTreatmentGastroesophageal Reflux Disease / GERD / Reflux Esophagitis (RE)1
4CompletedTreatmentGastric Ulcer (GU)1
4CompletedTreatmentGastritis / Indigestion / Peptic Ulcers1
4CompletedTreatmentGastro-Oesophageal Reflux1
4CompletedTreatmentGastro-Oesophageal Reflux Disease1
4CompletedTreatmentGastroesophageal Reflux Disease7
4CompletedTreatmentGastroesophageal Reflux Disease (GERD)2
4CompletedTreatmentGastroesophageal Reflux Disease / Heartburn1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHeartburn2
4CompletedTreatmentHeartburn / Reflux, Gastroesophageal1
4CompletedTreatmentHelicobacter Infection1
4CompletedTreatmentHelicobacter Infections1
4CompletedTreatmentIndigestion2
4CompletedTreatmentJuvenile Idiopathic Arthritis (JIA)1
4CompletedTreatmentNSAID Induced Gastropathy1
4CompletedTreatmentPeptic Ulcer Bleeding1
4CompletedTreatmentReflux, Gastroesophageal2
4CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
4CompletedTreatmentSchizophrenic Disorders1
4CompletedTreatmentBone destruction1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)3
4Not Yet RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4Not Yet RecruitingTreatmentPsoriasis1
4RecruitingDiagnosticIndigestion / Reflux, Gastroesophageal1
4RecruitingPreventionAcid-related Symptoms1
4RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)5
4RecruitingTreatmentIndigestion1
4RecruitingTreatmentLaryngopharyngeal Reflux1
4RecruitingTreatmentSynovitis of osteoarthritis1
4TerminatedTreatmentIndigestion1
4Unknown StatusScreening30 Healthy People1
4Unknown StatusTreatmentAspirin / Indigestion1
4Unknown StatusTreatmentGastroesophageal Reflux Disease / 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
4WithdrawnTreatmentPeptic Ulcers1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Gastroesophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableGERD / Quality of Life1
Not AvailableCompletedBasic ScienceReflux, Gastroesophageal1
Not AvailableCompletedDiagnosticGERD1
Not AvailableCompletedDiagnosticGastroesophageal Reflux Disease1
Not AvailableCompletedHealth Services ResearchGERD1
Not AvailableCompletedPreventionStomach Neoplasms1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
Not AvailableCompletedTreatmentGastritis1
Not AvailableCompletedTreatmentLaryngopharyngeal Reflux / Oesophageal pH-impedance1
Not AvailableCompletedTreatmentOesophagitis, Eosinophilic1
Not AvailableCompletedTreatmentReflux, Gastroesophageal1
Not AvailableCompletedTreatmentTreatment of Helicobacter Pylori1
Not AvailableCompletedTreatmentVasomotor Rhinitis1
Not AvailableEnrolling by InvitationTreatmentHelicobacter Infection1
Not AvailableNot Yet RecruitingTreatmentGastroesophageal Reflux Disease1
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 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 / Mortality / Rebleeding / Upper Gastrointestinal Hemorrhage1

Pharmacoeconomics

Manufacturers
  • Astrazeneca lp
Packagers
Dosage forms
FormRouteStrength
Capsule, delayed releaseOral20 mg/1
Capsule, delayed releaseOral20 1/1
Capsule, delayed releaseOral40 1/1
Capsule, delayed releaseOral40 mg/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/5mL
Injection, powder, lyophilized, for solutionIntravenous40 mg/1
Capsule, delayed releaseOral24.65 mg/1
Capsule, delayed releaseOral49.3 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
Kit
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 16, 2017 13:31