Identification

Name
Esomeprazole
Accession Number
DB00736
Description

Esomeprazole, sold under the brand name Nexium, is a proton pump inhibitor (PPI) medication used for the management of gastroesophageal reflux disease (GERD), for gastric protection to prevent recurrence of stomach ulcers or gastric damage from chronic use of NSAIDs, and for the treatment of pathological hypersecretory conditions including Zollinger-Ellison (ZE) Syndrome. It can also be found in quadruple regimens for the treatment of H. pylori infections along with other antibiotics including Amoxicillin, Clarithromycin, and Metronidazole, for example.7,9 Its efficacy is considered similar to other medications within the PPI class including Omeprazole, Pantoprazole, Lansoprazole, Dexlansoprazole, and Rabeprazole. Esomeprazole is the s-isomer of Omeprazole, which is a racemate of the S- and R-enantiomer. Esomeprazole has been shown to inhibit acid secretion to a similar extent as Omeprazole, without any significant differences between the two compounds in vitro.

Esomeprazole exerts its stomach acid-suppressing effects by preventing the final step in gastric acid production by covalently binding to sulfhydryl groups of cysteines found on the (H+, K+)-ATPase enzyme at the secretory surface of gastric parietal cells. This effect leads to inhibition of both basal and stimulated gastric acid secretion, irrespective of the stimulus. As the binding of esomeprazole to the (H+, K+)-ATPase enzyme is irreversible and new enzyme needs to be expressed in order to resume acid secretion, esomeprazole's duration of antisecretory effect persists longer than 24 hours.Label

PPIs such as esomeprazole have also been shown to inhibit the activity of dimethylarginine dimethylaminohydrolase (DDAH), an enzyme necessary for cardiovascular health. DDAH inhibition causes a consequent accumulation of the nitric oxide synthase inhibitor asymmetric dimethylarginie (ADMA), which is thought to cause the association of PPIs with increased risk of cardiovascular events in patients with unstable coronary syndromes.3,4

Due to their good safety profile and as several PPIs are available over the counter without a prescription, their current use in North America is widespread. Long term use of PPIs such as esomeprazole has been associated with possible adverse effects, however, including increased susceptibility to bacterial infections (including gastrointestinal C. difficile), reduced absorption of micronutrients such as iron and B12, and an increased risk of developing hypomagnesemia and hypocalcemia which may contribute to osteoporosis and bone fractures later in life.5

Rapid discontinuation of PPIs such as esomeprazole may cause a rebound effect and a short term increase in hypersecretion.6 Esomeprazole doses should be slowly lowered, or tapered, before discontinuing to prevent this rebound effect.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 345.416
Monoisotopic: 345.114712179
Chemical Formula
C17H19N3O3S
Synonyms
  • (−)-omeprazole
  • (S)-(−)-omeprazole
  • (S)-omeprazole
  • Esomeprazol
  • Ésoméprazole
  • Esomeprazole
  • Esomeprazolum
  • Omeprazole S-form
  • Perprazole
External IDs
  • A02BC05
  • H 199/18

Pharmacology

Indication

Esomeprazole is indicated for the treatment of acid-reflux disorders including healing and maintenance of erosive esophagitis, and symptomatic gastroesophageal reflux disease (GERD), peptic ulcer disease, H. pylori eradication, prevention of gastrointestinal bleeds with NSAID use, and for the long-term treatment of pathological hypersecretory conditions including Zollinger-Ellison Syndrome.

Associated Conditions
Contraindications & Blackbox Warnings
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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.

Esomeprazole is the s-isomer of Omeprazole, which is a racemate of the S- and R-enantiomer. Esomeprazole has been shown to inhibit acid secretion to a similar extent as Omeprazole, without any significant differences between the two compounds in vitro.

PPIs such as esomeprazole have also been shown to inhibit the activity of dimethylarginine dimethylaminohydrolase (DDAH), an enzyme necessary for cardiovascular health. DDAH inhibition causes a consequent accumulation of the nitric oxide synthase inhibitor asymmetric dimethylarginie (ADMA), which is thought to cause the association of PPIs with increased risk of cardiovascular events in patients with unstable coronary syndromes.3,4

Due to their good safety profile and as several PPIs are available over the counter without a prescription, their current use in North America is widespread. Long term use of PPIs such as esomeprazole has been associated with possible adverse effects, however, including increased susceptibility to bacterial infections (including gastrointestinal C. difficile), reduced absorption of micronutrients including iron and B12, and an increased risk of developing hypomagnesemia and hypocalcemia which may contribute to osteoporosis and bone fractures later in life.5

Mechanism of action

Esomeprazole exerts its stomach acid-suppressing effects by preventing the final step in gastric acid production by covalently binding to sulfhydryl groups of cysteines found on the (H+, K+)-ATPase enzyme at the secretory surface of gastric parietal cells. This effect leads to inhibition of both basal and stimulated gastric acid secretion, irrespective of the stimulus. As the binding of esomeprazole to the (H+, K+)-ATPase enzyme is irreversible and new enzyme needs to be expressed in order to resume acid secretion, esomeprazole's duration of antisecretory effect that persists longer than 24 hours.Label

TargetActionsOrganism
APotassium-transporting ATPase alpha chain 1
inhibitor
Humans
UN(G),N(G)-dimethylarginine dimethylaminohydrolase 1Not AvailableHumans
Absorption

After oral administration, peak plasma levels (Cmax) occur at approximately 1.5 hours (Tmax). The Cmax increases proportionally when the dose is increased, and there is a three-fold increase in the area under the plasma concentration-time curve (AUC) from 20 to 40 mg. At repeated once-daily dosing with 40 mg, the systemic bioavailability is approximately 90% compared to 64% after a single dose of 40 mg. The mean exposure (AUC) to esomeprazole increases from 4.32 μmolhr/L on Day 1 to 11.2 μmolhr/L on Day 5 after 40 mg once daily dosing. The AUC after administration of a single 40 mg dose of Esomeprazole is decreased by 43% to 53% after food intake compared to fasting conditions. Esomeprazole should be taken at least one hour before meals.Label

Combination Therapy with Antimicrobials:

Esomeprazole magnesium 40 mg once daily was given in combination with Clarithromycin 500 mg twice daily and Amoxicillin 1000 mg twice daily for 7 days to 17 healthy male and female subjects. The mean steady state AUC and Cmax of esomeprazole increased by 70% and 18%, respectively during triple combination therapy compared to treatment with esomeprazole alone. The observed increase in esomeprazole exposure during co-administration with clarithromycin and amoxicillin is not expected to produce significant safety concerns.

Volume of distribution

The apparent volume of distribution at steady state in healthy volunteers is approximately 16 L.Label

Protein binding

Esomeprazole is 97% bound to plasma proteins. Plasma protein binding is constant over the concentration range of 2 to 20 µmol/L.Label

Metabolism

Esomeprazole is extensively metabolized in the liver by the cytochrome P450 (CYP) enzyme system. The metabolites of esomeprazole lack antisecretory activity. The major part of esomeprazole’s metabolism is dependent upon the CYP2C19 isoenzyme, which forms the hydroxy and desmethyl metabolites. The remaining amount is dependent on CYP3A4 which forms the sulphone metabolite. CYP2C19 isoenzyme exhibits polymorphism in the metabolism of esomeprazole, since some 3% of Caucasians and 15 to 20% of Asians lack CYP2C19 and are termed Poor Metabolizers.Label However, the influence of CYP 2C19 polymorphism is less pronounced for esomeprazole than for omeprazole.8 At steady state, the ratio of AUC in Poor Metabolizers to AUC in the rest of the population (Extensive Metabolizers) is approximately 2.

Following administration of equimolar doses, the S- and R-isomers are metabolized differently by the liver, resulting in higher plasma levels of the S- than of the R-isomer.Label

Nine major urinary metabolites have been detected. The two main metabolites have been identified as hydroxyesomeprazole and the corresponding carboxylic acid. Three major metabolites have been identified in plasma: the 5-O-desmethyl- and sulphone derivatives and hydroxyesomeprazole. The major metabolites of esomeprazole have no effect on gastric acid secretion.8

Hover over products below to view reaction partners

Route of elimination

The plasma elimination half-life of esomeprazole is approximately 1 to 1.5 hours. Less than 1% of parent drug is excreted in the urine. Approximately 80% of an oral dose of esomeprazole is excreted as inactive metabolites in the urine, and the remainder is found as inactive metabolites in the feces.

Half-life

1-1.5 hours

Clearance
Not Available
Adverse Effects
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Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Esomeprazole Metabolism PathwayDrug metabolism
Esomeprazole Action PathwayDrug action
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
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Esomeprazole can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Esomeprazole can be increased when combined with Abatacept.
AbirateroneThe metabolism of Esomeprazole can be decreased when combined with Abiraterone.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Esomeprazole.
AcyclovirThe excretion of Acyclovir can be decreased when combined with Esomeprazole.
AdalimumabThe metabolism of Esomeprazole can be increased when combined with Adalimumab.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Esomeprazole.
Alendronic acidThe therapeutic efficacy of Alendronic acid can be decreased when used in combination with Esomeprazole.
AllopurinolThe excretion of Allopurinol can be decreased when combined with Esomeprazole.
AlpelisibThe metabolism of Esomeprazole can be decreased when combined with Alpelisib.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food. Co-administration with food slightly alters pharmacokinetics, but not to a clinically significant extent.

Products

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
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) / Esolok (Ibn Sina) / Esomarfan (Marfan) / Esomenta (RAK) / Esomep (ACI) / Esomeprazol Genfar (Genfar S.A) / Esopral (Maquifarma) / Esorest (Centaur) / Inexium paranova / Lucen (Malesci) / Nexiam (AstraZeneca)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
EsomeprazoleTablet, delayed release40 mgOralEthypharmNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release20 mgOralPro Doc Limitee2013-06-06Not applicableCanada
EsomeprazoleTablet, delayed release20 mgOralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
EsomeprazoleTablet, delayed release40 mgOralTEVA Canada LimitedNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release20 mgOralEthypharmNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release40 mgOralSanis Health Inc2014-09-22Not applicableCanada
EsomeprazoleTablet, delayed release40 mgOralRanbaxy Inc.Not applicableNot applicableCanada
EsomeprazoleTablet, delayed release20 mgOralTEVA Canada LimitedNot applicableNot applicableCanada
EsomeprazoleTablet, delayed release40 mgOralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
EsomeprazoleTablet, delayed release40 mgOralPro Doc Limitee2012-11-22Not applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-esomeprazoleTablet, delayed releaseOralApotex Corporation2011-03-07Not applicableCanada
Apo-esomeprazoleTablet, delayed releaseOralApotex Corporation2012-03-02Not applicableCanada
Esomeprazole Magneisum D/rCapsule, delayed release40 mg/1OralDirect_Rx2019-06-04Not applicableUs
Esomeprazole magnesiumCapsule, delayed release40 mg/1OralA-S Medication Solutions2017-10-01Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release pellets20 mg/1OralLannett Company, Inc.2017-09-01Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralNorthStar Rx LLC2017-08-14Not applicableUs
Esomeprazole magnesiumCapsule, delayed release20 mg/1OralSun Pharmaceutical Industries, Inc2018-05-31Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralCamber Pharmaceuticals, Inc.2015-09-21Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release40 mg/1OralNucare Pharmaceuticals,inc.2016-04-21Not applicableUs
Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralTeva Pharmaceuticals USA, Inc.2015-02-17Not applicableUs00093 6450 56 nlmimage10 c542e2e7
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Basic Care Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralL. Perrigo Company2018-01-09Not applicableUs
Basic Care Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralAmazon.Com Services Inc.2020-06-15Not applicableUs
Basic Care Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralAmazon.Com Services Inc.2020-07-22Not 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/1OralDOLGENCORP, LLC2020-07-14Not applicableUs
DG Health Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralDOLGENCORP, LLC2017-09-22Not applicableUs
Equaline Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralSUPERVALU INC2017-09-25Not applicableUs
Equate Esomeprazole MagnesiumCapsule, delayed release20 mg/1OralWAL-MART STORES INC2017-10-05Not applicableUs
EsomeprazoleCapsule, delayed release20 mg/1OralSun Pharmaceutical Industries, Inc.2019-11-30Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Anodyne IleEsomeprazole magnesium trihydrate (40 mg/1) + Ibuprofen (100 mg/5mL) + Levomenthol (1 g/100g) + Lidocaine (4 g/100g)KitOral; TopicalFortus 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
Naproxen and Esomeprazole MagnesiumEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralLupin Pharmaceuticals, Inc.2020-03-04Not applicableUs
Naproxen and esomeprazole magnesiumEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)Tablet, delayed releaseOralDr. Reddy's Laboratories Limited2020-02-18Not applicableUs
Naproxen and esomeprazole magnesiumEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralDr. Reddy's Laboratories Limited2020-02-18Not applicableUs
Naproxen and Esomeprazole MagnesiumEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)Tablet, delayed releaseOralLupin Pharmaceuticals, Inc.2020-03-04Not applicableUs
VimovoEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)Tablet, delayed releaseOralHorizon Medicines LLC2010-07-06Not applicableUs
VimovoEsomeprazole (20 mg) + Naproxen (500 mg)Tablet, delayed releaseOralAstra Zeneca2011-02-04Not applicableCanada
VimovoEsomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)Tablet, delayed releaseOralHorizon Medicines LLC2010-07-06Not applicableUs

Categories

ATC Codes
A02BD06 — Esomeprazole, amoxicillin and clarithromycinA02BC05 — EsomeprazoleM01AE52 — Naproxen and esomeprazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidazole
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)

Chemical Identifiers

UNII
N3PA6559FT
CAS number
119141-88-7
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

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]
  3. Ghebremariam YT, LePendu P, Lee JC, Erlanson DA, Slaviero A, Shah NH, Leiper J, Cooke JP: Unexpected effect of proton pump inhibitors: elevation of the cardiovascular risk factor asymmetric dimethylarginine. Circulation. 2013 Aug 20;128(8):845-53. doi: 10.1161/CIRCULATIONAHA.113.003602. Epub 2013 Jul 3. [PubMed:23825361]
  4. Tommasi S, Elliot DJ, Hulin JA, Lewis BC, McEvoy M, Mangoni AA: Human dimethylarginine dimethylaminohydrolase 1 inhibition by proton pump inhibitors and the cardiovascular risk marker asymmetric dimethylarginine: in vitro and in vivo significance. Sci Rep. 2017 Jun 6;7(1):2871. doi: 10.1038/s41598-017-03069-1. [PubMed:28588208]
  5. Haastrup PF, Thompson W, Sondergaard J, Jarbol DE: Side Effects of Long-Term Proton Pump Inhibitor Use: A Review. Basic Clin Pharmacol Toxicol. 2018 Aug;123(2):114-121. doi: 10.1111/bcpt.13023. Epub 2018 May 24. [PubMed:29658189]
  6. Reimer C, Sondergaard B, Hilsted L, Bytzer P: Proton-pump inhibitor therapy induces acid-related symptoms in healthy volunteers after withdrawal of therapy. Gastroenterology. 2009 Jul;137(1):80-7, 87.e1. doi: 10.1053/j.gastro.2009.03.058. Epub 2009 Apr 10. [PubMed:19362552]
  7. Fallone CA, Chiba N, van Zanten SV, Fischbach L, Gisbert JP, Hunt RH, Jones NL, Render C, Leontiadis GI, Moayyedi P, Marshall JK: The Toronto Consensus for the Treatment of Helicobacter pylori Infection in Adults. Gastroenterology. 2016 Jul;151(1):51-69.e14. doi: 10.1053/j.gastro.2016.04.006. Epub 2016 Apr 19. [PubMed:27102658]
  8. Health Canada Label - Esomeprazole [File]
  9. TOP Guidelines - H pylori [File]
Human Metabolome Database
HMDB0005009
KEGG Drug
D07917
PubChem Compound
9568614
PubChem Substance
46504894
ChemSpider
7843323
RxNav
283742
ChEBI
50275
ChEMBL
CHEMBL1201320
ZINC
ZINC000004693574
Therapeutic Targets Database
DCL000524
PharmGKB
PA10075
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Esomeprazole
AHFS Codes
  • 56:28.36 — Proton-pump Inhibitors
FDA label
Download (1.02 MB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Active Not RecruitingTreatmentHelicobacter Pylori Gastrointestinal Tract Infection1
4CompletedNot AvailableErosive Esophagitis (EE) / Gastro-esophageal Reflux Disease (GERD) / Reflux Esophagitis (RE)1
4CompletedNot AvailableHealthy Volunteers2
4CompletedBasic ScienceHeartburn1
4CompletedDiagnosticAcute Coronary Syndromes (ACS) / Acute Myocardial Infarction (AMI)1
4CompletedDiagnosticBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4CompletedDiagnosticDyspepsia / Gastroesophageal Reflux1
4CompletedDiagnosticGastro-esophageal Reflux Disease (GERD)1
4CompletedDiagnosticGastroesophageal Reflux1

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
KitOral; Topical
Capsule, delayed releaseOral20 MG
Capsule, delayed releaseOral40 MG
Tablet, delayed releaseOral40 MG
CapsuleOral20 mg/1
Tablet, delayed releaseOral20 mg/1
Capsule, delayed releaseOral40 1/1
Capsule, delayed release pelletsOral20 mg/1
Capsule, delayed release pelletsOral40 mg/1
For suspensionOral20 mg/1
For suspensionOral40 mg/1
Granule, for suspension, extended releaseOral10 mg/1
InjectionIntravenous40 mg/5mL
Injection, powder, lyophilized, for solutionIntravenous20 mg/5mL
Injection, powder, lyophilized, for solutionIntravenous20 mg/1
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 releaseOral2.5 mg/1
Granule, delayed releaseOral20 mg/1
Granule, delayed releaseOral40 mg/1
Granule, delayed releaseOral5 mg/1
Tablet, delayed releaseOral
Granule, delayed releaseOral10 MG
TabletOral20 mg/1
Tablet, delayed releaseOral20 mg
InjectionIntravenous20 mg/5mL
KitOral20 mg/1
Capsule, delayed releaseOral
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)Region
US5877192No1999-03-022014-05-27Us
CA1338377No1996-06-112013-06-11Canada
CA2346988No2009-02-102019-11-03Canada
US6191148Yes2001-02-202019-04-09Us
US6147103Yes2000-11-142019-04-09Us
US6166213Yes2000-12-262019-04-09Us
US5900424Yes1999-05-042016-11-04Us
US6369085Yes2002-04-092018-11-25Us
US6428810Yes2002-08-062020-05-03Us
US7411070Yes2008-08-122018-11-25Us
US8466175Yes2013-06-182018-11-25Us
US8852636No2014-10-072022-05-31Us
US8858996No2014-10-142022-05-31Us
US6926907No2005-08-092023-02-28Us
US7745466No2010-06-292018-10-13Us
US9161920No2015-10-202022-05-31Us
US9198888No2015-12-012022-05-31Us
US8945621No2015-02-032031-10-17Us
US8557285No2013-10-152022-05-31Us
US9220698No2015-12-292031-03-10Us
US5714504Yes1998-02-032015-08-03Us
US9345695No2016-05-242022-05-31Us
US9393208No2016-07-192029-09-03Us
US9707181No2017-07-182022-05-31Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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

Targets

Kind
Protein
Organism
Humans
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Hydrolyzes N(G),N(G)-dimethyl-L-arginine (ADMA) and N(G)-monomethyl-L-arginine (MMA) which act as inhibitors of NOS. Has therefore a role in the regulation of nitric oxide generation.
Gene Name
DDAH1
Uniprot ID
O94760
Uniprot Name
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
Molecular Weight
31121.5 Da
References
  1. Ghebremariam YT, LePendu P, Lee JC, Erlanson DA, Slaviero A, Shah NH, Leiper J, Cooke JP: Unexpected effect of proton pump inhibitors: elevation of the cardiovascular risk factor asymmetric dimethylarginine. Circulation. 2013 Aug 20;128(8):845-53. doi: 10.1161/CIRCULATIONAHA.113.003602. Epub 2013 Jul 3. [PubMed:23825361]
  2. Tommasi S, Elliot DJ, Hulin JA, Lewis BC, McEvoy M, Mangoni AA: Human dimethylarginine dimethylaminohydrolase 1 inhibition by proton pump inhibitors and the cardiovascular risk marker asymmetric dimethylarginine: in vitro and in vivo significance. Sci Rep. 2017 Jun 6;7(1):2871. doi: 10.1038/s41598-017-03069-1. [PubMed:28588208]

Enzymes

Kind
Protein
Organism
Humans
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. 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]
  2. Modak AS, Klyarytska I, Kriviy V, Tsapyak T, Rabotyagova Y: The effect of proton pump inhibitors on the CYP2C19 enzyme activity evaluated by the pantoprazole-(13)C breath test in GERD patients: clinical relevance for personalized medicine. J Breath Res. 2016 Dec 17;10(4):046017. doi: 10.1088/1752-7163/10/4/046017. [PubMed:27991432]
  3. Esomeprazole Therapy and CYP2C19 Genotype [Link]
Kind
Protein
Organism
Humans
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

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. [PubMed:11770010]
  2. Wedemeyer RS, Blume H: Pharmacokinetic drug interaction profiles of proton pump inhibitors: an update. Drug Saf. 2014 Apr;37(4):201-11. doi: 10.1007/s40264-014-0144-0. [PubMed:24550106]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Chioukh R, Noel-Hudson MS, Ribes S, Fournier N, Becquemont L, Verstuyft C: Proton pump inhibitors inhibit methotrexate transport by renal basolateral organic anion transporter hOAT3. Drug Metab Dispos. 2014 Dec;42(12):2041-8. doi: 10.1124/dmd.114.058529. Epub 2014 Sep 19. [PubMed:25239859]

Drug created on June 13, 2005 07:24 / Updated on August 14, 2020 04:24

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