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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Esomeprazole (DB00736)

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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

• Bacterial Infection Due to Helicobacter Pylori (H. Pylori)
• Erosive Esophagitis (EE)
• Gastro-esophageal Reflux Disease (GERD)
• Heartburn
• NSAID Associated Gastric Ulcers
• Stress Ulcers
• Zollinger-Ellison Syndrome
• Maintenance of healing Erosive esophagitis
• Postendoscopy Bleeding

Contraindications & Blackbox Warnings

Learn about our commercial Contraindications & Blackbox Warnings data.

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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

Target	Actions	Organism
APotassium-transporting ATPase alpha chain 1	inhibitor	Humans
UN(G),N(G)-dimethylarginine dimethylaminohydrolase 1	Not Available	Humans

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

• Esomeprazole
  • 5-hydroxyesomeprazole
  • Active Metabolite of Esomeprazole
  • Omeprazole sulfone
  • 5-O-Desmethylomeprazole

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

Pathway	Category
Esomeprazole Metabolism Pathway	Drug metabolism
Esomeprazole Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Cytochrome P450 2C19	CYP2C19*2	(A;A)	A Allele, homozygote	Effect Directly Studied	Patients with this genotype have reduced metabolism of esomeprazole.	Details
Cytochrome P450 2C19	CYP2C19*3	(A;A)	A Allele, homozygote	Effect Directly Studied	Patients with this genotype have reduced metabolism of esomeprazole.	Details
Cytochrome P450 2C19	CYP2C19*2A	Not Available	681G>A	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details
Cytochrome P450 2C19	CYP2C19*2B	Not Available	681G>A	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details
Cytochrome P450 2C19	CYP2C19*4	Not Available	1A>G	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details
Cytochrome P450 2C19	CYP2C19*5	Not Available	1297C>T	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details
Cytochrome P450 2C19	CYP2C19*6	Not Available	395G>A	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details
Cytochrome P450 2C19	CYP2C19*7	Not Available	19294T>A	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details
Cytochrome P450 2C19	CYP2C19*22	Not Available	557G>C / 991A>G	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details
Cytochrome P450 2C19	CYP2C19*24	Not Available	99C>T / 991A>G  … show all	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details
Cytochrome P450 2C19	CYP2C19*35	Not Available	12662A>G	Effect Inferred	Poor metabolizer, lower dose requirement, improved drug efficacy	Details

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Unlock Additional Data
Abametapir	The serum concentration of Esomeprazole can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Esomeprazole can be increased when combined with Abatacept.
Abiraterone	The metabolism of Esomeprazole can be decreased when combined with Abiraterone.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Esomeprazole.
Acyclovir	The excretion of Acyclovir can be decreased when combined with Esomeprazole.
Adalimumab	The metabolism of Esomeprazole can be increased when combined with Adalimumab.
Albendazole	The metabolism of Albendazole can be decreased when combined with Esomeprazole.
Alendronic acid	The therapeutic efficacy of Alendronic acid can be decreased when used in combination with Esomeprazole.
Allopurinol	The excretion of Allopurinol can be decreased when combined with Esomeprazole.
Alpelisib	The 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
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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

Ingredient	UNII	CAS	InChI Key
Esomeprazole magnesium	925R0D7W1O	161973-10-0	KWORUUGOSLYAGD-YPPDDXJESA-N
Esomeprazole magnesium dihydrate	36H71644EQ	217087-10-0	DBOUSUONOXEWHU-VCKZSRROSA-N
Esomeprazole magnesium trihydrate	R6DXU4WAY9	217087-09-7	VEVZQDGATGBLIC-UHFFFAOYSA-N
Esomeprazole sodium	L2C9GWQ43H	161796-78-7	RYXPMWYHEBGTRV-JIDHJSLPSA-N
Esomeprazole strontium	SCC2RK476A	914613-86-8	FEVPVZSYBDUVGY-YPPDDXJESA-N
Esomeprazole strontium hydrate	C5N25H3803	934714-36-0	NCGHIAKEJNQSMS-QLGOZJDFSA-N

Product Images

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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
Esomeprazole	Tablet, delayed release	40 mg	Oral	Ethypharm	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	20 mg	Oral	Pro Doc Limitee	2013-06-06	Not applicable
Esomeprazole	Tablet, delayed release	20 mg	Oral	Sivem Pharmaceuticals Ulc	2015-07-22	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	TEVA Canada Limited	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	20 mg	Oral	Ethypharm	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	Sanis Health Inc	2014-09-22	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	Ranbaxy Inc.	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	20 mg	Oral	TEVA Canada Limited	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	Sivem Pharmaceuticals Ulc	2015-07-22	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	Pro Doc Limitee	2012-11-22	Not applicable

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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
Apo-esomeprazole	Tablet, delayed release		Oral	Apotex Corporation	2011-03-07	Not applicable
Apo-esomeprazole	Tablet, delayed release		Oral	Apotex Corporation	2012-03-02	Not applicable
Esomeprazole Magneisum D/r	Capsule, delayed release	40 mg/1	Oral	Direct_Rx	2019-06-04	Not applicable
Esomeprazole magnesium	Capsule, delayed release	40 mg/1	Oral	A-S Medication Solutions	2017-10-01	Not applicable
Esomeprazole Magnesium	Capsule, delayed release pellets	20 mg/1	Oral	Lannett Company, Inc.	2017-09-01	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	NorthStar Rx LLC	2017-08-14	Not applicable
Esomeprazole magnesium	Capsule, delayed release	20 mg/1	Oral	Sun Pharmaceutical Industries, Inc	2018-05-31	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	Camber Pharmaceuticals, Inc.	2015-09-21	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	40 mg/1	Oral	Nucare Pharmaceuticals,inc.	2016-04-21	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	Teva Pharmaceuticals USA, Inc.	2015-02-17	Not applicable

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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Unlock Additional Data
Basic Care Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	L. Perrigo Company	2018-01-09	Not applicable
Basic Care Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	Amazon.Com Services Inc.	2020-06-15	Not applicable
Basic Care Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	Amazon.Com Services Inc.	2020-07-22	Not applicable
Berkley and Jensen Heartburn Treatment	Capsule, delayed release	20 mg/1	Oral	BJWC	2017-09-25	Not applicable
Careone Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	American Sales Company	2017-09-26	Not applicable
Dg Health Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	DOLGENCORP, LLC	2020-07-14	Not applicable
DG Health Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	DOLGENCORP, LLC	2017-09-22	Not applicable
Equaline Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	SUPERVALU INC	2017-09-25	Not applicable
Equate Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	WAL-MART STORES INC	2017-10-05	Not applicable
Esomeprazole	Capsule, delayed release	20 mg/1	Oral	Sun Pharmaceutical Industries, Inc.	2019-11-30	Not applicable

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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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Anodyne Ile	Esomeprazole magnesium trihydrate (40 mg/1) + Ibuprofen (100 mg/5mL) + Levomenthol (1 g/100g) + Lidocaine (4 g/100g)	Kit	Oral; Topical	Fortus Pharma, Llc	2017-10-16	2018-08-27
Mylan-naproxen/esomeprazole Mr	Esomeprazole (20 mg) + Naproxen (375 mg)	Tablet, delayed release	Oral	Mylan Pharmaceuticals	2017-02-27	Not applicable
Mylan-naproxen/esomeprazole Mr	Esomeprazole (20 mg) + Naproxen (500 mg)	Tablet, delayed release	Oral	Mylan Pharmaceuticals	2017-02-10	Not applicable
Naproxen and Esomeprazole Magnesium	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)	Tablet, delayed release	Oral	Lupin Pharmaceuticals, Inc.	2020-03-04	Not applicable
Naproxen and esomeprazole magnesium	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)	Tablet, delayed release	Oral	Dr. Reddy's Laboratories Limited	2020-02-18	Not applicable
Naproxen and esomeprazole magnesium	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)	Tablet, delayed release	Oral	Dr. Reddy's Laboratories Limited	2020-02-18	Not applicable
Naproxen and Esomeprazole Magnesium	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)	Tablet, delayed release	Oral	Lupin Pharmaceuticals, Inc.	2020-03-04	Not applicable
Vimovo	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)	Tablet, delayed release	Oral	Horizon Medicines LLC	2010-07-06	Not applicable
Vimovo	Esomeprazole (20 mg) + Naproxen (500 mg)	Tablet, delayed release	Oral	Astra Zeneca	2011-02-04	Not applicable
Vimovo	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)	Tablet, delayed release	Oral	Horizon Medicines LLC	2010-07-06	Not applicable

Categories

ATC Codes

A02BD06 — Esomeprazole, amoxicillin and clarithromycin

• A02BD — Combinations for eradication of Helicobacter pylori
• A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
• A02 — DRUGS FOR ACID RELATED DISORDERS
• A — ALIMENTARY TRACT AND METABOLISM

A02BC05 — Esomeprazole

• A02BC — Proton pump inhibitors
• A02B — DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
• A02 — DRUGS FOR ACID RELATED DISORDERS
• A — ALIMENTARY TRACT AND METABOLISM

M01AE52 — Naproxen and esomeprazole

• M01AE — Propionic acid derivatives
• M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
• M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
• M — MUSCULO-SKELETAL SYSTEM

Drug Categories

• 2-Pyridinylmethylsulfinylbenzimidazoles
• Acid Reducers
• Alimentary Tract and Metabolism
• Anti-Ulcer Agents
• Antiinflammatory and Antirheumatic Products
• Antiinflammatory and Antirheumatic Products, Non-Steroids
• Benzimidazoles
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 Inhibitors (weak)
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• Drugs causing inadvertant photosensitivity
• Drugs for Acid Related Disorders
• Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
• Enzyme Inhibitors
• Gastric Acid Lowering Agents
• Gastrointestinal Agents
• Heterocyclic Compounds, Fused-Ring
• Musculo-Skeletal System
• OAT3/SLC22A8 Inhibitors
• P-glycoprotein inhibitors
• P-glycoprotein substrates
• Photosensitizing Agents
• Propionates
• Proton Pump Inhibitors
• Proton-pump Inhibitors
• Pyridines
• Sulfoxides
• Sulfur Compounds

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 / Organic oxides / Hydrocarbon derivatives

show 2 more

Substituents

Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Methylpyridine / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Organosulfur compound / Pyridine / Sulfinyl compound / Sulfinylbenzimidazole / 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)

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]

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
4	Active Not Recruiting	Treatment	Helicobacter Pylori Gastrointestinal Tract Infection	1
4	Completed	Not Available	Erosive Esophagitis (EE) / Gastro-esophageal Reflux Disease (GERD) / Reflux Esophagitis (RE)	1
4	Completed	Not Available	Healthy Volunteers	2
4	Completed	Basic Science	Heartburn	1
4	Completed	Diagnostic	Acute Coronary Syndromes (ACS) / Acute Myocardial Infarction (AMI)	1
4	Completed	Diagnostic	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
4	Completed	Diagnostic	Dyspepsia / Gastroesophageal Reflux	1
4	Completed	Diagnostic	Gastro-esophageal Reflux Disease (GERD)	1
4	Completed	Diagnostic	Gastroesophageal Reflux	1

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

Form	Route	Strength
Kit	Oral; Topical
Capsule, delayed release	Oral	20 MG
Capsule, delayed release	Oral	40 MG
Tablet, delayed release	Oral	40 MG
Capsule	Oral	20 mg/1
Tablet, delayed release	Oral	20 mg/1
Capsule, delayed release	Oral	40 1/1
Capsule, delayed release pellets	Oral	20 mg/1
Capsule, delayed release pellets	Oral	40 mg/1
For suspension	Oral	20 mg/1
For suspension	Oral	40 mg/1
Granule, for suspension, extended release	Oral	10 mg/1
Injection	Intravenous	40 mg/5mL
Injection, powder, lyophilized, for solution	Intravenous	20 mg/5mL
Injection, powder, lyophilized, for solution	Intravenous	20 mg/1
Injection, powder, lyophilized, for solution	Intravenous	40 mg/1
Injection, powder, lyophilized, for solution	Intravenous	40 mg/5mL
Capsule, delayed release	Oral	24.65 mg/1
Capsule, delayed release	Oral	49.3 mg/1
Capsule, delayed release	Oral	20 mg/1
Capsule, delayed release	Oral	40 mg/1
Granule, delayed release	Oral	10 mg/1
Granule, delayed release	Oral	2.5 mg/1
Granule, delayed release	Oral	20 mg/1
Granule, delayed release	Oral	40 mg/1
Granule, delayed release	Oral	5 mg/1
Tablet, delayed release	Oral
Granule, delayed release	Oral	10 MG
Tablet	Oral	20 mg/1
Tablet, delayed release	Oral	20 mg
Injection	Intravenous	20 mg/5mL
Kit	Oral	20 mg/1
Capsule, delayed release	Oral
Tablet, delayed release	Oral

Prices

Unit description	Cost	Unit
Nexium i.v. 20 mg vial	33.91USD	vial
Nexium i.v. 40 mg vial	33.91USD	vial
NexIUM 20 mg Delayed Release Capsule	6.76USD	capsule
NexIUM 40 mg Delayed Release Capsule	6.76USD	capsule
Nexium 10 mg packet	6.5USD	each
Nexium 20 mg capsule	6.5USD	capsule
Nexium 20 mg packet	6.5USD	each
Nexium 40 mg capsule	6.5USD	capsule
Nexium 40 mg packet	6.5USD	each

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
Unlock Additional Data
US5877192	No	1999-03-02	2014-05-27
CA1338377	No	1996-06-11	2013-06-11
CA2346988	No	2009-02-10	2019-11-03
US6191148	Yes	2001-02-20	2019-04-09
US6147103	Yes	2000-11-14	2019-04-09
US6166213	Yes	2000-12-26	2019-04-09
US5900424	Yes	1999-05-04	2016-11-04
US6369085	Yes	2002-04-09	2018-11-25
US6428810	Yes	2002-08-06	2020-05-03
US7411070	Yes	2008-08-12	2018-11-25
US8466175	Yes	2013-06-18	2018-11-25
US8852636	No	2014-10-07	2022-05-31
US8858996	No	2014-10-14	2022-05-31
US6926907	No	2005-08-09	2023-02-28
US7745466	No	2010-06-29	2018-10-13
US9161920	No	2015-10-20	2022-05-31
US9198888	No	2015-12-01	2022-05-31
US8945621	No	2015-02-03	2031-10-17
US8557285	No	2013-10-15	2022-05-31
US9220698	No	2015-12-29	2031-03-10
US5714504	Yes	1998-02-03	2015-08-03
US9345695	No	2016-05-24	2022-05-31
US9393208	No	2016-07-19	2029-09-03
US9707181	No	2017-07-18	2022-05-31

Additional Data Available

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

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	155 °C	Not Available
water solubility	Very slightly soluble in water	Not Available
logP	0.6	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.353 mg/mL	ALOGPS
logP	1.66	ALOGPS
logP	2.43	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	4.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.1 Å2	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.66 m3·mol-1	ChemAxon
Polarizability	35.81 Å3	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9968
Blood Brain Barrier	-	0.6326
Caco-2 permeable	+	0.8867
P-glycoprotein substrate	Non-substrate	0.5573
P-glycoprotein inhibitor I	Inhibitor	0.6622
P-glycoprotein inhibitor II	Non-inhibitor	0.968
Renal organic cation transporter	Non-inhibitor	0.542
CYP450 2C9 substrate	Non-substrate	0.7838
CYP450 2D6 substrate	Substrate	0.6175
CYP450 3A4 substrate	Substrate	0.6901
CYP450 1A2 substrate	Inhibitor	0.7505
CYP450 2C9 inhibitor	Non-inhibitor	0.907
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Inhibitor	0.8994
CYP450 3A4 inhibitor	Inhibitor	0.796
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.7895
Ames test	Non AMES toxic	0.5692
Carcinogenicity	Non-carcinogens	0.8318
Biodegradation	Not ready biodegradable	0.9778
Rat acute toxicity	2.2254 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.719
hERG inhibition (predictor II)	Non-inhibitor	0.8977

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

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