Esomeprazole
Identification
- Name
- Esomeprazole
- Accession Number
- DB00736 (APRD00363)
- Type
- Small Molecule
- Groups
- Approved, Investigational
- 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 cell. 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 have 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.
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.
- Structure
Structure for Esomeprazole (DB00736)
- Synonyms
- (−)-omeprazole
- (S)-(−)-omeprazole
- (S)-omeprazole
- Esomeprazol
- Ésoméprazole
- Esomeprazole
- Esomeprazolum
- Omeprazole S-form
- Perprazole
- External IDs
- A02BC05 / H 199/18
- 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
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Unlock Additional DataAct Esomeprazole Tablet, delayed release 40 mg Oral Teva 2015-11-09 Not applicable Canada 
Act Esomeprazole Tablet, delayed release 20 mg Oral Teva 2015-11-09 Not applicable Canada Esomeprazole Tablet, delayed release 20 mg Oral Pro Doc Limitee 2013-06-06 Not applicable Canada Esomeprazole Tablet, delayed release 40 mg Oral Sivem Pharmaceuticals Ulc 2015-07-22 Not applicable Canada Esomeprazole Tablet, delayed release 40 mg Oral Ranbaxy Inc. Not applicable Not applicable Canada Esomeprazole Tablet, delayed release 40 mg Oral Ethypharm Not applicable Not applicable Canada Esomeprazole Tablet, delayed release 20 mg Oral Ranbaxy Inc. Not applicable Not applicable Canada Esomeprazole Tablet, delayed release 20 mg Oral Sivem Pharmaceuticals Ulc 2015-07-22 Not applicable Canada Esomeprazole Tablet, delayed release 20 mg Oral Ethypharm Not applicable Not applicable Canada Esomeprazole Tablet, delayed release 40 mg Oral Sanis Health Inc 2014-09-22 Not applicable Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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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 Unlock Additional DataApo-esomeprazole Tablet, delayed release 40 mg Oral Apotex Corporation 2011-03-07 Not applicable Canada Apo-esomeprazole Tablet, delayed release 20 mg Oral Apotex Corporation 2012-03-02 Not applicable Canada Esomeprazole magnesium Capsule, delayed release 40 mg/1 Oral bryant ranch prepack 2017-10-20 Not applicable US 
Esomeprazole Magnesium Capsule, delayed release pellets 20 mg/1 Oral Mylan Institutional Inc. 2016-06-01 Not applicable US Esomeprazole Magnesium Capsule, delayed release 40 mg/1 Oral Nucare Pharmaceuticals,inc. 2016-04-21 Not applicable US Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral Sunshine Lake Pharma Co., Ltd. 2018-05-18 Not applicable US Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral Amneal Pharmaceuticals LLC 2019-04-10 Not applicable US Esomeprazole Magnesium Capsule, delayed release 40 mg/1 Oral A-S Medication Solutions 2015-10-19 2018-08-17 US Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral American Health Packaging 2017-03-22 2019-03-31 US Esomeprazole Magnesium Capsule, delayed release 40 mg/1 Oral Unit Dose Services 2015-02-17 Not applicable US 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct 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 Unlock Additional DataBasic Care Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral L. Perrigo Company 2018-01-09 Not applicable US Berkley and Jensen Heartburn Treatment Capsule, delayed release 20 mg/1 Oral BJWC 2017-09-25 Not applicable US Careone Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral American Sales Company 2017-09-26 Not applicable US DG Health Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral Dolgencorp 2017-09-22 Not applicable US Equaline Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral SUPERVALU INC 2017-09-25 Not applicable US Equate Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral Walmart Stores 2017-10-05 Not applicable US Esomeprazole Capsule 20 mg/1 Oral Reliable 1 Laboratories 2018-11-01 Not applicable US Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral Publix Super Markets Inc 2017-09-29 Not applicable US Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral McKesson Corporation 2017-10-16 Not applicable US Esomeprazole Magnesium Capsule, delayed release 20 mg/1 Oral Best Choice 2017-10-16 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct 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 Anodyne Ile Esomeprazole magnesium trihydrate (40 mg/1) + Ibuprofen (100 mg/5mL) + Levomenthol (1 g/100g) + Lidocaine (4 g/100g) Kit Fortus Pharma, Llc 2017-10-16 2018-08-27 US Mylan-naproxen/esomeprazole Mr Esomeprazole (20 mg) + Naproxen (375 mg) Tablet, delayed release Oral Mylan Pharmaceuticals 2017-02-27 Not applicable Canada Mylan-naproxen/esomeprazole Mr Esomeprazole (20 mg) + Naproxen (500 mg) Tablet, delayed release Oral Mylan Pharmaceuticals 2017-02-10 Not applicable Canada Vimovo Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1) Tablet, delayed release Oral Astra Zeneca Lp 2010-07-06 2017-03-31 US 
Vimovo Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1) Tablet, delayed release Oral Astra Zeneca Lp 2010-07-06 2017-03-31 US Vimovo Esomeprazole (20 mg) + Naproxen (500 mg) Tablet, delayed release Oral Astra Zeneca 2011-02-04 Not applicable Canada Vimovo Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1) Tablet, delayed release Oral Horizon Pharma, Inc. 2014-01-01 Not applicable US Vimovo Esomeprazole (20 mg) + Naproxen (375 mg) Tablet, delayed release Oral Astra Zeneca 2011-02-04 Not applicable Canada Vimovo Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1) Tablet, delayed release Oral Stat Rx USA 2011-07-01 Not applicable US Vimovo Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1) Tablet, delayed release Oral Horizon Pharma, Inc. 2014-01-01 Not applicable US - 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)
- 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 CYP3A4 Substrates (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P450 2C19 Inhibitors
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Gastric Acid Lowering Agents
- Gastrointestinal Agents
- Musculo-Skeletal System
- OAT3/SLC22A8 Inhibitors
- Omeprazole
- P-glycoprotein/ABCB1 Inhibitors
- P-glycoprotein/ABCB1 Substrates
- Propionates
- Proton Pump Inhibitors
- Proton-pump Inhibitors
- Pyridines
- Sulfoxides
- Sulfur Compounds
- UNII
- N3PA6559FT
- CAS number
- 119141-88-7
- Weight
- Average: 345.416
Monoisotopic: 345.114712179 - Chemical Formula
- C17H19N3O3S
- InChI Key
- SUBDBMMJDZJVOS-DEOSSOPVSA-N
- InChI
- InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1
- IUPAC Name
- 5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
- SMILES
- COC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1
Pharmacology
- Indication
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
- 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 have 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 cell. 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 inhibitorHumans 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 mealsLabel.
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 omeprazole8. 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 secretion8.
- 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
- 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
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn moreStructured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn moreStructured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- Drug Interactions
Drug Interaction Unlock Additional Data(R)-warfarin The metabolism of (R)-warfarin can be decreased when combined with Esomeprazole. (S)-Warfarin The metabolism of (S)-Warfarin can be decreased when combined with Esomeprazole. 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid Esomeprazole can cause a decrease in the absorption of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy. 3,5-diiodothyropropionic acid The metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Esomeprazole. 4-hydroxycoumarin The metabolism of 4-hydroxycoumarin can be decreased when combined with Esomeprazole. 5-androstenedione The metabolism of 5-androstenedione can be decreased when combined with Esomeprazole. 6-Deoxyerythronolide B The metabolism of Esomeprazole can be decreased when combined with 6-Deoxyerythronolide B. 6-O-benzylguanine The metabolism of 6-O-benzylguanine can be decreased when combined with Esomeprazole. 7-ethyl-10-hydroxycamptothecin The metabolism of Esomeprazole can be decreased when combined with 7-ethyl-10-hydroxycamptothecin. 9-aminocamptothecin The metabolism of 9-aminocamptothecin can be decreased when combined with Esomeprazole. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionEvidence Level
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Health Canada Label - Esomeprazole [File]
- TOP Guidelines - H pylori [File]
- External Links
- Human Metabolome Database
- HMDB0005009
- KEGG Drug
- D07917
- PubChem Compound
- 9568614
- PubChem Substance
- 46504894
- ChemSpider
- 7843323
- ChEBI
- 50275
- ChEMBL
- CHEMBL1201320
- Therapeutic Targets Database
- DCL000524
- PharmGKB
- PA10075
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Esomeprazole
- 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
- 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
- AHFS Codes
- 56:28.36 — Proton-pump Inhibitors
- FDA label
- Download (1.02 MB)
Clinical Trials
- Clinical Trials
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 Capsule Oral 20 mg/1 Capsule, delayed release Oral 20 1/1 Capsule, delayed release Oral 40 1/1 Capsule, delayed release pellets Oral 20 mg/1 Capsule, delayed release pellets Oral 40 mg/1 Injection, powder, lyophilized, for solution Intravenous 20 mg/1 Injection, powder, lyophilized, for solution Intravenous 20 mg/5mL 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 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 20 mg Tablet, delayed release Oral 40 mg Tablet Oral 20 mg/1 Injection Intravenous 20 mg/5mL Injection Intravenous 40 mg/5mL Kit 20 mg/1 Capsule, delayed release Oral 20 mg Capsule, delayed release Oral 40 mg 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) Unlock Additional DataUS5877192 No 1999-03-02 2014-05-27 US CA1338377 No 1996-06-11 2013-06-11 Canada CA2346988 No 2009-02-10 2019-11-03 Canada US6191148 Yes 2001-02-20 2019-04-09 US US6147103 Yes 2000-11-14 2019-04-09 US US6166213 Yes 2000-12-26 2019-04-09 US US5900424 Yes 1999-05-04 2016-11-04 US US6369085 Yes 2002-04-09 2018-11-25 US US6428810 Yes 2002-08-06 2020-05-03 US US7411070 Yes 2008-08-12 2018-11-25 US US8466175 Yes 2013-06-18 2018-11-25 US US8852636 No 2014-10-07 2022-05-31 US US8858996 No 2014-10-14 2022-05-31 US US6926907 No 2005-08-09 2023-02-28 US US7745466 No 2010-06-29 2018-10-13 US US9161920 No 2015-10-20 2022-05-31 US US9198888 No 2015-12-01 2022-05-31 US US8945621 No 2015-02-03 2031-10-17 US US8557285 No 2013-10-15 2022-05-31 US US9220698 No 2015-12-29 2031-03-10 US US5714504 Yes 1998-02-03 2015-08-03 US US9345695 No 2016-05-24 2022-05-31 US US9393208 No 2016-07-19 2029-09-03 US US9707181 No 2017-07-18 2022-05-31 US Additional Data Available- Filed On
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
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
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
- 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
- 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]
- 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]
- 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]
- 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
- 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]
- 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
- SubstrateInhibitor
- 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
- 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]
- 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
- 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
- SubstrateInhibitor
- 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
- 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]
- 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
- 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 May 21, 2019 12:45