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Properties

Spectra

Taxonomy

Esomeprazole

Targets (1)Enzymes (2)Biointeractions (4)

Identification

Name

Esomeprazole

Accession Number

DB00736 (APRD00363)

Type

Small Molecule

Groups

Approved, Investigational

Description

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

Structure

Similar Structures

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
Act Esomeprazole	Tablet, delayed release	40 mg	Oral	Teva	2015-11-09	Not applicable
Act Esomeprazole	Tablet, delayed release	20 mg	Oral	Teva	2015-11-09	Not applicable
Esomeprazole	Tablet, delayed release	20 mg	Oral	Ethypharm	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	Teva	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	Pro Doc Limitee	2012-11-22	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	Ranbaxy Inc.	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	20 mg	Oral	Teva	Not applicable	Not applicable
Esomeprazole	Tablet, delayed release	40 mg	Oral	Sivem Pharmaceuticals Ulc	2015-07-22	Not applicable
Esomeprazole	Tablet, delayed release	20 mg	Oral	Pro Doc Limitee	2013-06-06	Not applicable
Esomeprazole	Tablet, delayed release	20 mg	Oral	Ranbaxy Inc.	Not applicable	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-esomeprazole	Tablet, delayed release	40 mg	Oral	Apotex Corporation	2011-03-07	Not applicable
Apo-esomeprazole	Tablet, delayed release	20 mg	Oral	Apotex Corporation	2012-03-02	Not applicable
Esomeprazole Magnesium	Capsule, delayed release pellets	20 mg/1	Oral	Mylan Institutional Inc.	2016-06-01	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	40 mg/1	Oral	Directrx	2014-01-01	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	medsourcer pharmaceuticals	2016-04-21	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	40 1/1	Oral	Nucare Pharmaceuticals,inc.	2015-10-19	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	bryant ranch prepack	2016-04-21	Not applicable
Esomeprazole Magnesium	Capsule, delayed release pellets	40 mg/1	Oral	Lannett Company, Inc..	2016-04-01	Not applicable
Esomeprazole magnesium	Capsule, delayed release	20 mg/1	Oral	Ascend Laboratories, LLC	2017-10-20	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	40 mg/1	Oral	A-S Medication Solutions	2015-10-19	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Basic Care Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	L. Perrigo Company	2018-01-09	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	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	Walmart Stores	2017-10-05	Not applicable
Esomeprazole	Capsule	20 mg/1	Oral	Reliable 1 Laboratories	2018-11-01	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	Amerisource Bergen	2017-10-16	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	Best Choice	2017-10-16	Not applicable
Esomeprazole Magnesium	Capsule, delayed release	20 mg/1	Oral	Kroger	2017-09-22	Not applicable

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
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
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 Pharma, Inc.	2014-01-01	Not applicable
Vimovo	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)	Tablet, delayed release	Oral	Stat Rx USA	2011-07-01	Not applicable
Vimovo	Esomeprazole (20 mg) + Naproxen (375 mg)	Tablet, delayed release	Oral	Astra Zeneca	2011-02-04	Not applicable
Vimovo	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)	Tablet, delayed release	Oral	Astra Zeneca Lp	2010-07-06	2017-03-31
Vimovo	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (375 mg/1)	Tablet, delayed release	Oral	Astra Zeneca Lp	2010-07-06	2017-03-31
Vimovo	Esomeprazole magnesium trihydrate (20 mg/1) + Naproxen (500 mg/1)	Tablet, delayed release	Oral	Horizon Pharma, Inc.	2014-01-01	Not applicable

International/Other Brands

Alenia (Delta) / Awa-Block (Usawa) / Axagon (Simesa) / Cor (Prater) / Cronopep (Biotoscana) / Emanera (Krka) / Emep (Aristopharma) / Emozul (HYGIA) / ES-OD (Piramal Healthcare) / Esmep (HYGIA) / Eso (Asiatic Lab) / Esofag (Micro Labs) / Esogastrosedol (Nova Argentia) / Esolok (Ibn Sina) / Esomarfan (Marfan) / Esomenta (RAK) / Esomep (ACI) / Esomeprazol Genfar (Genfar S.A) / Esopral (Maquifarma) / Esorest (Centaur) / Inexium paranova / Lucen (Malesci) / Nexiam (AstraZeneca)

Categories

UNII

N3PA6559FT

CAS number

119141-88-7

Weight

Average: 345.416
Monoisotopic: 345.114712179

Chemical Formula

C₁₇H₁₉N₃O₃S

InChI Key

SUBDBMMJDZJVOS-DEOSSOPVSA-N

InChI

InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1

IUPAC Name

5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

SMILES

COC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1

Pharmacology

Indication

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

Associated Conditions

Pharmacodynamics

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

Mechanism of action

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

Target	Actions	Organism
APotassium-transporting ATPase alpha chain 1	inhibitor	Humans

Absorption

90%

Volume of distribution

16 L [healthy volunteers]

Protein binding

97%

Metabolism

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

Route of elimination

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

Half life

1-1.5 hours

Clearance

Not Available

Toxicity

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

Affected organisms

Humans and other mammals

Pathways

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

Drug	Interaction
(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.

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]

External Links

Human Metabolome Database: HMDB0005009
KEGG Drug: D07917
PubChem Compound: 9568614
PubChem Substance: 46504894
ChemSpider: 7843323
ChEBI: 50275
ChEMBL: CHEMBL1201320
Therapeutic Targets Database: DCL000524
PharmGKB: PA10075
IUPHAR: 4279
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Esomeprazole

ATC Codes

A02BD06 — Esomeprazole, amoxicillin and clarithromycin

A02BC05 — Esomeprazole

M01AE52 — Naproxen and esomeprazole

AHFS Codes

56:28.36 — Proton-pump Inhibitors

FDA label

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Not Available	Bone and Bones / Homeostasis	1
1	Completed	Not Available	Endoscopically-Proven GERD / Reflux	1
1	Completed	Not Available	Healthy Volunteers	3
1	Completed	Not Available	Healthy Volunteers / Ilaprazole / Pharmacodynamics / Pharmacokinetics	1
1	Completed	Not Available	Ulcers / Upper GI Symptoms	1
1	Completed	Basic Science	Arthritis	1
1	Completed	Basic Science	Bioequivalence Study	2
1	Completed	Basic Science	Bioequivalence / Healthy Volunteers	1
1	Completed	Basic Science	Gastro-esophageal Reflux Disease (GERD)	1
1	Completed	Basic Science	Healthy Volunteers	10
1	Completed	Basic Science	Healthy Volunteers / Pharmacokinetics of Isavuconazole	1
1	Completed	Basic Science	Juvenile Idiopathic Arthritis (JIA)	1
1	Completed	Other	Healthy Participants	1
1	Completed	Prevention	Peptic Ulcers	1
1	Completed	Supportive Care	Healthy Volunteers	1
1	Completed	Treatment	Dose Finding Study	1
1	Completed	Treatment	Gastro-esophageal Reflux Disease (GERD)	3
1	Completed	Treatment	Healthy Volunteers	5
1	Completed	Treatment	Malignant Lymphomas / Tumors, Solid	1
1	Completed	Treatment	Pharmacokinetics	1
1	Completed	Treatment	Pulmonary Arterial Hypertension (PAH) / Pulmonary Hypertension (PH)	1
1	Enrolling by Invitation	Treatment	Healthy Volunteers	1
1	Not Yet Recruiting	Basic Science	Healthy Volunteers	1
1	Not Yet Recruiting	Other	Neoplasms, Advanced Solid	1
1	Recruiting	Basic Science	Healthy Male Volunteers / Pharmacodynamics / Pharmacokinetics	1
1	Recruiting	Treatment	Healthy Volunteers	1
1	Terminated	Not Available	Peptic Ulcer Disease	1
1	Terminated	Treatment	Exercise Triggered Asthma / Reflux, Gastroesophageal	1
1	Terminated	Treatment	Pancreatitis, Chronic	1
1	Unknown Status	Treatment	Esophagitis / Esophagus, Barrett / Reflux	1
1, 2	Completed	Diagnostic	Tooth Erosion	1
1, 2	Completed	Treatment	Healthy Volunteers With Ileostomy	1
1, 2	Unknown Status	Treatment	Gastro-esophageal Reflux Disease (GERD) / Heartburn / Indigestion	1
2	Completed	Diagnostic	Gastro-esophageal Reflux Disease (GERD) / Reflux, Gastroesophageal	1
2	Completed	Prevention	Esophageal Cancers / Esophagus, Barrett	1
2	Completed	Prevention	Peptic Ulcers	1
2	Completed	Treatment	Asthma Bronchial	1
2	Completed	Treatment	Asthma Bronchial / Gastro-esophageal Reflux Disease (GERD)	1
2	Completed	Treatment	Cancer, Breast / Neoplasms Metastasis	1
2	Completed	Treatment	Erosive Esophagitis(EE) / Gastro-esophageal Reflux Disease (GERD)	1
2	Completed	Treatment	Erosive Gastroesophageal Reflux Disease	1
2	Completed	Treatment	Esophagitis	1
2	Completed	Treatment	Gram-Negative Bacterial Infections / Helicobacter Infections / Indigestion	1
2	Completed	Treatment	Indigestion	2
2	Completed	Treatment	Non-erosive Reflux Disease (NERD)	1
2	Completed	Treatment	Reflux Esophagitis (RE)	1
2	Completed	Treatment	Reflux, Gastroesophageal	2
2	Not Yet Recruiting	Treatment	Acid Dyspepsia / Gastritis	1
2	Not Yet Recruiting	Treatment	Autism Spectrum Conditions/Disorders / Autism, Early Infantile	1
2	Recruiting	Prevention	Pain, Neuropathic	1
2	Recruiting	Treatment	Autism Spectrum Conditions/Disorders	1
2	Recruiting	Treatment	Gastrointestinal Erosions and/or Ulcers	1
2	Recruiting	Treatment	Knee Replacement Surgery / Manipulation	1
2	Terminated	Treatment	Cystic Fibrosis (CF)	1
2	Terminated	Treatment	Gastro-esophageal Reflux Disease (GERD)	1
2	Terminated	Treatment	Hemorrhage, Gastrointestinal	1
2	Unknown Status	Treatment	Gastro-esophageal Reflux Disease (GERD)	1
2, 3	Completed	Treatment	EE / Gastro-esophageal Reflux Disease (GERD) / Oesophagitis, Eosinophilic	1
2, 3	Recruiting	Treatment	Hepatic Encephalopathy	1
2, 3	Recruiting	Treatment	Preeclampsia	1
2, 3	Unknown Status	Treatment	Gastro-esophageal Reflux Disease (GERD)	1
3	Active Not Recruiting	Prevention	Esophageal Cancers / Precancerous Conditions	1
3	Completed	Not Available	Airway Responsiveness	1
3	Completed	Prevention	Back Pain Lower Back / Duodenal Ulcer / Gastric Ulcer (GU) / Osteoarthritis (OA) / Rheumatoid Arthritis	2
3	Completed	Prevention	Bleeding / ERCP	1
3	Completed	Prevention	Duodenal Ulcer / Gastric Ulcer (GU)	1
3	Completed	Prevention	Hemorrhage, Gastrointestinal	1
3	Completed	Prevention	NSAID Associated Gastric Ulcers	2
3	Completed	Prevention	Peptic ulcer haemorrhage	1
3	Completed	Prevention	Prevention	1
3	Completed	Prevention	Reflux, Gastroesophageal	1
3	Completed	Prevention	Stress Ulcer Prophylaxis	1
3	Completed	Treatment	Arthritis / Bleeding Ulcers	1
3	Completed	Treatment	Asthma Bronchial	1
3	Completed	Treatment	Asthma Bronchial / Chronic Lung Diseases / Lung Diseases, Obstructive	1
3	Completed	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
3	Completed	Treatment	Bleeding / Peptic Ulcers	1
3	Completed	Treatment	Dyslipidemia (Fredrickson Type Ⅱa)	1
3	Completed	Treatment	Erosive Esophagitis(EE)	2
3	Completed	Treatment	Gastric Ulcer (GU)	4
3	Completed	Treatment	Gastro-esophageal Reflux Disease (GERD)	9
3	Completed	Treatment	Gastrointestinal Diseases / Indigestion / Signs and Symptoms, Digestive	2
3	Completed	Treatment	Healthy Volunteers	1
3	Completed	Treatment	Heartburn	2
3	Completed	Treatment	Heartburn / Indigestion / Reflux, Gastroesophageal	1
3	Completed	Treatment	Hemorrhage, Gastrointestinal	1
3	Completed	Treatment	NSAID Associated Gastric Ulcers	2
3	Completed	Treatment	NSAIDs / Upper GI Symptoms	2
3	Completed	Treatment	Osteoarthritis (OA)	2
3	Completed	Treatment	Reflux Esophagitis (RE)	2
3	Completed	Treatment	Reflux, Gastroesophageal	2
3	Completed	Treatment	Reflux, Gastroesophageal / Thoracic Pain	1
3	Completed	Treatment	Symptomatic Gastroesophageal Reflux Disease (sGERD)	1
3	Completed	Treatment	Type 2 Diabetes Mellitus	1
3	Completed	Treatment	Zollinger-Ellison Syndrome	1
3	Not Yet Recruiting	Treatment	Erosive Esophagitis(EE)	1
3	Not Yet Recruiting	Treatment	Sepsis / Shock, Septic	1
3	Recruiting	Prevention	Duodenal Ulcer / Gastric Ulcer (GU) / Reflux Esophagitis (RE)	1
3	Recruiting	Prevention	Prophylaxis of preeclampsia	1
3	Recruiting	Treatment	Acute and Chronic Inflammation / Indigestion	1
3	Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
3	Recruiting	Treatment	Dry Eye Syndrome (DES) / Ophthalmopathy, Thyroid-Associated	1
3	Recruiting	Treatment	Erosive Esophagitis (EE)	1
3	Recruiting	Treatment	Indigestion	1
3	Terminated	Treatment	Gastric Ulcer (GU)	1
3	Terminated	Treatment	Nausea	1
3	Unknown Status	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastritis Chronic	1
3	Unknown Status	Treatment	Gastro-esophageal Reflux Disease (GERD)	1
3	Unknown Status	Treatment	Lymphocytic Gastritis	1
3	Withdrawn	Treatment	Gastro-esophageal Reflux Disease (GERD)	1
3	Withdrawn	Treatment	Larynx Disease	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	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
4	Completed	Diagnostic	Gastro-esophageal Reflux Disease (GERD)	1
4	Completed	Diagnostic	Indigestion / Reflux, Gastroesophageal	1
4	Completed	Diagnostic	Reflux, Gastroesophageal	1
4	Completed	Prevention	Abdominal Pain (AP) / Nausea / Vomiting	1
4	Completed	Prevention	Postoperative Bariatric Surgery	1
4	Completed	Prevention	Ulcers	1
4	Completed	Supportive Care	Impacted Third Molar Tooth / Other Surgical Procedures / Pain NOS	1
4	Completed	Treatment	Acid Regurgitation / Heartburn / Nausea / Upper Abdominal Pain	1
4	Completed	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	5
4	Completed	Treatment	Chronic Posterior Laryngitis (CPL)	1
4	Completed	Treatment	Colorectal Cancers	1
4	Completed	Treatment	Coughing / Gastro-esophageal Reflux Disease (GERD)	1
4	Completed	Treatment	Critically Ill Patients / Indication for Stress Ulcer Prophylaxis	1
4	Completed	Treatment	Erosive Esophagitis(EE)	3
4	Completed	Treatment	Erosive Esophagitis(EE) / Gastro-esophageal Reflux Disease (GERD) / Non-erosive Esophagitis	1
4	Completed	Treatment	Esophagus, Barrett	3
4	Completed	Treatment	Functional Dyspepsia / Helicobacter Pylori / Peptic Ulcers	1
4	Completed	Treatment	Functional Dyspepsia / Nonulcer Dyspepsia	1
4	Completed	Treatment	Gastric Ulcer (GU)	1
4	Completed	Treatment	Gastritis Chronic / Non Erosive Reflux Disease	1
4	Completed	Treatment	Gastritis / Indigestion / Peptic Ulcers	1
4	Completed	Treatment	Gastro-Oesophageal Reflux	1
4	Completed	Treatment	Gastro-esophageal Reflux Disease (GERD)	15
4	Completed	Treatment	Gastro-esophageal Reflux Disease (GERD) / Heartburn	1
4	Completed	Treatment	Gastro-esophageal Reflux Disease (GERD) / Reflux Esophagitis (RE)	1
4	Completed	Treatment	Healthy Volunteers	1
4	Completed	Treatment	Heartburn	2
4	Completed	Treatment	Heartburn / Reflux, Gastroesophageal	1
4	Completed	Treatment	Helicobacter Infection	1
4	Completed	Treatment	Helicobacter Infections	1
4	Completed	Treatment	Indigestion	2
4	Completed	Treatment	Juvenile Idiopathic Arthritis (JIA)	1
4	Completed	Treatment	NSAID Induced Gastropathy	1
4	Completed	Treatment	Osteoporosis	1
4	Completed	Treatment	Peptic Ulcer Bleeding	1
4	Completed	Treatment	Reflux, Gastroesophageal	3
4	Completed	Treatment	Relapsing Remitting Multiple Sclerosis (RRMS)	1
4	Completed	Treatment	Schizophrenic Disorders	1
4	Not Yet Recruiting	Treatment	Psoriasis	1
4	Recruiting	Prevention	Acid-related Symptoms / Stomach Diseases	1
4	Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	10
4	Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastric Ulcer (GU) / Gastritis / Gastritis Chronic / Malignant Neoplasm of Stomach	1
4	Recruiting	Treatment	Indigestion	1
4	Recruiting	Treatment	Osteoarthritis (OA)	1
4	Terminated	Treatment	Indigestion	1
4	Unknown Status	Screening	30 Healthy People	1
4	Unknown Status	Treatment	Aspirin / Indigestion	1
4	Unknown Status	Treatment	Gastro-esophageal Reflux Disease (GERD) / Heartburn / Sleep Disturbances	1
4	Unknown Status	Treatment	Gastroesophageal Refluxdisease / Indigestion / Ulcers	1
4	Unknown Status	Treatment	Healthy Volunteers	1
4	Unknown Status	Treatment	Peptic Ulcers	1
4	Unknown Status	Treatment	Upper Gastrointestinal Hemorrhage	2
4	Withdrawn	Prevention	Anastomotic Stricture / Obesity, Morbid	1
4	Withdrawn	Treatment	Helicobacter Pylori Gastrointestinal Tract Infection	1
4	Withdrawn	Treatment	Laryngopharyngeal Reflux	1
4	Withdrawn	Treatment	Peptic Ulcers	1
Not Available	Completed	Not Available	Community Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD)	1
Not Available	Completed	Not Available	Gastro-esophageal Reflux Disease (GERD) / Quality of Life	1
Not Available	Completed	Not Available	Pharmacokinetics / Voriconazole	1
Not Available	Completed	Basic Science	Reflux, Gastroesophageal	1
Not Available	Completed	Diagnostic	Gastro-esophageal Reflux Disease (GERD)	2
Not Available	Completed	Health Services Research	Gastro-esophageal Reflux Disease (GERD)	1
Not Available	Completed	Health Services Research	Kidney Transplant; Complications	1
Not Available	Completed	Prevention	Stomach Neoplasms	1
Not Available	Completed	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	2
Not Available	Completed	Treatment	Gastritis	1
Not Available	Completed	Treatment	Laryngopharyngeal Reflux / Oesophageal pH-impedance	1
Not Available	Completed	Treatment	Oesophagitis, Eosinophilic	1
Not Available	Completed	Treatment	Reflux, Gastroesophageal	1
Not Available	Completed	Treatment	Treatment of Helicobacter Pylori	1
Not Available	Completed	Treatment	Type 2 Diabetes Mellitus	1
Not Available	Completed	Treatment	Vasomotor Rhinitis	1
Not Available	Not Yet Recruiting	Not Available	Gastro-esophageal Reflux Disease (GERD)	1
Not Available	Not Yet Recruiting	Treatment	Gastro-esophageal Reflux Disease (GERD)	1
Not Available	Recruiting	Not Available	Reflux, Gastroesophageal	1
Not Available	Recruiting	Diagnostic	Non-erosive Reflux Disease (NERD)	1
Not Available	Recruiting	Diagnostic	Non-erosive Reflux Disease (NERD) / Reflux, Gastroesophageal	1
Not Available	Recruiting	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	3
Not Available	Recruiting	Treatment	Gastric Peroral Endoscopic Pyloromyotomy (G-POEM)	1
Not Available	Recruiting	Treatment	Helicobacter Infection	1
Not Available	Recruiting	Treatment	Preeclampsia	1
Not Available	Recruiting	Treatment	Prophylaxis of preeclampsia	1
Not Available	Terminated	Diagnostic	Achalasia / GORD	1
Not Available	Terminated	Prevention	Esophagus, Barrett	1
Not Available	Terminated	Treatment	Duodenal Ulcer Induced by Anti-platelet Agent / Gastric Ulcer Induced by Anti-platelet Agent / OGD	1
Not Available	Terminated	Treatment	Gastro-Esophageal Reflux	1
Not Available	Unknown Status	Treatment	Bacterial Infection Due to Helicobacter Pylori (H. Pylori)	1
Not Available	Unknown Status	Treatment	Hemostasis / Hexacapron / Rebleeding / The Mortality Rate / Upper Gastrointestinal Hemorrhage	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
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/1
Granule, delayed release	Oral	10 mg
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)
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

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

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

Details1. Potassium-transporting ATPase alpha chain 1

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]

Enzymes

Details1. Cytochrome P450 2C19

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

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]

Details2. Cytochrome P450 3A4

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

Drug created on June 13, 2005 07:24 / Updated on February 22, 2019 22:55

Esomeprazole

Identification

Structure for Esomeprazole (DB00736)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

Enzymes

References