Omeprazole

Identification

Name

Omeprazole

Accession Number

DB00338

Description

Originally approved by the FDA in 1989, omeprazole is a proton-pump inhibitor, used to treat gastric acid-related disorders. These disorders may include gastroesophageal reflux disease (GERD), peptic ulcer disease, and other diseases characterized by the oversecretion of gastric acid. This drug was the first clinical useful drug in its class, and its approval was followed by the formulation of many other proton pump inhibitor drugs ⁶. Omeprazole is generally effective and well-tolerated, promoting its popular use in children and adults ^Label.

Type

Small Molecule

Groups

Approved, Investigational, Vet approved

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Omeprazole (DB00338)

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Weight

Average: 345.416
Monoisotopic: 345.114712179

Chemical Formula

C₁₇H₁₉N₃O₃S

Synonyms

• OMEP
• Omeprazol
• Omeprazole
• Omeprazolum

Pharmacology

Indication

Omeprazole, according to the FDA label ^Label is a proton pump inhibitor (PPI) used for the following purposes:

• Treatment of active duodenal ulcer in adults

• Eradication of Helicobacter pylori to reduce the risk of duodenal ulcer recurrence in adults

• Treatment of active benign gastric ulcer in adults

• Treatment of symptomatic gastroesophageal reflux disease (GERD) in patients 1 year of age and older

• Treatment of erosive esophagitis (EE) due to acid-mediated GERD in patients 1 month of age and older

• Maintenance of healing of EE due to acid-mediated GERD in patients 1 year of age and older

• Pathologic hypersecretory conditions in adults

Associated Conditions

• Ankylosing Spondylitis (AS)
• Duodenal Ulcer
• Erosive Esophagitis
• Gastric Ulcer
• Gastro-esophageal Reflux Disease (GERD)
• Healing
• Heartburn
• Helicobacter Pylori Infection
• NSAID Associated Gastric Ulcers
• Osteoarthritis (OA)
• Rheumatoid Arthritis
• Zollinger-Ellison Syndrome
• Hypersecretory conditions
• Multiple endocrine adenomas

Contraindications & Blackbox Warnings

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Pharmacodynamics

Effects on gastric acid secretion

This drug decreases gastric acid secretion ^Label. After oral administration, the onset of the antisecretory effect of omeprazole is usually achieved within one hour, with the maximum effect occurring by 2 hours after administration. The inhibitory effect of omeprazole on acid secretion increases with repeated once-daily dosing, reaching a plateau after four days ^Label.

Effects on serum gastrin

In studies of 200 or more patients, serum gastrin levels increased during the first 1-2 weeks of daily administration of therapeutic doses of omeprazole. This occurred in a parallel fashion with the inhibition of acid secretion. No further increase in serum gastrin occurred with continued omeprazole administration. Increased gastrin causes enterochromaffin-like cell hyperplasia and increased serum Chromogranin A (CgA) levels. The increased CgA levels may lead to false positive results in diagnostic studies for neuroendocrine tumors ^Label.

Enterochromaffin-like (ECL) cell effects

Human gastric biopsy samples have been obtained from more than 3000 pediatric and adult patients treated with omeprazole in long-term clinical studies. The incidence of enterochromaffin-like cell hyperplasia in these studies increased with time; however, no case of ECL cell carcinoids, dysplasia, or neoplasia have been identified in these patients. These studies, however, are of insufficient in power and duration to draw conclusions on the possible influence of long-term administration of omeprazole in the development of any premalignant or malignant conditions ^Label.

Other effects

Systemic effects of omeprazole in the central nervous system, cardiovascular and respiratory systems have not been found to date. Omeprazole, given in oral doses of 30 or 40 mg for 2-4 weeks, showed no effect on thyroid function, carbohydrate metabolism, or circulating levels of parathyroid hormone, cortisol, estradiol, testosterone, prolactin, cholecystokinin or secretin ^Label.

Mechanism of action

Hydrochloric acid (HCl) secretion into the gastric lumen is a process regulated mainly by the H(+)/K(+)-ATPase of the proton pump ¹⁰, expressed in high quantities by the parietal cells of the stomach. ATPase is an enzyme on the parietal cell membrane that facilitates hydrogen and potassium exchange through the cell, which normally results in the extrusion of potassium and formation of HCl (gastric acid) ⁹.

Omeprazole is a member of a class of antisecretory compounds, the substituted benzimidazoles, that stop gastric acid secretion by selective inhibition of the H+/K+ ATPase enzyme system. Proton-pump inhibitors such as omeprazole bind covalently to cysteine residues via disulfide bridges on the alpha subunit of the H+/K+ ATPase pump, inhibiting gastric acid secretion for up to 36 hours ¹¹. This antisecretory effect is dose-related and leads to the inhibition of both basal and stimulated acid secretion, regardless of the stimulus ^Label.

Mechanism of H. pylori eradication

Peptic ulcer disease (PUD) is frequently associated with Helicobacter pylori bacterial infection (NSAIDs) ¹². The treatment of H. pylori infection may include the addition of omeprazole or other proton pump inhibitors as part of the treatment regimen ^Label, ¹³. H. pylori replicates most effectively at a neutral pH ¹⁴. Acid inhibition in H. pylori eradication therapy, including proton-pump inhibitors such as omeprazole, raises gastric pH, discouraging the growth of H.pylori ¹³. It is generally believed that proton pump inhibitors inhibit the urease enzyme, which increases the pathogenesis of H. pylori in gastric-acid related conditions ¹⁵.

Target	Actions	Organism
APotassium-transporting ATPase alpha chain 1	inhibitor	Humans
UAryl hydrocarbon receptor	agonist	Humans

Absorption

Omeprazole delayed-release capsules contain an enteric-coated granule formulation of omeprazole (because omeprazole is acid-labile), so that absorption of omeprazole begins only after the granules exit the stomach ^Label.

Absorption of omeprazole occurs rapidly, with peak plasma concentrations of omeprazole achieved within 0.5-3.5 hours ^Label.

Absolute bioavailability (compared with intravenous administration) is approximately 30-40% at doses of 20-40 mg, largely due to pre-systemic metabolism. The bioavailability of omeprazole increases slightly upon repeated administration of omeprazole delayed-release capsules ^Label.

Volume of distribution

Approximately 0.3 L/kg, corresponding to the volume of extracellular water ⁵.

Protein binding

Approximately 95% bound to human plasma proteins ^Label.

Metabolism

Omeprazole is heavily metabolized in the liver by the cytochrome P450 (CYP) enzyme system. The main part of its metabolism depends on the polymorphically expressed CYP2C19, which is responsible for the formation of hydroxyomeprazole, the major metabolite found in plasma. The remaining part depends on CYP3A4, responsible for the formation of omeprazole sulphone ^Label.

Hover over products below to view reaction partners

• Omeprazole
  • 5-Hydroxyomeprazole
  • 5'-O-Desmethyl omeprazole
  • Omeprazole sulfone
  • 3-Hydroxyomeprazole

Route of elimination

After a single dose oral dose of a buffered solution of omeprazole, negligible (if any) amounts of unchanged drug were excreted in urine. Most of the dose (about 77%) was eliminated in urine as at least six different metabolites. Two metabolites were identified as hydroxyomeprazole and the corresponding carboxylic acid. The remainder of the dose was found in the feces. This suggests significant biliary excretion of omeprazole metabolites. Three metabolites have been identified in the plasma, the sulfide and sulfone derivatives of omeprazole, and hydroxyomeprazole. These metabolites possess minimal or no antisecretory activity ^Label.

Half-life

0.5-1 hour (healthy subjects, delayed-release capsule) ^Label
Approximately 3 hours (hepatic impairment) ^Label

Clearance

Healthy subject (delayed release capsule), total body clearance 500 - 600 mL/min ^Label

Geriatric plasma clearance: 250 mL/min ^Label

Hepatic impairment plasma clearance: 70 mL/min ^Label

Adverse Effects

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Toxicity

Oral acute (LD50): 4000 mg/kg (mouse), 2210 mg/kg (rat) ^MSDS.

Overdose

Symptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.

Carcinogenesis and mutagenesis

In 24-month studies in rats, a dose-related significant increase in gastric carcinoid tumors and ECL cell hyperplasia was seen in male and female animals. Carcinoid tumors have also been found in rats treated with a fundectomy or long-term treatment with other proton pump inhibitors, or high doses of H2-receptor antagonists ^Label.

Omeprazole showed positive clastogenic effects in an in vitro human lymphocyte chromosomal aberration study, in one of two in vivo mouse micronucleus tests, and in an in vivo bone marrow cell chromosomal aberration test. Omeprazole tested negative in the in vitro Ames test, an in vitro mouse lymphoma cell forward mutation assay, and an in vivo rat liver DNA damage assay ^Label.

The use in breastfeeding

Limited data indicate that omeprazole may be present in human milk. There is currently no information on the effects of omeprazole on the breastfed infant or production of milk. The benefits of breastfeeding should be considered along with the level of need for omeprazole and any potential adverse effects on the breastfed infant from omeprazole ^Label.

Effects on fertility

Effects of omeprazole at oral doses up to 138 mg/kg/day in rats (about 34 times an oral human dose) was found to have no impact on fertility and reproductive performance ^Label.

Affected organisms

• Humans and other mammals

Pathways

Pathway	Category
Omeprazole Metabolism Pathway	Drug metabolism
Omeprazole 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 omeprazole.	Details
Cytochrome P450 2C19	CYP2C19*3	(A;A)	A Allele, homozygote	Effect Directly Studied	Patients with this genotype have reduced metabolism of omeprazole.	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
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Abametapir	The serum concentration of Omeprazole can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Omeprazole can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be increased when combined with Omeprazole.
Abiraterone	The metabolism of Omeprazole can be decreased when combined with Abiraterone.
Acalabrutinib	The metabolism of Acalabrutinib can be increased when combined with Omeprazole.
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Omeprazole.
Acenocoumarol	The metabolism of Acenocoumarol can be increased when combined with Omeprazole.
Acetaminophen	The metabolism of Acetaminophen can be increased when combined with Omeprazole.
Acetohexamide	The metabolism of Acetohexamide can be decreased when combined with Omeprazole.
Acetyl sulfisoxazole	The metabolism of Omeprazole can be decreased when combined with Acetyl sulfisoxazole.

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Severity
Severity
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Evidence Level
Evidence Level
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Action
Action
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Food Interactions

• Take before a meal. Allow 30-60 minutes before a meal.

Products

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Omeprazole magnesium	426QFE7XLK	95382-33-5	KWORUUGOSLYAGD-UHFFFAOYSA-N
Omeprazole sodium	KV03YZ6QLW	95510-70-6	RYXPMWYHEBGTRV-UHFFFAOYSA-N

Product Images

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International/Other Brands

Antra / Audazol / Belmazol / Ceprandal / Danlox / Desec / Elgam / Emeproton / Gasec / Gastrimut / Gastroloc / Indurgan / Inhibitron / Logastric / Losec / Mepral / Mopral / Olexin / Omapren / Omepral / Omeprazon / Omeprol / Omezol / Omisec / Omizac / Ortanol / Parizac / Prazidec / Prazolit / Procelac / Ramezol / Regulacid / Sanamidol / Ulceral / Ulcesep / Ultop / Zepral

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Leader Omeprazole	Tablet, delayed release	20 mg/1	Oral	Remedy Repack	2013-04-24	2014-04-24
Losec	Capsule, delayed release		Oral	Cheplapharm Arzneimittel Gmbh	1989-12-31	Not applicable
Losec	Tablet, delayed release		Oral	Cheplapharm Arzneimittel Gmbh	1996-12-31	Not applicable
Losec 10 mg	Tablet, delayed release		Oral	Astra Zeneca	1997-04-28	2019-11-16
Losec Capsules 10mg	Capsule, delayed release		Oral	Astra Zeneca	2000-10-03	2013-12-04
Losec Capsules 40mg	Capsule, delayed release		Oral	Astra Zeneca	2003-10-17	2010-06-30
Losec Mups	Tablet, delayed release		Oral	Cheplapharm Arzneimittel Gmbh	2001-02-22	Not applicable
Losec Mups	Tablet, delayed release		Oral	Cheplapharm Arzneimittel Gmbh	2001-02-22	Not applicable
Nra-omeprazole	Tablet, delayed release		Oral	Nora Pharma Inc	Not applicable	Not applicable
Omeprazole	Tablet, delayed release	20 mg	Oral	Altamed Pharma	2020-03-12	Not applicable

Additional Data Available

Application Number
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Product Code
Product Code
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Ag-omeprazole Dr	Tablet, delayed release		Oral	Angita Pharma Inc.	Not applicable	Not applicable
Apo-omeprazole	Capsule, delayed release		Oral	Apotex Corporation	2004-01-28	Not applicable
Apo-omeprazole	Capsule, delayed release		Oral	Apotex Corporation	Not applicable	Not applicable
Auro-omeprazole	Capsule, delayed release		Oral	Auro Pharma Inc	2014-03-26	2014-03-26
Auro-omeprazole	Capsule, delayed release		Oral	Auro Pharma Inc	2014-03-26	2014-03-26
Ava-omeprazole	Capsule, delayed release		Oral	Avanstra Inc	2011-11-28	2014-08-21
Bio-omeprazole	Tablet, delayed release		Oral	Biomed Pharma	2016-09-07	Not applicable
Dom-omeprazole Dr	Tablet, delayed release		Oral	Dominion Pharmacal	Not applicable	Not applicable
Dom-omeprazole Dr	Tablet, delayed release		Oral	Dominion Pharmacal	2013-01-23	2019-01-04
Jamp-omeprazole Dr	Tablet, delayed release		Oral	Jamp Pharma Corporation	2014-02-11	Not applicable

Additional Data Available

Application Number
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Product Code
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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
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Acid Reducer	Tablet, delayed release	20 mg/1	Oral	FRED'S, INC.	2018-06-06	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	Cardinal Health	2018-06-06	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	Winco Foods, Llc.	2018-06-06	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	Aurohealth LLC	2020-05-16	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	Bi-Mart	2018-06-06	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	CVS Pharmacy, Inc.	2020-09-23	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	Wal-Mart Stores, Inc.	2018-06-06	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	Discount Drug Mart	2018-06-06	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	Aurohealth LLC	2018-06-06	Not applicable
Acid Reducer	Capsule, delayed release	20 mg/1	Oral	Cardinal Health	2017-03-07	Not applicable

Additional Data Available

Application Number
Application Number
Available for Purchase
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
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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Aspirin and Omeprazole Delayed-release Tab	Omeprazole (40 mg/1) + Acetylsalicylic acid (81 mg/1)	Tablet, film coated	Oral	Innovida Therapeutique Corporation	2019-11-13	Not applicable
Aspirin and Omeprazole Delayed-release Tab	Omeprazole (40 mg/1) + Acetylsalicylic acid (325 mg/1)	Tablet, film coated	Oral	Innovida Phamaceutique Corporation	2019-07-17	Not applicable
Aspirin and Omeprazole Delayed-release Tab	Omeprazole (40 mg/1) + Acetylsalicylic acid (81 mg/1)	Tablet, film coated	Oral	Innovida Phamaceutique Corporation	2019-07-17	Not applicable
Good Sense Omeprazole and Sodium Bicarbonate	Omeprazole (20 mg/1) + Sodium bicarbonate (1100 mg/1)	Capsule, gelatin coated	Oral	L. Perrigo Company	2017-06-19	Not applicable
medPREDkit	Omeprazole (20 mg/1) + Methylprednisolone (4 mg/1) + Sodium bicarbonate (1100 mg/1)	Kit	Oral	Medarbor Llc	2017-12-25	2018-01-15
Not Applicable	Omeprazole (40 mg/1) + Sodium bicarbonate (1100 mg/1)	Capsule	Oral	Sterling Knight Pharmaceuticals, Llc	2017-07-13	Not applicable
Omeclamox-Pak	Omeprazole (20 mg/1) + Amoxicillin Trihydrate (500 mg/1) + Clarithromycin (500 mg/1)	Kit	Oral	Cumberland Pharmaceuticals Inc.	2012-04-27	Not applicable
Omeclamox-Pak	Omeprazole (20 mg/1) + Amoxicillin Trihydrate (500 mg/1) + Clarithromycin (500 mg/1)	Kit	Oral	Pernix Therapeutics	2012-04-27	2016-07-31
Omeprazole and Sodium Bicarbonate	Omeprazole (20 mg/1) + Sodium bicarbonate (1100 mg/1)	Capsule	Oral	Zydus Pharmaceuticals (USA) Inc.	2018-07-19	Not applicable
Omeprazole and Sodium Bicarbonate	Omeprazole (20 mg/1) + Sodium bicarbonate (1100 mg/1)	Capsule, gelatin coated	Oral	Meijer Distribution Inc	2020-04-03	Not applicable

Categories

ATC Codes

A02BC01 — Omeprazole

• 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

A02BD05 — Omeprazole, 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

A02BD01 — Omeprazole, amoxicillin and metronidazole

• 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

Drug Categories

• 2-Pyridinylmethylsulfinylbenzimidazoles
• Acid Reducers
• Alimentary Tract and Metabolism
• Anti-Ulcer Agents
• BCRP/ABCG2 Inhibitors
• Benzimidazoles
• Cytochrome P-450 CYP1A2 Inducers
• Cytochrome P-450 CYP1A2 Inducers (strength unknown)
• Cytochrome P-450 CYP1A2 Inhibitors
• Cytochrome P-450 CYP2C18 Substrates
• Cytochrome P-450 CYP2C19 Inhibitors
• Cytochrome P-450 CYP2C19 Inhibitors (weak)
• Cytochrome P-450 CYP2C19 Substrates
• Cytochrome P-450 CYP2C8 Substrates
• Cytochrome P-450 CYP2C9 Substrates
• Cytochrome P-450 CYP2D6 Inhibitors
• Cytochrome P-450 CYP2D6 Inhibitors (weak)
• Cytochrome P-450 CYP3A Inducers
• Cytochrome P-450 CYP3A Inhibitors
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Inducers
• Cytochrome P-450 CYP3A4 Inducers (strength unknown)
• Cytochrome P-450 CYP3A4 Inhibitors
• Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Enzyme Inducers
• Cytochrome P-450 Enzyme Inhibitors
• Cytochrome P-450 Substrates
• 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
• P-glycoprotein inhibitors
• P-glycoprotein substrates
• Photosensitizing Agents
• 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

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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

aromatic ether, sulfoxide, pyridines, benzimidazoles (CHEBI:77260)

Chemical Identifiers

UNII

KG60484QX9

CAS number

73590-58-6

InChI Key

SUBDBMMJDZJVOS-UHFFFAOYSA-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)

IUPAC Name

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

SMILES

COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(C)C(OC)=C1C

References

Synthesis Reference

Arne E. Brandstrom, Bo R. Lamm, "Processes for the preparation of omeprazole and intermediates therefore." U.S. Patent US4620008, issued October, 1982.

US4620008

General References

1. Yang YX, Lewis JD, Epstein S, Metz DC: Long-term proton pump inhibitor therapy and risk of hip fracture. JAMA. 2006 Dec 27;296(24):2947-53. [PubMed:17190895]
2. Castell D: Review of immediate-release omeprazole for the treatment of gastric acid-related disorders. Expert Opin Pharmacother. 2005 Nov;6(14):2501-10. doi: 10.1517/14656566.6.14.2501 . [PubMed:16259581]
3. Higuera-de-la-Tijera F: Efficacy of omeprazole/sodium bicarbonate treatment in gastroesophageal reflux disease: a systematic review. Medwave. 2018 Mar 14;18(2):e7179. doi: 10.5867/medwave.2018.02.7179. [PubMed:29547594]
4. Welage LS, Berardi RR: Evaluation of omeprazole, lansoprazole, pantoprazole, and rabeprazole in the treatment of acid-related diseases. J Am Pharm Assoc (Wash). 2000 Jan-Feb;40(1):52-62; quiz 121-3. [PubMed:10665250]
5. Cederberg C, Andersson T, Skanberg I: Omeprazole: pharmacokinetics and metabolism in man. Scand J Gastroenterol Suppl. 1989;166:33-40; discussion 41-2. [PubMed:2690330]
6. Strand DS, Kim D, Peura DA: 25 Years of Proton Pump Inhibitors: A Comprehensive Review. Gut Liver. 2017 Jan 15;11(1):27-37. doi: 10.5009/gnl15502. [PubMed:27840364]
7. McTavish D, Buckley MM, Heel RC: Omeprazole. An updated review of its pharmacology and therapeutic use in acid-related disorders. Drugs. 1991 Jul;42(1):138-70. doi: 10.2165/00003495-199142010-00008. [PubMed:1718683]
8. Langtry HD, Wilde MI: Omeprazole. A review of its use in Helicobacter pylori infection, gastro-oesophageal reflux disease and peptic ulcers induced by nonsteroidal anti-inflammatory drugs. Drugs. 1998 Sep;56(3):447-86. doi: 10.2165/00003495-199856030-00012. [PubMed:9777317]
9. Lewin MJ: Cellular mechanisms and inhibitors of gastric acid secretion. Drugs Today (Barc). 1999 Oct;35(10):743-52. [PubMed:12973369]
10. Sachs G, Wallmark B: The gastric H+,K+-ATPase: the site of action of omeprazole. Scand J Gastroenterol Suppl. 1989;166:3-11. [PubMed:2557669]
11. Sachs G, Shin JM, Howden CW: Review article: the clinical pharmacology of proton pump inhibitors. Aliment Pharmacol Ther. 2006 Jun;23 Suppl 2:2-8. doi: 10.1111/j.1365-2036.2006.02943.x. [PubMed:16700898]
12. Sung JJ, Kuipers EJ, El-Serag HB: Systematic review: the global incidence and prevalence of peptic ulcer disease. Aliment Pharmacol Ther. 2009 May 1;29(9):938-46. doi: 10.1111/j.1365-2036.2009.03960.x. [PubMed:19220208]
13. Vcev A, Stimac D, Vceva A, Takac B, Pezerovic D, Ivandic A: High dose omeprazole plus amoxicillin and azithromycin in eradication of Helicobacter pylori in duodenal ulcers. Helicobacter. 1999 Mar;4(1):54-7. [PubMed:10352088]
14. Scott DR, Sachs G, Marcus EA: The role of acid inhibition in Helicobacter pylori eradication. F1000Res. 2016 Jul 19;5. doi: 10.12688/f1000research.8598.1. eCollection 2016. [PubMed:30023042]
15. Mobley HL: The role of Helicobacter pylori urease in the pathogenesis of gastritis and peptic ulceration. Aliment Pharmacol Ther. 1996 Apr;10 Suppl 1:57-64. [PubMed:8730260]
16. FDA Approved Drug Products: Talicia Amoxicillin, Omeprazole, and Rifabutin Oral Delayed Release Capsules [Link]
17. NIH StatPearls: Omeprazole [Link]
18. FDA Approved Products: Prilosec (omeprazole) delayed release capsules [Link]

External Links

Human Metabolome Database

HMDB0001913

KEGG Drug

D00455

KEGG Compound

C07324

PubChem Compound

4594

PubChem Substance

46509065

ChemSpider

4433

BindingDB

50241343

RxNav

7646

ChEBI

77260

ChEMBL

CHEMBL1503

Therapeutic Targets Database

DAP000180

PharmGKB

PA450704

Guide to Pharmacology

GtP Drug Page

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

PDRhealth

PDRhealth Drug Page

Wikipedia

Omeprazole

AHFS Codes

• 56:28.36 — Proton-pump Inhibitors

FDA label

Download (1.01 MB)

MSDS

Download (73.8 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Prevention	Helicobacter Pylori Infection / Obesity, Morbid	1
4	Completed	Not Available	Achlorhydria / Gastro-esophageal Reflux Disease (GERD) / Hip Fracture / Osteoporosis	1
4	Completed	Not Available	Normal Healthy Subject Population	1
4	Completed	Basic Science	Clostridium Difficile	1
4	Completed	Basic Science	Healthy Volunteers	1
4	Completed	Basic Science	Probiotics	1
4	Completed	Basic Science	Rejection, Transplant	1
4	Completed	Basic Science	Tolerance	1
4	Completed	Basic Science	Type 2 Diabetes Mellitus	1
4	Completed	Diagnostic	Food Allergy	1

Pharmacoeconomics

Manufacturers

• Apotex inc
• Dr reddys laboratories ltd
• Impax laboratories inc
• Kremers urban development co
• Lek pharmaceuticals d d
• Mylan pharmaceuticals inc
• Sandoz inc
• Watson laboratories inc florida
• Astrazeneca lp
• Dexcel pharma technologies ltd
• Santarus, Inc.

Packagers

• Aidarex Pharmacuticals LLC
• Altura Pharmaceuticals Inc.
• Amerisource Health Services Corp.
• Apotex Inc.
• A-S Medication Solutions LLC
• Astra Pharma Inc.
• AstraZeneca Inc.
• Atlantic Biologicals Corporation
• Blenheim Pharmacal
• Bryant Ranch Prepack
• Cardinal Health
• Caremark LLC
• Comprehensive Consultant Services Inc.
• Concern Stirol
• Contract Packaging Resources Inc.
• Corepharma LLC
• Coupler Enterprises Inc.
• CVS Pharmacy
• Dept Health Central Pharmacy
• Dexcel Ltd.
• DHHS Program Support Center Supply Service Center
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• Doctor Reddys Laboratories Ltd.
• Ftl International Inc.
• Global Pharmaceuticals
• Golden State Medical Supply Inc.
• H.J. Harkins Co. Inc.
• Heartland Repack Services LLC
• Impax Laboratories Inc.
• Innoviant Pharmacy Inc.
• Kaiser Foundation Hospital
• Keltman Pharmaceuticals Inc.
• Laboratorios Dr Esteve SA
• Lake Erie Medical and Surgical Supply
• Lek Pharmaceuticals Inc.
• Major Pharmaceuticals
• Mckesson Corp.
• Medisca Inc.
• Medsource Pharmaceuticals
• Merck & Co.
• Merial Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Nucare Pharmaceuticals Inc.
• Palmetto Pharmaceuticals Inc.
• Par Pharmaceuticals
• Patheon Inc.
• PD-Rx Pharmaceuticals Inc.
• Perrigo Co.
• Physicians Total Care Inc.
• Preferred Pharmaceuticals Inc.
• Prepak Systems Inc.
• Prescript Pharmaceuticals
• Procter & Gamble
• Ranbaxy Laboratories
• Rebel Distributors Corp.
• Remedy Repack
• S&P Healthcare
• Sandhills Packaging Inc.
• Sandoz
• Santarus Inc.
• Schwarz Pharma Inc.
• Southwood Pharmaceuticals
• St Mary's Medical Park Pharmacy
• Stat Rx Usa
• Teva Pharmaceutical Industries Ltd.
• Torpharm Inc.
• UDL Laboratories
• Vangard Labs Inc.
• Watson Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet, delayed release	Oral
Tablet, delayed release	Oral	10 MG
Tablet, delayed release	Oral	20 MG
Capsule, delayed release	Oral	75 mg
Capsule; kit; tablet	Oral	250 mg
Tablet, delayed release	Oral	250 mg
Injection, powder, lyophilized, for solution	Intravenous	40 mg
Capsule, coated	Oral	20 mg
Injection	Intravenous	40 mg/ml
Capsule, delayed release; capsule, extended release	Oral	20 mg
Tablet	Oral	10 MG
Tablet	Oral	20 MG
Capsule, extended release	Oral	10 mg
Injection, powder, for solution	Intravenous	40 MG
Capsule, delayed release	Oral	20 MG
Capsule	Oral	40 mg
Kit	Oral
Capsule, coated pellets	Oral	20 mg
Capsule, delayed release	Oral	10 MG
Capsule, delayed release	Oral	40 MG
Tablet, delayed release	Oral	40 MG
Capsule	Oral	20 MG
Powder, for solution	Intravenous	40 MG
Capsule, coated	Oral	10 mg
Capsule, coated	Oral	40 mg
Capsule, coated	Oral	470.59 mg
Capsule, coated	Oral	21 mg
Capsule, coated	Oral	232.8 mg
Capsule	Oral	40 mg/1
Capsule, delayed release	Oral	20.6 mg/1
Capsule, delayed release	Oral	235.3 mg
Capsule, delayed release	Oral	236 mg
Capsule, delayed release pellets	Oral	10 mg/1
Capsule, delayed release pellets	Oral	20 mg/1
Capsule, delayed release pellets	Oral	40 mg/1
Powder	Not applicable	1 kg/1kg
Syrup		2 mg/1mL
Tablet, delayed release	Oral	20 mg/1
Tablet, orally disintegrating, delayed release	Oral	20 mg/1
For suspension	Oral
Capsule	Oral	10 mg/1
Capsule, delayed release	Oral	10 mg/1
Capsule, delayed release	Oral	20 mg/1
Capsule, delayed release	Oral	40 mg/1
Capsule	Oral	20.6 mg/1
Injection, powder, for solution	Intravenous	126 mg
Tablet	Oral
Powder, for suspension	Oral
Capsule, delayed release	Oral	15 MG
Capsule	Oral	10 MG
Capsule, delayed release pellets	Oral	10 MG
Capsule, delayed release pellets	Oral	20 MG
Capsule, delayed release pellets	Oral	40 MG
Injection, solution	Intravenous	40 mg
Injection	Intravenous	40 mg
Capsule	Oral
Capsule, delayed release	Oral	250 mg
Capsule, coated	Oral	191.945 mg
Injection, powder, lyophilized, for solution	Parenteral	40 mg
Kit	Oral; Topical
Capsule	Oral	20 mg/1
Granule, delayed release	Oral	10 mg/1
Granule, delayed release	Oral	2.5 mg/1
Tablet, delayed release	Oral	20.6 mg/1
Capsule, delayed release	Oral
Tablet, coated	Oral	250 mg
Capsule, delayed release	Oral
Capsule, gelatin coated	Oral
Capsule, coated	Oral	20.00007 mg
Tablet, film coated	Oral
Capsule	Oral
Tablet, chewable	Oral

Prices

Unit description	Cost	Unit
PriLOSEC 30 20 mg Delayed Release Capsule Bottle	459.99USD	bottle
Zegerid 30 20-1680 mg Packets Packet	224.27USD	packet
Zegerid 30 40-1680 mg Packets Packet	224.27USD	packet
PriLOSEC 30 10 mg Delayed Release Capsule Bottle	174.37USD	bottle
Omeprazole 28 20 mg Enteric Coated Tabs Box	25.99USD	box
PriLOSEC OTC 14 20 mg Enteric Coated Tabs Box	19.99USD	box
PriLOSEC 40 mg Delayed Release Capsule	9.59USD	capsule
Prilosec dr 40 mg capsule	9.22USD	capsule
Omeprazole 40 mg Delayed Release Capsule	7.69USD	capsule
Zegerid 40-1100 mg capsule	7.48USD	capsule
Zegerid 20 mg capsule	7.19USD	capsule
Zegerid 40 mg capsule	6.46USD	capsule
Prilosec dr 20 mg capsule	6.24USD	capsule
Prilosec 20 mg capsule dr	6.15USD	capsule
Prilosec dr 10 mg capsule	5.59USD	capsule
Omeprazole powder	5.05USD	g
Omeprazole 20 mg Delayed Release Capsule	4.32USD	capsule
Omeprazole 10 mg Delayed Release Capsule	3.13USD	capsule
Losec (Sustained-Release Tablet) 20 mg Capsule/Sustained Release Tablet	2.48USD	tablet
Losec (Sustained-Release Tablet) 10 mg Capsule/Sustained Release Tablet	1.97USD	tablet
Losec (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet	1.24USD	tablet
Apo-Omeprazole 20 mg Capsule/Sustained Release Tablet	1.15USD	tablet
Mylan-Omeprazole 20 mg Capsule/Sustained Release Tablet	1.15USD	tablet
Pms-Omeprazole (Delayed Release Tablet) 20 mg Capsule/Sustained Release Tablet	1.15USD	tablet
Pms-Omeprazole (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet	1.15USD	tablet
Ratio-Omeprazole (Sustained-Release Tablet) 20 mg Capsule/Sustained Release Tablet	1.15USD	tablet
Sandoz Omeprazole (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet	1.15USD	tablet
Mylan-Omeprazole 10 mg Capsule/Sustained Release Tablet	0.86USD	tablet
Sandoz Omeprazole (Sustained-Release Capsule) 10 mg Capsule/Sustained Release Tablet	0.86USD	tablet
Zegerid otc 20-1100 mg capsule	0.78USD	capsule
Prilosec otc 20 mg tablet	0.76USD	tablet
Omeprazole dr 20 mg tablet	0.66USD	tablet
CVS Pharmacy omeprazole dr 20 mg tablet	0.53USD	tablet

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
US5690960	No	1997-11-25	2014-11-25
CA2180535	No	2004-03-23	2014-01-05
CA1338377	No	1996-06-11	2013-06-11
US6489346	No	2002-12-03	2016-07-16
US6699885	No	2004-03-02	2016-07-16
USRE45198	No	2014-10-14	2016-07-16
US6645988	No	2003-11-11	2016-07-16
US7399772	No	2008-07-15	2016-07-16
US6150380	Yes	2000-11-21	2019-05-10
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
US6428810	Yes	2002-08-06	2020-05-03
US9023391	No	2015-05-05	2025-08-16
US6403616	No	2002-06-11	2019-11-15
US5817338	No	1998-10-06	2015-10-06
US5840737	No	1998-11-24	2016-07-15
US6780882	No	2004-08-24	2016-07-15
US6926907	No	2005-08-09	2023-02-28
US9539214	No	2017-01-10	2033-03-13
US9364439	No	2016-06-14	2022-05-31
US8206741	No	2012-06-26	2023-02-28
US9987231	No	2018-06-05	2033-01-02
US10076494	No	2018-09-18	2036-12-08
US9603806	No	2017-03-28	2034-02-12
US9498445	No	2016-11-22	2034-02-12
US9050263	No	2015-06-09	2034-02-12
US10238606	No	2019-03-26	2034-02-12

Additional Data Available

Filed On
Filed On
Available for Purchase
The date on which a patent was filed with the relevant government.
Learn more

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	155 °C	FDA label
boiling point (°C)	599.991 °C at 760 mmHg	https://www.lookchem.com/Omeprazole/
water solubility	0.359 mg/ml	http://www.thepharmajournal.com/archives/2015/vol4issue8/PartA/4-8-12.pdf
logP	2.23	http://www.thepharmajournal.com/archives/2015/vol4issue8/PartA/4-8-12.pdf
pKa	9.29 (acid), 4.77 (base)	https://www.chemicalbook.com/ChemicalProductProperty_US_CB8160492.aspx

Predicted Properties

Property	Value	Source
Water Solubility	0.359 mg/mL	ALOGPS
logP	1.66	ALOGPS
logP	2.43	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.29	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	37.45 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
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-002f-0900000000-412912cbbcdbd1b34699
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0002-0901000000-189e81fb724041d50498
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0f6t-0900000000-db101d248a4e861d4c3b
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0uds-0900000000-f579fb74ac97c56dd3eb
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-0900000000-eefbf9686f0313da581e
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-0900000000-363d6954875894f433ba
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0f6t-1900000000-d8c64d496f1d9b3ed465
MS/MS Spectrum - , positive	LC-MS/MS	splash10-014i-1669000000-51f9342d7e4bbd0356b2
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0f6t-0900000000-d21755acc44ff2d29cfa
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0f80-2900000000-9989d19c171c612ea3dc
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0002-0900000000-f74adb7f41e2d390b602
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

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Drug created on June 13, 2005 07:24 / Updated on January 25, 2021 22:38