Omeprazole

Identification

Summary

Omeprazole is a proton pump inhibitor used to treat GERD associated conditions such as heartburn and gastric acid hypersecretion, and to promote healing of tissue damage and ulcers caused by gastric acid and H. pylori infection.

Brand Names

Konvomep, Losec, Omeclamox, Omesec, Previdolrx Analgesic Pak, Prilosec, Talicia, Yosprala, Zegerid, Zegerid Reformulated Aug 2006, Zegerid With Magnesium Hydroxide

Generic Name

Omeprazole

DrugBank Accession Number

DB00338

Background

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

Similar Structures

Weight: Average: 345.416
Monoisotopic: 345.114712179
Chemical Formula: C₁₇H₁₉N₃O₃S

Synonyms

OMEP
Omeprazol
Omeprazole
Omeprazolum

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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

• Reduction of risk of upper gastrointestinal (GI) bleeding in critically ill adult patients.

• 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

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination for symptomatic treatment of	Ankylosing spondylitis (as)	Combination Product in combination with: Diclofenac (DB00586)	••••••••••••	•••••	•••• •••• •••••••••••••• ••••••	•••••••• ••••••• •••••••
Treatment of	Duodenal ulcers		••••••••••••	•••••
Management of	Erosive esophagitis		••••••••••••
Treatment of	Gastric ulcer		••••••••••••	•••••
Symptomatic treatment of	Gastroesophageal reflux disease		••••••••••••

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.

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Omeprazole

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.

Pathways

Pathway	Category
Omeprazole Metabolism Pathway	Drug metabolism
Omeprazole Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

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 Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

Drug	Interaction
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Abatacept	The metabolism of Omeprazole can be increased when combined with Abatacept.
Abrocitinib	The metabolism of Abrocitinib can be decreased when combined with Omeprazole.
Acenocoumarol	The metabolism of Acenocoumarol can be decreased when combined with Omeprazole.
Adalimumab	The metabolism of Omeprazole can be increased when combined with Adalimumab.
Albendazole	The metabolism of Albendazole can be decreased when combined with Omeprazole.

Food Interactions

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

Products

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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

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
Leader Omeprazole	Tablet, delayed release	20 mg/1	Oral	Remedy Repack	2013-04-24	2014-04-24
Losec	Tablet, delayed release	20 mg	Oral	Cheplapharm Arzneimittel Gmbh	1996-12-31	2021-10-31
Losec	Capsule, delayed release	20 mg	Oral	Cheplapharm Arzneimittel Gmbh	1989-12-31	Not applicable
Losec 10 mg	Tablet, delayed release	10 mg	Oral	Astra Zeneca	1997-04-28	2019-11-16
Losec Capsules 10mg	Capsule, delayed release	10 mg	Oral	Astra Zeneca	2000-10-03	2013-12-04

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Ag-omeprazole Dr	Tablet, delayed release	20 mg	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Apo-omeprazole	Capsule, delayed release	40 mg	Oral	Apotex Corporation	Not applicable	Not applicable
Apo-omeprazole	Capsule, delayed release	20 mg	Oral	Apotex Corporation	2004-01-28	Not applicable
Auro-omeprazole	Capsule, delayed release	20 mg	Oral	Auro Pharma Inc	2014-03-26	2014-03-26
Auro-omeprazole	Capsule, delayed release	10 mg	Oral	Auro Pharma Inc	2014-03-26	2014-03-26

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
24 Hr Omeprazole	Tablet, delayed release	20 mg/1	Oral	MEIJER, INC.	2022-05-25	Not applicable
Acid Reducer	Tablet, delayed release	20 mg/1	Oral	Northeast Pharma	2021-07-05	Not applicable
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

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
ArthroComb 75 mg/20 mg Hartkapseln mit veränderter Wirkstofffreisetzung	Omeprazole (20 mg) + Diclofenac sodium (75 mg)	Capsule, delayed release	Oral	Aristo Pharma Gmb H	2017-04-27	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	2021-11-30
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	2022-01-31
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
Basic Care Omeprazole and Sodium Bicarbonate	Omeprazole (20 mg/1) + Sodium bicarbonate (1100 mg/1)	Capsule, gelatin coated	Oral	Amazon.com Services LLC	2021-07-22	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
OMEPROL 20 MG MIKROPELLET KAPSUL, 28 ADET	Omeprazole (20 mg)	Capsule, coated pellets	Oral	SANDOZ İLAÇ SAN. VE TİC. A.Ş.	2014-11-11	Not applicable

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

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. [Article]
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 . [Article]
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. [Article]
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. [Article]
Cederberg C, Andersson T, Skanberg I: Omeprazole: pharmacokinetics and metabolism in man. Scand J Gastroenterol Suppl. 1989;166:33-40; discussion 41-2. [Article]
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. [Article]
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. [Article]
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. [Article]
Lewin MJ: Cellular mechanisms and inhibitors of gastric acid secretion. Drugs Today (Barc). 1999 Oct;35(10):743-52. [Article]
Sachs G, Wallmark B: The gastric H+,K+-ATPase: the site of action of omeprazole. Scand J Gastroenterol Suppl. 1989;166:3-11. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
FDA Approved Drug Products: Talicia Amoxicillin, Omeprazole, and Rifabutin Oral Delayed Release Capsules [Link]
NIH StatPearls: Omeprazole [Link]
FDA Approved Products: Prilosec (omeprazole) oral delayed release capsules [Link]
FDA Approved Drug Products: KONVOMEP™ (omeprazole and sodium bicarbonate for oral suspension) [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: PA10075
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Omeprazole

FDA label

Download (1.01 MB)

MSDS

Download (73.8 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
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 Subjects (HS)	1
4	Completed	Basic Science	Probiotics	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
Solution	Intravenous	44.632 mg
Capsule	Oral	20.0 mg
Capsule	Oral	20.0000 ml
Capsule	Oral	40 MG
Capsule; kit; tablet	Oral
Tablet, delayed release	Oral
Capsule	Oral	235.3 mg
Solution	Intravenous	40.000 mg
Injection	Intravenous
Solution	Parenteral	44.630 mg
Capsule	Oral	10.000 mg
Capsule	Oral	40.000 mg
Kit; solution; suspension	Oral
Solution	Parenteral
Capsule, delayed release; capsule, extended release	Oral
Tablet, delayed release	Oral	10 mg
Capsule	Oral	235.300 mg
Capsule, delayed release	Oral	40 mg
Tablet, delayed release	Oral	20 mg
Tablet	Oral	10 MG
Tablet	Oral	20 MG
Tablet, film coated	Oral	10 mg
Capsule	Oral	235.290 mg
Injection, powder, lyophilized, for solution	Intravenous
Capsule, extended release	Oral	10 mg
Injection, solution	Intravenous	40 mg
Capsule, coated pellets	Oral
Injection, powder, for solution	Intravenous	40 MG
Capsule, delayed release	Oral	10 MG
Capsule	Oral
Capsule; capsule, delayed release; kit; tablet	Oral
Kit	Oral
Capsule, coated pellets	Oral	20 mg
Tablet, delayed release	Oral	40 MG
Tablet, coated	Oral	20 mg
Capsule	Oral	20 MG
Powder, for solution	Intravenous	40 MG
Capsule, coated	Oral	10 mg
Capsule, coated	Oral
Capsule, coated	Oral	20 mg
Capsule, coated	Oral	40 mg
Capsule, coated	Oral	4000000 mg
Powder	Intravenous	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 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
Tablet, delayed release	Oral	20 mg/1
Tablet, orally disintegrating, delayed release	Oral	20 mg/1
Injection, powder, lyophilized, for solution	Intravenous	40 mg
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
Tablet, film coated	Oral	20 mg
Injection, powder, for solution	Intravenous	126 mg
Tablet	Oral
Powder, for suspension	Oral
Capsule, delayed release	Oral	15 MG
Capsule, delayed release pellets	Oral	10 MG
Capsule, delayed release pellets	Oral	20 MG
Capsule	Oral	10 MG
Capsule, delayed release pellets	Oral	40 MG
Capsule, delayed release pellets	Oral
Injection, solution	Intravenous
Injection	Intravenous	40 MG
Capsule	Oral	20.00 mg
Capsule, coated	Oral
Injection, powder, lyophilized, for solution	Parenteral	40 mg
Kit	Oral; Topical
Solution	Parenteral	40.000 mg
Capsule; capsule, delayed release	Oral	20 mg
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	20.000 mg
Solution	Oral	20.000 mg
Capsule	Oral	235.294 mg
Solution	Intravenous
Capsule, delayed release	Oral
Solution	Intravenous	42.400 mg
Tablet, coated	Oral
Capsule, delayed release	Oral
Capsule, gelatin coated	Oral
Capsule, coated	Oral	2000000 mg
Capsule, coated	Oral	20.00007 mg
Tablet, film coated	Oral
Solution	Intravenous	40.00 mg
Capsule	Oral
Tablet, chewable	Oral
Capsule	Oral	20.000 mg
Injection, powder, for solution	Intravenous
Capsule, delayed release	Oral	20 mg
Powder	Intravenous	40 mg/1vial
Injection, powder, for solution	Intravenous	40 mg/1vial

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)
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
US10835488	No	2020-11-17	2036-12-08
US11135172	No	2021-10-05	2034-02-12
US10751333	No	2020-08-25	2039-07-16
US11103492	No	2021-08-31	2039-07-16
US11633478	No	2019-07-16	2039-07-16
US11771686	No	2020-03-01	2040-03-01

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	splash10-0udj-0902000000-cfa5184c794ea62ab995
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-014i-1669000000-51f9342d7e4bbd0356b2
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f6t-0049000000-dd6465ff98d6ab7b732e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0005-1904000000-2c0b41fb687c7276742c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f6t-0935000000-8e10633e2e9d56c4305a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-0900000000-9fd0b7267901f29c8a26
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0910000000-3cb2734362e389c7f316
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004i-4900000000-c49d95c2f14e14dc5350
1H NMR Spectrum	1D NMR	Not Applicable
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	204.6499042	predicted	DarkChem Lite v0.1.0
[M-H]-	179.86778	predicted	DeepCCS 1.0 (2019)
[M+H]+	205.1663042	predicted	DarkChem Lite v0.1.0
[M+H]+	182.22575	predicted	DeepCCS 1.0 (2019)
[M+Na]+	205.0830042	predicted	DarkChem Lite v0.1.0
[M+Na]+	189.21736	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	50000	N/A	N/A	A27833
IC 50 (nM)	2000	N/A	N/A	A27834
IC 50 (nM)	250	N/A	N/A	A27835
IC 50 (nM)	280	N/A	N/A	A27835
IC 50 (nM)	370	N/A	N/A	A27836
IC 50 (nM)	3800	N/A	N/A	A27837
IC 50 (nM)	22400	N/A	N/A	A27838

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

Shi S, Klotz U: Proton pump inhibitors: an update of their clinical use and pharmacokinetics. Eur J Clin Pharmacol. 2008 Oct;64(10):935-51. doi: 10.1007/s00228-008-0538-y. Epub 2008 Aug 5. [Article]
Kirchheiner J, Glatt S, Fuhr U, Klotz U, Meineke I, Seufferlein T, Brockmoller J: Relative potency of proton-pump inhibitors-comparison of effects on intragastric pH. Eur J Clin Pharmacol. 2009 Jan;65(1):19-31. doi: 10.1007/s00228-008-0576-5. Epub 2008 Oct 17. [Article]
Shin JM, Munson K, Vagin O, Sachs G: The gastric HK-ATPase: structure, function, and inhibition. Pflugers Arch. 2009 Jan;457(3):609-22. doi: 10.1007/s00424-008-0495-4. Epub 2008 Jun 6. [Article]
Munson K, Law RJ, Sachs G: Analysis of the gastric H,K ATPase for ion pathways and inhibitor binding sites. Biochemistry. 2007 May 8;46(18):5398-417. doi: 10.1021/bi062305h. Epub 2007 Apr 11. [Article]
Zuger B: Effeminate behavior present in boys from childhood: ten additional years of follow-up. Compr Psychiatry. 1978 Jul-Aug;19(4):363-9. [Article]
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. [Article]
FDA label, Omeprazole [File]

Details2. Aryl hydrocarbon receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Transcription regulatory region dna binding
Specific Function: Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name: AHR
Uniprot ID: P35869
Uniprot Name: Aryl hydrocarbon receptor
Molecular Weight: 96146.705 Da

References

Dzeletovic N, McGuire J, Daujat M, Tholander J, Ema M, Fujii-Kuriyama Y, Bergman J, Maurel P, Poellinger L: Regulation of dioxin receptor function by omeprazole. J Biol Chem. 1997 May 9;272(19):12705-13. [Article]

Enzymes

Details1. Cytochrome P450 1A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inducer

General Function: Vitamin d 24-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 oxidizes a variety of structurally un...
Gene Name: CYP1A1
Uniprot ID: P04798
Uniprot Name: Cytochrome P450 1A1
Molecular Weight: 58164.815 Da

References

Harvey JL, Paine AJ, Maurel P, Wright MC: Effect of the adrenal 11-beta-hydroxylase inhibitor metyrapone on human hepatic cytochrome P-450 expression: induction of cytochrome P-450 3A4. Drug Metab Dispos. 2000 Jan;28(1):96-101. [Article]
Kikuchi H, Hossain A: Signal transduction-mediated CYP1A1 induction by omeprazole in human HepG2 cells. Exp Toxicol Pathol. 1999 Jul;51(4-5):342-6. doi: 10.1016/S0940-2993(99)80018-9. [Article]
Lee DY, Jung YS, Shin HS, Lee I, Kim YC, Lee MG: Faster clearance of omeprazole in rats with acute renal failure induced by uranyl nitrate: contribution of increased expression of hepatic cytochrome P450 (CYP) 3A1 and intestinal CYP1A and 3A subfamilies. J Pharm Pharmacol. 2008 Jul;60(7):843-51. doi: 10.1211/jpp.60.7.0005. [Article]

Details2. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Frick A, Kopitz J, Bergemann N: Omeprazole reduces clozapine plasma concentrations. A case report. Pharmacopsychiatry. 2003 May;36(3):121-3. doi: 10.1055/s-2003-39980. [Article]
Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. [Article]
Zhou Q, Zhou S, Chan E: Effect of omeprazole on the hydroxylation of warfarin enantiomers in human: in-vitro studies with liver microsomes and cDNA-expressed cytochrome P450 isozymes. Curr Drug Metab. 2005 Oct;6(5):399-411. [Article]
Han XM, Ouyang DS, Chen XP, Shu Y, Jiang CH, Tan ZR, Zhou HH: Inducibility of CYP1A2 by omeprazole in vivo related to the genetic polymorphism of CYP1A2. Br J Clin Pharmacol. 2002 Nov;54(5):540-3. [Article]
Rost KL, Fuhr U, Thomsen T, Zaigler M, Brockmoller J, Bohnemeier H, Roots I: Omeprazole weakly inhibits CYP1A2 activity in man. Int J Clin Pharmacol Ther. 1999 Nov;37(11):567-74. [Article]
Rost KL, Brosicke H, Brockmoller J, Scheffler M, Helge H, Roots I: Increase of cytochrome P450IA2 activity by omeprazole: evidence by the 13C-[N-3-methyl]-caffeine breath test in poor and extensive metabolizers of S-mephenytoin. Clin Pharmacol Ther. 1992 Aug;52(2):170-80. [Article]
Daujat M, Peryt B, Lesca P, Fourtanier G, Domergue J, Maurel P: Omeprazole, an inducer of human CYP1A1 and 1A2, is not a ligand for the Ah receptor. Biochem Biophys Res Commun. 1992 Oct 30;188(2):820-5. [Article]
Flockhart Table of Drug Interactions [Link]

Details3. Cytochrome P450 1B1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer

General Function: Oxygen binding
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 oxidizes a variety of structurally un...
Gene Name: CYP1B1
Uniprot ID: Q16678
Uniprot Name: Cytochrome P450 1B1
Molecular Weight: 60845.33 Da

References

Krusekopf S, Roots I, Hildebrandt AG, Kleeberg U: Time-dependent transcriptional induction of CYP1A1, CYP1A2 and CYP1B1 mRNAs by H+/K+ -ATPase inhibitors and other xenobiotics. Xenobiotica. 2003 Feb;33(2):107-18. [Article]

Details4. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid 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 oxidizes a variety of structurally un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

Karam WG, Goldstein JA, Lasker JM, Ghanayem BI: Human CYP2C19 is a major omeprazole 5-hydroxylase, as demonstrated with recombinant cytochrome P450 enzymes. Drug Metab Dispos. 1996 Oct;24(10):1081-7. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	45000	N/A	N/A	A27342

Details5. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid 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 oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Lasker JM, Wester MR, Aramsombatdee E, Raucy JL: Characterization of CYP2C19 and CYP2C9 from human liver: respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations. Arch Biochem Biophys. 1998 May 1;353(1):16-28. [Article]
Du H, Wei Z, Yan Y, Xiong Y, Zhang X, Shen L, Ruan Y, Wu X, Xu Q, He L, Qin S: Functional Characterization of Human CYP2C9 Allelic Variants in COS-7 Cells. Front Pharmacol. 2016 Apr 25;7:98. doi: 10.3389/fphar.2016.00098. eCollection 2016. [Article]

Details6. Cytochrome P450 2C18

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid 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 oxidizes a variety of structurally un...
Gene Name: CYP2C18
Uniprot ID: P33260
Uniprot Name: Cytochrome P450 2C18
Molecular Weight: 55710.075 Da

References

Karam WG, Goldstein JA, Lasker JM, Ghanayem BI: Human CYP2C19 is a major omeprazole 5-hydroxylase, as demonstrated with recombinant cytochrome P450 enzymes. Drug Metab Dispos. 1996 Oct;24(10):1081-7. [Article]

Details7. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Furuta S, Kamada E, Suzuki T, Sugimoto T, Kawabata Y, Shinozaki Y, Sano H: Inhibition of drug metabolism in human liver microsomes by nizatidine, cimetidine and omeprazole. Xenobiotica. 2001 Jan;31(1):1-10. doi: 10.1080/00498250110035615. [Article]
Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	7.80E+04	N/A	N/A	A27395

Details8. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor
Inducer
Curator comments: Omeprazole and 5'-O-desmethylomeprazole were found to be time-dependent inhibitors of CYP3A4.

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

References

Li XQ, Weidolf L, Simonsson R, Andersson TB: Enantiomer/enantiomer interactions between the S- and R- isomers of omeprazole in human cytochrome P450 enzymes: major role of CYP2C19 and CYP3A4. J Pharmacol Exp Ther. 2005 Nov;315(2):777-87. Epub 2005 Aug 10. [Article]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Botsch S, Gautier JC, Beaune P, Eichelbaum M, Kroemer HK: Identification and characterization of the cytochrome P450 enzymes involved in N-dealkylation of propafenone: molecular base for interaction potential and variable disposition of active metabolites. Mol Pharmacol. 1993 Jan;43(1):120-6. [Article]
Turpeinen M, Uusitalo J, Jalonen J, Pelkonen O: Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. Eur J Pharm Sci. 2005 Jan;24(1):123-32. [Article]
Park EJ, Cho HY, Lee YB: Effect of Cimetidine and Phenobarbital on metabolite kinetics of Omeprazole in rats. Arch Pharm Res. 2005 Oct;28(10):1196-202. [Article]
Zhou Q, Zhou S, Chan E: Effect of omeprazole on the hydroxylation of warfarin enantiomers in human: in-vitro studies with liver microsomes and cDNA-expressed cytochrome P450 isozymes. Curr Drug Metab. 2005 Oct;6(5):399-411. [Article]
Roymans D, Van Looveren C, Leone A, Parker JB, McMillian M, Johnson MD, Koganti A, Gilissen R, Silber P, Mannens G, Meuldermans W: Determination of cytochrome P450 1A2 and cytochrome P450 3A4 induction in cryopreserved human hepatocytes. Biochem Pharmacol. 2004 Feb 1;67(3):427-37. doi: 10.1016/j.bcp.2003.09.022. [Article]
Abelo A, Andersson TB, Antonsson M, Naudot AK, Skanberg I, Weidolf L: Stereoselective metabolism of omeprazole by human cytochrome P450 enzymes. Drug Metab Dispos. 2000 Aug;28(8):966-72. [Article]
Tassaneeyakul W, Vannaprasaht S, Yamazoe Y: Formation of omeprazole sulphone but not 5-hydroxyomeprazole is inhibited by grapefruit juice. Br J Clin Pharmacol. 2000 Feb;49(2):139-44. [Article]
Shirasaka Y, Sager JE, Lutz JD, Davis C, Isoherranen N: Inhibition of CYP2C19 and CYP3A4 by omeprazole metabolites and their contribution to drug-drug interactions. Drug Metab Dispos. 2013 Jul;41(7):1414-24. doi: 10.1124/dmd.113.051722. Epub 2013 Apr 25. [Article]
Prilosec FDA label [File]

Details9. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor
Curator comments: Omeprazole and 5'-O-desmethylomeprazole were found to be time-dependent inhibitors of CYP3A4.

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

Foti RS, Wahlstrom JL: CYP2C19 inhibition: the impact of substrate probe selection on in vitro inhibition profiles. Drug Metab Dispos. 2008 Mar;36(3):523-8. Epub 2007 Nov 29. [Article]
Li XQ, Andersson TB, Ahlstrom M, Weidolf L: Comparison of inhibitory effects of the proton pump-inhibiting drugs omeprazole, esomeprazole, lansoprazole, pantoprazole, and rabeprazole on human cytochrome P450 activities. Drug Metab Dispos. 2004 Aug;32(8):821-7. [Article]
Li XQ, Weidolf L, Simonsson R, Andersson TB: Enantiomer/enantiomer interactions between the S- and R- isomers of omeprazole in human cytochrome P450 enzymes: major role of CYP2C19 and CYP3A4. J Pharmacol Exp Ther. 2005 Nov;315(2):777-87. Epub 2005 Aug 10. [Article]
Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Yamazaki H, Inoue K, Shaw PM, Checovich WJ, Guengerich FP, Shimada T: Different contributions of cytochrome P450 2C19 and 3A4 in the oxidation of omeprazole by human liver microsomes: effects of contents of these two forms in individual human samples. J Pharmacol Exp Ther. 1997 Nov;283(2):434-42. [Article]
McGinnity DF, Parker AJ, Soars M, Riley RJ: Automated definition of the enzymology of drug oxidation by the major human drug metabolizing cytochrome P450s. Drug Metab Dispos. 2000 Nov;28(11):1327-34. [Article]
Ko JW, Sukhova N, Thacker D, Chen P, Flockhart DA: Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos. 1997 Jul;25(7):853-62. [Article]
Ieiri I, Kubota T, Urae A, Kimura M, Wada Y, Mamiya K, Yoshioka S, Irie S, Amamoto T, Nakamura K, Nakano S, Higuchi S: Pharmacokinetics of omeprazole (a substrate of CYP2C19) and comparison with two mutant alleles, C gamma P2C19m1 in exon 5 and C gamma P2C19m2 in exon 4, in Japanese subjects. Clin Pharmacol Ther. 1996 Jun;59(6):647-53. doi: 10.1016/S0009-9236(96)90004-1. [Article]
Liu S, Wang Z, Tian X, Cai W: Predicting the Effects of CYP2C19 and Carboxylesterases on Vicagrel, a Novel P2Y12 Antagonist, by Physiologically Based Pharmacokinetic/Pharmacodynamic Modeling Approach. Front Pharmacol. 2020 Dec 8;11:591854. doi: 10.3389/fphar.2020.591854. eCollection 2020. [Article]
Shirasaka Y, Sager JE, Lutz JD, Davis C, Isoherranen N: Inhibition of CYP2C19 and CYP3A4 by omeprazole metabolites and their contribution to drug-drug interactions. Drug Metab Dispos. 2013 Jul;41(7):1414-24. doi: 10.1124/dmd.113.051722. Epub 2013 Apr 25. [Article]
Flockhart Table of Drug Interactions [Link]
Prilosec FDA label [File]

Transporters

Details1. ATP-binding cassette sub-family G member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: This transporter action is based on data from in vitro studies.

General Function: Xenobiotic-transporting atpase activity
Specific Function: High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name: ABCG2
Uniprot ID: Q9UNQ0
Uniprot Name: ATP-binding cassette sub-family G member 2
Molecular Weight: 72313.47 Da

References

Breedveld P, Zelcer N, Pluim D, Sonmezer O, Tibben MM, Beijnen JH, Schinkel AH, van Tellingen O, Borst P, Schellens JH: Mechanism of the pharmacokinetic interaction between methotrexate and benzimidazoles: potential role for breast cancer resistance protein in clinical drug-drug interactions. Cancer Res. 2004 Aug 15;64(16):5804-11. [Article]
Suzuki K, Doki K, Homma M, Tamaki H, Hori S, Ohtani H, Sawada Y, Kohda Y: Co-administration of proton pump inhibitors delays elimination of plasma methotrexate in high-dose methotrexate therapy. Br J Clin Pharmacol. 2009 Jan;67(1):44-9. doi: 10.1111/j.1365-2125.2008.03303.x. Epub 2008 Nov 17. [Article]

Details2. Canalicular multispecific organic anion transporter 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inducer
Curator comments: This transporter action is based on in vitro data.

General Function: Organic anion transmembrane transporter activity
Specific Function: May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name: ABCC3
Uniprot ID: O15438
Uniprot Name: Canalicular multispecific organic anion transporter 2
Molecular Weight: 169341.14 Da

References

Hitzl M, Klein K, Zanger UM, Fritz P, Nussler AK, Neuhaus P, Fromm MF: Influence of omeprazole on multidrug resistance protein 3 expression in human liver. J Pharmacol Exp Ther. 2003 Feb;304(2):524-30. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	17700	N/A	N/A	A16156
IC 50 (nM)	97200	N/A	N/A	A27451
IC 50 (nM)	91200	N/A	N/A	A27451
IC 50 (nM)	89000	N/A	N/A	A27451

Details3. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

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. [Article]
Li W, Zeng S, Yu LS, Zhou Q: Pharmacokinetic drug interaction profile of omeprazole with adverse consequences and clinical risk management. Ther Clin Risk Manag. 2013;9:259-71. doi: 10.2147/TCRM.S43151. Epub 2013 May 27. [Article]
Shah Y, Iqbal Z, Ahmad L, Khuda F, Khan A, Khan A, Khan MI, Ismail: Effect of Omeprazole on the Pharmacokinetics of Rosuvastatin in Healthy Male Volunteers. Am J Ther. 2016 Nov/Dec;23(6):e1514-e1523. doi: 10.1097/MJT.0000000000000221. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Omeprazole

Identification

Structure for Omeprazole (DB00338)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

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Enzymes

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Transporters

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