Identification

Name
Omeprazole
Accession Number
DB00338  (APRD00446)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Description

A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and Zollinger-Ellison syndrome. Omeprazole belongs to a class of antisecretory compounds, the substituted benzimidazoles, that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase enzyme system at the secretory surface of the gastric parietal cell.

Structure
Thumb
Synonyms
  • OMEP
  • Omeprazol
  • Omeprazolum
Product Ingredients
IngredientUNIICASInChI Key
Omeprazole magnesium426QFE7XLK95382-33-5KWORUUGOSLYAGD-UHFFFAOYSA-N
Omeprazole sodiumKV03YZ6QLW95510-70-6RYXPMWYHEBGTRV-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Leader OmeprazoleTablet, delayed release20 mg/1OralRemedy Repack2013-04-242014-04-24Us
Losec 10 mgTablet, delayed release10 mgOralAstra Zeneca1997-04-28Not applicableCanada
Losec 20 mgTablet, delayed release20 mgOralAstra Zeneca1996-12-31Not applicableCanada
Losec Capsules 10mgCapsule, delayed release10 mgOralAstra Zeneca2000-10-032013-12-04Canada
Losec Capsules 20mgCapsule, delayed release20 mgOralAstra Zeneca1989-12-31Not applicableCanada
Losec Capsules 40mgCapsule, delayed release40 mgOralAstra Zeneca2003-10-172010-06-30Canada
Losec Mups - 10mgTablet, delayed release10 mgOralAstra Zeneca2001-02-222009-12-01Canada
Losec Mups - 20mgTablet, delayed release20 mgOralAstra Zeneca2001-02-222009-12-01Canada
OmeprazoleCapsule, delayed release20 mgOralSanis Health Inc2010-06-16Not applicableCanada
OmeprazoleCapsule, delayed release10 mgOralSivem Pharmaceuticals UlcNot applicableNot applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-omeprazoleCapsule, delayed release20 mgOralApotex Corporation2004-01-28Not applicableCanada
Apo-omeprazoleCapsule, delayed release40 mgOralApotex CorporationNot applicableNot applicableCanada
Auro-omeprazoleCapsule, delayed release10 mgOralAuro Pharma Inc2014-03-26Not applicableCanada
Auro-omeprazoleCapsule, delayed release20 mgOralAuro Pharma Inc2014-03-26Not applicableCanada
Ava-omeprazoleCapsule, delayed release20 mgOralAvanstra Inc2011-11-282014-08-21Canada
Bio-omeprazoleTablet, delayed release20 mgOralBiomed Pharma2016-09-07Not applicableCanada
Dom-omeprazole DrTablet, delayed release20 mgOralDominion Pharmacal2013-01-23Not applicableCanada
Dom-omeprazole DrTablet, delayed release10 mgOralDominion PharmacalNot applicableNot applicableCanada
Jamp-omeprazole DrTablet, delayed release20 mgOralJamp Pharma Corporation2014-02-11Not applicableCanada
Mylan-omeprazoleCapsule, delayed release10 mgOralMylan Pharmaceuticals2009-08-04Not applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acid ReducerTablet, delayed release20 mg/1OralBest Choice2018-06-06Not applicableUs
Acid ReducerTablet, delayed release20 mg/1OralWinco Foods, Llc.2018-06-06Not applicableUs
Acid ReducerTablet, delayed release20 mg/1OralAurohealth LLC2018-06-06Not applicableUs
Acid ReducerTablet, delayed release20 mg/1OralBi-Mart2018-06-06Not applicableUs
Acid ReducerTablet, delayed release20 mg/1OralFamily Dollar2018-06-06Not applicableUs
Acid ReducerTablet, delayed release20 mg/1OralDiscount Drug Mart2018-06-06Not applicableUs
Acid ReducerCapsule, delayed release20 mg/1OralCardinal Health2017-03-07Not applicableUs
Acid ReducerTablet, delayed release20 mg/1OralAurohealth LLC2018-06-06Not applicableUs
Ahi-omeprazoleTablet, delayed release20 mgOralAccord Healthcare LimitedNot applicableNot applicableCanada
Basic Care OmeprazoleTablet, orally disintegrating, delayed release20 mg/1OralL. Perrigo Company2018-08-30Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Good Sense Omeprazole and Sodium BicarbonateOmeprazole (20 mg/1) + Sodium bicarbonate (1100 mg/1)Capsule, gelatin coatedOralL. Perrigo Company2017-06-19Not applicableUs
medPREDkitOmeprazole (20 mg/1) + Methylprednisolone (4 mg/1) + Sodium bicarbonate (1100 mg/1)KitMedarbor Llc2017-12-252018-01-15Us
Not ApplicableOmeprazole (40 mg/1) + Sodium bicarbonate (1100 mg/1)CapsuleOralSterling Knight Pharmaceuticals, Llc2017-07-13Not applicableUs
Omeclamox-PakOmeprazole (20 mg/1) + Amoxycillin trihydrate (500 mg/1) + Clarithromycin (500 mg/1)KitPernix Therapeutics2012-04-272016-07-31Us
Omeclamox-PakOmeprazole (20 mg/1) + Amoxycillin trihydrate (500 mg/1) + Clarithromycin (500 mg/1)KitCumberland Pharmaceuticals2012-04-27Not applicableUs
Omeprazole and Sodium BicarbonateOmeprazole (40 mg/1) + Sodium bicarbonate (1100 mg/1)CapsuleOralZydus Pharmaceuticals Usa, Inc.2018-05-29Not applicableUs
Omeprazole and Sodium BicarbonateOmeprazole (20 mg/1) + Sodium bicarbonate (1100 mg/1)CapsuleOralCadila Pharnmaceuticals2018-07-19Not applicableUs
Omeprazole and Sodium BicarbonateOmeprazole (40 mg/1) + Sodium bicarbonate (1100 mg/1)CapsuleOralNorth Star Rx Llc2016-11-30Not applicableUs
Omeprazole and Sodium BicarbonateOmeprazole (20 mg/1) + Sodium bicarbonate (1100 mg/1)CapsuleOralOceanside Pharmaceuticals2006-02-27Not applicableUs
Omeprazole and Sodium BicarbonateOmeprazole (20 mg/1) + Sodium bicarbonate (1100 mg/1)CapsuleOralAurolife Pharma, LLC2016-11-21Not applicableUs
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
Categories
UNII
KG60484QX9
CAS number
73590-58-6
Weight
Average: 345.416
Monoisotopic: 345.114712179
Chemical Formula
C17H19N3O3S
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

Pharmacology

Indication

Omeprazole is indicated for the treatment of duodenal ulcers, benign gastric ulcers, gastroesophageal reflux disease (GERD), heartburn and other symptoms associated with GERD, erosive esophagitis, and long-term treatment of pathological hypersecretory conditions like Zollinger-Ellison syndrome, multiple endocrine adenomas, and systemic mastocytosis.

Associated Conditions
Pharmacodynamics

After oral administration, the onset of the anti-secretory effect of omeprazole occurs within one hour and maximum effect occurring within two hours. At 24 hours, inhibition of secretion is approximately 50% of maximum and duration of inhibition lasts up to 72 hours. Although omeprazole has a very short plasma half-life, the anti-secretory effect lasts for a long time due to prolonged binding to parietal H+/K+ ATPase enzyme. When the drug has been discontinued, secretory activity will return to baseline over 3-5 days. The inhibitory effect of omeprazole on acid secretion increases with repeated once-daily dosing, reaching a plateau after four days. In studies involving more than 200 patients, serum gastrin levels increased during the first 1 to 2 weeks of once-daily administration of therapeutic doses of omeprazole in parallel with inhibition of acid secretion. Systemic effects of omeprazole in the CNS, cardiovascular and respiratory systems have not been found to date.

Mechanism of action

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

TargetActionsOrganism
APotassium-transporting ATPase alpha chain 1
inhibitor
Human
UAryl hydrocarbon receptor
agonist
Human
Absorption

The delayed-release capsule are enteric-coated (as omeprazole is acid-labile) so the absorption of omprazole begins once the granules leave the stomach. Absorption is rapid. Peak plasma levels occur within 0.5 - 3.5 hours. The absolute bioavailability (compared with intravenous administration) of the delayed-release capsule is 30-40% at doses of 20 - 40 mg, due to presystemic metabolism. This value increases slightly when given repeatedly. Based on a relative bioavailability study, the AUC and Cmax of PRILOSEC (omeprazole magnesium) for Delayed-Release Oral Suspension were 87% and 88% of those for PRILOSEC Delayed-Release Capsules, respectively. Interestingly, when the 40 mg delayed release capsule is given with or without applesauce, it is bioequivalent. However, when the 20 mg delayed release capsule is given with the same conditions, it is not bioequivalent. When the same capsule is given to the elderly, bioavailability increases. Omeprazole was 76% bioavailable.

Volume of distribution
Not Available
Protein binding

95% bound to human plasma protein.

Metabolism

Hepatic. Omeprazole is extensively metabolized by the cytochrome P450 (CYP) enzyme system. The two primary CYP isozymes involved are CYP2C19 and CYP3A4. Metabolism is stereoselective in which the S-isomer is converted to 5'O-desmethylomeprazole via CYP2C19. CYP3A4 converts the S-isomer to 3-hydroxyomeprazole. The R-isomer is converted to 5-hydroxyomeprazole by CYP2C19. CYP3A4 converts the R-isomer to any four different metabolites: 5-hydroxyomeprazole (5-OH OME), omeprazole sulfone (OME sulfone), 5'-O-desmethylomeprazole (5'-desmethyl OME), and 3-hydroxyomeprazole (3-OH OME).

Route of elimination

Urinary excretion is a primary route of excretion of omeprazole metabolites. Little, if any unchanged drug was excreted in the urine. The majority of the dose (about 77%) was eliminated in urine as at least six metabolites. Two were identified as hydroxyomeprazole and the corresponding carboxylic acid. The remainder of the dose was recovered in the feces.

Half life

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

Clearance
  • 500 - 600 mL/min [Total body clearance, healthy subjects, delayed-release capsule]
  • 250 mL/min [Plasma clearance, Geriatric]
  • 70 mL/min [Plasma clearance, Hepatic Impairment]
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Omeprazole Metabolism PathwayDrug metabolism
Omeprazole Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 2C19CYP2C19*2(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of omeprazole.Details
Cytochrome P450 2C19CYP2C19*3(A;A)A Allele, homozygoteEffect Directly StudiedPatients with this genotype have reduced metabolism of omeprazole.Details
Cytochrome P450 2C19CYP2C19*2ANot Available681G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*2BNot Available681G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*4Not Available1A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*5Not Available1297C>TEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*6Not Available395G>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*7Not Available19294T>AEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*22Not Available557G>C / 991A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*24Not Available99C>T / 991A>G  … show all Effect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails
Cytochrome P450 2C19CYP2C19*35Not Available12662A>GEffect InferredPoor metabolizer, lower dose requirement, improved drug efficacyDetails

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Omeprazole.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Omeprazole.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidOmeprazole can cause a decrease in the absorption of 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Omeprazole.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Omeprazole.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Omeprazole.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Omeprazole.
6-Deoxyerythronolide BThe metabolism of Omeprazole can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be increased when combined with Omeprazole.
8-azaguanineThe metabolism of 8-azaguanine can be increased when combined with Omeprazole.
Food Interactions
  • Avoid alcohol.
  • Take 30-60 minutes before meals.

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]
External Links
Human Metabolome Database
HMDB0001913
KEGG Drug
D00455
KEGG Compound
C07324
PubChem Compound
4594
PubChem Substance
46509065
ChemSpider
4433
BindingDB
50241343
ChEBI
77260
ChEMBL
CHEMBL1503
Therapeutic Targets Database
DAP000180
PharmGKB
PA450704
IUPHAR
4279
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Omeprazole
ATC Codes
A02BD01 — Omeprazole, amoxicillin and metronidazoleA02BC01 — OmeprazoleA02BD05 — Omeprazole, amoxicillin and clarithromycin
AHFS Codes
  • 56:28.36 — Proton-pump Inhibitors
FDA label
Download (218 KB)
MSDS
Download (73.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceHealthy Volunteers2
0CompletedPreventionLong Segment Barrett's Esophagus / Short Segment Barrett's Esophagus1
0WithdrawnTreatmentEsophagitis1
1Active Not RecruitingOtherNeoplasms1
1Active Not RecruitingTreatmentBreast Neoplasm, Male / Neoplasms, Breast / Triple Negative Breast Cancer (TNBC)1
1CompletedNot AvailableAlzheimer's Disease (AD) / Huntington's Disease (HD)1
1CompletedNot AvailableClostridium Difficile Infection (CDI) / Healthy Volunteers1
1CompletedNot AvailableDrug Drug Interaction (DDI)1
1CompletedNot AvailableGastric Acid-related Disorders / Hepatitis C Virus (HCV) Infection1
1CompletedNot AvailableHealthy Volunteers5
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedNot AvailablePain, Chronic1
1CompletedNot AvailablePharmacodynamics Study1
1CompletedBasic Science(t1/2,λz) / Cmax / Pharmacokinetics / Plasma [AUC(0-672)] / Plasma [AUC(0-t)] / Plasma AUC / Tmax1
1CompletedBasic ScienceAlzheimer's Disease (AD) / Metabolism1
1CompletedBasic ScienceAtopic Dermatitis (AD)1
1CompletedBasic ScienceBioequivalence, AUC, Cmax, Pharmacokinetics1
1CompletedBasic ScienceDrug Drug Interaction (DDI)2
1CompletedBasic ScienceEvaluation of Pharmacokinetics of Sativex in the Absence and Presence of a CYP2C19 Inhibitor / Evaluation of Pharmacokinetics of Sativex in the Absence and Presence of a Known Inducer of CYP3A4 / Evaluation of Pharmacokinetics of Sativex in the Absence and Presence of a Potent Inhibitor of CYP3A41
1CompletedBasic ScienceGastric Ulcer (GU)1
1CompletedBasic ScienceHealthy Volunteers8
1CompletedBasic ScienceHealthy Volunteers / Pharmacologic Actions1
1CompletedBasic SciencePharmacodynamics of ASP8477 / Pharmacokinetics of ASP84771
1CompletedBasic SciencePharmacokinetic Assessments in Healthy Volunteers1
1CompletedBasic ScienceReflux Esophagitis (RE)1
1CompletedBasic ScienceRheumatoid Arthritis2
1CompletedDiagnosticCytochrome / Pharmacokinetics1
1CompletedDiagnosticDrug Drug Interaction (DDI)1
1CompletedDiagnosticHealthy Volunteers1
1CompletedHealth Services ResearchHealthy Volunteers1
1CompletedOtherHealthy Volunteers3
1CompletedOtherHealthy Volunteers / Rheumatoid Arthritis1
1CompletedOtherTumors, Solid1
1CompletedSupportive CareHealthy Volunteers1
1CompletedTreatmentAcid Reflux / Gastro Oesophageal Reflux Disease1
1CompletedTreatmentAdult Solid Neoplasm1
1CompletedTreatmentAdvanced Solid Tumors, Excluding Breast Cancer1
1CompletedTreatmentAnemias / Healthy Volunteers1
1CompletedTreatmentCastration Resistant Prostate Cancer (CRPC) / Pharmacokinetics of MDV31001
1CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
1CompletedTreatmentCrohn's Disease (CD)1
1CompletedTreatmentDiabetes Mellitus (DM) / Healthy Volunteers1
1CompletedTreatmentDrug Drug Interaction (DDI)1
1CompletedTreatmentDrug Interaction of Clopidogrel1
1CompletedTreatmentErectile Dysfunction (ED)1
1CompletedTreatmentGastric Ulcer (GU) / Reflux, Gastroesophageal1
1CompletedTreatmentHealthy Volunteers28
1CompletedTreatmentHeartburn1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I1
1CompletedTreatmentInfectious Diseases1
1CompletedTreatmentNeoplasms1
1CompletedTreatmentNon-Hodgkin's Lymphoma (NHL) / Tumors1
1CompletedTreatmentProton Pubm Inhibitor / Reflux, Gastroesophageal / Sclerosis, Progressive Systemic1
1CompletedTreatmentPsoriasis2
1CompletedTreatmentPulmonary Disease, Chronic Obstructive1
1CompletedTreatmentReflux, Gastroesophageal1
1CompletedTreatmentTumors, Solid2
1Not Yet RecruitingOtherHepatitis C Viral Infection / Swallowing Disorders1
1Not Yet RecruitingTreatmentHIV-1-infection1
1Not Yet RecruitingTreatmentHeathy Volunteer1
1RecruitingBasic ScienceAutoimmune Diseases / Drug Drug Interaction (DDI) / Fibrotic Disease1
1RecruitingOtherCrohn's Disease (CD)1
1RecruitingTreatmentAdvanced Solid Tumors / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Mantle Cell Lymphoma (MCL) / Marginal Zone Lymphoma / Primary Mediastinal Lymphoma1
1RecruitingTreatmentAtopic Dermatitis (AD)1
1RecruitingTreatmentGastro Esophageal Reflux Disorder / Gastroesophageal Reflux Disorder1
1RecruitingTreatmentTumors, Solid1
1TerminatedTreatmentHealthy Volunteers1
1Unknown StatusTreatmentGlaucoma1
1WithdrawnTreatmentHealthy Volunteers1
1WithdrawnTreatmentLaryngomalacia1
1WithdrawnTreatmentObstructive Sleep Apnea (OSA) / Reflux, Gastroesophageal / Upper Airway Resistance Syndrome1
1WithdrawnTreatmentTumors, Solid1
1, 2CompletedTreatmentAutism Spectrum Conditions/Disorders / Gastrointestinal Problems1
1, 2CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
1, 2CompletedTreatmentCentral Serous Chorioretinopathy (CSC)1
1, 2CompletedTreatmentUlcerative Colitis (UC)1
1, 2RecruitingTreatmentCrohn's Disease (CD)1
2Active Not RecruitingTreatmentIntestinal Colonization With Multidrug-resistant Bacteria1
2Active Not RecruitingTreatmentSquamous Cell Carcinoma of the Oral Cavity1
2CompletedNot AvailableReflux, Gastroesophageal1
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentDuodenal Ulcer1
2CompletedTreatmentFatty Liver / Insulin Resistance / Liver Dysfunction1
2CompletedTreatmentGastrinoma / Zollinger-Ellison Syndrome1
2CompletedTreatmentGastro-esophageal Reflux Disease (GERD)1
2CompletedTreatmentIdiopathic Pulmonary Fibrosis (IPF)1
2CompletedTreatmentMalignant Lymphomas2
2CompletedTreatmentNonalcoholic Steatohepatitis1
2CompletedTreatmentPeptic ulcer haemorrhage1
2CompletedTreatmentSquamous Cell Carcinoma of the Head and Neck (SCCHN)1
2Not Yet RecruitingTreatmentNAFLD / NASH - Nonalcoholic Steatohepatitis / Type 2 Diabetes Mellitus1
2Not Yet RecruitingTreatmentNon-erosive Reflux Disease (NERD)1
2RecruitingTreatmentCancer of the Breast1
2RecruitingTreatmentCervical Squamous Cell Carcinoma In Situ / Vulvar High Grade Squamous Intraepithelial Lesion1
2RecruitingTreatmentCystic Fibrosis (CF) / Pancreatic Insufficiency1
2TerminatedTreatmentIndigestion1
2WithdrawnTreatmentCancer of Head and Neck1
2WithdrawnTreatmentContact Ulcer of Vocal Folds / Granuloma / Granuloma of Vocal Cords / Granuloma, Laryngeal1
2, 3CompletedTreatmentNon-erosive Reflux Disease (NERD)1
3Active Not RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Indigestion1
3Active Not RecruitingTreatmentGastro-esophageal Reflux Disease (GERD)1
3Active Not RecruitingTreatmentMyocardial Injury After Noncardiac Surgery (MINS)1
3CompletedNot AvailableGastric Acid / Human Experimentation2
3CompletedNot AvailableIntragastric Acidity1
3CompletedPreventionAnkylosing Spondylitis (AS) / Osteoarthritis (OA) / Rheumatoid Arthritis1
3CompletedPreventionPrecancerous Gastric Lesions1
3CompletedTreatmentAspirin-Associated Gastric Ulcers1
3CompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
3CompletedTreatmentBleeding Peptic Ulcers Disease1
3CompletedTreatmentDuodenal Ulcer1
3CompletedTreatmentErosive Esophagitis(EE)1
3CompletedTreatmentExocrine Pancreatic Insufficiency / Pancreatitis, Chronic / Post-pancreatectomy1
3CompletedTreatmentGastric Ulcer (GU)3
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD)1
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD) / Heartburn1
3CompletedTreatmentGlobus1
3CompletedTreatmentHelicobacter Infections1
3CompletedTreatmentHemorrhage, Gastrointestinal1
3CompletedTreatmentHuman Experimentation1
3CompletedTreatmentNeurocysticercosis1
3CompletedTreatmentNon-erosive Reflux Disease (NERD)2
3CompletedTreatmentPeptic Ulcers / Upper Gastrointestinal Hemorrhage1
3CompletedTreatmentPeptic ulcer haemorrhage2
3CompletedTreatmentReflux Esophagitis (RE)2
3CompletedTreatmentReflux, Gastroesophageal1
3RecruitingTreatmentHelicobacter-associated Gastritis1
3RecruitingTreatmentIndigestion1
3RecruitingTreatmentNon-Bleeding Peptic Ulcers1
3RecruitingTreatmentRefractory Chronic Cough1
3TerminatedHealth Services ResearchCoughing1
3TerminatedTreatmentHelicobacter Infections / Motor Fluctuations / Parkinson's Disease (PD)1
3Unknown StatusPreventionEsophagus, Barrett1
3Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
3Unknown StatusTreatmentMalignant Neoplasm of Stomach1
3WithdrawnTreatmentDiabetes, Diabetes Mellitus Type 11
4Active Not RecruitingPreventionBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Obesity, Morbid1
4Active Not RecruitingTreatmentAcute Gouty Arthritis1
4CompletedNot AvailableAchlorhydria / Gastro-esophageal Reflux Disease (GERD) / Hip Fractures / Osteoporosis1
4CompletedNot AvailableNormal Healthy Subject Population1
4CompletedBasic ScienceHealthy Volunteers1
4CompletedBasic ScienceRejection, Transplant1
4CompletedBasic ScienceTolerance1
4CompletedDiagnosticBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4CompletedDiagnosticFood Allergy1
4CompletedDiagnosticGastro-esophageal Reflux Disease (GERD)1
4CompletedDiagnosticLaryngopharyngeal Reflux (LPR)1
4CompletedOtherBariatric Surgery Candidate1
4CompletedPreventionMarginal Ulcers1
4CompletedSupportive CareOther Surgical Procedures / Pain NOS1
4CompletedTreatmentChronic Rhinosinusitis (Diagnosis) / Laryngopharyngeal Reflux1
4CompletedTreatmentCompliance / Depression / Indigestion1
4CompletedTreatmentCoronary Artery Disease / Drug Interaction Potentiation / VA Drug Interactions [VA Drug Interaction]1
4CompletedTreatmentErosive Esophagitis(EE)1
4CompletedTreatmentEsophagus, Barrett / Inflammatory Reaction1
4CompletedTreatmentGastric Ulcer (GU)1
4CompletedTreatmentGastro-esophageal Reflux Disease (GERD)2
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHeartburn1
4CompletedTreatmentHemorrhage / Peptic Ulcers1
4CompletedTreatmentHypoalbuminemia / Peptic Ulcer Bleeding1
4CompletedTreatmentIndigestion1
4CompletedTreatmentOsteoarthritis (OA) / Rheumatoid Arthritis1
4CompletedTreatmentPeptic Ulcers1
4CompletedTreatmentReflux, Gastroesophageal1
4Not Yet RecruitingBasic ScienceProbiotics1
4RecruitingBasic ScienceType 2 Diabetes Mellitus1
4RecruitingTreatmentBack Pain Lower Back Chronic2
4RecruitingTreatmentCrohn's Disease (CD) / Ulcerative Colitis (UC)1
4RecruitingTreatmentEPS / Gastro-esophageal Reflux Disease (GERD)1
4RecruitingTreatmentHeartburn1
4RecruitingTreatmentTinea Cruris / Tinea Pedis1
4SuspendedTreatmentRotator Cuff Syndrome1
4TerminatedPreventionLaryngopharyngeal Reflux / Throat Pain1
4TerminatedTreatmentPeptic ulcer haemorrhage1
4TerminatedTreatmentReflux, Gastroesophageal1
4Unknown StatusPreventionAcute Coronary Syndromes (ACS)1
4Unknown StatusTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1
4Unknown StatusTreatmentCDA Type I1
4Unknown StatusTreatmentCoronary Artery Disease1
4Unknown StatusTreatmentGastro-esophageal Reflux Disease (GERD)1
4Unknown StatusTreatmentNonvariceal Upper Gastrointestinal Bleeding1
4WithdrawnPreventionPeptic Ulcers1
4WithdrawnTreatmentCoronary Artery Disease1
4WithdrawnTreatmentEustachian Tube Dysfunction / Laryngopharyngeal Reflux1
4WithdrawnTreatmentGastroduodenal Ulcers / Marginal Ulcers / Peptic ulcer haemorrhage1
4WithdrawnTreatmentLaryngopharyngeal Reflux1
Not AvailableActive Not RecruitingNot AvailableGastroduodenal Ulcers / Marginal Ulcers / Peptic ulcer haemorrhage1
Not AvailableActive Not RecruitingTreatmentCRE-induced SBO1
Not AvailableCompletedNot AvailableAnthocyanin Metabolism1
Not AvailableCompletedNot AvailableAspirin Blood Level / Proton Pump Inhiditor Treatment1
Not AvailableCompletedNot AvailableChronic Laryngitis / Gastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableCommunity Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers1
Not AvailableCompletedBasic ScienceGastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedDiagnosticBile Reflux / Gastro-esophageal Reflux Disease (GERD) / Indigestion1
Not AvailableCompletedDiagnosticHealthy Volunteers / Liver Cirrhosis1
Not AvailableCompletedPreventionCritical Illness1
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)2
Not AvailableCompletedTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Functional Dyspepsia1
Not AvailableCompletedTreatmentGastric MALT Lymphoma1
Not AvailableCompletedTreatmentMetabolism of Clopidogrel1
Not AvailableNot Yet RecruitingNot AvailableGastro-esophageal Reflux Disease (GERD)1
Not AvailableRecruitingNot AvailableDepression1
Not AvailableRecruitingBasic ScienceClostridium Difficile Infection (CDI)1
Not AvailableRecruitingDiagnosticNon-erosive Reflux Disease (NERD) / Reflux, Gastroesophageal1
Not AvailableTerminatedScreeningCytochrome P450 Phenotype and Genotype Metrics1
Not AvailableUnknown StatusTreatmentEsophagus, Barrett / Reflux, Gastroesophageal1
Not AvailableWithdrawnDiagnosticGastro-esophageal Reflux Disease (GERD) / Indigestion / Non Erosive Reflux Disease1

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
FormRouteStrength
Capsule, delayed releaseOral20 mg
Tablet, orally disintegrating, delayed releaseOral20 mg/1
Tablet, delayed releaseOral10 mg
Tablet, delayed releaseOral20 mg
Capsule, delayed releaseOral40 mg
Kit
CapsuleOral10 mg/1
CapsuleOral40 mg/1
Capsule, delayed release pelletsOral10 mg/1
Capsule, delayed release pelletsOral20 mg/1
Capsule, delayed release pelletsOral40 mg/1
Tablet, delayed releaseOral20 mg/1
Capsule, delayed releaseOral10 mg/1
Capsule, delayed releaseOral20 mg/1
Capsule, delayed releaseOral40 mg/1
CapsuleOral20.6 mg/1
Capsule, delayed releaseOral20.6 mg/1
TabletOral
Powder, for suspensionOral
CapsuleOral20 mg/1
Granule, delayed releaseOral10 mg/1
Granule, delayed releaseOral2.5 mg/1
Tablet, delayed releaseOral20.6 mg/1
Capsule, delayed releaseOral10 mg
Capsule, gelatin coatedOral
Tablet, film coatedOral
CapsuleOral
Tablet, chewableOral
Prices
Unit descriptionCostUnit
PriLOSEC 30 20 mg Delayed Release Capsule Bottle459.99USD bottle
Zegerid 30 20-1680 mg Packets Packet224.27USD packet
Zegerid 30 40-1680 mg Packets Packet224.27USD packet
PriLOSEC 30 10 mg Delayed Release Capsule Bottle174.37USD bottle
Omeprazole 28 20 mg Enteric Coated Tabs Box25.99USD box
PriLOSEC OTC 14 20 mg Enteric Coated Tabs Box19.99USD box
PriLOSEC 40 mg Delayed Release Capsule9.59USD capsule
Prilosec dr 40 mg capsule9.22USD capsule
Omeprazole 40 mg Delayed Release Capsule7.69USD capsule
Zegerid 40-1100 mg capsule7.48USD capsule
Zegerid 20 mg capsule7.19USD capsule
Zegerid 40 mg capsule6.46USD capsule
Prilosec dr 20 mg capsule6.24USD capsule
Prilosec 20 mg capsule dr6.15USD capsule
Prilosec dr 10 mg capsule5.59USD capsule
Omeprazole powder5.05USD g
Omeprazole 20 mg Delayed Release Capsule4.32USD capsule
Omeprazole 10 mg Delayed Release Capsule3.13USD capsule
Losec (Sustained-Release Tablet) 20 mg Capsule/Sustained Release Tablet2.48USD tablet
Losec (Sustained-Release Tablet) 10 mg Capsule/Sustained Release Tablet1.97USD tablet
Losec (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet1.24USD tablet
Apo-Omeprazole 20 mg Capsule/Sustained Release Tablet1.15USD tablet
Mylan-Omeprazole 20 mg Capsule/Sustained Release Tablet1.15USD tablet
Pms-Omeprazole (Delayed Release Tablet) 20 mg Capsule/Sustained Release Tablet1.15USD tablet
Pms-Omeprazole (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet1.15USD tablet
Ratio-Omeprazole (Sustained-Release Tablet) 20 mg Capsule/Sustained Release Tablet1.15USD tablet
Sandoz Omeprazole (Sustained-Release Capsule) 20 mg Capsule/Sustained Release Tablet1.15USD tablet
Mylan-Omeprazole 10 mg Capsule/Sustained Release Tablet0.86USD tablet
Sandoz Omeprazole (Sustained-Release Capsule) 10 mg Capsule/Sustained Release Tablet0.86USD tablet
Zegerid otc 20-1100 mg capsule0.78USD capsule
Prilosec otc 20 mg tablet0.76USD tablet
Omeprazole dr 20 mg tablet0.66USD tablet
CVS Pharmacy omeprazole dr 20 mg tablet0.53USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5690960No1997-11-252014-11-25Us
CA2180535No2004-03-232014-01-05Canada
CA1338377No1996-06-112013-06-11Canada
US6489346No2002-12-032016-07-16Us
US6699885No2004-03-022016-07-16Us
USRE45198No2014-10-142016-07-16Us
US6645988No2003-11-112016-07-16Us
US7399772No2008-07-152016-07-16Us
US6150380Yes2000-11-212019-05-10Us
US6191148Yes2001-02-202019-04-09Us
US6147103Yes2000-11-142019-04-09Us
US6166213Yes2000-12-262019-04-09Us
US5900424Yes1999-05-042016-11-04Us
US6428810Yes2002-08-062020-05-03Us
US9023391No2015-05-052025-08-16Us
US6403616No2002-06-112019-11-15Us
US5817338No1998-10-062015-10-06Us
US5840737No1998-11-242016-07-15Us
US6780882No2004-08-242016-07-15Us
US6926907No2005-08-092023-02-28Us
US9539214No2017-01-102033-03-13Us
US9364439No2016-06-142022-05-31Us
US8206741No2012-06-262023-02-28Us
US9987231No2013-01-022033-01-02Us
US10076494No2016-12-082036-12-08Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)155 °CFDA label
water solubilityVery slightly soluble FDA label
logP2.23SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.359 mg/mLALOGPS
logP1.66ALOGPS
logP2.43ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.29ChemAxon
pKa (Strongest Basic)4.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.1 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.66 m3·mol-1ChemAxon
Polarizability37.45 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9968
Blood Brain Barrier-0.6326
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.5573
P-glycoprotein inhibitor IInhibitor0.6622
P-glycoprotein inhibitor IINon-inhibitor0.968
Renal organic cation transporterNon-inhibitor0.542
CYP450 2C9 substrateNon-substrate0.7838
CYP450 2D6 substrateSubstrate0.6175
CYP450 3A4 substrateSubstrate0.6901
CYP450 1A2 substrateInhibitor0.7505
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7895
Ames testNon AMES toxic0.5692
CarcinogenicityNon-carcinogens0.8318
BiodegradationNot ready biodegradable0.9778
Rat acute toxicity2.2254 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.719
hERG inhibition (predictor II)Non-inhibitor0.8977
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-002f-0900000000-412912cbbcdbd1b34699
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0901000000-189e81fb724041d50498
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f6t-0900000000-db101d248a4e861d4c3b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uds-0900000000-f579fb74ac97c56dd3eb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-eefbf9686f0313da581e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-363d6954875894f433ba
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f6t-1900000000-d8c64d496f1d9b3ed465
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-1669000000-51f9342d7e4bbd0356b2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f6t-0900000000-d21755acc44ff2d29cfa
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0f80-2900000000-9989d19c171c612ea3dc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-f74adb7f41e2d390b602
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzimidazoles
Sub Class
Sulfinylbenzimidazoles
Direct Parent
Sulfinylbenzimidazoles
Alternative Parents
Anisoles / Methylpyridines / Alkyl aryl ethers / Imidazoles / Heteroaromatic compounds / Sulfoxides / Sulfinyl compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds
show 2 more
Substituents
Sulfinylbenzimidazole / Anisole / Alkyl aryl ether / Methylpyridine / Pyridine / Benzenoid / Azole / Imidazole / Heteroaromatic compound / Sulfoxide
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether, sulfoxide, pyridines, benzimidazoles (CHEBI:77260)

Targets

Kind
Protein
Organism
Human
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
  1. Tajima A, Koizumi K, Suzuki K, Higashi N, Takahashi M, Shimada T, Terano A, Hiraishi H, Kuwayama H: Proton pump inhibitors and recurrent bleeding in peptic ulcer disease. J Gastroenterol Hepatol. 2008 Dec;23 Suppl 2:S237-41. doi: 10.1111/j.1440-1746.2008.05557.x. [PubMed:19120905]
  2. 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. [PubMed:18679668]
  3. 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. [PubMed:18925391]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:9139728]

Enzymes

Kind
Protein
Organism
Human
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
  1. 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. [PubMed:10611146]
  2. 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. [PubMed:10445394]
  3. 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. [PubMed:18549670]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
  1. 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. [PubMed:12806570]
  2. 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. [PubMed:12623754]
  3. 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. [PubMed:16248835]
  4. 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. [PubMed:12445035]
  5. 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. [PubMed:10584979]
  6. 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. [PubMed:1505152]
  7. 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. [PubMed:1280125]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:12623754]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:8894508]
Details
5. Cytochrome P450 2C9
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:9578596]
  2. 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. [PubMed:27199745]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:8894508]
Kind
Protein
Organism
Human
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
  1. 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 . [PubMed:11334262]
  2. 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. [PubMed:15258107]
Details
8. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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
  1. 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. [PubMed:16093273]
  2. 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. [PubMed:19515014]
  3. 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. [PubMed:8423765]
  4. 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. [PubMed:15626586]
  5. 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. [PubMed:16276979]
  6. 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. [PubMed:16248835]
  7. 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. [PubMed:15037195]
  8. 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. [PubMed:10901708]
  9. 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. [PubMed:10671908]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name
CYP11A1
Uniprot ID
P05108
Uniprot Name
Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight
60101.87 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. 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. [PubMed:18048485]
  2. 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. [PubMed:15258107]
  3. 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. [PubMed:16093273]
  4. 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. [PubMed:19515014]
  5. 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. [PubMed:9353355]
  6. 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. [PubMed:11038161]
  7. 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. [PubMed:9224780]
  8. 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. [PubMed:8681489]
  9. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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
  1. 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. [PubMed:15313923]
  2. 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. [PubMed:19076159]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
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
  1. 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. [PubMed:12538803]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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
  1. Pauli-Magnus C, Rekersbrink S, Klotz U, Fromm MF: Interaction of omeprazole, lansoprazole and pantoprazole with P-glycoprotein. Naunyn Schmiedebergs Arch Pharmacol. 2001 Dec;364(6):551-7. [PubMed:11770010]

Drug created on June 13, 2005 07:24 / Updated on December 12, 2018 07:03