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OMEP;Omeprazol [INN-Spanish];omeprazole;Omeprazole magnesium;Omeprazolum [INN-Latin];OMP;OMZ;

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

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

• 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

Synthesis Reference	Not Available
General Reference	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

Type	small molecule

Classes

Phenols and Derivatives Benzimidazoles Ethers Anisoles

Substructures

Phenols and Derivatives Benzimidazoles Pyridines and Derivatives Ethers Benzene and Derivatives Imidazoles Heterocyclic compounds Aromatic compounds Anisoles Imines Cyanamides Phenyl Esters Sulfoxides

gastric acid RELATED DISORDERS 中和胃酸;

Indication	For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Pharmacodynamics	Omeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Omeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase at the secretory surface of the gastric parietal cell. As a result, it inhibits acid secretion into the gastric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.
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.
Absorption	Absorption is rapid, absolute bioavailability (compared to intravenous administration) is about 30-40% at doses of 20-40 mg.
Volume of distribution	Not Available
Protein binding	95%
Metabolism	Hepatic. Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us. Substrate Enzymes Product Omeprazole Cytochrome P450 2C9 Cytochrome P450 2C19 Cytochrome P450 3A4 5-Hydroxyomeprazole Details Omeprazole Cytochrome P450 2C19 5'-O-Desmethyl omeprazole Details Omeprazole Cytochrome P450 3A4 Omeprazole sulfone Details Omeprazole Cytochrome P450 3A4 3-Hydroxyomeprazole Details
Route of elimination	Urinary excretion is a primary route of excretion of omeprazole metabolites.
Half life	0.5-1 hour
Clearance	total body cl=500-600 mL/min [healthy] 250 mL/min [Geriatric] 70 mL/min [Hepatic Impairment] 10 – 62 mL/min/1.73 m2 [Renal 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	Pathway Name SMPDB ID Omeprazole Pathway SMP00226

Properties
State	solid
Experimental Properties	Property Value Source melting point 156 °C PhysProp water solubility 82.3 mg/L Not Available logP 2.23 SANGSTER (1994)
Predicted Properties	Property Value Source water solubility 3.59e-01 g/l 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 ChemAxon rotatable bond count 5 ChemAxon refractivity 93.66 ChemAxon polarizability 37.45 ChemAxon

Drug	Interaction
Alprazolam	Omeprazole may increase the effect of the benzodiazepine, alprazolam.
Atazanavir	This gastric pH modifier decreases the levels/effects of atazanavir
Avanafil	Nineteen healthy male volunteers received a single 40 omeprazole delayed-release capsule once daily for 8 days (Days 1-8), and a single 200 mg avanafil on Day 8. Twelve hour pharmacokinetics of omeprazole on Days 7 and 8 were compared. Co-administration with avanafil resulted in an approximate 5.9% increase in AUC0-inf and 8.6% increase in Cmax of omeprazole.
Bendamustine	Affects hepatic CYP1A2 metabolism, thus increasing bendamustine levels. Concentration of active metabolites may be decreased due to decreased conversion.
Cefditoren	Proton pump inhibitors such as omeprazole may decrease the serum concentration of cefditoren. If possible, avoid use of cefditoren with proton pump inhibitors (PPIs). Consider alternative methods to minimize/control acid reflux (eg, diet modification) or alternative antimicrobial therapy if use of PPIs can not be avoided.
Chlordiazepoxide	Omeprazole may increase the effect of the benzodiazepine, chlordiazepoxide.
Cilostazol	Omeprazole increases the effect of cilostazol
Clonazepam	Omeprazole may increase the effect of the benzodiazepine, clonazepam.
Clopidogrel	Omeprazole may decrease serum concentrations of the active metabolite(s) of clopidogrel. Clopidogrel prescribing information recommends avoiding concurrent use with omeprazole, due to the possibility that combined use may result in decreased clopidogrel effectiveness.
Clorazepate	Omeprazole may increase the effect of the benzodiazepine, clorazepate.
Cyclosporine	Omeprazole increases the effect and toxicity of cyclosporine
Dasatinib	Omeprazole may decrease the serum level of dasatinib.
Diazepam	Omeprazole may increase the effect of the benzodiazepine, diazepam.
Disopyramide	The beta-blocker increases toxicity of disopyramide
Enoxacin	Omeprazole may decrease the absorption of enoxacin.
Estazolam	Omeprazole may increase the effect of the benzodiazepine, estazolam.
Ethotoin	Omeprazole increases the effect of hydantoin
Flurazepam	Omeprazole may increase the effect of the benzodiazepine, flurazepam.
Fosphenytoin	Omeprazole increases the effect of hydantoin
Halazepam	Omeprazole may increase the effect of the benzodiazepine, halazepam.
Indinavir	Omeprazole decreases the absorption of indinavir
Itraconazole	The proton pump inhibitor, omeprazole, may decrease the absorption of itraconazole.
Ketazolam	Omeprazole may increase the effect of the benzodiazepine, ketazolam.
Ketoconazole	The proton pump inhibitor, omeprazole, may decrease the absorption of ketoconazole.
Mephenytoin	Omeprazole increases the effect of hydantoin
Methotrexate	Omeprazole increases the levels of methotrexate
Midazolam	Omeprazole may increase the effect of the benzodiazepine, midazolam.
Ospemifene	Moderate CYP2C19 inhibitors may increase levels of ospemifene. Monitor concomitant therapy closely.
Phenytoin	Omeprazole increases the effect of hydantoin
Prazepam	Omeprazole may increase the effect of the benzodiazepine, prazepam.
Quazepam	Omeprazole may increase the effect of the benzodiazepine, quazepam.
Rilpivirine	Proton-pump inhibitors increase gastric pH which causes a decrease in the exposure of rilpivirine thus reducing efficacy.
Roflumilast	Affects CYP1A2 metabolism; decreases level or effect of roflumilast.
St. John's Wort	St. John's Wort decreases the levels/effects of omeprazole
Tacrolimus	Omeprazole may increase the blood concentration of Tacrolimus. Monitor for changes in the therapeutic/toxic effects of Tacrolimus if Omeprazole therapy is initiated, discontinued or altered.
Tipranavir	Tipranavir, co-administered with Ritonavir, may decrease the plasma concentration of Omeprazole. Consider alternate therapy or increase the dose of Omeprazole based on the therapeutic response.
Tocilizumab	Omeprazole is a CYP2C19 and CYP3A4 substrate. Exposure of omeprazole decreases following administration of tocilizumab..
Triazolam	Omeprazole may increase the effect of the benzodiazepine, triazolam.
Trimipramine	The strong CYP2C19 inhibitor, Omeprazole, may decrease the metabolism and clearance of Trimipramine, a CYP2C19 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimipramine if Omeprazole is initiated, discontinued or dose changed.
Vismodegib	Vismodegib serum concentrations may be decreased by proton pump inhibitors such as omeprazole.
Voriconazole	Voriconazole increases the effect and toxicity of omeprazole

• Avoid alcohol.
• Take 30-60 minutes before meals.