小中大Identification
Name Esomeprazole
Accession Number DB00736 (APRD00363)
Type small molecule
Groups approved
Description
A highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and zollinger-ellison syndrome. The drug inhibits the H()-K()-ATPase (H()-K()-exchanging ATPase) in the proton pump of gastric parietal cells. [PubChem]
Structure
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms •(-)-Omeprazole
•(S)-Omeprazole
•Esomperazole
Synonyms (-)-Omeprazole
(S)-Omeprazole
Esomperazole
Salts Not Available
Brand names Name Company
Axagon
Esopral
Lucen
Nexiam AstraZeneca
Nexium AstraZeneca
Brand mixtures Not Available
Categories •Anti-Ulcer Agents
•Enzyme Inhibitors
•Proton-pump Inhibitors
•Antihistamines
CAS number 161796-78-7
Weight Average: 345.416
Monoisotopic: 345.114712179
Chemical Formula C17H19N3O3S
InChI Key InChIKey=SUBDBMMJDZJVOS-XMMPIXPASA-N
InChI InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m1/s1Plain Text
IUPAC Name 5-methoxy-2-[(R)-[(4-methoxy-3,5-dimethylpyridin-2-yl)methane]sulfinyl]-1H-1,3-benzodiazole
SMILES COC1=CC2=C(NC(=N2)[S@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Pharmacodynamics Esomeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Esomeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase at the secretory surface of the gastric parietal cell. By doing so, it inhibits acid secretion into the gsatric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.
Mechanism of action Esomeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H+/K+-ATPase in the gastric parietal cell. By acting specifically on the proton pump, Esomeprazole blocks the final step in acid production, thus reducing gastric acidity.
Absorption 90%
Volume of distribution •16 L [healthy volunteers]
Protein binding 97%
Metabolism Mainly hepatic. Esomeprazole is completely metabolized by the cytochrome P450 system via CYP2C19 and CYP3A4. Metabolism produces inactive hydroxy and desmethyl metabolites, which have no effect on gastric acid secretion. Less than 1% of the parent drug is excreted in urine.
Route of elimination Approximately 80% of the administered dose of esomeprazole is excreted as metabolites in urine and the remaining 20% is excreted in feces.
Half life 1-1.5 hours
Clearance Not Available
Toxicity Blurred vision, confusion, drowsiness, dry mouth, flushing headache, nausea, rapid heartbeat, sweating
Affected organisms •Humans and other mammals
Pathways Pathway Name SMPDB ID
=true] Esomeprazole Pathway =true]SMP00225
Pharmacoeconomics
Manufacturers •Astrazeneca lp
Packagers •AQ Pharmaceuticals Inc.
•A-S Medication Solutions LLC
•AstraZeneca Inc.
•Cardinal Health
•Direct Pharmaceuticals Inc.
•Diversified Healthcare Services Inc.
•Innoviant Pharmacy Inc.
•Lake Erie Medical and Surgical Supply
•Merck & Co.
•Nucare Pharmaceuticals Inc.
•Palmetto Pharmaceuticals Inc.
•Physicians Total Care Inc.
•Prepackage Specialists
•Rebel Distributors Corp.
•Southwood Pharmaceuticals
•Stat Rx Usa
Dosage forms Form Route Strength
Capsule, delayed release Oral 20 mg
Capsule, delayed release Oral 40 mg
Granule, for suspension Oral 10 mg per packet
Granule, for suspension Oral 20 mg per packet
Granule, for suspension Oral 40 mg per packet
Injection Intravenous 20 mg
Injection Intravenous 40 mg
Prices Unit description Cost Unit
Nexium i.v. 20 mg vial 33.91 USD vial
Nexium i.v. 40 mg vial 33.91 USD vial
NexIUM 20 mg Delayed Release Capsule 6.76 USD capsule
NexIUM 40 mg Delayed Release Capsule 6.76 USD capsule
Nexium 10 mg packet 6.5 USD each
Nexium 20 mg capsule 6.5 USD capsule
Nexium 20 mg packet 6.5 USD each
Nexium 40 mg capsule 6.5 USD capsule
Nexium 40 mg packet 6.5 USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Country Patent Number Approved Expires (estimated)
United States 6428810 2000-05-03 2020-05-03
United States 5877192 1994-05-27 2014-05-27
Canada 2346988 2009-02-10 2019-11-03
Canada 1338377 1996-06-11 2013-06-11
Properties
State solid
Melting point 155 oC
Experimental Properties Property Value Source
water solubility Very slightly soluble in water PhysProp
logP 0.6 PhysProp
Predicted Properties Property Value Source
water solubility 3.53e-01 g/l ALOGPS
logP 1.66 ALOGPS
logP 2.43 ChemAxon Molconvert
logS -3 ALOGPS
pKa 18.31 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 77.1 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 93.66 ChemAxon Molconvert
polarizability 37.43 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference 1.Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7. Pubmed
External Links Resource Link
KEGG Drug D01984
ChEBI 50275
ChEMBL 50275
Therapeutic Targets Database DCL000524
PharmGKB PA10075
IUPHAR 4279
Guide to Pharmacology 4279
Drug Product Database 2244521
RxList cuturl('http://www.rxlist.com/cgi/generic3/esomeprazole.htm')
Drugs.com cuturl('http://www.drugs.com/cdi/esomeprazole.html')
Wikipedia cuturl('http://en.wikipedia.org/wiki/Esomeprazole')
ATC Codes •A02BC05
•A02BC01
AHFS Codes •56:28.36
PDB Entries Not Available
FDA label show (104 KB)
MSDS Not Available
Interactions
Drug Interactions Drug Interaction
Atazanavir This gastric pH modifier decreases the levels/effects of atazanavir
Cefditoren Proton pump inhibitors such as esomeprazole 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.
Clopidogrel Esomeprazole may decrease serum concentrations of the active metabolite(s) of clopidogrel. Due to the possible risk for impaired clopidogrel effectiveness with this combination, clinicians should carefully consider the need for concurrent esomeprazole therapy in patients receiving clopidogrel. Monitor response to clopidogrel closely when using clopidogrel with esomeprazole. Whether there are differences among individual proton pump inhibitors is unclear. Other acid-lowering therapies (e.g., H2-receptor antagonists, antacids, etc.) do not appear to share this interaction with clopidogrel.
Enoxacin Esomeprazole may decrease the absorption of enoxacin.
Indinavir Omeprazole decreases the absorption of indinavir
Itraconazole The proton pump inhibitor, esomeprazole, may decrease the absorption of itraconazole.
Ketoconazole The proton pump inhibitor, esomeprazole, may decrease the absorption of ketoconazole.
Tipranavir Tipranavir, co-administered with Ritonavir, may decrease the plasma concentration of Esomeprazole. Consider alternate therapy or increase the dose of Esomeprazole based on the therapeutic response.
Food Interactions •Take without regard to meals.
