You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameEsomeprazole
Accession NumberDB00736  (APRD00363)
TypeSmall Molecule
GroupsApproved, Investigational
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
Thumb
Synonyms
(−)-omeprazole
(S)-(−)-omeprazole
(S)-omeprazole
Esomeprazol
Ésoméprazole
Esomeprazolum
Omeprazole S-form
Perprazole
External Identifiers
  • H 199/18
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act Esomeprazoletablet (delayed-release)40 mgoralActavis Pharma Company2015-11-09Not applicableCanada
Act Esomeprazoletablet (delayed-release)20 mgoralActavis Pharma Company2015-11-09Not applicableCanada
Esomeprazoletablet (delayed-release)20 mgoralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
Esomeprazoletablet (delayed-release)20 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Esomeprazoletablet (delayed-release)40 mgoralSanis Health Inc2014-09-22Not applicableCanada
Esomeprazoletablet (delayed-release)40 mgoralSivem Pharmaceuticals Ulc2015-07-22Not applicableCanada
Esomeprazoletablet (delayed-release)40 mgoralPro Doc Limitee2012-11-22Not applicableCanada
Esomeprazoletablet (delayed-release)20 mgoralPro Doc Limitee2013-06-06Not applicableCanada
Esomeprazoletablet (delayed-release)40 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Esomeprazoletablet (delayed-release)20 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Esomeprazoletablet (delayed-release)40 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Esomeprazole Drcapsule (delayed release)40 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Esomeprazole Drcapsule (delayed release)20 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Esomeprazole Strontiumcapsule, delayed release20 mg/1oralAmneal Pharmaceuticals of New York, LLC2013-08-12Not applicableUs
Esomeprazole Strontiumcapsule, delayed release40 mg/1oralAmneal Pharmaceuticals, LLC2013-08-12Not applicableUs
Esomeprazole Strontiumcapsule, delayed release20 mg/1oralAmneal Pharmaceuticals, LLC2013-08-12Not applicableUs
Esomeprazole Strontiumcapsule, delayed release40 mg/1oralAmneal Pharmaceuticals of New York, LLC2013-08-12Not applicableUs
Mylan-esomeprazolecapsule (delayed release)20 mgoralMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Mylan-esomeprazoletablet (delayed-release)40 mgoralMylan Pharmaceuticals Ulc2012-08-14Not applicableCanada
Mylan-esomeprazolecapsule (delayed release)40 mgoralMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Mylan-esomeprazoletablet (delayed-release)20 mgoralMylan Pharmaceuticals Ulc2012-08-14Not applicableCanada
Nexiumcapsule, delayed release40 mg/1oralRebel Distributors Corp2011-07-08Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralbryant ranch prepack2001-03-19Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralUnit Dose Services2001-03-19Not applicableUs
Nexiumgranule, delayed release10 mg/1oralAstra Zeneca Lp2008-07-07Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralAstra Zeneca Lp2001-03-19Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralPhysicians Total Care, Inc.2002-06-17Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralClinical Solutions Wholesale2001-03-19Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralRebel Distributors Corp2011-07-08Not applicableUs
Nexiumgranules for suspension, delayed release10 mgoralAstrazeneca Canada Inc2008-01-02Not applicableCanada
Nexiumcapsule, delayed release40 mg/1oralPhysicians Total Care, Inc.2002-05-02Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralAstra Zeneca Lp2001-03-19Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralCardinal Health2001-03-19Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralSTAT Rx USA LLC2010-08-19Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralA S Medication Solutions Llc2001-06-28Not applicableUs
Nexiumgranule, delayed release5 mg/1oralAstra Zeneca Lp2012-06-01Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralREMEDYREPACK INC.2013-02-22Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralA S Medication Solutions Llc2001-06-28Not applicableUs
Nexiumgranule, delayed release40 mg/1oralAstra Zeneca Lp2007-03-19Not applicableUs
Nexiumgranule, delayed release40 mg/1oralCardinal Health2007-03-19Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralAvera Mc Kennan Hospital2015-04-06Not applicableUs
Nexiumgranule, delayed release2.5 mg/1oralAstra Zeneca Lp2012-06-01Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralCardinal Health2010-08-19Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralAstra Zeneca Lp2001-03-19Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralAvera Mc Kennan Hospital2015-03-31Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2011-02-25Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralbryant ranch prepack2001-03-19Not applicableUs
Nexiumgranule, delayed release20 mg/1oralAstra Zeneca Lp2007-03-19Not applicableUs
Nexiumcapsule, delayed release20 mg/1oralCardinal Health2010-08-19Not applicableUs
Nexiumcapsule, delayed release40 mg/1oralAstra Zeneca Lp2001-03-19Not applicableUs
Nexium - 20mgtablet (delayed-release)20 mgoralAstrazeneca Canada Inc2001-08-20Not applicableCanada
Nexium - 40mgtablet (delayed-release)40 mgoralAstrazeneca Canada Inc2001-08-20Not applicableCanada
Nexium I.V.injection40 mg/5mLintravenousCardinal Health2005-05-03Not applicableUs
Nexium I.V.injection40 mg/5mLintravenousAstra Zeneca Lp2005-05-03Not applicableUs
Nexium I.V.injection20 mg/5mLintravenousAstra Zeneca Lp2005-05-03Not applicableUs
PMS-esomeprazole Drcapsule (delayed release)40 mgoralPharmascience Inc2014-06-12Not applicableCanada
PMS-esomeprazole Drcapsule (delayed release)20 mgoralPharmascience IncNot applicableNot applicableCanada
Ran-esomeprazoletablet (delayed-release)40 mgoralRanbaxy Pharmaceuticals Canada Inc.2014-10-09Not applicableCanada
Ran-esomeprazoletablet (delayed-release)20 mgoralRanbaxy Pharmaceuticals Canada Inc.2014-10-09Not applicableCanada
Riva-esomeprazole Drcapsule (delayed release)40 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Riva-esomeprazole Drcapsule (delayed release)20 mgoralLaboratoire Riva IncNot applicableNot applicableCanada
Teva-esomeprazoletablet (delayed-release)40 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Teva-esomeprazoletablet (delayed-release)20 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-esomeprazoletablet (delayed-release)20 mgoralApotex Inc2012-03-02Not applicableCanada
Apo-esomeprazoletablet (delayed-release)40 mgoralApotex Inc2011-03-07Not applicableCanada
Esomeprazole Magnesiumcapsule, delayed release40 mg/1oralUnit Dose Services2015-02-17Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release40 mg/1oralDr. Reddy's Laboratories Limited2015-09-25Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release20 mg/1oralTeva Pharmaceuticals USA Inc2015-02-17Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release40 1/1oralTorrent Pharmaceuticals Limited2015-10-19Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release20 1/1oralTorrent Pharmaceuticals Limited2015-10-19Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release40 mg/1oralDr. Reddy's Laboratories Inc2015-12-10Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release pellets40 mg/1oralMylan Pharmaceuticals Inc.2015-08-03Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release20 mg/1oralDr. Reddy's Laboratories Inc2015-12-10Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release pellets20 mg/1oralMylan Pharmaceuticals Inc.2015-08-03Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release40 mg/1oralCamber Pharmaceuticals, Inc.2015-09-21Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release20 mg/1oralDr. Reddy's Laboratories Limited2015-09-25Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release40 mg/1oralDIRECT RX2014-01-01Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release40 mg/1oralTeva Pharmaceuticals USA Inc2015-02-17Not applicableUs
Esomeprazole Magnesiumcapsule, delayed release20 mg/1oralCamber Pharmaceuticals, Inc.2015-09-21Not applicableUs
Esomeprazole Magnesium D/rcapsule, delayed release40 mg/1oralDIRECT RX2015-01-01Not applicableUs
Esomeprazole Sodiuminjection40 mg/5mLintravenousAccord Healthcare Inc.2015-12-10Not applicableUs
Esomeprazole Sodiuminjection, powder, lyophilized, for solution40 mg/5mLintravenousSun Pharma Global FZE2014-01-03Not applicableUs
Esomeprazole Sodiuminjection, powder, lyophilized, for solution40 mg/5mLintravenousSun Pharmaceutical Industries Limited2014-12-15Not applicableUs
Esomeprazole Sodiuminjection, powder, lyophilized, for solution20 mg/5mLintravenousSun Pharma Global FZE2014-01-03Not applicableUs
Esomeprazole Sodiuminjection, powder, lyophilized, for solution20 mg/5mLintravenousSun Pharmaceutical Industries Limited2014-12-15Not applicableUs
Nexiumgranule, delayed release40 mg/1oralDIRECT RX2014-01-01Not applicableUs
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nexium 24hrcapsule, delayed release20 mg/1oralPfizer Consumer Healthcare2014-05-27Not applicableUs
Nexium 24hrtablet20 mg/1oralPfizer Consumer Healthcare2016-02-06Not applicableUs
Unapproved/Other Products Not Available
International Brands
NameCompany
AleniaDelta
Awa-BlockUsawa
AxagonSimesa
CorPrater
CronopepBiotoscana
EmaneraKrka
EmepAristopharma
EmozulHYGIA
ES-ODPiramal Healthcare
EsmepHYGIA
EsoAsiatic Lab
EsofagMicro Labs
EsogastrosedolNova Argentia
EsolokIbn Sina
EsomarfanMarfan
EsomentaRAK
EsomepACI
Esomeprazol GenfarGenfar S.A
EsopralMaquifarma
EsorestCentaur
Inexium paranovaNot Available
LucenMalesci
NexiamAstraZeneca
Brand mixtures
NameLabellerIngredients
VimovoAstra Zeneca Lp
Salts
Name/CASStructureProperties
Esomeprazole magnesium
161973-10-0
Thumb
  • InChI Key: KWORUUGOSLYAGD-YPPDDXJESA-N
  • Monoisotopic Mass: 712.19881695
  • Average Mass: 713.12
DBSALT001222
Esomeprazole magnesium dihydrate
217087-10-0
Thumb
  • InChI Key: DBOUSUONOXEWHU-VCKZSRROSA-N
  • Monoisotopic Mass: 748.21994632
  • Average Mass: 749.15
DBSALT001223
Esomeprazole magnesium trihydrate
217087-09-7
Thumb
  • InChI Key: VEVZQDGATGBLIC-UHFFFAOYSA-N
  • Monoisotopic Mass: 766.230511
  • Average Mass: 767.17
DBSALT001836
Esomeprazole sodium
161796-78-7
Thumb
  • InChI Key: RYXPMWYHEBGTRV-JIDHJSLPSA-N
  • Monoisotopic Mass: 367.09665691
  • Average Mass: 367.4
DBSALT000968
Esomeprazole strontium
914613-86-8
Thumb
  • InChI Key: FEVPVZSYBDUVGY-YPPDDXJESA-N
  • Monoisotopic Mass: 776.119388
  • Average Mass: 776.44
DBSALT001224
Esomeprazole strontium hydrate
934714-36-0
Thumb
  • InChI Key: NCGHIAKEJNQSMS-QLGOZJDFSA-N
  • Monoisotopic Mass: 848.161647
  • Average Mass: 848.5
DBSALT001837
Categories
UNIIN3PA6559FT
CAS number119141-88-7
WeightAverage: 345.416
Monoisotopic: 345.114712179
Chemical FormulaC17H19N3O3S
InChI KeySUBDBMMJDZJVOS-DEOSSOPVSA-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-/m0/s1
IUPAC Name
5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
SMILES
COC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub ClassSulfinylbenzimidazoles
Direct ParentSulfinylbenzimidazoles
Alternative Parents
Substituents
  • Sulfinylbenzimidazole
  • Anisole
  • Methylpyridine
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Sulfoxide
  • Azacycle
  • Sulfinyl compound
  • Ether
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • 5-methoxy-2-\{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl\}-1H-benzimidazole (CHEBI:50275 )
Pharmacology
IndicationFor the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
PharmacodynamicsEsomeprazole 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 actionEsomeprazole 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.
Related Articles
Absorption90%
Volume of distribution
  • 16 L [healthy volunteers]
Protein binding97%
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.

SubstrateEnzymesProduct
Esomeprazole
5-hydroxyesomeprazoleDetails
Esomeprazole
Not Available
Active Metabolite of EsomeprazoleDetails
Route of eliminationApproximately 80% of the administered dose of esomeprazole is excreted as metabolites in urine and the remaining 20% is excreted in feces.
Half life1-1.5 hours
ClearanceNot Available
ToxicityBlurred vision, confusion, drowsiness, dry mouth, flushing headache, nausea, rapid heartbeat, sweating
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Esomeprazole Action PathwayDrug actionSMP00225
Esomeprazole Metabolism PathwayDrug metabolismSMP00612
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2C19
Gene symbol: CYP2C19
UniProt: P33261
rs4244285 CYP2C19*2A Allele, homozygotePoor metabolizer, lower dose requirement, improved drug efficacy9867757
Cytochrome P450 2C19
Gene symbol: CYP2C19
UniProt: P33261
rs4986893 CYP2C19*3A Allele, homozygotePoor metabolizer, lower dose requirement, improved drug efficacy9867757
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Astrazeneca lp
Packagers
Dosage forms
FormRouteStrength
Capsule, delayed releaseoral20 mg/1
Capsule, delayed releaseoral20 1/1
Capsule, delayed releaseoral40 1/1
Capsule, delayed releaseoral40 mg/1
Capsule, delayed release pelletsoral20 mg/1
Capsule, delayed release pelletsoral40 mg/1
Injection, powder, lyophilized, for solutionintravenous20 mg/5mL
Injection, powder, lyophilized, for solutionintravenous40 mg/5mL
Granule, delayed releaseoral10 mg/1
Granule, delayed releaseoral2.5 mg/1
Granule, delayed releaseoral20 mg/1
Granule, delayed releaseoral40 mg/1
Granule, delayed releaseoral5 mg/1
Granules for suspension, delayed releaseoral10 mg
Tablet (delayed-release)oral20 mg
Tablet (delayed-release)oral40 mg
Tabletoral20 mg/1
Injectionintravenous20 mg/5mL
Injectionintravenous40 mg/5mL
Capsule (delayed release)oral20 mg
Capsule (delayed release)oral40 mg
Tablet (immediate and delayed-release)oral
Tablet, delayed releaseoral
Prices
Unit descriptionCostUnit
Nexium i.v. 20 mg vial33.91USD vial
Nexium i.v. 40 mg vial33.91USD vial
NexIUM 20 mg Delayed Release Capsule6.76USD capsule
NexIUM 40 mg Delayed Release Capsule6.76USD capsule
Nexium 10 mg packet6.5USD each
Nexium 20 mg capsule6.5USD capsule
Nexium 20 mg packet6.5USD each
Nexium 40 mg capsule6.5USD capsule
Nexium 40 mg packet6.5USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA1338377 No1996-06-112013-06-11Canada
CA2346988 No2009-02-102019-11-03Canada
US5714504 Yes1995-08-032015-08-03Us
US5877192 No1994-05-272014-05-27Us
US5900424 Yes1996-11-042016-11-04Us
US6147103 Yes1999-04-092019-04-09Us
US6166213 Yes1999-04-092019-04-09Us
US6191148 Yes1999-04-092019-04-09Us
US6369085 Yes1998-11-252018-11-25Us
US6428810 Yes2000-05-032020-05-03Us
US6926907 No2003-02-282023-02-28Us
US7411070 Yes1998-11-252018-11-25Us
US7745466 No1998-10-132018-10-13Us
US8466175 Yes1998-11-252018-11-25Us
US8557285 No2002-05-312022-05-31Us
US8852636 No2002-05-312022-05-31Us
US8858996 No2002-05-312022-05-31Us
US8945621 No2011-10-172031-10-17Us
US9161920 No2002-05-312022-05-31Us
US9198888 No2002-05-312022-05-31Us
US9220698 No2011-03-102031-03-10Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point155 °CNot Available
water solubilityVery slightly soluble in waterNot Available
logP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.353 mg/mLALOGPS
logP1.66ALOGPS
logP2.43ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.68ChemAxon
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
Polarizability35.81 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Manne Reddy, “Amorphous hydrates of esomeprazole magnesium and process for the preparation thereof.” U.S. Patent US20040167173, issued August 26, 2004.

US20040167173
General References
  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:10886041 ]
External Links
ATC CodesA02BC05A02BD06M01AE52
AHFS Codes
  • 56:28.36
PDB EntriesNot Available
FDA labelDownload (104 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Esomeprazole.
Alendronic acidThe therapeutic efficacy of Alendronate can be decreased when used in combination with Esomeprazole.
AmphetamineEsomeprazole can cause an increase in the absorption of Amphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Esomeprazole.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Esomeprazole.
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Esomeprazole.
CefditorenThe serum concentration of Cefditoren can be decreased when it is combined with Esomeprazole.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Esomeprazole.
CitalopramThe serum concentration of Citalopram can be increased when it is combined with Esomeprazole.
ClodronateThe therapeutic efficacy of Clodronate can be decreased when used in combination with Esomeprazole.
ClopidogrelEsomeprazole may decrease the antiplatelet activities of Clopidogrel.
CysteamineThe therapeutic efficacy of Cysteamine can be decreased when used in combination with Esomeprazole.
Dabigatran etexilateThe serum concentration of the active metabolites of Dabigatran etexilate can be reduced when Dabigatran etexilate is used in combination with Esomeprazole resulting in a loss in efficacy.
DabrafenibThe serum concentration of Esomeprazole can be decreased when it is combined with Dabrafenib.
DasatinibThe serum concentration of Dasatinib can be decreased when it is combined with Esomeprazole.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Esomeprazole.
DexmethylphenidateEsomeprazole can cause an increase in the absorption of Dexmethylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.
DextroamphetamineEsomeprazole can cause an increase in the absorption of Dextroamphetamine resulting in an increased serum concentration and potentially a worsening of adverse effects.
DicoumarolThe serum concentration of Dicoumarol can be increased when it is combined with Esomeprazole.
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Esomeprazole.
FluconazoleThe serum concentration of Esomeprazole can be increased when it is combined with Fluconazole.
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Esomeprazole.
IbandronateThe therapeutic efficacy of Ibandronate can be decreased when used in combination with Esomeprazole.
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Esomeprazole.
Iron DextranEsomeprazole can cause a decrease in the absorption of Iron Dextran resulting in a reduced serum concentration and potentially a decrease in efficacy.
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Esomeprazole.
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Esomeprazole.
LedipasvirThe serum concentration of Ledipasvir can be decreased when it is combined with Esomeprazole.
LumacaftorThe serum concentration of Esomeprazole can be decreased when it is combined with Lumacaftor.
MesalazineThe therapeutic efficacy of Mesalazine can be decreased when used in combination with Esomeprazole.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Esomeprazole.
MethylphenidateEsomeprazole can cause an increase in the absorption of Methylphenidate resulting in an increased serum concentration and potentially a worsening of adverse effects.
Mycophenolate mofetilThe serum concentration of Mycophenolate mofetil can be decreased when it is combined with Esomeprazole.
Mycophenolic acidThe serum concentration of Mycophenolic acid can be decreased when it is combined with Esomeprazole.
NelfinavirThe serum concentration of the active metabolites of Nelfinavir can be reduced when Nelfinavir is used in combination with Esomeprazole resulting in a loss in efficacy.
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Esomeprazole.
PamidronateThe therapeutic efficacy of Pamidronate can be decreased when used in combination with Esomeprazole.
PantoprazoleThe metabolism of Pantoprazole can be decreased when combined with Esomeprazole.
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Esomeprazole.
PhenytoinThe metabolism of Esomeprazole can be increased when combined with Phenytoin.
PosaconazoleThe serum concentration of Posaconazole can be decreased when it is combined with Esomeprazole.
RaltegravirThe serum concentration of Raltegravir can be increased when it is combined with Esomeprazole.
RifampicinThe serum concentration of Esomeprazole can be decreased when it is combined with Rifampicin.
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Esomeprazole.
RiociguatThe serum concentration of Riociguat can be decreased when it is combined with Esomeprazole.
RisedronateThe therapeutic efficacy of Risedronate can be decreased when used in combination with Esomeprazole.
SaquinavirThe serum concentration of Saquinavir can be increased when it is combined with Esomeprazole.
SofosbuvirThe serum concentration of Sofosbuvir can be decreased when it is combined with Esomeprazole.
St. John's WortThe serum concentration of Esomeprazole can be decreased when it is combined with St. John's Wort.
TacrolimusThe serum concentration of Tacrolimus can be increased when it is combined with Esomeprazole.
TiludronateThe therapeutic efficacy of Tiludronate can be decreased when used in combination with Esomeprazole.
TipranavirThe serum concentration of Esomeprazole can be decreased when it is combined with Tipranavir.
VoriconazoleThe serum concentration of Esomeprazole can be increased when it is combined with Voriconazole.
WarfarinThe serum concentration of Warfarin can be increased when it is combined with Esomeprazole.
Zoledronic acidThe therapeutic efficacy of Zoledronate can be decreased when used in combination with Esomeprazole.
Food Interactions
  • Take without regard to meals.

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
Molecular Weight:
114117.74 Da
References
  1. Saccar CL: The pharmacology of esomeprazole and its role in gastric acid related diseases. Expert Opin Drug Metab Toxicol. 2009 Sep;5(9):1113-24. doi: 10.1517/17425250903124363. [PubMed:19606942 ]
  2. McKeage K, Blick SK, Croxtall JD, Lyseng-Williamson KA, Keating GM: Esomeprazole: a review of its use in the management of gastric acid-related diseases in adults. Drugs. 2008;68(11):1571-607. [PubMed:18627213 ]
  3. Vachhani R, Olds G, Velanovich V: Esomeprazole: a proton pump inhibitor. Expert Rev Gastroenterol Hepatol. 2009 Feb;3(1):15-27. doi: 10.1586/17474124.3.1.15. [PubMed:19210109 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 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 ]
  2. Klotz U: Clinical impact of CYP2C19 polymorphism on the action of proton pump inhibitors: a review of a special problem. Int J Clin Pharmacol Ther. 2006 Jul;44(7):297-302. [PubMed:16961157 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on July 28, 2016 03:05