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Record Information
Version4.0
Creation Date2006-05-17 14:44:52 UTC
Update Date2017-09-27 08:24:09 UTC
HMDB IDHMDB0001913
Secondary Accession Numbers
  • HMDB01913
Metabolite Identification
Common NameOmeprazole
DescriptionOmeprazole is a highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers, dyspepsia, peptic ulcer disease , gastroesophageal reflux disease and Zollinger-Ellison syndrome. The drug inhibits the H(+)-K(+)-ATPase (H(+)-K(+)-exchanging ATPase) in the proton pump of Gastric Parietal Cells.--Pubchem. Omeprazole is one of the most widely prescribed drugs internationally and is available over the counter in some countries.
Structure
Thumb
Synonyms
ValueSource
PrilosecKegg
( -)-OmeprazoleHMDB
(-)-OmeprazoleHMDB
(S)-(-)-OmeprazoleHMDB
(S)-OmeprazoleHMDB
2,3,5-Trimethylpyridine/OmeprazoleHMDB
AntraHMDB
Antra mupsHMDB
AudazolHMDB
AulcerHMDB
BelmazolHMDB
CeprandalHMDB
DanloxHMDB
DemeprazolHMDB
DesecHMDB
DizprazolHMDB
DudencerHMDB
ElgamHMDB
EmeprotonHMDB
EpirazoleHMDB
ErbolinHMDB
EsomeprazoleHMDB
EsomperazoleHMDB
ExterHMDB
GasecHMDB
GastrimutHMDB
GastrolocHMDB
GibancerHMDB
IndurganHMDB
InhibitronHMDB
InhipumpHMDB
LensorHMDB
LogastricHMDB
LomacHMDB
LosecHMDB
MepralHMDB
MiolHMDB
MiracidHMDB
MopralHMDB
MoreconHMDB
NexiamHMDB
NexiumHMDB
Nexium IVHMDB
NilsecHMDB
NopraminHMDB
NuclosinaHMDB
OcidHMDB
OlexinHMDB
OmaprenHMDB
Omebeta 20HMDB
OmedHMDB
OmegastHMDB
OMEPHMDB
OmepradexHMDB
OmepralHMDB
OmeprazolHMDB
Omeprazole pelletsHMDB
OmeprazolumHMDB
OmeprazonHMDB
OmeprolHMDB
OmesekHMDB
OmezHMDB
OmezolHMDB
OmezolanHMDB
OmidHMDB
OmisecHMDB
OmizacHMDB
OmpanytHMDB
OMZHMDB
OrtanolHMDB
OsirenHMDB
OzokenHMDB
PaprazolHMDB
ParizacHMDB
PepticumHMDB
PepticusHMDB
PeptilcerHMDB
PrazentolHMDB
PrazidecHMDB
PrazolitHMDB
Prestwick_808HMDB
Prilosec otcHMDB
ProcelacHMDB
ProclorHMDB
PrysmaHMDB
RamezolHMDB
RegulacidHMDB
ResultHMDB
SanamidolHMDB
SecrepinaHMDB
Tedec ulceralHMDB
UlceralHMDB
UlcesepHMDB
UlcometionHMDB
UlcozolHMDB
UlcsepHMDB
UlsenHMDB
UltopHMDB
UlzolHMDB
VictrixHMDB
ZefxonHMDB
ZegeridHMDB
ZepralHMDB
ZimorHMDB
ZoltumHMDB
Magnesium, omeprazoleMeSH
Omeprazole magnesiumMeSH
Omeprazole sodiumMeSH
Sodium, omeprazoleMeSH
Chemical FormulaC17H19N3O3S
Average Molecular Weight345.416
Monoisotopic Molecular Weight345.114712179
IUPAC Name6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
Traditional Nameomeprazole
CAS Registry Number73590-58-6
SMILES
COC1=CC2=C(C=C1)N=C(N2)S(=O)CC1=NC=C(C)C(OC)=C1C
InChI Identifier
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)
InChI KeySUBDBMMJDZJVOS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzimidazoles
Direct ParentSulfinylbenzimidazoles
Alternative Parents
Substituents
  • Sulfinylbenzimidazole
  • Anisole
  • Alkyl aryl ether
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Sulfoxide
  • Azacycle
  • Ether
  • Sulfinyl compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Enteral:

  Parenteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    Nervous system disorders:

    Psychiatric disorders:

    Eye disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point156 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.5 mg/mLNot Available
LogP2.23SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.66 m³·mol⁻¹ChemAxon
Polarizability37.45 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udj-0902000000-cfa5184c794ea62ab995View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-1669000000-51f9342d7e4bbd0356b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-002f-0900000000-412912cbbcdbd1b34699View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0901000000-189e81fb724041d50498View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f6t-0900000000-db101d248a4e861d4c3bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0uds-0900000000-f579fb74ac97c56dd3ebView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-eefbf9686f0313da581eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-363d6954875894f433baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f6t-1900000000-d8c64d496f1d9b3ed465View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-1669000000-51f9342d7e4bbd0356b2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f6t-0900000000-d21755acc44ff2d29cfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0f80-2900000000-9989d19c171c612ea3dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-f74adb7f41e2d390b602View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0509000000-a35086072388d122723eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0902000000-cf6c80499c6b8e76c5d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ul9-3900000000-2356754b2ae17bd3bc19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0709000000-1b29375937cfcb406414View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0900000000-3383df9e4bfd7979d5e5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0900000000-4fb7ec8321857498646dView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Omeprazole Metabolism PathwayPw000589Pw000589 greyscalePw000589 simpleNot Available
Omeprazole PathwayPw000316Pw000316 greyscalePw000316 simpleNot Available
Displaying all 2 entries
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.34 (0.014-7.24) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB021863
KNApSAcK IDNot Available
Chemspider ID4433
KEGG Compound IDC07324
BioCyc IDNot Available
BiGG ID2299956
Wikipedia LinkOmeprazole
METLIN ID1632
PubChem Compound4594
PDB IDNot Available
ChEBI ID7772
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase 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 xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase 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:
55944.565
General function:
Involved in ATP binding
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
General function:
Involved in monooxygenase 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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915