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Record Information
Version3.6
Creation Date2006-05-17 14:44:52 UTC
Update Date2016-02-11 01:05:05 UTC
HMDB IDHMDB01913
Secondary Accession NumbersNone
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
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 KeyInChIKey=SUBDBMMJDZJVOS-UHFFFAOYSA-N
Chemical 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
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
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 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Omeprazole Metabolism PathwaySMP00613Not Available
Omeprazole PathwaySMP00226Not Available
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
NuGOwiki LinkHMDB01913
Metagene LinkHMDB01913
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