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Record Information
Version3.6
Creation Date2006-10-16 12:33:19 UTC
Update Date2016-02-11 01:07:01 UTC
HMDB IDHMDB05008
Secondary Accession NumbersNone
Metabolite Identification
Common NameLansoprazole
DescriptionLansoprazole is a proton pump inhibitor similar to omeprazole which prevents the stomach from producing acid. Lansoprazole's plasma elimination half-life is not proportional to the duration of the drug's effects (i.e. gastric acid suppression). The plasma elimination half-life is 1.5 hours or less, and the effects of the drug last for over 24 hours after it has been given for 5 days or more.
Structure
Thumb
Synonyms
ValueSource
AG 1749ChEBI
BamaliteChEBI
LansoprazolChEBI
LansoprazolumChEBI
LanzolChEBI
LanzopralChEBI
LanzulChEBI
LimpidexChEBI
MonolitumChEBI
OgastroChEBI
OpirenChEBI
PrevacidChEBI
AgoptonHMDB
AmarinHMDB
AprazolHMDB
BlasonHMDB
KetianHMDB
LancidHMDB
LanfastHMDB
LanprotonHMDB
LansopepHMDB
LansophedHMDB
LansoxHMDB
LanstonHMDB
LanzHMDB
LanzoHMDB
LanzorHMDB
LaprazHMDB
LasoprolHMDB
LinamarinHMDB
MesactolHMDB
Chemical FormulaC16H14F3N3O2S
Average Molecular Weight369.361
Monoisotopic Molecular Weight369.075882012
IUPAC Name2-{[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
Traditional Namelansoprazole
CAS Registry Number103577-45-3
SMILES
CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1
InChI Identifier
InChI=1S/C16H14F3N3O2S/c1-10-13(20-7-6-14(10)24-9-16(17,18)19)8-25(23)15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)
InChI KeyInChIKey=MJIHNNLFOKEZEW-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
  • Methylpyridine
  • Alkyl aryl ether
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Sulfoxide
  • Azacycle
  • Sulfinyl compound
  • Ether
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178 - 182 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.25 mg/mLALOGPS
logP2.84ALOGPS
logP3.03ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)4.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.87 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.61 m3·mol-1ChemAxon
Polarizability34.59 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-502b719a981f262577baView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uxr-0890000000-2734547f6dc584ba4877View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053i-0930000000-94e6e179919ee803d567View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Liver
Pathways
NameSMPDB LinkKEGG Link
Lansoprazole Metabolism PathwaySMP00614Not Available
Lansoprazole PathwaySMP00227Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
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 IDFDB023581
KNApSAcK IDNot Available
Chemspider ID3746
KEGG Compound IDC01594
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLansoprazole
NuGOwiki LinkHMDB05008
Metagene LinkHMDB05008
METLIN ID919
PubChem Compound3883
PDB IDNot Available
ChEBI ID6375
References
Synthesis ReferenceNohara, Akira; Maki, Yoshitaka. (Pyridylmethylthio)benzimidazoles and their sulfoxides. Eur. Pat. Appl. (1986), 23 pp. CODEN: EPXXDW EP 174726 A1 19860319 CAN 105:133883 AN 1986:533883
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Katsuki H, Hamada A, Nakamura C, Arimori K, Nakano M: High-performance liquid chromatographic assay for the simultaneous determination of lansoprazole enantiomers and metabolites in human liver microsomes. J Chromatogr B Biomed Sci Appl. 2001 Jun 5;757(1):127-33. [11419737 ]
  2. Katsuki H, Hamada A, Nakamura C, Arimori K, Nakano M: Role of CYP3A4 and CYP2C19 in the stereoselective metabolism of lansoprazole by human liver microsomes. Eur J Clin Pharmacol. 2001 Dec;57(10):709-15. [11829200 ]

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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
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