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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-10-16 12:33:19 UTC
Update Date2020-02-26 21:25:39 UTC
HMDB IDHMDB0005008
Secondary Accession Numbers
  • HMDB05008
Metabolite Identification
Common NameLansoprazole
DescriptionLansoprazole, also known as ogastro or prevacid, 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. Lansoprazole is a drug. It is available as a generic medication. Lansoprazole is a strong basic compound (based on its pKa). In humans, lansoprazole is involved in lansoprazole metabolism pathway. Since 2009, lansoprazole has been available over the counter (OTC) in the U.S. in a marketed by Novartis as Prevacid 24HR. It is taken by mouth. In the United States, it was approved for medical use in 1995. Side effects of PPIs in general and lansoprazole in particular may include:Common: diarrhea, abdominal painInfrequent: dry mouth, insomnia, drowsiness, blurred vision, rash, pruritusRarely and very rarely: taste disturbance, liver dysfunction, peripheral oedema, hypersensitivity reactions (including bronchospasm, urinary, angioedema, anaphylaxis), photosensitivity, fever, sweating, depression, interstitial nephritis, blood disorders (including leukopenia, leukocytosis, pancytopenia, thrombocytopenia), arthralgia, myalgia, skin reactions including (erythroderma Stevens–Johnson syndrome, toxic epidermal necrolysis, bullous eruption)PPIs may be associated with a greater risk of hip fractures and Clostridium difficile-associated diarrhea. Serious side effects may include osteoporosis, low blood magnesium, Clostridium difficile infection, and pneumonia.
Structure
Data?1582752339
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
2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl)methyl)sulfinyl)benzimidazoleHMDB
Lansoprazole hormona brandHMDB
Lansoprazole sodiumHMDB
Lansoprazole tecnobio brandHMDB
Lansoprazole wyeth brandHMDB
LansoprazolesHMDB
OgastHMDB
Pro ulcoHMDB
TakepronHMDB
Vinas brand OF lansoprazoleHMDB
Wyeth brand OF lansoprazoleHMDB
Almirall brand OF lansoprazoleHMDB
Lansoprazole abbot brandHMDB
Lansoprazole hoechst brandHMDB
Lansoprazole takeda brandHMDB
Salvar brand OF lansoprazoleHMDB
Sodium, lansoprazoleHMDB
Takeda brand OF lansoprazoleHMDB
Tecnobio brand OF lansoprazoleHMDB
Abbot brand OF lansoprazoleHMDB
Hoechst brand OF lansoprazoleHMDB
LansolHMDB
Lansoprazole lederle brandHMDB
Lansoprazole promeco brandHMDB
Lansoprazole vinas brandHMDB
Lederle brand OF lansoprazoleHMDB
PromecoHMDB
UlpaxHMDB
Hormona brand OF lansoprazoleHMDB
Lansoprazole almirall brandHMDB
Lansoprazole salvar brandHMDB
Lansoprazole tap brandHMDB
PrezalHMDB
Promeco brand OF lansoprazoleHMDB
TAP brand OF lansoprazoleHMDB
ZotonHMDB
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 KeyMJIHNNLFOKEZEW-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Alkyl aryl ether
  • Methylpyridine
  • Pyridine
  • Benzenoid
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Sulfoxide
  • Azacycle
  • Sulfinyl compound
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Alkyl halide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity87.61 m³·mol⁻¹ChemAxon
Polarizability34.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3692000000-7bae74d48caf51b77e10Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-502b719a981f262577baSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0uxr-0890000000-2734547f6dc584ba4877Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-053i-0930000000-94e6e179919ee803d567Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-0339000000-30ca3e1162573d0632ebSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-1676d647709a023eb1d8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-95a3126e9d69aa2812d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-0bb1e54ec8c7d6bb5746Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-52d969183040eb21720cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03di-0900000000-bba914a2bd85fb3b0823Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-02u0-0900000000-10a04626464fa2bcd6f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014i-2900000000-14157d06ad23e343435eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-02t9-8900000000-025e7246e314127a8422Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-03xr-9300000000-6a804721218ef90d3f61Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0290000000-a108432755e4f5916f6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0390000000-b8a59093f6b667fae5e4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fs9-0790000000-a2f5e86f6faaab508112Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00li-0940000000-cc60a0c246e3fc1399d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0pvr-0910000000-3c73fbb04b031d6b077dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-1900000000-731f4b8d7ac3ecfe924eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0179000000-5cfcc8f944fb98b8de94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0392000000-337f7fc96032201fb855Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pi0-3910000000-4c5108c4c3adf0b5f96dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0719000000-5e77bdceea9908f5d4ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-3ed397c90e44d64dd400Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3901000000-0a4de90a6a2e2069b266Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Liver
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00448
Phenol Explorer Compound IDNot Available
FooDB IDFDB023581
KNApSAcK IDNot Available
Chemspider ID3746
KEGG Compound IDC01594
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLansoprazole
METLIN ID919
PubChem Compound3883
PDB IDNot Available
ChEBI ID6375
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. [PubMed: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. [PubMed: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