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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-16 12:33:19 UTC
Update Date2022-03-07 02:49:25 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. In humans, lansoprazole is involved in the lansoprazole metabolism pathway. Lansoprazole is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Lansoprazole.
Structure
Data?1582752339
Synonyms
ValueSource
AG 1749ChEBI
BamaliteChEBI
LansoprazolChEBI
LansoprazolumChEBI
LanzolChEBI
LanzopralChEBI
LanzulChEBI
LimpidexChEBI
MonolitumChEBI
OgastroChEBI
OpirenChEBI
PrevacidChEBI
PrezalMeSH
UlpaxMeSH
LansolMeSH
Lansoprazole sodiumMeSH
Pro ulcoMeSH
PromecoMeSH
ZotonMeSH
AgoptonMeSH
OgastMeSH
TakepronMeSH
2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl)methyl)sulfinyl)benzimidazoleMeSH
LansoprazolesMeSH
LanzorMeSH
Sodium, lansoprazoleMeSH
AmarinHMDB
AprazolHMDB
BlasonHMDB
KetianHMDB
LancidHMDB
LanfastHMDB
LanprotonHMDB
LansopepHMDB
LansophedHMDB
LansoxHMDB
LanstonHMDB
LanzHMDB
LanzoHMDB
LaprazHMDB
LasoprolHMDB
LinamarinHMDB
MesactolHMDB
Lansoprazole hormona brandMeSH, HMDB
Lansoprazole tecnobio brandMeSH, HMDB
Lansoprazole wyeth brandMeSH, HMDB
Vinas brand OF lansoprazoleMeSH, HMDB
Wyeth brand OF lansoprazoleMeSH, HMDB
Almirall brand OF lansoprazoleMeSH, HMDB
Lansoprazole abbot brandMeSH, HMDB
Lansoprazole hoechst brandMeSH, HMDB
Lansoprazole takeda brandMeSH, HMDB
Salvar brand OF lansoprazoleMeSH, HMDB
Takeda brand OF lansoprazoleMeSH, HMDB
tecnobio Brand OF lansoprazoleMeSH, HMDB
Abbot brand OF lansoprazoleMeSH, HMDB
Hoechst brand OF lansoprazoleMeSH, HMDB
Lansoprazole lederle brandMeSH, HMDB
Lansoprazole promeco brandMeSH, HMDB
Lansoprazole vinas brandMeSH, HMDB
Lederle brand OF lansoprazoleMeSH, HMDB
Hormona brand OF lansoprazoleMeSH, HMDB
Lansoprazole almirall brandMeSH, HMDB
Lansoprazole salvar brandMeSH, HMDB
Lansoprazole tap brandMeSH, HMDB
promeco Brand OF lansoprazoleMeSH, HMDB
TAP brand OF lansoprazoleMeSH, HMDB
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 - 182 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available185.83http://allccs.zhulab.cn/database/detail?ID=AllCCS00001059
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+175.93430932474
DeepCCS[M-H]-173.57630932474
DeepCCS[M-2H]-206.46230932474
DeepCCS[M+Na]+182.02830932474
AllCCS[M+H]+181.632859911
AllCCS[M+H-H2O]+178.732859911
AllCCS[M+NH4]+184.332859911
AllCCS[M+Na]+185.132859911
AllCCS[M-H]-177.732859911
AllCCS[M+Na-2H]-177.032859911
AllCCS[M+HCOO]-176.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LansoprazoleCC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N13255.2Standard polar33892256
LansoprazoleCC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N12575.7Standard non polar33892256
LansoprazoleCC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N12781.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lansoprazole,1TMS,isomer #1CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1[Si](C)(C)C2611.9Semi standard non polar33892256
Lansoprazole,1TMS,isomer #1CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1[Si](C)(C)C2611.2Standard non polar33892256
Lansoprazole,1TMS,isomer #1CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1[Si](C)(C)C3025.0Standard polar33892256
Lansoprazole,1TBDMS,isomer #1CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1[Si](C)(C)C(C)(C)C2781.4Semi standard non polar33892256
Lansoprazole,1TBDMS,isomer #1CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1[Si](C)(C)C(C)(C)C2815.1Standard non polar33892256
Lansoprazole,1TBDMS,isomer #1CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC=CC=C2N1[Si](C)(C)C(C)(C)C3094.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lansoprazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3692000000-7bae74d48caf51b77e102017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lansoprazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lansoprazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lansoprazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-0090000000-502b719a981f262577ba2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0uxr-0890000000-2734547f6dc584ba48772012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-053i-0930000000-94e6e179919ee803d5672012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-qTof , Positive-QTOFsplash10-0006-0339000000-30ca3e1162573d0632eb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-03di-0900000000-1676d647709a023eb1d82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-03di-0900000000-95a3126e9d69aa2812d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-03di-0900000000-0bb1e54ec8c7d6bb57462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-03di-0900000000-52d969183040eb21720c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-03di-0900000000-bba914a2bd85fb3b08232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-02u0-0900000000-10a04626464fa2bcd6f92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-014i-2900000000-14157d06ad23e343435e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-02t9-8900000000-025e7246e314127a84222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , negative-QTOFsplash10-03xr-9300000000-6a804721218ef90d3f612017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , positive-QTOFsplash10-0udi-0290000000-a108432755e4f5916f6e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , positive-QTOFsplash10-0udi-0390000000-b8a59093f6b667fae5e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , positive-QTOFsplash10-0fs9-0790000000-a2f5e86f6faaab5081122017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , positive-QTOFsplash10-00li-0940000000-cc60a0c246e3fc1399d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , positive-QTOFsplash10-0pvr-0910000000-3c73fbb04b031d6b077d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Lansoprazole LC-ESI-QFT , positive-QTOFsplash10-0a4i-1900000000-731f4b8d7ac3ecfe924e2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansoprazole 10V, Positive-QTOFsplash10-0fk9-0179000000-5cfcc8f944fb98b8de942017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansoprazole 20V, Positive-QTOFsplash10-0udi-0392000000-337f7fc96032201fb8552017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansoprazole 40V, Positive-QTOFsplash10-0pi0-3910000000-4c5108c4c3adf0b5f96d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansoprazole 10V, Negative-QTOFsplash10-014i-0719000000-5e77bdceea9908f5d4ec2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansoprazole 20V, Negative-QTOFsplash10-014i-0900000000-3ed397c90e44d64dd4002017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansoprazole 40V, Negative-QTOFsplash10-014i-3901000000-0a4de90a6a2e2069b2662017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLansoprazole
METLIN IDNot Available
PubChem Compound3883
PDB IDNot Available
ChEBI ID6375
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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