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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-16 23:01:43 UTC
Update Date2019-07-23 14:38:50 UTC
HMDB IDHMDB0240216
Secondary Accession NumbersNone
Metabolite Identification
Common NameLafutidine
DescriptionLafutidine, also known as protecadin, belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group. It also activates calcitonin gene-related peptide, resulting in the stimulation of nitric oxide (NO) and regulation of gastric mucosal blood flow, increases somatostatin levels also resulting in less gastric acid secretion, causes the stomach lining to generate more mucin, inhibits neutrophil activation thus preventing injury from inflammation, and blocks the attachment of Helicobacter pylori to gastric cells. Lafutidine is a very strong basic compound (based on its pKa). In humans, lafutidine is involved in lafutidine h2-antihistamine action. It is marketed in Japan and India. Like other H2 receptor antagonists, lafutidine acts by preventing the secretion of gastric acid. Lafutidine (INN) is a second generation histamine H2 receptor antagonist having multimodal mechanism of action and used to treat gastrointestinal disorders. It is marketed in Japan as Stogar by UCB and in India as Lafaxid by Zuventus Healthcare. Lafutidine is used to treat gastric ulcers, duodenal ulcers, as well as wounds in the lining of the stomach associated with acute gastritis and acute exacerbation of chronic gastritis. Adverse events observed during clinical trials included constipation, diarrhea, drug rash, nausea, vomiting and dizziness.
Structure
Data?1563892730
Synonyms
ValueSource
ProtecadinKegg
(+)-2-[(2-Furanylmethyl)sulfinyl]-N-[(2Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl]-acetamideHMDB
(Z)-(+)-2-[(2-Furanylmethyl)sulfinyl]-N-[4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl]-acetamideHMDB
(+)-2-[(2-Furanylmethyl)sulfinyl]-N-[(2Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-yl]acetamideHMDB
(+)-2-(Furfurylsulfinyl)-N-[(Z)-4-[[4-(piperidinomethyl)-2-pyridyl]oxy]-2-butenyl]acetamideHMDB
(+)-LafutidineHMDB
FRG 8813HMDB
LaflutidineHMDB
LafukemHMDB
StogarHMDB
LafutidineHMDB, MeSH
2-(Furan-2-ylmethylsulphinyl)-N-[(Z)-4-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxybut-2-enyl]acetamideGenerator, HMDB
N-(4-(4-Piperidinylmethyl)pyridyl-2-oxy)-(Z)-butenyl-2-(furfurylsulfinyl)acetamideMeSH, HMDB
N-(4-(4-Piperidinylmethyl)pyridyl-2-oxy)butenyl-2-(furfurylsulfinyl)acetamideMeSH, HMDB
Chemical FormulaC22H29N3O4S
Average Molecular Weight431.55
Monoisotopic Molecular Weight431.1878776
IUPAC Name2-[(furan-2-yl)methanesulfinyl]-N-[(2Z)-4-({4-[(piperidin-1-yl)methyl]pyridin-2-yl}oxy)but-2-en-1-yl]acetamide
Traditional Namelafutidine
CAS Registry Number118288-08-7
SMILES
O=C(CS(=O)CC1=CC=CO1)NC\C=C/COC1=NC=CC(CN2CCCCC2)=C1
InChI Identifier
InChI=1S/C22H29N3O4S/c26-21(18-30(27)17-20-7-6-14-28-20)23-9-2-5-13-29-22-15-19(8-10-24-22)16-25-11-3-1-4-12-25/h2,5-8,10,14-15H,1,3-4,9,11-13,16-18H2,(H,23,26)/b5-2-
InChI KeyKMZQAVXSMUKBPD-DJWKRKHSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentAlkyl aryl ethers
Alternative Parents
Substituents
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Pyridine
  • Furan
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Sulfoxide
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfinyl compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organosulfur compound
  • Amine
  • Organopnictogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.59ALOGPS
logP0.86ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)8.87ChemAxon
pKa (Strongest Basic)7.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area84.67 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity120.24 m³·mol⁻¹ChemAxon
Polarizability45.27 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0319500000-21e5d3163103c305767bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uec-0629700000-2cad78fc15f4386b3645Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0319500000-21e5d3163103c305767bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-1676900000-3adc00bef17a159fb17eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-2971000000-7ee0ab341e67b0ccb95dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-4930000000-1265ca526856cae249ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1930700000-aec8e386acbf098257aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0059-2920100000-149ac7afce52861c0b08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0016-6900000000-695b1fd2b230388122f4Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12770
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLafutidine
METLIN IDNot Available
PubChem Compound5282136
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shimatani T, Inoue M, Kuroiwa T, Xu J, Nakamura M, Tazuma S, Ikawa K, Morikawa N: Lafutidine, a newly developed antiulcer drug, elevates postprandial intragastric pH and increases plasma calcitonin gene-related peptide and somatostatin concentrations in humans: comparisons with famotidine. Dig Dis Sci. 2006 Jan;51(1):114-20. [PubMed:16416222 ]