Mosapride citrate (CHEM018829)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:34:10 UTC
Update Date2016-11-09 01:15:52 UTC
Accession NumberCHEM018829
Identification
Common NameMosapride citrate
ClassSmall Molecule
DescriptionMosapride is a gastroprokinetic agent that acts as a selective 5HT4 agonist. The major active metabolite of mosapride, known as M1, additionally acts as a 5HT3 antagonist, which accelerates gastric emptying throughout the whole of the gastrointestinal tract in humans, and is used for the treatment of gastritis, gastroesophageal reflux disease, functional dyspepsia and irritable bowel syndrome. It is recommended to be taken on an empty stomach (i.e. at least one hour before food or two hours after food).In addition to its prokinetic properties, mosapride also exerts anti-inflammatory effects on the gastrointestinal tract which may contribute to some of its therapeutic effects. Mosapride also promotes neurogenesis in the gastrointestinal tract which may prove useful in certain bowel disorders. The neurogenesis is due to mosapride's effect on the 5-HT4 receptor where it acts as an agonist.Its common side effects include dry mouth, abdominal pain, dizziness, headache, insomnia, malaise, nausea, diarrhea and sometimes constipation. Unlike some other prokinetic agents, mosapride has little effect on potassium channels, no effect on hERG transfected cells, and no effect on cardiovascular function that could be detected in tests on humans. Due to the pharmacokinetics of mosapride, it would take 1,000–3,000 times the therapeutic dose to elicit cardiovascular effects.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Mosapride citric acidGenerator
MosaprideMeSH
Mosapride ui05MSP015CTMeSH
4-Amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)-2-morpholinyl)methyl)benzamideMeSH
Mosapride citrateMeSH
2-Hydroxypropane-1,2,3-tricarboxylate
4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzene-1-carboximidate
2-Hydroxypropane-1,2,3-tricarboxylate; 4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzene-1-carboximidateGenerator
Chemical FormulaC27H33ClFN3O10
Average Molecular Mass614.020 g/mol
Monoisotopic Mass613.184 g/mol
CAS Registry Number112885-42-4
IUPAC Name2-hydroxypropane-1,2,3-tricarboxylic acid; 4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzene-1-carboximidic acid
Traditional Namecitric acid; mosapride
SMILESOC(=O)CC(O)(CC(O)=O)C(O)=O.CCOC1=C(C=C(Cl)C(N)=C1)C(O)=NCC1CN(CC2=CC=C(F)C=C2)CCO1
InChI IdentifierInChI=1S/C21H25ClFN3O3.C6H8O7/c1-2-28-20-10-19(24)18(22)9-17(20)21(27)25-11-16-13-26(7-8-29-16)12-14-3-5-15(23)6-4-14;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-6,9-10,16H,2,7-8,11-13,24H2,1H3,(H,25,27);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChI KeyHUZTYZBFZKRPFG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Aminophenyl ether
  • Tricarboxylic acid or derivatives
  • Phenoxy compound
  • Phenol ether
  • Phenylmethylamine
  • Benzylamine
  • Aniline or substituted anilines
  • Alkyl aryl ether
  • Halobenzene
  • Fluorobenzene
  • Aralkylamine
  • Chlorobenzene
  • Morpholine
  • Oxazinane
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Aryl halide
  • Benzenoid
  • Aryl fluoride
  • Hydroxy acid
  • Aryl chloride
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Azacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Dialkyl ether
  • Ether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organohalogen compound
  • Organochloride
  • Organofluoride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP3.04ALOGPS
logP3.46ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)7.9ChemAxon
pKa (Strongest Basic)6.06ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.31 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity112.86 m³·mol⁻¹ChemAxon
Polarizability43.82 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dj-1920400000-661fa2874767aad68d12Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00dj-2910000000-0cf829215035f4f15409Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-4fae3fa34ad0cb8b7224Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-4fae3fa34ad0cb8b7224Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0000009000-4fae3fa34ad0cb8b7224Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000009000-e750f76dc7ef3027218fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000009000-e750f76dc7ef3027218fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0000009000-e750f76dc7ef3027218fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT002047
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMosapride
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID119583
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available