Basic information
- CAS
112885-41-3- Standard SMILES
CCOc1cc(N)c(Cl)cc1C(=O)NCC1CN(Cc2ccc(F)cc2)CCO1- InChIKey
YPELFRMCRYSPKZ-UHFFFAOYSA-N- Molecular formula
- C21H25ClFN3O3
- Average molar mass
- 421.9 g/mol
- Monoisotopic mass
- 421.15684756
Overview
Mosapride is a racemate comprising equimolar amounts of (R)- and (S)-mosapride. It is a gastroprokinetic agent which acts on 5-hydroxytryptamine type 4 (5-HT4) receptors in the gastrointestinal plexus, consequently increasing the release of acetylcholine and hence enhancing gastrointestinal motility and gastric emptying. It has a role as a serotonergic agonist and a gastrointestinal drug. It contains a (R)-mosapride and a (S)-mosapride.
Names & identifiers
- Preferred name
- Mosapride
- IUPAC
- 4-amino-5-chloro-2-ethoxy-N-[[4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl]benzamide
- English name
- Mosapride
- Molecular formula
- C21H25ClFN3O3
- Molecular weight
- 421.89
Names & synonyms
Mosapride112885-41-34-amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)-2-morpholinyl)methyl)benzamideMosart4-amino-5-chloro-2-ethoxy-N-[[4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl]benzamidemosapridaI8MFJ1C0BY4-amino-5-chloro-2-ethoxy-N-({4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl)benzamideDTXSID2048408CHEBI:94373CHEBI:167204mosapridum
Show more names
MozaMosapidTAK-370Mosid-MTMoxabiliMosapride referenceMosapride USP/EP/BPMosapride, 10 mM in DMSO((4-(4-fluorobenzyl)-2-morpholinyl)methyl)benzamide/mosapride
4-amino-5-chloro-2-ethoxy-N-((4-((4-fluorophenyl)methyl)morpholin-2-yl)methyl)benzamide4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamideRefChem:159818DTXCID4028381A03FA09Benzamide, 4-amino-5-chloro-2-ethoxy-N-((4-((4-fluorophenyl)methyl)-2-morpholinyl)methyl)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)Mosapride [INN]C21H25ClFN3O3
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 76.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 521
Experimental & physicochemical properties
DrugsPharmaceuticals -> Alimentary tract and metabolism -> Drugs for acid related disorders
Collision Cross Section195.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID7046207]
Physicochemical properties
- Melting point
- 151 · 151-153°C
- Boiling point
- 549.2 · 549.2±50.0 °C(Predicted)
- Density
- 1.272 · 1.272±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 13.52 · 13.52±0.46(Predicted)
- color
- White to Off-White
- CAS DataBase Reference
- 112885 · 112885-41-3(CAS DataBase Reference)
- FDA UNII
- 8 MFJ1C0BY · I8MFJ1C0BY
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
Mosapride
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
MeSH Pharmacological Classification
Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion.
Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Applications
DescriptionMosapride citrate, a new gastroprokinetic benzamide was introduced in Japan as Gasmotin for the relief of gastrointestinal symptoms in patients with chronic gastritis, gastro-oesophageal reflux, dyspepsia and post-surgery use. Mosapride is synthesized by final amidation between the corresponding benzoic acid, itself obtained in 3 steps from methyl 4-acetamido salicylate, and the appropriate 2-aminomethyl-morpholine. Mosapride is a 5-HT4 partial agonist without notable activity for D2, 5-HT1 , 5-HT2, alpha-1 and alpha-2 receptors. In dogs, mosapride was as potent as cisapride to stimulate antral and duodenal motility. In most of species including man, mosapride undergoes extensive cleavage to a N-debenzylated metabolite which retains partial 5-HT4 activity but has potent 5-HT3 antagonist activity.
UsesA selective 5-HT4 receptor agonist. Gastroprokinetic.
Usesgastroprokinetic agent
Upstream & downstream products
Upstream raw materials
Related reactions
8 records
Compound notes
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