| Identification | More | [Name]
Mosapride citrate | [CAS]
112885-42-4 | [Synonyms]
4-AMINO-5-CHLORO-2-ETHOXY-N-[[4-(4-FLUOROBENZYL)-2-MORPHOLINYL]METHYL]BENZAMIDE CITRATE DIHYDRATE
MOSAPRIDE CITRATE
MOSAPRIDE CITRATE DIHYDRATE
(+-)-4-amino-5-chloro-2-ethoxy-n-((4-(4-fluorobenzyl)-2-morpholinyl)methyl)b
as4370
benzamide,4-amino-5-chloro-2-ethoxy-n-((4-((4-fluorophenyl)methyl)-2-morpholin
enzamidecitrate
yl)methyl)-,2-hydroxy-1,2,3-propanetricarboxylate(1:1)
4-Amino-5-chloro-2-ethoxy-N-[[4-[(4-fluorophenyl)methyl]-2-morpholinyl]methyl]-benzamide 2-hydroxy-1,2,3-propanetricarboxylate
Gasmotin | [EINECS(EC#)]
601-211-6 | [Molecular Formula]
C27H37ClFN3O12 | [MDL Number]
MFCD00874415 | [Molecular Weight]
650.05 | [MOL File]
112885-42-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
143-145° | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO (Slightly), Ethanol (Slightly, Sonicated) | [form ]
Solid | [color ]
White to Off-White | [Stability:]
Hygroscopic | [InChIKey]
HUZTYZBFZKRPFG-UHFFFAOYSA-N | [SMILES]
C(O)(C(=O)O)(CC(=O)O)CC(=O)O.C(C1C=C(Cl)C(N)=CC=1OCC)(=O)NCC1OCCN(CC2C=CC(F)=CC=2)C1 | [CAS DataBase Reference]
112885-42-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Mosapride is an agonist of the serotonin (5-HT) receptor subtype 5-HT4 (Ki = 69.9 nM).1,2 It is selective for 5-HT4 over 5-HT1, 5-HT2, dopamine D2, and α1- and α2-adrenergic receptors but acts as a partial antagonist at 5-HT3 (Ki = 1,189 nM).1,2 It induces relaxation of precontracted rat esophageal thoracic muscularis mucosa preparations and enhances electrically evoked contractions in isolated guinea pig ileum (EC50s = 208.4 and 73.2 nM, respectively).3 Mosapride (0.5 and 1 mg/kg, i.v.) increases antral and duodenal, but not ileal or colonic, motility in conscious dogs.1 It also increases gastric emptying in rats when administered at doses ranging from 0.03 to 30 mg/kg. | [Uses]
A selective SR-4 activator and a SR-3 inhibitor | [Uses]
As a selective SR-4 activator and a SR-3 inhibitor, Mosapride(Mosapride citrate) is a gastroprokinetic agent that acts as a selective 5HT4 agonist which accelerates gastric emptying and is used for the treatment of acid reflux, irritable bowel syndrome and functional dyspepsia.
| [Biological Activity]
5-HT 4 receptor agonist and 5-HT 3 receptor antagonist. Displays no activity at D 2 , α 1 , α 2 , 5-HT 1 and 5-HT 2 receptors. Gastroprokinetic agent; increases gastric emptying in rats and stimulates gastric motor actvity in conscious dogs. | [Synthesis]
GENERAL STEPS: To a suspension of 1.3 g (2.5 mmol) of 4-amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)morpholin-2-yl)methyl)benzamide (Compound VIII) and 3 mL of water was added 12 mL of 117% aqueous hydrochloric acid. The resulting solution was stirred at 40°C for 3 hours, cooled to 10°C and 38 mL of 4M aqueous sodium hydroxide solution was added dropwise. The precipitated mosapride base (Compound IX) was filtered and washed twice with water to give 1.05 g (100%) of Compound IX.1.01 g of the above obtained Compound IX was warmed to boiling with 25 mL of 10% aqueous citric acid solution with stirring, cooled to 0°C, the precipitated product was filtered, and washed twice with water to give 1.34 g (86%) of 4-amino-5-chloro-2-ethanol oxy-N-((4-(4-fluorobenzyl)morpholin-2-yl)methyl)benzamide 2-hydroxypropane-1,2,3-tricarboxylate. Melting point: 110-113°C. | [storage]
room temperature (desiccate) | [References]
[1] Patent: WO2003/106440, 2003, A2. Location in patent: Page 10 |
| Safety Data | Back Directory | [Toxicity]
LD50 in male, female mice, rats (mg/kg): >3000, >3000, >3000, 1905 orally; >1000, 914, >1000, >1000 i.p.; all species >1000 s.c.; in male, female dogs (mg/kg): both >400 orally (Yatera) |
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