Norcisapride, (+)-
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Basic information
- CAS
202590-69-0- Standard SMILES
COc1cc(N)c(Cl)cc1C(=O)N[C@@H]1CCNC[C@@H]1OC- InChIKey
OMLDMGPCWMBPAN-YPMHNXCESA-N- Molecular formula
- C14H20ClN3O3
- Average molar mass
- 313.78 g/mol
- Monoisotopic mass
- 313.1193192
Names & identifiers
- Preferred name
- Norcisapride, (+)-
- IUPAC
- 4-amino-5-chloro-2-methoxy-N-[(3S,4R)-3-methoxypiperidin-4-yl]benzamide
- English name
- CIS-4-AMINO-5-CHLORO-2-METHOXY-N-(3-METHOXY-PIPERIDIN-4-YL)-BENZAMIDE
- Molecular formula
- C14H20ClN3O3
- Molecular weight
- 313.78
Names & synonyms
Ticalopride202590-69-0(+)-NorcisaprideTicalopride [INN]4-amino-5-chloro-2-methoxy-n-[(3s,4r)-3-methoxypiperidin-4-yl]benzamideTicalopridaNaronapride metabolite m4QNG273A81ONORCISAPRIDE, (+)-4-amino-5-chloro-2-methoxy-N-((3S,4R)-3-methoxypiperidin-4-yl)benzamideBenzamide, 4-amino-5-chloro-2-methoxy-N-[(3S,4R)-3-methoxy-4-piperidinyl]-4-AMINO-5-CHLORO-2-METHOXY-N-((3S,4R)-3-METHOXY-4-PIPERIDINYL)BENZAMIDE
Show more names
Unii-qng273A81o
BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-((3S,4R)-3-METHOXY-4-PIPERIDINYL)-BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-(3-METHOXY-4-PIPERIDINYL)-, CIS-(+)-ticalopridumRefChem:854710Norcisapride83863-69-8CIS-4-AMINO-5-CHLORO-2-METHOXY-N-(3-METHOXY-PIPERIDIN-4-YL)-BENZAMIDEU221XI117N
Database identifiers
- CAS
202590-69-0、83863-69-8- PubChem CID
- 216236
- DTXSID
DTXSID501351857- ChEMBL
CHEMBL1748、CHEMBL2107465- UNII
- QNG273A81O、U221XI117N
- EC Number
- 281-134-9
- Nikkaji
- J324.227G
Properties
Computed structural propertiesFilling in
- XLogP
- 0.8
- Topological polar surface area
- 85.6 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 4
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 358
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 461.014 · 461.014±45.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.295 · 1.295±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- pka
- 13.039 · 13.039±0.40(predicted)
- FDA UNII
- 273 A81O · QNG273A81O
Chemistry & industry
Pharmacology
Mechanism of Action
Ticalopride is an isomer of the active metabolite of cisapride. Cisapride acts through the stimulation of the serotonin 5-HT4 receptors which increases acetylcholine release in the enteric nervous system (specifically the myenteric plexus). This results in increased tone and amplitude of gastric (especially antral) contractions, relaxation of the pyloric sphincter and the duodenal bulb, and increased peristalsis of the duodenum and jejunum resulting in accelerated gastric emptying and intestinal transit.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Applications
Uses(+)-Norcisapride (Ticalopride) is a potent 5-HT4 agonist and a 5-HT3 antagonist. (+)-Norcisapride has activity in animals models of constipation[1].
Related reactions
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Compound notes
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