Cisapride Impurity 3
Basic information
- CAS
104860-66-4- Standard SMILES
COc1cc(N)c(Cl)cc1C(=O)N[C@@H]1CCN(CCCOc2ccc(F)cc2)C[C@H]1OC- InChIKey
DCSUBABJRXZOMT-IFMALSPDSA-N- Molecular formula
- C23H29ClFN3O4
- Average molar mass
- 465.9 g/mol
Names & identifiers
- Preferred name
- Cisapride Impurity 3
- IUPAC
- 4-amino-5-chloro-N-[(3R,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
- English name
- TRANS-CISAPRIDE
- Molecular formula
- C23H29ClFN3O4
- Molecular weight
- 465.95
Names & synonyms
104860-66-4Cisapride Impurity 34-amino-5-chloro-N-((3R,4R)-1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamideTRANS-CISAPRIDECisapride Impurity 4Cisapride Impurity 2 (trans Cisapride)Benzamide, 4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxy-, trans- (9CI)
Database identifiers
- CAS
104860-66-4
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 86.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 9
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 581
Physicochemical properties
- Boiling point
- 605.4 · 605.4±55.0 °C(Predicted)
- Density
- 1.29 · 1.29±0.1 g/cm3(Predicted)
- pka
- 13.01 · 13.01±0.40(Predicted)
Chemistry & industry
Additional notes
DefinitionChEBI: Cisapride is the amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere. It has a role as a serotonergic agonist, an anti-ulcer drug and a gastrointestinal drug. It is a member of piperidines, a member of benzamides, a member of monochlorobenzenes, a substituted aniline, an organofluorine compound and an aromatic ether.
Related reactions
0 records
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Compound notes
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