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81098-60-4

81098-60-4 structural image
Product Name: Cisapride
Formula: C23H29ClFN3O4
Synonyms: cis-4-Amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxybenxamide monohydrate;Acenalin;Cipril;Cisapride monohydrate
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CHEMICAL AND PHYSICAL PROPERTIES

Physical Description Solid
Color/Form White to slightly biege powder
Odor Odorless
Melting Point 110 °C
Solubility 2.71 mg/L
LogP 3.3
Other Experimental Properties Crystals from 2-propanol /monohydrate/

COMPUTED DESCRIPTORS

Molecular Weight 465.9 g/mol
XLogP3 3.4
Hydrogen Bond Donor Count 2
Hydrogen Bond Acceptor Count 7
Rotatable Bond Count 9
Exact Mass 465.1830623 g/mol
Monoisotopic Mass 465.1830623 g/mol
Topological Polar Surface Area 86 Ų
Heavy Atom Count 32
Formal Charge 0
Complexity 581
Isotope Atom Count 0
Defined Atom Stereocenter Count 2
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes

PRODUCT INTRODUCTION

description

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.