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Cisapride

CAT: 1596-AR-C02946-02Size: 25 UnitsDry Ice: NoHazardous: No
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CAT#:1596-AR-C02946-02Size:25 Units
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CAS Number
81098-60-4
Synonyms
4-amino-5-chloro-N- (1- (3- (4-fluorophenoxy) propyl) -3-methoxypiperidin-4-yl) -2-methoxybenzamide; (.+-.) -Cisapride; Acenalin; Alimix; Benzamide, 4-amino-5-chloro-N-[1-[ (3R,4S) -3- (4-fluorophenoxy) propyl]-3-methoxy-4-piperidinyl]-2-methoxy-, rel-; Benzamide, 4-amino-5-chloro-N-[1-[3- (4-fluorophenoxy) propyl]-3-methoxy-4-piperidinyl]-2-methoxy-, cis-; Cipril; cis-2-Methoxy-4-amino-5-chloro-N-[1-[3- (4-fluorophenoxy) propyl]-3-methoxy-4-piperidinyl]benzamide; Cisaprid; cisaprida; cisapride; Coordinax; Prepulsid; Propulsid; Propulsin; R 51619; Risamal; T 1341; rel-4-Amino-5-chloro-N-[1-[ (3R,4S) -3- (4-fluorophenoxy) propyl]-3-methoxy-4-piperidinyl]-2-methoxybenzamide; (+/-) -Cisapride; Acenalin; Alimix; Cipril; Coordinax; Prepulsid; Propulsid; Propulsin; R 51619; Risamal; T 1341; cis-2-Methoxy-4-amino-5-chloro-N-[1-[3- (4-fluorophenoxy) propyl]-3-methoxy-4-piperidinyl]benzamide
Molecular Formula
C23H29ClFN3O4
Molecular Weight
465.96
API Name
Cisapride

Chemical Information

Cisapride

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 benzamides, a member of piperidines, an aromatic ether, an organofluorine compound, a substituted aniline and a member of monochlorobenzenes.

CAS Number81098-60-4
PubChem CID6917698
IUPAC Name4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
Molecular FormulaC23H29ClFN3O4
Molecular Weight465.9
XLogP3.4
Topological Polar Surface Area86.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count9
Heavy Atom Count32
Formal Charge0
Complexity581
SMILES
CO[C@H]1CN(CC[C@H]1NC(=O)C2=CC(=C(C=C2OC)N)Cl)CCCOC3=CC=C(C=C3)F
InChI
InChI=1S/C23H29ClFN3O4/c1-30-21-13-19(26)18(24)12-17(21)23(29)27-20-8-10-28(14-22(20)31-2)9-3-11-32-16-6-4-15(25)5-7-16/h4-7,12-13,20,22H,3,8-11,14,26H2,1-2H3,(H,27,29)/t20-,22+/m1/s1
InChIKey
DCSUBABJRXZOMT-IRLDBZIGSA-N
Chemical Structure
2D Structure
2D structure of Cisapride
CAS: 81098-60-4
CID: 6917698
Formula: C23H29ClFN3O4
MW: 465.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight465.9
XLogP33.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count9
Exact Mass465.1830623
Monoisotopic Mass465.1830623
Topological Polar Surface Area86.1 Ų
Heavy Atom Count32
Formal Charge0
Complexity581
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
HY-14149-01Cisapride
50R-R51619Cisapride (powder)
HY-14149R-01Cisapride (Standard)
T70070-01Cisapride tartrate
444789-01Cisapride Monohydrate
ESS0464-01Trans-Cisapride
ESS0442-01Cisapride Demethoxy

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