Cisapride monohydrateProduct ingredient for Cisapride

Show full entry for Cisapride
Name
Cisapride monohydrate
Drug Entry
Cisapride

In many countries (including Canada) cisapride has been either withdrawn or has had its indications limited due to reports about long QT syndrome due to cisapride, which predisposes to arrhythmias. The FDA issued a warning letter regarding this risk to health care professionals and patients.

See full entry for Cisapride
Accession Number
DBSALT001018
Structure
Similar Structures
Synonyms
Not Available
UNII
VZV0A4I38W
CAS Number
260779-88-2
Weight
Average: 483.97
Monoisotopic: 483.193627
Chemical Formula
C23H31ClFN3O5
InChI Key
QBYYXIDJOFZORM-LBPAWUGGSA-N
InChI
InChI=1S/C23H29ClFN3O4.H2O/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);1H2/t20-,22+;/m1./s1
IUPAC Name
4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide hydrate
SMILES
O.CO[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC
ChemSpider
5292926
ChEMBL
CHEMBL1546244
Wikipedia
Cisapride
Predicted Properties
PropertyValueSource
Water Solubility0.012 mg/mLALOGPS
logP2.95ALOGPS
logP2.49Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.58Chemaxon
pKa (Strongest Basic)8.24Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area86.05 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity122.93 m3·mol-1Chemaxon
Polarizability47.95 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon