(sis' a pride).
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C23H29ClFN3O4 465.95

Benzamide, 4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxy-, cis-
cis-4-Amino-5-chloro-N-[1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidyl]-o-anisamide [81098-60-4].

Monohydrate 484.0 [260779-88-2].
» Cisapride contains not less than 99.0 percent and not more than 101.0 percent of C23H29ClFN3O4, calculated on the anhydrous basis.
Packaging and storage— Preserve in well-closed, light-resistant containers, and store at room temperature.
USP Reference standards 11
USP Cisapride RS
USP Haloperidol RS Click to View Structure
Completeness of solution 641 A solution, 10 mg per mL in methylene chloride, meets the requirements.
Identification, Infrared Absorption 197K.
Specific rotation 781S: between 10 and +10, measured at 20.
Test solution: 10 mg per mL, in methylene chloride.
Water, Method I 921: between 3.4% and 4.0%.
Residue on ignition 281: not more than 0.1%.
Chromatographic purity—
Solution A— Prepare a 20 g per L solution of tetrabutylammonium hydrogen sulfate in water.
Solution B— Use methanol.
Mobile phase— Use variable mixtures of Solution A and Solution B as directed for Chromatographic system. Make adjustments if necessary (see System Suitability under Chromatography 621).
Blank solution— Use methanol.
System suitability solution— Prepare a solution of USP Cisapride RS and USP Haloperidol RS in methanol containing about 0.05 mg per mL and 0.4 mg per mL, respectively.
Test solution 1— Dissolve an accurately weighed quantity of Cisapride, in methanol to obtain a solution having a known concentration of about 10 mg per mL.
Test solution 2— Dilute quantitatively and stepwise Test solution 1 in methanol to obtain a solution having a known concentration of about 0.05 mg per mL.
Chromatographic system (see Chromatography 621) The liquid chromatograph is equipped with a 275-nm detector and a 4.0-mm × 10-cm column that contains 3-µm base-deactivated packing L1. The flow rate is about 1.2 mL per minute. The chromatograph is programmed as follows.
Solution A
Solution B
0–20 80®55 20®45 linear gradient
20–21 55®5 45®95 linear gradient
21–25 5 95 isocratic
25–26 5®80 95®20 return to initial
26–30 80 20 re-equilibration
Chromatograph the System suitability solution, and record the peak responses as directed for Procedure: the order of elution is cisapride followed by haloperidol, the resolution, R, between these two peaks is not less than 2.5; and the relative standard deviation for replicate injections is not more than 2.0% for the cisapride peak.
Procedure— Inject a volume (about 10 µL) of the Blank solution, Test solution 1, and Test solution 2 into the chromatograph, record the chromatograms, and measure the peak areas. Calculate the percentage of cisapride impurities in the portion of Cisapride taken by the formula:
100(CS / Ci)(ri / rS)
in which CS and Ci are the concentration of cisapride, in mg per mL, of Test solution 2 and Test solution 1, respectively; ri is the individual peak response of cisapride inpurities in Test solution 1; and rS is cisapride peak area in Test solution 2: not more than 0.5% of any cisapride impurity is found, and not more than 1.0% of total impurities is found. Disregard any peak also found in the Blank solution and any peak with an area less than 0.1 times the area of the principal peak in the Test solution 2 chromatogram.
Assay— Dissolve about 0.350 g of Cisapride, accurately weighed, in 70 mL of a mixture of methyl ethyl ketone and acetic acid (7:1). Titrate with 0.1 N perchloric acid VS, determining the endpoint potentiometrically. Perform a blank determination, and make any necessary correction (see Titrimetry 541). Each mL of 0.1 N perchloric acid is equivalent to 46.60 mg of C23H29ClFN3O4.
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Monograph Morgan Puderbaugh, B.S.
Associate Scientific Liaison
(SM32010) Monographs - Small Molecules 3
Reference Standards RS Technical Services
USP35–NF30 Page 2677
Pharmacopeial Forum: Volume No. 34(2) Page 253