Cisapride

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  • Identifiers

    CAS number
    81098-60-4

    Molecular formula
    C23H29ClFN3O4

    SMILES
    CO[C@H]1CN(CC[C@H]1NC(=O)C2=CC(=C(C=C2OC)N)Cl)CCCOC3=CC=C(C=C3)F

    Safety labels

    Corrosive
    Corrosive

  • Odor profile

    Fragrance
    Odorless 57.89%
    Savory 32.73%
    Cooling 27.0%
    Meaty 26.16%
    Animal 22.04%
    Milky 21.56%
    Grape 20.9%
    Cooked 20.53%
    Bitter 19.76%
    Sweet 19.44%

     

    Flavor
    Bitter 81.91%
    Odorless 34.85%
    Bland 26.75%
    Mild 22.33%
    Sweet-like 22.1%
    Orange flower 19.7%
    Cedarleaf 19.52%
    Fruity 19.2%
    Orange blossom 19.05%
    Nitrile 18.93%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    3.4

    pKa est.
    7.09 (neutral)

    Molecular weight
    465.9 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    905°C

    Melting point expt.

    • 110 °C

    Flash point

    • 238.33 ˚C est.

    Solubility expt.

    • 2.71 mg/L
    • Sparingly soluble in methanol. Soluble in acetone
    • Practically insoluble in water.
    • 1.20e-02 g/L

  • Synonyms

    • cisapride
    • 81098-60-4
    • Cisaprida
    • Cisapridum
    • Prepulsid
    • (+-)-Cisapride
    • CHEBI:3720
    • Propulsid
    • Risamol
    • R 51619
    • 86718-70-9
    • UVL329170W
    • cis-4-Amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamide
    • CHEMBL560739
    • DTXSID3022825
    • R-51,619
    • Enteropride
    • Acenalin
    • Kinestase
    • Propulsin
    • CISAPRIDE (USP-RS)
    • CISAPRIDE [USP-RS]
    • 4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
    • CISAPRIDE (USP MONOGRAPH)
    • CISAPRIDE [USP MONOGRAPH]
    • Acpulsif
    • Alipride
    • Cipride
    • Cisapron
    • Cisawal
    • Colinorm
    • Kaudalit
    • Pridesia
    • Rapulid
    • Syspride
    • Unipride
    • Vomiprid
    • Vomipride
    • Dispep
    • Esorid
    • Guptro
    • Presid
    • Pulsid
    • Unamol
    • R-51619
    • Alimix Forte
    • 4-Amino-5-chloro-N-{(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide
    • BENZAMIDE, 4-AMINO-5-CHLORO-N-(1-(3-(4-FLUOROPHENOXY)PROPYL)-3-METHOXY-4-PIPERIDINYL)-2-METHOXY-, CIS
    • Cisapridum [Latin]
    • Cisaprida [Spanish]
    • T 1341
    • SR-01000597514
    • Cisapridum [INN-Latin]
    • Cisaprida [INN-Spanish]
    • DTXCID402825
    • CISAPRIDE [JAN]
    • Cisaprid
    • UNII-UVL329170W
    • HSDB 3571
    • cis-4-amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-o-anisamide
    • cis-4-amino-5-chloro-N-{1-[3-(p-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-o-anisamide
    • 4-Amino-5-chloro-N-(1-(3-(4-fluoro-phenoxy)-propyl)-3-methoxy-piperidin-4-yl)-2-methoxy-benzamide
    • 4-amino-5-chloro-N-(cis-1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide
    • 4-Amino-5-chloro-N-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamide
    • 4-amino-5-chloro-N-{cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl}-2-methoxybenzamide
    • cis-4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxybenzamide
    • cis-4-amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide
    • EINECS 279-689-7
    • Cisapride (Standard)
    • Cisapride [USAN:USP:INN:BAN:JAN]
    • CISAPRIDE [INN]
    • CISAPRIDE [MI]
    • CISAPRIDE [HSDB]
    • CISAPRIDE [USAN]
    • CISAPRIDE [VANDF]
    • CISAPRIDE [WHO-DD]
    • SCHEMBL16132
    • BIDD:GT0774
    • 81098-60-4 , anhydride
    • A03FA02
    • DCSUBABJRXZOMT-IRLDBZIGSA-N
    • HMS3268O13
    • HMS3412B22
    • HMS3676B22
    • Benzamide, 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, cis-
    • GDA09860
    • BDBM50462032
    • HY-14149R
    • NSC785572
    • AKOS024456750
    • DB00604
    • NSC-785572
    • 104860-66-4
    • AS-56067
    • Q425295
    • R 51619;( inverted exclamation markA)-Cisaprid
    • SR-01000597514-1
    • SR-01000597514-3
    • BRD-K06895174-001-01-0
    • BRD-K06895174-001-02-8
    • 279-689-7

  • Applications

    Primarily used in pharmaceutical development as an active pharmaceutical ingredient (API) and historically as a gastroprokinetic agent; its clinical use is now highly restricted in many markets due to safety concerns and regulatory actions. In medicinal chemistry, cisapride serves as a lead compound and building block for exploring 5-HT4 receptor–mediated gastrointestinal motility, and it is frequently referenced in SAR studies and related drug design. In analytical and quality-control laboratories, cisapride is utilized as an analytical reference material and for method development and validation in pharmaceutical analysis. It also functions as a synthetic intermediate in organic chemistry work and in the development of related heterocyclic compounds during medicinal chemistry research. In controlled lab settings and with appropriate regulatory compliance, it may be encountered as a research chemical within pharmaceutical R&D programs.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 6.62
    methanol 11.13
    isopropanol 3.76
    water 0.12
    ethyl acetate 6.01
    n-propanol 6.0
    acetone 12.51
    n-butanol 4.74
    acetonitrile 3.16
    DMF 30.62
    toluene 1.29
    isobutanol 3.63
    1,4-dioxane 10.21
    methyl acetate 6.34
    THF 30.26
    2-butanone 9.2
    n-pentanol 3.4
    sec-butanol 4.05
    n-hexane 0.04
    ethylene glycol 5.73
    NMP 41.36
    cyclohexane 0.12
    DMSO 81.54
    n-butyl acetate 1.62
    n-octanol 1.45
    chloroform 25.46
    n-propyl acetate 2.82
    acetic acid 65.47
    dichloromethane 25.82
    cyclohexanone 18.9
    propylene glycol 9.51
    isopropyl acetate 3.53
    DMAc 83.63
    2-ethoxyethanol 22.08
    isopentanol 3.65
    n-heptane 0.07
    ethyl formate 7.66
    1,2-dichloroethane 8.87
    n-hexanol 1.4
    2-methoxyethanol 37.84
    isobutyl acetate 1.63
    tetrachloromethane 2.49
    n-pentyl acetate 3.13
    transcutol 43.47
    n-heptanol 1.98
    ethylbenzene 0.45
    MIBK 3.29
    2-propoxyethanol 12.37
    tert-butanol 3.27
    MTBE 1.57
    2-butoxyethanol 11.32
    propionic acid 11.62
    o-xylene 0.92
    formic acid 42.58
    diethyl ether 1.42
    m-xylene 0.83
    p-xylene 0.66
    chlorobenzene 1.92
    dimethyl carbonate 7.2
    n-octane 0.04
    formamide 41.07
    cyclopentanone 25.34
    2-pentanone 6.15
    anisole 1.98
    cyclopentyl methyl ether 4.52
    gamma-butyrolactone 27.36
    1-methoxy-2-propanol 21.72
    pyridine 9.26
    3-pentanone 4.32
    furfural 28.91
    n-dodecane 0.04
    diethylene glycol 16.9
    diisopropyl ether 0.37
    tert-amyl alcohol 3.69
    acetylacetone 14.49
    n-hexadecane 0.04
    acetophenone 4.07
    methyl propionate 6.84
    isopentyl acetate 1.85
    trichloroethylene 31.68
    n-nonanol 1.62
    cyclohexanol 4.78
    benzyl alcohol 5.4
    2-ethylhexanol 0.84
    isooctanol 1.62
    dipropyl ether 0.95
    1,2-dichlorobenzene 2.23
    ethyl lactate 5.96
    propylene carbonate 13.31
    n-methylformamide 17.25
    2-pentanol 1.95
    n-pentane 0.06
    1-propoxy-2-propanol 6.67
    1-methoxy-2-propyl acetate 6.57
    2-(2-methoxypropoxy) propanol 12.05
    mesitylene 0.45
    ε-caprolactone 16.81
    p-cymene 0.41
    epichlorohydrin 34.41
    1,1,1-trichloroethane 6.82
    2-aminoethanol 11.52
    morpholine-4-carbaldehyde 37.05
    sulfolane 47.16
    2,2,4-trimethylpentane 0.06
    2-methyltetrahydrofuran 7.57
    n-hexyl acetate 3.2
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 15.52
    sec-butyl acetate 1.76
    tert-butyl acetate 3.3
    decalin 0.07
    glycerin 22.2
    diglyme 29.05
    acrylic acid 15.88
    isopropyl myristate 1.09
    n-butyric acid 15.66
    acetyl acetate 8.22
    di(2-ethylhexyl) phthalate 2.71
    ethyl propionate 2.76
    nitromethane 61.76
    1,2-diethoxyethane 4.49
    benzonitrile 3.01
    trioctyl phosphate 1.75
    1-bromopropane 2.1
    gamma-valerolactone 50.47
    n-decanol 1.04
    triethyl phosphate 2.49
    4-methyl-2-pentanol 1.18
    propionitrile 2.31
    vinylene carbonate 13.33
    1,1,2-trichlorotrifluoroethane 71.16
    DMS 4.32
    cumene 0.35
    2-octanol 1.08
    2-hexanone 3.49
    octyl acetate 1.8
    limonene 0.57
    1,2-dimethoxyethane 18.22
    ethyl orthosilicate 2.25
    tributyl phosphate 1.96
    diacetone alcohol 9.71
    N,N-dimethylaniline 1.64
    acrylonitrile 4.57
    aniline 4.46
    1,3-propanediol 16.36
    bromobenzene 1.65
    dibromomethane 9.04
    1,1,2,2-tetrachloroethane 22.76
    2-methyl-cyclohexyl acetate 2.48
    tetrabutyl urea 3.28
    diisobutyl methanol 0.54
    2-phenylethanol 3.08
    styrene 0.56
    dioctyl adipate 3.03
    dimethyl sulfate 18.36
    ethyl butyrate 2.14
    methyl lactate 14.31
    butyl lactate 5.47
    diethyl carbonate 2.12
    propanediol butyl ether 11.4
    triethyl orthoformate 2.72
    p-tert-butyltoluene 0.4
    methyl 4-tert-butylbenzoate 6.6
    morpholine 17.81
    tert-butylamine 0.87
    n-dodecanol 0.67
    dimethoxymethane 19.03
    ethylene carbonate 9.85
    cyrene 18.54
    2-ethoxyethyl acetate 8.37
    2-ethylhexyl acetate 1.37
    1,2,4-trichlorobenzene 3.89
    4-methylpyridine 6.76
    dibutyl ether 1.06
    2,6-dimethyl-4-heptanol 0.54
    DEF 11.13
    dimethyl isosorbide 15.74
    tetrachloroethylene 14.22
    eugenol 7.71
    triacetin 8.46
    span 80 8.77
    1,4-butanediol 6.82
    1,1-dichloroethane 6.33
    2-methyl-1-pentanol 3.1
    methyl formate 14.41
    2-methyl-1-butanol 3.98
    n-decane 0.07
    butyronitrile 2.6
    3,7-dimethyl-1-octanol 1.23
    1-chlorooctane 0.43
    1-chlorotetradecane 0.17
    n-nonane 0.06
    undecane 0.05
    tert-butylcyclohexane 0.05
    cyclooctane 0.05
    cyclopentanol 7.29
    tetrahydropyran 5.4
    tert-amyl methyl ether 1.72
    2,5,8-trioxanonane 20.4
    1-hexene 0.23
    2-isopropoxyethanol 10.6
    2,2,2-trifluoroethanol 27.03
    methyl butyrate 4.43

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction