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Cisapride

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Name

Cisapride

EINECS 279-689-7
CAS No. 81098-60-4 Density 1.29 g/cm3
PSA 86.05000 LogP 4.26810
Solubility DMSO: ~30 mg/mL Melting Point 107 - 111oC
Formula C23H29ClFN3O4 Boiling Point 605.4 °C at 760 mmHg
Molecular Weight 465.952 Flash Point 319.9 °C
Transport Information N/A Appearance White to slightly beige powder
Safety 26-39 Risk Codes 41
Molecular Structure Molecular Structure of 81098-60-4 (Cisapride) Hazard Symbols IrritantXi
Synonyms

Benzamide,4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxy-,cis-;Acenalin;Coordinax;Prepulsid;Propulsin;R 51619;Risamal;T 1341;cis-2-Methoxy-4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]benzamide;4-Amino-5-chloro-N-{(3R,4S)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl}-2-methoxybenzamide;

Article Data 4

Cisapride History

Cisapride  was discovered by Janssen Pharmaceutica in 1980.

Cisapride Specification

The CAS register number of Cisapride is 81098-60-4. It also can be called as (+/-)-cis-4-Amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxybenzamide and the IUPAC name about this chemical is 4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide. The molecular formula about this chemical is C23H29ClFN3O4 and the molecular weight is 465.95. It belongs to the following product categories, such as Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals; Serotonin receptor and so on. This chemical is a substituted benzamide used for its prokinetic properties. It is used in the management of gastroesophageal reflux disease, functional dyspepsia, and other disorders associated with impaired gastrointestinal motility. (Martindale The Extra Pharmacopoeia, 31st ed). This chemical is a parasympathomimetic and gastroprokinetic agent that acts as a serotonin 5-HT4 receptor agonist. It has been used to treat bowel constipation and it is still available in the United States for use in animals and is commonly prescribed by veterinarians to treat megacolon in cats.

Physical properties about Cisapride are: (1)ACD/LogP: 3.12; (2)ACD/LogD (pH 5.5): 0.82; (3)ACD/LogD (pH 7.4): 2.52; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 34.82; (6)ACD/KOC (pH 5.5): 5.92; (7)ACD/KOC (pH 7.4): 298.29; (8)#H bond acceptors: 7; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 10; (11)Polar Surface Area: 54.48Å2; (12)Index of Refraction: 1.593; (13)Molar Refractivity: 121.73 cm3; (14)Molar Volume: 359 cm3; (15)Polarizability: 48.26x10-24cm3; (16)Surface Tension: 54.6 dyne/cm; (17)Enthalpy of Vaporization: 90.01 kJ/mol; (18)Boiling Point: 605.4 °C at 760 mmHg; (19)Vapour Pressure: 1.32E-14 mmHg at 25°C.

The dehydration of 3-methox -4-amino-piperidine and 4-acetamido-2-methoxy-5-chlorobenzoic acid amide can produce 4-acetamido-2-methoxy-5-chloro-N-( 3-methoxy-4-piperidinyl) benzamide, and then react with fluorophenyl ether of chlorpromazine on the alkylation of nitrogen, last through acidification and hydrolysis can get Cisapride.

When you are using this chemical, please be cautious about it as the following:
This chemical has risk of serious damage to the eyes. When you are using it, wear eye / face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(c(OC)cc1N)C(=O)NC3CCN(CCCOc2ccc(F)cc2)CC3OC
(2)InChI: InChI=1/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)
(3)InChIKey: DCSUBABJRXZOMT-UHFFFAOYAV
(4)Std. 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)
(5)Std. InChIKey: DCSUBABJRXZOMT-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 900ug/kg (0.9mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

GASTROINTESTINAL: NAUSEA OR VOMITING
Veterinary and Human Toxicology. Vol. 39, Pg. 231, 1997.
dog LCLo oral 640mg/kg (640mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Veterinary and Human Toxicology. Vol. 38, Pg. 118, 1996.
mouse LD50 intraperitoneal > 1gm/kg (1000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
mouse LD50 intravenous 32200ug/kg (32.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
mouse LD50 oral 8715mg/kg (8715mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
mouse LD50 subcutaneous > 1gm/kg (1000mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
rat LD50 intraperitoneal 3435mg/kg (3435mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
rat LD50 intravenous 27400ug/kg (27.4mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
rat LD50 oral 4166mg/kg (4166mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
rat LD50 subcutaneous > 2250mg/kg (2250mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
women TDLo unreported 200ug/kg (0.2mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED Medical Journal of Australia. Vol. 160, Pg. 579, 1994.
women TDLo unreported 400ug/kg/2D-I (0.4mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES Medical Journal of Australia. Vol. 160, Pg. 579, 1994.
 

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