Cisapride

Cisapride  was discovered by Janssen Pharmaceutica in 1980.

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: 54.48Ų; (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.