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Substance Name: Cisapride [USAN:USP:INN:BAN:JAN]
RN: 81098-60-4
UNII: UVL329170W
InChIKey: DCSUBABJRXZOMT-IRLDBZIGSA-N

Note

  • 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)

Molecular Formula

  • C23-H29-Cl-F-N3-O4

Molecular Weight

  • 465.9501
 

Classification Codes

  • Anti-Ulcer Agents
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Human Data
  • Neurotransmitter Agents
  • Serotonin Agents
  • Serotonin Receptor Agonists
  • Stimulant (Peristaltic)

Names and Synonyms

Name of Substance

  • Cisapride
  • Cisapride [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Cisapride

Synonyms

  • (+-)-Cisapride
  • Acenalin
  • Acpulsif
  • Alimix
  • Alimix Forte
  • Alipride
  • Benzamide, 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, cis-
  • Cipride
  • cis-4-Amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamide
  • Cisaprida
  • Cisaprida [INN-Spanish]
  • Cisaprida [Spanish]
  • Cisapride
  • Cisapridum
  • Cisapridum [INN-Latin]
  • Cisapridum [Latin]
  • Cisapron
  • Cisawal
  • Colinorm
  • Dispep
  • EINECS 279-689-7
  • Enteropride
  • Esorid
  • Guptro
  • HSDB 3571
  • Kaudalit
  • Kinestase
  • Prepulsid
  • Presid
  • Pridesia
  • Propulsid
  • Propulsin
  • Pulsid
  • R 51619
  • R-51,619
  • Rapulid
  • Risamol
  • Syspride
  • T 1341
  • Unamol
  • UNII-UVL329170W
  • Unipride
  • Vomiprid
  • Vomipride

Systematic Names

  • Benzamide, 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, cis-
  • Cisapride

Registry Numbers

CAS Registry Number

  • 81098-60-4

FDA UNII

  • UVL329170W

Other Registry Number

  • 86718-68-5

System Generated Number

  • 0081098604

Structure Descriptors

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)/t20-,22+/m1/s1

InChIKey

DCSUBABJRXZOMT-IRLDBZIGSA-N

Smiles

CO[C@H]1CN(CCCOc2ccc(F)cc2)CC[C@H]1NC(=O)c3cc(Cl)c(N)cc3OC

Toxicity

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) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Veterinary and Human Toxicology. Vol. 38, Pg. 118, 1996.
mouse LD50 intraperitoneal > 1gm/kg (1000mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 19, Pg. 599, 1988.
mouse LD50 intravenous 32200ug/kg (32.2mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
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

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 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) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
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

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 oral 4166mg/kg (4166mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 3.090 (none)   EST
Water Solubility 2.710 mg/L 25 EST
Henry's Law Constant 5.44E-24 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.48E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.