Grundinformationen
- CAS
260779-88-2- Standard-SMILES
COc1cc(N)c(Cl)cc1C(=O)N[C@@H]1CCN(CCCOc2ccc(F)cc2)C[C@@H]1OC- InChIKey
DCSUBABJRXZOMT-IRLDBZIGSA-N- Summenformel
- C23H29ClFN3O4
- Durchschnittliche Molmasse
- 465,9 g/mol
- Monoisotopische Masse
- 465,1830623
Überblick
Cisapride is the amide resulting from formal condensation of 4-amino-5-chloro-2-methoxybenzoic acid with cis-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-amine. It has been used (as its monohydrate or as its tartrate) for the treatment of gastro-oesophageal reflux disease and for non-ulcer dyspepsia, but its propensity to cause cardiac arrhythmias resulted in its complete withdrawal from many countries, including the U.K., and restrictions on its use elsewhere. It has a role as a serotonergic agonist, an anti-ulcer drug and a gastrointestinal drug. It is a member of benzamides, a member of piperidines, an aromatic ether, an organofluorine compound, a substituted aniline and a member of monochlorobenzenes.
Namen und Bezeichner
- Bevorzugter Name
- Cisapride
- IUPAC
- 4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
- Lokaler Name
- Cisaprid
- Englischer Name
- Cisapride
- Summenformel
- C23H29ClFN3O4
- Molmasse
- 465.95
Namen und Synonyme
cisapride81098-60-4CisapridumCisapridaEnteroprideKinestasePridesiaPrepulsidR 51619Prepulsid quickletPropulsid QuicksolvCHEBI:3720
Weitere Namen anzeigen
CISAPRIDE MONOHYDRATEAlimixT 1341r51619CIPRILRisamalRisamolACENALINKaudalit
UVL329170W4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamidecis-4-Amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamideR-51,619R-51619Benzamide, 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, cis-DTXSID30228254-amino-5-chloro-N-((3S,4R)-1-(3-(4-fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide
Datenbank-Bezeichner
- CAS
260779-88-2、81098-60-4- PubChem CID
- 6917698
- DTXSID
DTXSID3022825- ChEMBL
CHEMBL1729、CHEMBL560739
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,4
- Polarare Oberfläche (TPSA)
- 86,1 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 9
- Schwere Atome
- 32
- Formalladung
- 0
- Komplexität
- 581
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.3
OdorOdorless
Color/FormWhite to slightly biege powder
Solubility
Sparingly soluble in methanol. Soluble in acetone
Practically insoluble in water.
1.20e-02 g/L
Human DrugsBreast Feeding; Lactation; Gastrointestinal Agents; Serotonin Agonists;
Melting Point110 °C
Physical DescriptionSolid
Other Experimental Properties
Crystals from 2-propanol /monohydrate/
109.8 °C /monohydrate/
Physikochemische Eigenschaften
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
P264+P265, P280, P305+P354+P338, and P317 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Danger
H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
Gefahrenhinweise
Other Safety InformationIMAP assessments - Benzamide, 4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxy-, cis-: Environment tier I assessment
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Hazard Classes and Categories
Eye Dam. 1 (100%)
Eye Dam. 1 (100%)
Sicherheit und Schutzausrüstung
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Chemie und Industrie
Pharmakologische Informationen
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Protein Binding97.5%
Pharmacodynamics
Cisapride is a parasympathomimetic which acts as a serotonin 5-HT<sub>4</sub> agonist; upon activation of the receptor signaling pathway, cisapride promotes the release of acetylcholine neurotransmitters in the enteric nervous system. Cisapride stimulates motility of the upper gastrointestinal tract without stimulating gastric, biliary, or pancreatic secretions. Cisapride increases the tone and amplitude of gastric (especially antral) contractions, relaxes the pyloric sphincter and the duodenal bulb, and increases peristalsis of the duodenum and jejunum resulting in accelerated gastric emptying and intestinal transit. It increases the resting tone of the lower esophageal sphincter. It has little, if any, effect on the motility of the colon or gallbladder. Cisapride does not induce muscarinic or nicotinic receptor stimulation, nor does it inhibit acetylcholinesterase activity.
Mechanism of Action
Cisapride acts through the stimulation of the serotonin 5-HT<sub>4</sub> receptors which increases acetylcholine release in the enteric nervous system (specifically the myenteric plexus). This results in increased tone and amplitude of gastric (especially antral) contractions, relaxation of the pyloric sphincter and the duodenal bulb, and increased peristalsis of the duodenum and jejunum resulting in accelerated gastric emptying and intestinal transit.
Cisapride exerts its effect by increasing the release of acetylcholine from the postganglionic nerve endings of the myenteric plexus. This release of acetylcholine increases esophageal activity and increases esophageal sphincter tone, thereby improving esophageal clearance and decreasing reflux of gastric and duodenal emptying as a result of increased gastric and duodenal contractility and antroduodenal coordination. Duodenogastric reflux is also decreased. Cisapride improves transit in both small and large bowel.
Biological Half-Life6-12 hours
Metabolism/Metabolites
Zugehörige Reaktionen
0
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Notizen zur Verbindung
Wird geladen…