Cisapride
Overview Mechanism of Action Pharmacokinetics Indications Adverse reactions Contraindication Precautions Drug Interactions- Product Name
- Cisapride
- CAS No.
- 81098-60-4
- Chemical Name
- Cisapride
- Synonyms
- Alimix;T 1341;r51619;CIPRIL;Risamal;Risamol;ACENALIN;Kaudalit;Pridesia;Propulsin
- CBNumber
- CB9121489
- Molecular Formula
- C23H29ClFN3O4
- Formula Weight
- 465.95
- MOL File
- 81098-60-4.mol
Cisapride Property
- Melting point:
- 109.8 °C
- Boiling point:
- 605.4±55.0 °C(Predicted)
- Density
- 1.29±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- DMSO: ~30 mg/mL
- form
- solid
- pka
- 13.01±0.40(Predicted)
- color
- white
- Water Solubility
- 9.319mg/L(30 ºC)
- CAS DataBase Reference
- 81098-60-4(CAS DataBase Reference)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 41
- Safety Statements
- 26-39
- WGK Germany
- 2
- RTECS
- CU9372000
- Hazardous Substances Data
- 81098-60-4(Hazardous Substances Data)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H318Causes serious eye damage
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P310Immediately call a POISON CENTER or doctor/physician.
N-Bromosuccinimide Price
- Product number
- 21657
- Product name
- Cisapride
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $44
- Updated
- 2024/03/01
- Product number
- 21657
- Product name
- Cisapride
- Purity
- ≥98%
- Packaging
- 10mg
- Price
- $84
- Updated
- 2024/03/01
- Product number
- 21657
- Product name
- Cisapride
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $193
- Updated
- 2024/03/01
- Product number
- 21657
- Product name
- Cisapride
- Purity
- ≥98%
- Packaging
- 50mg
- Price
- $341
- Updated
- 2024/03/01
- Product number
- 1695
- Product name
- Cisapride
- Purity
- ≥99%(HPLC)
- Packaging
- 10
- Price
- $141
- Updated
- 2021/12/16
Cisapride Chemical Properties,Usage,Production
Overview
Cisapride is a gastrointestinal pro-motility drug, and was listed in the UK in 1988. It is a benzamide compound without anti-dopaminergic properties and does not have direct cholinergic properties. Its mechanism of action is different from that of metoclopramide and domperidone. It does not affect dopamine receptors, instead acts through acting with different serotonin receptors on the parietal plexus ending of the posterior wall of gastrointestinal organ, promoting the release of wall muscle acetylcholine (in quantity and time), further stimulating the entire digestive system organs and exerting an pro-motility effect. It does not affect the submucosal plexus, does not change the secretion of mucous membranes, belonging to a driving force drugs. This product can enhance the contraction and peristalsis of the human esophagus, stomach and duodenum, further improving the coordination of gastric antral duodenal region and preventing gastroesophageal and duodenal reflux. It can strengthen the emptying of the stomach and duodenum, and can promote the peristalsis of the large intestine and small intestine. It is mainly used for the treatment of gastrointestinal motility disorders, such as functional dyspepsia, gastroesophageal reflux disease, chronic constipation, bile reflux gastritis, neonatal vomiting and non-ulcer dyspepsia. Second, it can also be used for the treatment of non-gastrointestinal motility disorders, such as diabetic neurogenic bladder, gallbladder contraction disorders.
Mechanism of Action
This product belongs to the whole gastrointestinal pro-motility drug. It can strengthen and coordinate gastrointestinal motility, further preventing food retention and reflux. Its mechanism of action is mainly through the selective promotion of the release of acetylcholine in the intestinal myenteric plexus postganglionic nerve, thereby enhancing gastrointestinal motility. Animal experiments confirmed that this product can accelerate the gastric motility, enhance the gastrointestinal - duodenal digestive activity, coordinate the action of gastric antrum - duodenum, small intestine and large intestine, and reduce intestinal movement time. In the human body, this product can enhance esophageal peristalsis, increase the tension of the lower esophageal sphincter to prevent the reflux of gastric contents into the esophagus and improve esophageal clearance; can enhance the contraction of stomach and duodenum and improve the gastric antrum – duodenum coordination. This effect can prevent duodenal - gastric reflux, promote gastric and duodenal emptying; promote small intestine and colon peristalsis.
This product does not affect the gastrointestinal submucosal plexus, it does not change the secretion of gastrointestinal mucosa. At the same time because this product does not inhibit the activity of acetylcholinesterase, nor has dopamine receptor blocking effect, it does not increase gastric acid secretion; does not affect the level of plasma prolactin. Therefore, it basically has no central inhibitory effect.
Pharmacokinetics
Oral administration leads to rapid absorption with plasma concentration reaching peak within 1 ~ 2h; protein binding rate: 98%; bioavailability: 40% to 50%; half-life:7 ~ 10h. It is subject to metabolism inside the body to demethylated cisapride. 90% is excreted through the urine with a small amount subjecting to milk excretion.
Indications
- It is mainly used for the treatment of functional dyspepsia, relieving abdominal fullness, fullness, nausea, vomiting, belching, abdominal pain and other symptoms. It may also be useful to apply this drug for the treatment of child chronic, excessive nausea and vomiting which are failed to be cured through taking physical posture and diet measures.
- It is used for the treatment of gastroesophageal reflux disease, including the treatment and maintenance of esophagitis.
- It is used for the gastroparesis caused by nerve injury, vagotomy and partial gastroparesis.
- Recover the colon propulsive movement for the long-term treatment of chronic constipation.
- It can be used for the treatment of motor function disorders associated with pseudo-intestinal obstruction caused by prophylactic peristalsis and gastrointestinal contents retention.
Adverse reactions
- A small number of patients can get transient abdominal cramps, abdominal vomiting and diarrhea. Loss can disappear easily.
- There are occasional reports on allergic reactions (such as rash, urticaria, itching and bronchospasm), mild brief headaches or dizziness, and dose-related frequent urination.
- Rare: ① There are few reports of arrhythmia (including ventricular tachycardia, ventricular fibrillation and torsades de pointes and QT prolongation). Most patients often take other drugs (including CYP 3A4 enzyme Inhibitor), or has been suffering from heart disease, or have other risk factors such as arrhythmias. ② there are some reports of rare reversible liver dysfunction (which may be associated with cholestasis). ③ There are also reports of men's breast development and milk overflow (the relationship with this product is not yet clear). Individual reports: the goods can affect the central nervous system, leading to epilepsy, extrapyramidal reactions.
Contraindication
- Allergic to the drug.
- Bradycardia.
- QT prolongation (including congenital QT prolongation) or congenital QT prolongation syndrome family history of patients.
- Lung, liver and kidney dysfunction.
- Infants.
Precautions
- Children failing in using posture and diet measures to control galactorrhea (nausea) and vomiting can take its suspension.
- To determine the dose of the drug associated with this product, it is appropriate to monitor the plasma concentration of these drugs.
- If syncope, heart rate or arrhythmia occurs, or QT interval is over 0.45 seconds, it should immediately stopped of using this product.
- If abdominal cramps occurs, the dose can be halved.
- Use with caution in the following cases: ① patients who may suffer from increased gastrointestinal function. ② patients with sudden death of family history.
- The FDA pregnancy safety rating for this drug is C.
Drug Interactions
- Combinations with drugs that prolong the QT interval such as Class Ia antiarrhythmic drugs (such as quinidine, disopyramide and procainamide), class III antiarrhythmic drugs (such as amiodarone, sotalol), tricyclic antidepressants (such as amitriptyline), tetracycline antidepressants (such as maprotiline), antipsychotics (such as phenothiazine, pimozide), anti-histamine drugs (such as Astemizole, Tefinatide), bepupi and halofantrine can increase the cardiotoxicity, so this good should be banned for combination with these drugs.
- Drug inhibiting the CYP3A4 enzyme such as nefazodone, azoles antifungal drugs (such as ketoconazole, itraconazole, miconazole, fluconazole), macrolide antibiotics (such as erythromycin , Clarithromycin, Troleandomycin), protease inhibitors (such as indinavir, ritonavir, amprenavir) can inhibit the metabolism of the goods, increased blood concentration and cause cardiotoxicity ( Such as QT prolongation, torsades de pointes ventricular tachycardia, ventricular fibrillation, cardiac arrest, etc.), so the treatment of these goods should be prohibited during taking cisapride.
- Cimetidine can increase the blood concentration of this product, but with no clinical significance.
- Combination with bromipeline and haloperidol can promote the absorption of the latter, inhibiting its metabolism, so that mental symptoms are worsened.
- Combination with cyclosporine can increase the latter's absorption rate, enhance its toxicity (such as renal dysfunction, cholestasis, etc.).
- This product can accelerate the absorption of central nervous inhibitory drugs (such as barbiturates).
- This product can reduce the metabolism of tacrolimus, increasing its risk of causing adverse reactions (such as toxic renal damage, hyperglycemia and hyperkalemia).
- Combination with levodopa can increase the risk of the adverse reactions (such as involuntary movement, tremors, nausea and vomiting and cardiovascular irritation) caused by latter one.
- This product can accelerate gastric emptying, thereby reducing the rate of absorption of drugs to be absorbed through the stomach; on the contrary, it may increase the absorption rate of drugs absorbed by the intestine (such as anticoagulants, acetaminophen, H2 receptor antagonists, etc.) Absorption rate. When combined with anticoagulants, it can extend the clotting time. In this case, pay attention to check the clotting time to determine the appropriate dose of anticoagulant.
- Anticholinergic drugs (such as atropine, benztropine and belladonna preparations) can reduce the efficacy of this product.
- This product can reduce the absorption of digoxin, but have no clinical significance.
Description
Cisapride is a gastroprokinetic useful in the treatment of reflux esophagitis, constipation, and a variety of gastro-intestinal motility disorders. Its novel mechanism of action is thought to involve the enhancement of acetylcholine release in the mysenteric plexus of the gut. It is reportedly devoid of CNS and cardiac side-effects.
Chemical Properties
White Solid
Originator
Janssen (Belgium)
Uses
A Serotonin 5-HT4 receptro agonist. Used as a Gastroprokinetic
Uses
Cisapride Monohydrate is a cardioactive drug that causes prolongation of cardiac repolarization in human; selective serotonin 5-HT4 receptor agonist.
Uses
Peristaltic stimulant;5-HT antagonist
Uses
isoflavone used as a cholagogue and cathartic
Indications
Cisapride (Propulsid) is serotonin-4 (5-HT4) receptor agonists that stimulate GI motility. Cisapride appears to act by facilitating the release of acetylcholine from the myenteric plexus. It has no antiadrenergic, antidopaminergic, or cholinergic side effects. Following oral administration, peak plasma levels occur in 1.5 to 2 hours; the drug’s half-life is 10 hours.
Definition
ChEBI: 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-oeso hageal 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.
Manufacturing Process
A mixture of 1-[3-(4-fluorophenoxy)-propyl]-3-methoxy-4-piperidinone (140
mg), benzylamine (61 mg), Pd 10% on charcoal (100 mg) and a 0.02%
solution of thiophene in THF was reacted under hydrogen gas for 3 hours at
50°C. The catalyst was filtered off and fresh palladium 10% on charcoal (100
mg) was added. Debenzylation of the formed intermediate took place under
hydrogen atmosphere for 18 hours at 50°C. The reaction mixture was filtered
and evaporated under a stream of nitrogen to yield 1-[3-(4-fluorophenoxy)-
propyl]-3-methoxy-4-piperidinamine having a cis/trans ratio of about 93/7.
1-[3-(4-Fluorophenoxy)-propyl]-3-methoxy-4-piperidinamine (50 g) was
dissolved in methyl isobutylketone (250 ml) and a nitric acid solution (65%,
12.8 ml) was carefully added so that the temperature of the solution did not
exceed 45°C. The reaction mixture was stirred at a temperature of 30°C and
seeded. When crystallisation started, the reaction mixture was cooled to 0°C
and stirred for another 2 hours. The product was filtered off, washed with a
small amount of toluene and dried, yielding 1-[3-(4-fluorophenoxy)-propyl]-3-
methoxy-4-piperidinamine nitrate (m.p. 60°C).
1-[3-(4-Fluorophenoxy)-propyl]-3-methoxy-4-piperidinamine nitrate was
dissolved in water (95 ml). The reaction mixture was stirred and toluene (95
ml) was added. A NaOH solution (50%, 10.3 ml) was slowly added and the
temperature of the reaction mixture was raised to 75°C. After 30 min, the
aqueous layer was discarded and the organic layer was evaporated, yielding
1-[3-(4-fluorophenoxy)-propyl]-3-methoxy-4-piperidinamine having a
cis/trans ratio equal to or higher than 98/2.
To a solution of 4-amino-5-chloro-2-methoxybenzoic acid (20.2 g) in methyl
isobutylketone (250 ml) and triethyl amine (15.3 ml) was slowly dropped
ethyl chloroformate (9.6 ml). The reaction mixture was stirred for 30 min at
room temperature. To the formed mixed anhydride was then added 1-[3-(4-
fluorophenoxy)-propyl]-3-methoxy-4-piperidinamine (28.2 g) and the reaction
mixture was stirred for 2 hours at room temperature. Subsequently, the
reaction mixture was washed with water (80 ml) and a NaOH solution (6.5%
w/v, 50 ml). The organic layer was warmed to 65°C and methanol (50 ml)
and water (8.5 ml) were added. The solution was cooled slowly and stirred for
2 days during which crystallisation occurred, yielding benzamide, 4-amino-5-
chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-
, monohydrate, cis- (Cisapride) having a cis/trans ratio higher than 99/1.
brand name
Propulsid (Janssen);Calmax;Cisapid;Cismotil;Digenol;Prepulsid.
Therapeutic Function
Gastrointestinal drug
Biological Activity
5-HT 4 receptor agonist and gastrokinetic agent. Stimulates intestinal acetylcholine release, possibly via 5-HT 4 receptor-dependent and -independent mechanisms, leading to increased intestinal motility.
Clinical Use
Cisapride has been successfully used to treat gastroparesis and mild gastroesophageal reflux disease.
Side effects
The most frequent side effect has been diarrhea. A few patients had seizure activity that was reversible after medication was discontinued. Cisapride was pulled from the U. S. market after deaths from drug-associated cardiac arrhythmias, including ventricular tachycardia, ventricular fibrillation, torsades de pointes, and QT prolongation.
Veterinary Drugs and Treatments
Proposed uses for cisapride in small animals includes esophageal reflux and treatment of primary gastric stasis disorders. Cisapride has been found to be useful in the treatment of constipation and megacolon in cats.
Metabolic pathway
Cisapride 14C labeled at the carbonyl carbon and 3H labeled at the fluorophenyl moiety or at the piperidine ring is investigated using some animals. N- Dealkylation at the nitrogen of the piperidine ring, resulting in the main urinary metabolite norcisapride, and aromatic hydroxylation of the fluorinated phenyl ring are the major metabolic pathways in dogs and humans. Norcisapride excretion accounts for 14% of the dose in dogs and 41-45% in humans. Minor metabolic pathways are O-dearylation of the 4- fluorophenyl group and oxidation on the piperidine ring (rat, rabbits and dogs: Lavrijsen et al. (1986)15).
storage
Store at RT
Cisapride Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Cisapride manufacturers
- Product
- Cisapride 81098-60-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 100g
- Purity
- 99%min
- Supply Ability
- 10KG
- Release date
- 2021-06-01
- Product
- Cisapride 81098-60-4
- Price
- US $1.00-1.00/KG
- Min. Order
- 1g
- Purity
- 99%
- Supply Ability
- 50tons
- Release date
- 2020-05-06
- Product
- Cisapride 81098-60-4
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 10 ton
- Release date
- 2024-08-20