QuickView for Cisapride (compound)

Summary
General Info

PubChem

PubChem Compound 2769

Name:	Cisapride
PubChem Compound ID:	2769
Description:	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:	C₂₃H₂₉ClFN₃O₄
Molecular weight:	465.945 g/mol
Synonyms:	Propulsin; Cisapride; Benzamide, 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, cis-; Guptro; Cisapridum [INN-Latin]; Unamol; cis-4-Amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamide; Propulsid; D00274; Propulsid (TN). show more » Propulsin; Cisapride; Benzamide, 4-amino-5-chloro-N-(1-(3-(4-fluorophenoxy)propyl)-3-methoxy-4-piperidinyl)-2-methoxy-, cis-; Guptro; Cisapridum [INN-Latin]; Unamol; cis-4-Amino-5-chloro-N-(1-(3-(p-fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-o-anisamide; Propulsid; D00274; Propulsid (TN); Alimix; Cisapron; Alimix Forte; Kaudalit; Cisapride (JAN/USAN); Presid; Cisapride [USAN:BAN:INN:JAN]; Pulsid; (+-)-Cisapride; 86718-68-5; EINECS 279-689-7; Unipride; Prestwick1_000430; Vomiprid; R 51619; Syspride; SPBio_002359; Acenalin; Cisapridum [Latin]; Pridesia; Cisaprida [Spanish]; Enteropride; Esorid; Colinorm; 81098-60-4; HSDB 3571; Rapulid; T 1341; Acpulsif; Vomipride; Kinestase; Prestwick0_000430; Dispep; Prepulsid; Risamol; Cipride; Cisaprida [INN-Spanish]; Alipride; Benzamide, 4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl]-2-methoxy-, cis-; Prestwick_786; C06910; Cisawal show less «

DrugBank

Identification

Name:	Cisapride
Name (isomeric):	DB00604
Drug Type:	small molecule
Description:	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)
Brand:	Propulsin, Propulsid Quicksolv, Alimix, Propulsid, Prepulsid, Kinestase, Pridesia, Enteropride, Syspride, Cipril, Risamal, Acenalin
Category:	Serotonin Agonists, Anti-Ulcer Agents, Gastrointestinal Agents, Prokinetic Agents
CAS number:	81098-60-4

Pharmacology

Indication:	For the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease.
Pharmacology:	Cisapride is a parasympathomimetic which acts as a serotonin 5-HT₄ agonist. Stimulation of the serotonin receptors increases acetylcholine release in the enteric nervous system. Cisapride stimulates motility of the upper gastrointestinal tract without stimulating gastric, biliary, or pancreatic secretions. Cisapride increases the tone an... show more » Cisapride is a parasympathomimetic which acts as a serotonin 5-HT₄ agonist. Stimulation of the serotonin receptors increases acetylcholine release 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. show less «
Mechanism of Action:	Cisapride acts through the stimulation of the serotonin 5-HT₄ 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... show more » Cisapride acts through the stimulation of the serotonin 5-HT₄ 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. show less «
Absorption:	Cisapride is rapidly absorbed after oral administration, with an absolute bioavailability of 35-40%.
Protein binding:	97.5%
Biotransformation:	Hepatic. Extensively metabolized via cytochrome P450 3A4 enzyme.
Half Life:	6-12 hours
Affected organisms:	Humans and other mammals

Interactions

Food interaction:

Increases absorption, take 30 minutes before a meal.

Grapefruit and grapefruit juice should be avoided throughout treatment, grapefruit can significantly increase serum levels of this product.

Drug interaction:

Erythromycin	Increased risk of cardiotoxicity and arrhythmias
Triflupromazine	Increased risk of cardiotoxicity and arrhythmias
Ethopropazine	Increased risk of cardiotoxicity and arrhythmias
Fexofenadine	Increased risk of cardiotoxicity and arrhythmias
Bretylium	Increased risk of cardiotoxicity and arrhythmias

Erythromycin	Increased risk of cardiotoxicity and arrhythmias
Triflupromazine	Increased risk of cardiotoxicity and arrhythmias
Ethopropazine	Increased risk of cardiotoxicity and arrhythmias
Fexofenadine	Increased risk of cardiotoxicity and arrhythmias
Bretylium	Increased risk of cardiotoxicity and arrhythmias
Ibutilide	Increased risk of cardiotoxicity and arrhythmias
Telithromycin	Telithromycin may reduce clearance of Cisapride. Concomitant therapy is contraindicated.
Doxepin	Increased risk of cardiotoxicity and arrhythmias
Flecainide	Increased risk of cardiotoxicity and arrhythmias
Maprotiline	Increased risk of cardiotoxicity and arrhythmias
Clomipramine	Increased risk of cardiotoxicity and arrhythmias
Thiethylperazine	Increased risk of cardiotoxicity and arrhythmias
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Indinavir	Increased risk of cardiotoxicity and arrhythmias
Zafirlukast	Increased risk of cardiotoxicity and arrhythmias
Promethazine	Increased risk of cardiotoxicity and arrhythmias
Efavirenz	Increased risk of cardiotoxicity and arrhythmias
Anisindione	Cisapride may increase the anticoagulant effect of anisindione.
Methotrimeprazine	Increased risk of cardiotoxicity and arrhythmias
Sotalol	Increased risk of cardiotoxicity and arrhythmias
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy should be avoided.
Acetophenazine	Increased risk of cardiotoxicity and arrhythmias
Mibefradil	Mibefradil increases levels of cisapride
Methdilazine	Increased risk of cardiotoxicity and arrhythmias
Tipranavir	Tipranavir, co-administered with Ritonavir, may increase the plasma concentration of Cisapride. Concomitant therapy is contraindicated.
Clarithromycin	Increased risk of cardiotoxicity and arrhythmias
Amoxapine	Increased risk of cardiotoxicity and arrhythmias
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Bepridil	Increased risk of cardiotoxicity and arrhythmias
Nelfinavir	Increased risk of cardiotoxicity and arrhythmias
Prochlorperazine	Increased risk of cardiotoxicity and arrhythmias
Atazanavir	Increased risk of cardiotoxicity and arrhythmias
Itraconazole	Increased risk of cardiotoxicity and arrhythmias
Propafenone	Increased risk of cardiotoxicity and arrhythmias
Quinidine barbiturate	Increased risk of cardiotoxicity and arrhythmias
Propiomazine	Increased risk of cardiotoxicity and arrhythmias
Saquinavir	Increased risk of cardiotoxicity and arrhythmias
Astemizole	Increased risk of cardiotoxicity and arrhythmias
Protriptyline	Increased risk of cardiotoxicity and arrhythmias
Encainide	Increased risk of cardiotoxicity and arrhythmias
Quinupristin	This combination presents an increased risk of toxicity
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Ritonavir	Increased risk of cardiotoxicity and arrhythmias
Posaconazole	Contraindicated co-administration
Toremifene	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Quinidine	Increased risk of cardiotoxicity and arrhythmias
Diltiazem	Diltiazem, a moderate CYP3A4 inhibitor, may increase the serum concentration of cisapride by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of cisapride if diltiazem is initiated, discontinued or dose changed.
Aprepitant	Increased risk of cardiotoxicity and arrhythmias
Trifluoperazine	Increased risk of cardiotoxicity and arrhythmias
Dicumarol	Cisapride may increase the anticoagulant effect of dicumarol.
Fluconazole	Increased risk of cardiotoxicity and arrhythmias
Promazine	Increased risk of cardiotoxicity and arrhythmias
Disopyramide	Increased risk of cardiotoxicity and arrhythmias
Chlorpromazine	Increased risk of cardiotoxicity and arrhythmias
Nifedipine	Cisapride may increase the effect and toxicity of nifedipine.
Troleandomycin	Increased risk of cardiotoxicity and arrhythmias
Acenocoumarol	Cisapride may increase the anticoagulant effect of acenocoumarol.
Amprenavir	Amprenavir may increase the effect and toxicity of cisapride.
Imipramine	Increased risk of cardiotoxicity and arrhythmias
Nortriptyline	Increased risk of cardiotoxicity and arrhythmias
Trimeprazine	Increased risk of cardiotoxicity and arrhythmias
Dihydroquinidine barbiturate	Increased risk of cardiotoxicity and arrhythmias
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Warfarin	Cisapride may increase the anticoagulant effect of warfarin.
Desipramine	Increased risk of cardiotoxicity and arrhythmias
Perphenazine	Increased risk of cardiotoxicity and arrhythmias
Josamycin	Increased risk of cardiotoxicity and arrhythmias
Ketoconazole	Increased risk of cardiotoxicity and arrhythmias
Mesoridazine	Increased risk of cardiotoxicity and arrhythmias
Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Nefazodone	Nefazodone increases serum levels of cisapride
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
Voriconazole	Voriconazole may increase the serum concentration and toxicity of cisapride likely by decreasing its metabolism. Additive QTc prolongation may also occur. Concomitant therapy is contraindicated.
Procainamide	Increased risk of cardiotoxicity and arrhythmias
Amiodarone	Increased risk of cardiotoxicity and arrhythmias
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. Cisapride may also increase the concentration of Tacrolimus in the blood.
Fluphenazine	Increased risk of cardiotoxicity and arrhythmias
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Amitriptyline	Increased risk of cardiotoxicity and arrhythmias
Fosamprenavir	Amprenavir increases the effect and toxicity of cisapride
Delavirdine	Delavirdine, a strong CYP3A4 inhibitor, may increase the metabolism of cisapride. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of cisapride if delavirdine is initiated, discontinued or dose changed.

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Targets

5-hydroxytryptamine 4 receptor

5-hydroxytryptamine 3 receptor

5-hydroxytryptamine 2A receptor

Potassium voltage-gated channel subfamily H member 2

Enzymes