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Identification
NameCisapride
Accession NumberDB00604  (APRD00454)
TypeSmall Molecule
GroupsApproved, Investigational, Withdrawn
DescriptionIn many countries (including Canada) cisapride has been either withdrawn or has had its indications limited due to reports about long QT syndrome due to cisapride, which predisposes to arrhythmias. The FDA issued a warning letter regarding this risk to health care professionals and patients.
Structure
Thumb
Synonyms
(+-)-Cisapride
4-amino-5-chloro-N-(1-(3-(4-Fluorophenoxy)propyl)-3-methoxypiperidin-4-yl)-2-methoxybenzamide
4-Amino-5-chloro-N-{1-[3-(4-fluoro-phenoxy)-propyl]-3-methoxy-piperidin-4-yl}-2-methoxy-benzamide
cis-4-amino-5-chloro-N-(1-(3-(P-Fluorophenoxy)propyl)-3-methoxy-4-piperidyl)-O-anisamide
cis-4-amino-5-chloro-N-{1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-2-methoxybenzamide
cis-4-amino-5-chloro-N-{1-[3-(P-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl}-O-anisamide
Cisaprid
Cisaprida
Cisapride
Cisapridum
External Identifiers
  • R 51619
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Prepulsid Sus 1mg/mlSuspension1 mgOralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1992-12-312000-08-25Canada
Prepulsid Tab 10mgTablet10 mgOralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1990-12-312000-08-25Canada
Prepulsid Tab 20mgTablet20 mgOralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1993-12-312000-08-25Canada
Prepulsid Tab 5mgTablet5 mgOralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1990-12-312000-08-25Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EnteroprideNot Available
KinestaseNot Available
PrepulsidJanssen-Ortho
PridesiaNot Available
PropulsidJanssen-Ortho
Propulsid QuicksolvJanssen-Ortho
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cisapride Monohydrate
ThumbNot applicableDBSALT001018
Categories
UNIIUVL329170W
CAS number81098-60-4
WeightAverage: 465.945
Monoisotopic: 465.183062343
Chemical FormulaC23H29ClFN3O4
InChI KeyDCSUBABJRXZOMT-IRLDBZIGSA-N
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)/t20-,22+/m1/s1
IUPAC Name
4-amino-5-chloro-N-[(3S,4R)-1-[3-(4-fluorophenoxy)propyl]-3-methoxypiperidin-4-yl]-2-methoxybenzamide
SMILES
CO[[email protected]]1CN(CCCOC2=CC=C(F)C=C2)CC[[email protected]]1NC(=O)C1=CC(Cl)=C(N)C=C1OC
Pharmacology
IndicationFor the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease.
Structured Indications Not Available
PharmacodynamicsCisapride 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.
Mechanism of actionCisapride 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
5-hydroxytryptamine receptor 4Proteinyes
agonist
HumanQ13639 details
5-hydroxytryptamine receptor 3AProteinyes
agonist
HumanP46098 details
5-hydroxytryptamine receptor 2AProteinyes
agonist
HumanP28223 details
Potassium voltage-gated channel subfamily H member 2Proteinunknown
inhibitor
HumanQ12809 details
Related Articles
AbsorptionCisapride is rapidly absorbed after oral administration, with an absolute bioavailability of 35-40%.
Volume of distributionNot Available
Protein binding97.5%
Metabolism

Hepatic. Extensively metabolized via cytochrome P450 3A4 enzyme.

SubstrateEnzymesProduct
Cisapride
norcisaprideDetails
Route of eliminationNot Available
Half life6-12 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Cisapride can be increased when it is combined with 1,10-Phenanthroline.Experimental
2-HYDROXY-1,4-NAPHTHOQUINONEThe serum concentration of Cisapride can be increased when it is combined with 2-HYDROXY-1,4-NAPHTHOQUINONE.Experimental
2-mercaptobenzothiazoleThe serum concentration of Cisapride can be increased when it is combined with 2-mercaptobenzothiazole.Vet Approved
3,4-DichloroisocoumarinThe serum concentration of Cisapride can be increased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDEThe serum concentration of Cisapride can be increased when it is combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.Experimental
AbirateroneThe serum concentration of Cisapride can be increased when it is combined with Abiraterone.Approved
AlfuzosinAlfuzosin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
AlogliptinThe serum concentration of Cisapride can be increased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Cisapride can be increased when it is combined with Alpha-1-proteinase inhibitor.Approved
AmantadineAmantadine may increase the QTc-prolonging activities of Cisapride.Approved
AmiodaroneCisapride may increase the QTc-prolonging activities of Amiodarone.Approved, Investigational
AmitriptylineAmitriptyline may increase the arrhythmogenic activities of Cisapride.Approved
AmorolfineThe serum concentration of Cisapride can be increased when it is combined with Amorolfine.Approved
AmoxapineAmoxapine may increase the QTc-prolonging activities of Cisapride.Approved
Amphotericin BThe serum concentration of Cisapride can be increased when it is combined with Amphotericin B.Approved, Investigational
AmprenavirThe serum concentration of Cisapride can be increased when it is combined with Amprenavir.Approved
AN2690The serum concentration of Cisapride can be increased when it is combined with AN2690.Investigational
AnagrelideAnagrelide may increase the QTc-prolonging activities of Cisapride.Approved
AnidulafunginThe serum concentration of Cisapride can be increased when it is combined with Anidulafungin.Approved, Investigational
Antithrombin III humanThe serum concentration of Cisapride can be increased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Cisapride can be increased when it is combined with Apixaban.Approved
ApomorphineApomorphine may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
AprepitantThe serum concentration of Cisapride can be increased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Cisapride can be increased when it is combined with Aprotinin.Approved, Withdrawn
ArformoterolArformoterol may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
ArgatrobanThe serum concentration of Cisapride can be increased when it is combined with Argatroban.Approved, Investigational
AripiprazoleAripiprazole may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
ArmodafinilThe metabolism of Cisapride can be decreased when combined with Armodafinil.Approved, Investigational
Arsenic trioxideCisapride may increase the QTc-prolonging activities of Arsenic trioxide.Approved, Investigational
ArtemetherThe serum concentration of Cisapride can be increased when it is combined with Artemether.Approved
AsenapineCisapride may increase the QTc-prolonging activities of Asenapine.Approved
AsunaprevirThe serum concentration of Cisapride can be increased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Cisapride can be increased when it is combined with Atazanavir.Approved, Investigational
AtomoxetineAtomoxetine may increase the QTc-prolonging activities of Cisapride.Approved
AzithromycinAzithromycin may increase the QTc-prolonging activities of Cisapride.Approved
Bafilomycin A1The serum concentration of Cisapride can be increased when it is combined with Bafilomycin A1.Experimental
BatimastatThe serum concentration of Cisapride can be increased when it is combined with Batimastat.Experimental
BedaquilineBedaquiline may increase the QTc-prolonging activities of Cisapride.Approved
BenazeprilThe serum concentration of Cisapride can be increased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Cisapride can be increased when it is combined with Benzamidine.Experimental
Benzoic AcidThe serum concentration of Cisapride can be increased when it is combined with Benzoic Acid.Approved
BepridilCisapride may increase the QTc-prolonging activities of Bepridil.Approved, Withdrawn
BexaroteneThe serum concentration of Cisapride can be decreased when it is combined with Bexarotene.Approved, Investigational
Bi201335The serum concentration of Cisapride can be increased when it is combined with Bi201335.Investigational
BicalutamideThe serum concentration of Cisapride can be increased when it is combined with Bicalutamide.Approved
BifonazoleThe serum concentration of Cisapride can be increased when it is combined with Bifonazole.Approved
BivalirudinThe serum concentration of Cisapride can be increased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Cisapride can be increased when it is combined with Boceprevir.Approved
BortezomibBortezomib may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
BosentanThe serum concentration of Cisapride can be decreased when it is combined with Bosentan.Approved, Investigational
BuserelinBuserelin may increase the QTc-prolonging activities of Cisapride.Approved
ButenafineThe serum concentration of Cisapride can be increased when it is combined with Butenafine.Approved
ButoconazoleThe serum concentration of Cisapride can be increased when it is combined with Butoconazole.Approved
CaffeineThe metabolism of Cisapride can be decreased when combined with Caffeine.Approved
CandicidinThe serum concentration of Cisapride can be increased when it is combined with Candicidin.Withdrawn
CandoxatrilThe serum concentration of Cisapride can be increased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Cisapride can be increased when it is combined with Candoxatrilat.Experimental
CapecitabineThe metabolism of Cisapride can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilThe serum concentration of Cisapride can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Cisapride can be increased when combined with Carbamazepine.Approved, Investigational
CarbomycinThe metabolism of Cisapride can be decreased when combined with Carbomycin.Vet Approved
CaspofunginThe serum concentration of Cisapride can be increased when it is combined with Caspofungin.Approved
CelecoxibThe metabolism of Cisapride can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Cisapride can be increased when it is combined with Ceritinib.Approved
CeruleninThe serum concentration of Cisapride can be increased when it is combined with Cerulenin.Approved
ChloramphenicolThe metabolism of Cisapride can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineChloroquine may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
ChloroxineThe serum concentration of Cisapride can be increased when it is combined with Chloroxine.Approved
ChlorpromazineChlorpromazine may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
CholecalciferolThe metabolism of Cisapride can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
ChymostatinThe serum concentration of Cisapride can be increased when it is combined with Chymostatin.Experimental
CiclopiroxThe serum concentration of Cisapride can be increased when it is combined with Ciclopirox.Approved, Investigational
CilastatinThe serum concentration of Cisapride can be increased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Cisapride can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Cisapride can be increased when it is combined with Cimetidine.Approved
CiprofloxacinCiprofloxacin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
CitalopramCitalopram may increase the QTc-prolonging activities of Cisapride.Approved
ClarithromycinThe metabolism of Cisapride can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Cisapride can be decreased when combined with Clemastine.Approved
ClomipramineClomipramine may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
ClopidogrelThe metabolism of Cisapride can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe serum concentration of Cisapride can be increased when it is combined with Clotrimazole.Approved, Vet Approved
ClozapineClozapine may increase the QTc-prolonging activities of Cisapride.Approved
CobicistatThe serum concentration of Cisapride can be increased when it is combined with Cobicistat.Approved
ConivaptanThe serum concentration of Cisapride can be increased when it is combined with Conivaptan.Approved, Investigational
CordycepinThe serum concentration of Cisapride can be increased when it is combined with Cordycepin.Investigational
CrizotinibCrizotinib may increase the QTc-prolonging activities of Cisapride.Approved
CyclosporineThe serum concentration of Cisapride can be increased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Cisapride can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
Dabigatran etexilateThe serum concentration of Cisapride can be increased when it is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Cisapride can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe serum concentration of Cisapride can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Cisapride can be increased when it is combined with Dasatinib.Approved, Investigational
Decanoic AcidThe serum concentration of Cisapride can be increased when it is combined with Decanoic Acid.Experimental
DeferasiroxThe serum concentration of Cisapride can be decreased when it is combined with Deferasirox.Approved, Investigational
DegarelixDegarelix may increase the QTc-prolonging activities of Cisapride.Approved
DelavirdineThe metabolism of Cisapride can be decreased when combined with Delavirdine.Approved
DesfluraneDesflurane may increase the QTc-prolonging activities of Cisapride.Approved
DesipramineDesipramine may increase the QTc-prolonging activities of Cisapride.Approved
DexamethasoneThe serum concentration of Cisapride can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DihydroergotamineThe metabolism of Cisapride can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Cisapride can be decreased when combined with Diltiazem.Approved
DiphenhydramineDiphenhydramine may increase the QTc-prolonging activities of Cisapride.Approved
DisopyramideDisopyramide may increase the QTc-prolonging activities of Cisapride.Approved
DofetilideDofetilide may increase the QTc-prolonging activities of Cisapride.Approved
DolasetronDolasetron may increase the QTc-prolonging activities of Cisapride.Approved
DomperidoneCisapride may increase the QTc-prolonging activities of Domperidone.Approved, Investigational, Vet Approved
DoxepinDoxepin may increase the QTc-prolonging activities of Cisapride.Approved
DoxorubicinThe metabolism of Cisapride can be decreased when combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Cisapride can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneCisapride may increase the QTc-prolonging activities of Dronedarone.Approved
DroperidolDroperidol may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
EcabetThe serum concentration of Cisapride can be increased when it is combined with Ecabet.Approved, Investigational
EconazoleThe serum concentration of Cisapride can be increased when it is combined with Econazole.Approved
EdoxabanThe serum concentration of Cisapride can be increased when it is combined with Edoxaban.Approved
EfavirenzThe serum concentration of Cisapride can be decreased when it is combined with Efavirenz.Approved, Investigational
EfinaconazoleThe serum concentration of Cisapride can be increased when it is combined with Efinaconazole.Approved
ElafinThe serum concentration of Cisapride can be increased when it is combined with Elafin.Investigational
EliglustatCisapride may increase the QTc-prolonging activities of Eliglustat.Approved
EnalaprilThe serum concentration of Cisapride can be increased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Cisapride can be increased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Cisapride can be increased when it is combined with Enalkiren.Experimental
EnzalutamideThe serum concentration of Cisapride can be decreased when it is combined with Enzalutamide.Approved
EribulinEribulin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
ErythromycinThe metabolism of Cisapride can be decreased when combined with Erythromycin.Approved, Vet Approved
EscitalopramCisapride may increase the QTc-prolonging activities of Escitalopram.Approved, Investigational
Eslicarbazepine acetateThe serum concentration of Cisapride can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Cisapride can be decreased when combined with Esomeprazole.Approved, Investigational
EthanolThe risk or severity of adverse effects can be increased when Cisapride is combined with Ethanol.Approved
EtravirineThe serum concentration of Cisapride can be decreased when it is combined with Etravirine.Approved
EzogabineEzogabine may increase the QTc-prolonging activities of Cisapride.Approved
FamotidineFamotidine may increase the QTc-prolonging activities of Cisapride.Approved
FelbamateFelbamate may increase the QTc-prolonging activities of Cisapride.Approved
FelodipineThe metabolism of Cisapride can be decreased when combined with Felodipine.Approved, Investigational
FesoterodineThe serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Cisapride.Approved
FingolimodFingolimod may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
FlecainideFlecainide may increase the QTc-prolonging activities of Cisapride.Approved, Withdrawn
FloxuridineThe metabolism of Cisapride can be decreased when combined with Floxuridine.Approved
FluconazoleThe serum concentration of Cisapride can be increased when it is combined with Fluconazole.Approved
FlucytosineThe serum concentration of Cisapride can be increased when it is combined with Flucytosine.Approved
FluorouracilThe metabolism of Cisapride can be decreased when combined with Fluorouracil.Approved
FluoxetineFluoxetine may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
FlupentixolCisapride may increase the QTc-prolonging activities of Flupentixol.Approved, Withdrawn
FluvastatinThe metabolism of Cisapride can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Cisapride can be decreased when combined with Fluvoxamine.Approved, Investigational
FormoterolFormoterol may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
FosamprenavirThe serum concentration of Cisapride can be increased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Cisapride can be increased when it is combined with Fosaprepitant.Approved
FoscarnetFoscarnet may increase the QTc-prolonging activities of Cisapride.Approved
FosinoprilThe serum concentration of Cisapride can be increased when it is combined with Fosinopril.Approved
FosphenytoinThe metabolism of Cisapride can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Cisapride can be increased when it is combined with Fusidic Acid.Approved
GabexateThe serum concentration of Cisapride can be increased when it is combined with Gabexate.Investigational
Gadobenic acidGadobenic acid may increase the QTc-prolonging activities of Cisapride.Approved
GalantamineGalantamine may increase the QTc-prolonging activities of Cisapride.Approved
GeldanamycinThe serum concentration of Cisapride can be increased when it is combined with Geldanamycin.Experimental
GemfibrozilThe metabolism of Cisapride can be decreased when combined with Gemfibrozil.Approved
GemifloxacinGemifloxacin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
GlyphosateThe serum concentration of Cisapride can be increased when it is combined with Glyphosate.Experimental
GM6001The serum concentration of Cisapride can be increased when it is combined with GM6001.Experimental
GoserelinGoserelin may increase the QTc-prolonging activities of Cisapride.Approved
GranisetronGranisetron may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
GriseofulvinThe serum concentration of Cisapride can be increased when it is combined with Griseofulvin.Approved, Vet Approved
HaloperidolHaloperidol may increase the QTc-prolonging activities of Cisapride.Approved
HaloproginThe serum concentration of Cisapride can be increased when it is combined with Haloprogin.Approved, Withdrawn
HexetidineThe serum concentration of Cisapride can be increased when it is combined with Hexetidine.Approved
HirulogThe serum concentration of Cisapride can be increased when it is combined with Hirulog.Experimental
HistrelinHistrelin may increase the QTc-prolonging activities of Cisapride.Approved
HydroxyzineHydroxyzine may increase the QTc-prolonging activities of Cisapride.Approved
IbandronateIbandronate may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
IbutilideIbutilide may increase the QTc-prolonging activities of Cisapride.Approved
IdelalisibThe serum concentration of Cisapride can be increased when it is combined with Idelalisib.Approved
idraparinuxThe serum concentration of Cisapride can be increased when it is combined with idraparinux.Investigational
IloperidoneCisapride may increase the QTc-prolonging activities of Iloperidone.Approved
ImatinibThe metabolism of Cisapride can be decreased when combined with Imatinib.Approved
ImidaprilThe serum concentration of Cisapride can be increased when it is combined with Imidapril.Investigational
ImipramineImipramine may increase the QTc-prolonging activities of Cisapride.Approved
IndacaterolIndacaterol may increase the QTc-prolonging activities of Cisapride.Approved
IndapamideIndapamide may increase the QTc-prolonging activities of Cisapride.Approved
IndinavirThe serum concentration of Cisapride can be increased when it is combined with Indinavir.Approved
IrbesartanThe metabolism of Cisapride can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Cisapride can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoconazoleThe serum concentration of Cisapride can be increased when it is combined with Isoconazole.Approved
IsofluraneIsoflurane may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
IsoflurophateThe serum concentration of Cisapride can be increased when it is combined with Isoflurophate.Approved, Withdrawn
IsoniazidThe metabolism of Cisapride can be decreased when combined with Isoniazid.Approved
IsradipineIsradipine may increase the QTc-prolonging activities of Cisapride.Approved
ItraconazoleThe serum concentration of Cisapride can be increased when it is combined with Itraconazole.Approved, Investigational
IvabradineIvabradine may increase the QTc-prolonging activities of Cisapride.Approved
IvacaftorThe serum concentration of Cisapride can be increased when it is combined with Ivacaftor.Approved
IxazomibThe serum concentration of Cisapride can be increased when it is combined with Ixazomib.Approved
JosamycinThe metabolism of Cisapride can be decreased when combined with Josamycin.Approved
KetoconazoleThe serum concentration of Cisapride can be increased when it is combined with Ketoconazole.Approved, Investigational
KitasamycinThe metabolism of Cisapride can be decreased when combined with Kitasamycin.Experimental
LapatinibLapatinib may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
LeflunomideThe metabolism of Cisapride can be decreased when combined with Leflunomide.Approved, Investigational
LenvatinibLenvatinib may increase the QTc-prolonging activities of Cisapride.Approved
LepirudinThe serum concentration of Cisapride can be increased when it is combined with Lepirudin.Approved
LeuprolideLeuprolide may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
LevofloxacinLevofloxacin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
LidocaineThe metabolism of Cisapride can be decreased when combined with Lidocaine.Approved, Vet Approved
LinagliptinThe serum concentration of Cisapride can be increased when it is combined with Linagliptin.Approved
LisinoprilThe serum concentration of Cisapride can be increased when it is combined with Lisinopril.Approved, Investigational
LithiumLithium may increase the QTc-prolonging activities of Cisapride.Approved
LopinavirThe serum concentration of Cisapride can be increased when it is combined with Lopinavir.Approved
LosartanThe metabolism of Cisapride can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Cisapride can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Cisapride can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Cisapride can be increased when it is combined with Lumacaftor.Approved
LumefantrineCisapride may increase the QTc-prolonging activities of Lumefantrine.Approved
MaprotilineMaprotiline may increase the QTc-prolonging activities of Cisapride.Approved
MefloquineMefloquine may increase the QTc-prolonging activities of Cisapride.Approved
MethadoneMethadone may increase the QTc-prolonging activities of Cisapride.Approved
MethotrimeprazineMethotrimeprazine may increase the QTc-prolonging activities of Cisapride.Approved
MetoclopramideMetoclopramide may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
MetoprololThe serum concentration of Metoprolol can be increased when it is combined with Cisapride.Approved, Investigational
MetronidazoleMetronidazole may increase the QTc-prolonging activities of Cisapride.Approved
MevastatinThe serum concentration of Cisapride can be increased when it is combined with Mevastatin.Experimental
MexiletineThe metabolism of Cisapride can be decreased when combined with Mexiletine.Approved
MicafunginThe serum concentration of Cisapride can be increased when it is combined with Micafungin.Approved, Investigational
MiconazoleThe serum concentration of Cisapride can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MifepristoneMifepristone may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
MiltefosineThe serum concentration of Cisapride can be increased when it is combined with Miltefosine.Approved
MirabegronMirabegron may increase the QTc-prolonging activities of Cisapride.Approved
MirtazapineMirtazapine may increase the QTc-prolonging activities of Cisapride.Approved
MitotaneThe serum concentration of Cisapride can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Cisapride can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of Cisapride can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Cisapride can be increased when it is combined with Moexipril.Approved
MonensinThe serum concentration of Cisapride can be increased when it is combined with Monensin.Vet Approved
MoxifloxacinMoxifloxacin may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
MyxothiazolThe serum concentration of Cisapride can be increased when it is combined with Myxothiazol.Experimental
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Cisapride can be increased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NafamostatThe serum concentration of Cisapride can be increased when it is combined with Nafamostat.Investigational
NafcillinThe serum concentration of Cisapride can be decreased when it is combined with Nafcillin.Approved
NaftifineThe serum concentration of Cisapride can be increased when it is combined with Naftifine.Approved
NatamycinThe serum concentration of Cisapride can be increased when it is combined with Natamycin.Approved
NCX 4016The serum concentration of Cisapride can be increased when it is combined with NCX 4016.Investigational
NefazodoneThe serum concentration of Cisapride can be increased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Cisapride can be increased when it is combined with Nelfinavir.Approved
NetupitantThe serum concentration of Cisapride can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Cisapride can be increased when combined with Nevirapine.Approved
NicardipineNicardipine may increase the QTc-prolonging activities of Cisapride.Approved
NicotineThe metabolism of Cisapride can be decreased when combined with Nicotine.Approved
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Cisapride.Approved
NilotinibCisapride may increase the QTc-prolonging activities of Nilotinib.Approved, Investigational
NitroaspirinThe serum concentration of Cisapride can be increased when it is combined with Nitroaspirin.Investigational
NitroxolineThe serum concentration of Cisapride can be increased when it is combined with Nitroxoline.Approved
NorfloxacinNorfloxacin may increase the QTc-prolonging activities of Cisapride.Approved
NortriptylineNortriptyline may increase the QTc-prolonging activities of Cisapride.Approved
NystatinThe serum concentration of Cisapride can be increased when it is combined with Nystatin.Approved, Vet Approved
OctreotideOctreotide may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
OfloxacinOfloxacin may increase the QTc-prolonging activities of Cisapride.Approved
OlanzapineOlanzapine may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
OlaparibThe metabolism of Cisapride can be decreased when combined with Olaparib.Approved
OleandomycinThe metabolism of Cisapride can be decreased when combined with Oleandomycin.Vet Approved
OlodaterolOlodaterol may increase the QTc-prolonging activities of Cisapride.Approved
OmapatrilatThe serum concentration of Cisapride can be increased when it is combined with Omapatrilat.Investigational
OmeprazoleThe metabolism of Cisapride can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronOndansetron may increase the QTc-prolonging activities of Cisapride.Approved
OsimertinibThe serum concentration of Cisapride can be increased when it is combined with Osimertinib.Approved
OtamixabanThe serum concentration of Cisapride can be increased when it is combined with Otamixaban.Investigational
OxiconazoleThe serum concentration of Cisapride can be increased when it is combined with Oxiconazole.Approved
OxytocinOxytocin may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
pafuramidineThe serum concentration of Cisapride can be increased when it is combined with pafuramidine.Investigational
PalbociclibThe serum concentration of Cisapride can be increased when it is combined with Palbociclib.Approved
PaliperidoneCisapride may increase the QTc-prolonging activities of Paliperidone.Approved
PanobinostatPanobinostat may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
PantoprazoleThe metabolism of Cisapride can be decreased when combined with Pantoprazole.Approved
ParoxetineParoxetine may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
PasireotidePasireotide may increase the QTc-prolonging activities of Cisapride.Approved
PazopanibPazopanib may increase the QTc-prolonging activities of Cisapride.Approved
Peginterferon alfa-2bThe serum concentration of Cisapride can be increased when it is combined with Peginterferon alfa-2b.Approved
PentamidineThe serum concentration of Cisapride can be increased when it is combined with Pentamidine.Approved
PentobarbitalThe metabolism of Cisapride can be increased when combined with Pentobarbital.Approved, Vet Approved
PerflutrenPerflutren may increase the QTc-prolonging activities of Cisapride.Approved
PerindoprilThe serum concentration of Cisapride can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe metabolism of Cisapride can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Cisapride can be increased when combined with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Cisapride can be increased when it is combined with Phosphoramidon.Experimental
PimozideCisapride may increase the QTc-prolonging activities of Pimozide.Approved
PioglitazoneThe metabolism of Cisapride can be decreased when combined with Pioglitazone.Approved, Investigational
PosaconazoleThe serum concentration of Cisapride can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PrimaquinePrimaquine may increase the QTc-prolonging activities of Cisapride.Approved
PrimidoneThe metabolism of Cisapride can be increased when combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Cisapride can be increased when it is combined with Prinomastat.Investigational
ProcainamideCisapride may increase the QTc-prolonging activities of Procainamide.Approved
PromazinePromazine may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
PromethazinePromethazine may increase the QTc-prolonging activities of Cisapride.Approved
PropafenonePropafenone may increase the QTc-prolonging activities of Cisapride.Approved
PropofolPropofol may increase the QTc-prolonging activities of Cisapride.Approved, Investigational, Vet Approved
ProtriptylineProtriptyline may increase the arrhythmogenic activities of Cisapride.Approved
PyrimethamineThe metabolism of Cisapride can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe serum concentration of Cisapride can be increased when it is combined with Quazepam.Approved, Illicit
QuetiapineCisapride may increase the QTc-prolonging activities of Quetiapine.Approved
QuinaprilThe serum concentration of Cisapride can be increased when it is combined with Quinapril.Approved, Investigational
QuinidineCisapride may increase the QTc-prolonging activities of Quinidine.Approved
QuinineQuinine may increase the QTc-prolonging activities of Cisapride.Approved
RabeprazoleThe metabolism of Cisapride can be decreased when combined with Rabeprazole.Approved, Investigational
RacecadotrilThe serum concentration of Cisapride can be increased when it is combined with Racecadotril.Investigational
RadicicolThe serum concentration of Cisapride can be increased when it is combined with Radicicol.Experimental
RamiprilThe serum concentration of Cisapride can be increased when it is combined with Ramipril.Approved
RanolazineRanolazine may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
RemikirenThe serum concentration of Cisapride can be increased when it is combined with Remikiren.Approved
RifabutinThe metabolism of Cisapride can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Cisapride can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Cisapride can be increased when combined with Rifapentine.Approved
RilpivirineRilpivirine may increase the QTc-prolonging activities of Cisapride.Approved
RisperidoneRisperidone may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
RitonavirThe serum concentration of Cisapride can be increased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Cisapride can be increased when it is combined with Rivaroxaban.Approved
RopiniroleThe metabolism of Cisapride can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneThe metabolism of Cisapride can be decreased when combined with Rosiglitazone.Approved, Investigational
RoxithromycinThe metabolism of Cisapride can be decreased when combined with Roxithromycin.Approved, Withdrawn
SalbutamolSalbutamol may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
Salicylhydroxamic AcidThe serum concentration of Cisapride can be increased when it is combined with Salicylhydroxamic Acid.Experimental
Salicylic acidThe serum concentration of Cisapride can be increased when it is combined with Salicylic acid.Approved, Vet Approved
SalmeterolSalmeterol may increase the QTc-prolonging activities of Cisapride.Approved
SaquinavirThe serum concentration of Cisapride can be increased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Cisapride can be increased when it is combined with Saxagliptin.Approved
SecobarbitalThe metabolism of Cisapride can be increased when combined with Secobarbital.Approved, Vet Approved
SertaconazoleThe serum concentration of Cisapride can be increased when it is combined with Sertaconazole.Approved
SertralineSertraline may increase the QTc-prolonging activities of Cisapride.Approved
SevofluraneSevoflurane may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
SildenafilThe metabolism of Cisapride can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Cisapride can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Cisapride can be increased when it is combined with Simeprevir.Approved
SinefunginThe serum concentration of Cisapride can be increased when it is combined with Sinefungin.Experimental
SirolimusThe serum concentration of Cisapride can be increased when it is combined with Sirolimus.Approved, Investigational
SitagliptinThe serum concentration of Cisapride can be increased when it is combined with Sitagliptin.Approved, Investigational
SolifenacinSolifenacin may increase the QTc-prolonging activities of Cisapride.Approved
SolithromycinThe metabolism of Cisapride can be decreased when combined with Solithromycin.Investigational
SorafenibSorafenib may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
SotalolSotalol may increase the QTc-prolonging activities of Cisapride.Approved
SpiraprilThe serum concentration of Cisapride can be increased when it is combined with Spirapril.Approved
St. John's WortThe serum concentration of Cisapride can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Cisapride can be increased when it is combined with Stiripentol.Approved
SulconazoleThe serum concentration of Cisapride can be increased when it is combined with Sulconazole.Approved
SulfadiazineThe metabolism of Cisapride can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleSulfamethoxazole may increase the QTc-prolonging activities of Cisapride.Approved
SulfisoxazoleSulfisoxazole may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
SulpirideThe risk or severity of adverse effects can be increased when Cisapride is combined with Sulpiride.Approved
SunitinibSunitinib may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
TamoxifenTamoxifen may increase the QTc-prolonging activities of Cisapride.Approved
TavaboroleThe serum concentration of Cisapride can be increased when it is combined with Tavaborole.Approved
TelaprevirThe serum concentration of Cisapride can be increased when it is combined with Telaprevir.Approved
TelavancinTelavancin may increase the QTc-prolonging activities of Cisapride.Approved
TelithromycinThe metabolism of Cisapride can be decreased when combined with Telithromycin.Approved
TemocaprilThe serum concentration of Cisapride can be increased when it is combined with Temocapril.Experimental, Investigational
TenofovirThe metabolism of Cisapride can be decreased when combined with Tenofovir.Approved, Investigational
TerbinafineThe serum concentration of Cisapride can be increased when it is combined with Terbinafine.Approved, Investigational, Vet Approved
TerbutalineTerbutaline may increase the QTc-prolonging activities of Cisapride.Approved
TerconazoleThe serum concentration of Cisapride can be increased when it is combined with Terconazole.Approved
TeriflunomideThe serum concentration of Cisapride can be decreased when it is combined with Teriflunomide.Approved
TetrabenazineCisapride may increase the QTc-prolonging activities of Tetrabenazine.Approved
TheophyllineThe metabolism of Cisapride can be decreased when combined with Theophylline.Approved
ThioridazineThe serum concentration of Thioridazine can be increased when it is combined with Cisapride.Approved
ThiorphanThe serum concentration of Cisapride can be increased when it is combined with Thiorphan.Experimental
ThiotepaThe metabolism of Cisapride can be decreased when combined with Thiotepa.Approved
ThiothixeneThiothixene may increase the QTc-prolonging activities of Cisapride.Approved
ThymolThe serum concentration of Cisapride can be increased when it is combined with Thymol.Approved
TicagrelorThe metabolism of Cisapride can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Cisapride can be decreased when combined with Ticlopidine.Approved
TioconazoleThe serum concentration of Cisapride can be increased when it is combined with Tioconazole.Approved
TipranavirThe serum concentration of Cisapride can be increased when it is combined with Tipranavir.Approved, Investigational
TizanidineTizanidine may increase the QTc-prolonging activities of Cisapride.Approved
TocilizumabThe serum concentration of Cisapride can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Cisapride can be decreased when combined with Tolbutamide.Approved
TolnaftateThe serum concentration of Cisapride can be increased when it is combined with Tolnaftate.Approved, Vet Approved
TolterodineTolterodine may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
TopiramateThe metabolism of Cisapride can be decreased when combined with Topiramate.Approved
ToremifeneToremifene may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
TrandolaprilThe serum concentration of Cisapride can be increased when it is combined with Trandolapril.Approved
TranylcypromineThe metabolism of Cisapride can be decreased when combined with Tranylcypromine.Approved
TrazodoneTrazodone may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
TreprostinilTreprostinil may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
TrimethoprimTrimethoprim may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
TrimetrexateThe serum concentration of Cisapride can be increased when it is combined with Trimetrexate.Approved, Investigational
TrimipramineTrimipramine may increase the QTc-prolonging activities of Cisapride.Approved
TriptorelinTriptorelin may increase the QTc-prolonging activities of Cisapride.Approved, Vet Approved
TroleandomycinThe metabolism of Cisapride can be decreased when combined with Troleandomycin.Approved
TylosinThe metabolism of Cisapride can be decreased when combined with Tylosin.Vet Approved
UbenimexThe serum concentration of Cisapride can be increased when it is combined with Ubenimex.Experimental
UlinastatinThe serum concentration of Cisapride can be increased when it is combined with Ulinastatin.Investigational
Valproic AcidThe metabolism of Cisapride can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Cisapride can be decreased when combined with Valsartan.Approved, Investigational
VandetanibCisapride may increase the QTc-prolonging activities of Vandetanib.Approved
VardenafilVardenafil may increase the QTc-prolonging activities of Cisapride.Approved
VemurafenibThe serum concentration of Cisapride can be increased when it is combined with Vemurafenib.Approved
VenlafaxineVenlafaxine may increase the QTc-prolonging activities of Cisapride.Approved
VerapamilThe metabolism of Cisapride can be decreased when combined with Verapamil.Approved
VilanterolVilanterol may increase the QTc-prolonging activities of Cisapride.Approved
VildagliptinThe serum concentration of Cisapride can be increased when it is combined with Vildagliptin.Approved, Investigational
VoriconazoleThe serum concentration of Cisapride can be increased when it is combined with Voriconazole.Approved, Investigational
VorinostatVorinostat may increase the QTc-prolonging activities of Cisapride.Approved, Investigational
XimelagatranThe serum concentration of Cisapride can be increased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Ym150The serum concentration of Cisapride can be increased when it is combined with Ym150.Investigational
ZafirlukastThe metabolism of Cisapride can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneZiprasidone may increase the QTc-prolonging activities of Cisapride.Approved
ZuclopenthixolCisapride may increase the QTc-prolonging activities of Zuclopenthixol.Approved, Investigational
Food Interactions
  • Grapefruit and grapefruit juice should be avoided throughout treatment, grapefruit can significantly increase serum levels of this product.
  • Increases absorption, take 30 minutes before a meal.
References
Synthesis Reference

Alfons Gaston Maria De Knaep, Luc Jozef Raphael Moens, Max Rey, “Synthesis of cisapride.” U.S. Patent US6218542, issued January, 1988.

US6218542
General References
  1. Pearce RE, Gotschall RR, Kearns GL, Leeder JS: Cytochrome P450 Involvement in the biotransformation of cisapride and racemic norcisapride in vitro: differential activity of individual human CYP3A isoforms. Drug Metab Dispos. 2001 Dec;29(12):1548-54. [PubMed:11717173 ]
External Links
ATC CodesA03FA02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74.5 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9666
Blood Brain Barrier+0.9383
Caco-2 permeable+0.5835
P-glycoprotein substrateSubstrate0.8103
P-glycoprotein inhibitor IInhibitor0.5422
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.5978
CYP450 2C9 substrateNon-substrate0.8718
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7375
CYP450 1A2 substrateNon-inhibitor0.6912
CYP450 2C9 inhibitorNon-inhibitor0.8868
CYP450 2D6 inhibitorInhibitor0.8933
CYP450 2C19 inhibitorNon-inhibitor0.8269
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.524
Ames testNon AMES toxic0.6505
CarcinogenicityNon-carcinogens0.8915
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.0806 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8918
hERG inhibition (predictor II)Inhibitor0.8616
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Ortho mcneil janssen pharmaceuticals inc
  • Janssen pharmaceutica products lp
Packagers
Dosage forms
FormRouteStrength
SuspensionOral1 mg
TabletOral10 mg
TabletOral20 mg
TabletOral5 mg
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5648093 No1994-07-152014-07-15Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point110 °CNot Available
water solubility2.71 mg/LNot Available
logP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 mg/mLALOGPS
logP2.95ALOGPS
logP2.49ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)8.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.05 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity122.93 m3·mol-1ChemAxon
Polarizability49.11 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminobenzoic acids and derivatives. These are benzoic acids (or derivative thereof) containing an amine group attached to the benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentAminobenzoic acids and derivatives
Alternative Parents
Substituents
  • 3-halobenzoic acid or derivatives
  • Salicylamide
  • Aminobenzoic acid or derivatives
  • Methoxyaniline
  • Benzamide
  • Aminobenzamide
  • Methoxybenzene
  • Substituted aniline
  • Phenol ether
  • Benzoyl
  • Anisole
  • Halobenzene
  • Fluorobenzene
  • Chlorobenzene
  • Aniline
  • 4-aminopiperidine
  • Alkyl aryl ether
  • Primary aromatic amine
  • Piperidine
  • Aryl halide
  • Aryl fluoride
  • Aryl chloride
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Serotonin receptor activity
Specific Function:
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase.
Gene Name:
HTR4
Uniprot ID:
Q13639
Molecular Weight:
43760.975 Da
References
  1. Crema F, Modini C, Croci T, Langlois M, de Ponti F: Intestinal prokinesia by two esters of 4-amino-5-chloro-2- methoxybenzoic acid: involvement of 5-hydroxytryptamine-4 receptors and dissociation from cardiac effects in vivo. J Pharmacol Exp Ther. 1999 Mar;288(3):1045-52. [PubMed:10027842 ]
  2. Nagakura Y, Akuzawa S, Miyata K, Kamato T, Suzuki T, Ito H, Yamaguchi T: Pharmacological properties of a novel gastrointestinal prokinetic benzamide selective for human 5-HT4 receptor versus human 5-HT3 receptor. Pharmacol Res. 1999 May;39(5):375-82. [PubMed:10328995 ]
  3. Rahme MM, Cotter B, Leistad E, Wadhwa MK, Mohabir R, Ford AP, Eglen RM, Feld GK: Electrophysiological and antiarrhythmic effects of the atrial selective 5-HT(4) receptor antagonist RS-100302 in experimental atrial flutter and fibrillation. Circulation. 1999 Nov 9;100(19):2010-7. [PubMed:10556228 ]
  4. Bharucha AE, Camilleri M, Haydock S, Ferber I, Burton D, Cooper S, Tompson D, Fitzpatrick K, Higgins R, Zinsmeister AR: Effects of a serotonin 5-HT(4) receptor antagonist SB-207266 on gastrointestinal motor and sensory function in humans. Gut. 2000 Nov;47(5):667-74. [PubMed:11034583 ]
  5. Bach T, Syversveen T, Kvingedal AM, Krobert KA, Brattelid T, Kaumann AJ, Levy FO: 5HT4(a) and 5-HT4(b) receptors have nearly identical pharmacology and are both expressed in human atrium and ventricle. Naunyn Schmiedebergs Arch Pharmacol. 2001 Feb;363(2):146-60. [PubMed:11218067 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Voltage-gated potassium channel activity
Specific Function:
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel.
Gene Name:
HTR3A
Uniprot ID:
P46098
Molecular Weight:
55279.835 Da
References
  1. Nagakura Y, Akuzawa S, Miyata K, Kamato T, Suzuki T, Ito H, Yamaguchi T: Pharmacological properties of a novel gastrointestinal prokinetic benzamide selective for human 5-HT4 receptor versus human 5-HT3 receptor. Pharmacol Res. 1999 May;39(5):375-82. [PubMed:10328995 ]
  2. Talley NJ: Review article: 5-hydroxytryptamine agonists and antagonists in the modulation of gastrointestinal motility and sensation: clinical implications. Aliment Pharmacol Ther. 1992 Jun;6(3):273-89. [PubMed:1600046 ]
  3. de Ridder WJ, Schuurkes JA: Cisapride and 5-hydroxytryptamine enhance motility in the canine antrum via separate pathways, not involving 5-hydroxytryptamine1,2,3,4 receptors. J Pharmacol Exp Ther. 1993 Jan;264(1):79-88. [PubMed:8093733 ]
  4. Haga N, Suzuki H, Shiba Y, Mochiki E, Mizumoto A, Itoh Z: Effect of TKS159, a novel 5-hydroxytryptamine4 agonist, on gastric contractile activity in conscious dogs. Neurogastroenterol Motil. 1998 Aug;10(4):295-303. [PubMed:9697104 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Virus receptor activity
Specific Function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular Weight:
52602.58 Da
References
  1. Nieto JE, Snyder JR, Kollias-Baker C, Stanley S: In vitro effects of 5-hydroxytryptamine and cisapride on the circular smooth muscle of the jejunum of horses. Am J Vet Res. 2000 Dec;61(12):1561-5. [PubMed:11131599 ]
  2. Cushing DJ, Cohen ML: Serotonin-induced contraction in porcine coronary artery: use of ergolines to support vascular 5-hydroxytryptamine2-receptor heterogeneity. J Pharmacol Exp Ther. 1993 Jan;264(1):193-200. [PubMed:8423526 ]
  3. Beubler E, Coupar IM, Hardcastle J, Hardcastle PT: Stimulatory effects of 5-hydroxytryptamine on fluid secretion and transmural potential difference in rat small intestine are mediated by different receptor subtypes. J Pharm Pharmacol. 1990 Jan;42(1):35-9. [PubMed:1969947 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function:
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoforms USO have no channel activity by themself, but modulates channel characteristics by forming heterotetramers with other isoforms which are r...
Gene Name:
KCNH2
Uniprot ID:
Q12809
Molecular Weight:
126653.52 Da
References
  1. Walker BD, Singleton CB, Bursill JA, Wyse KR, Valenzuela SM, Qiu MR, Breit SN, Campbell TJ: Inhibition of the human ether-a-go-go-related gene (HERG) potassium channel by cisapride: affinity for open and inactivated states. Br J Pharmacol. 1999 Sep;128(2):444-50. [PubMed:10510456 ]
  2. Chen J, Seebohm G, Sanguinetti MC: Position of aromatic residues in the S6 domain, not inactivation, dictates cisapride sensitivity of HERG and eag potassium channels. Proc Natl Acad Sci U S A. 2002 Sep 17;99(19):12461-6. Epub 2002 Sep 3. [PubMed:12209010 ]
  3. Lin J, Guo J, Gang H, Wojciechowski P, Wigle JT, Zhang S: Intracellular K+ is required for the inactivation-induced high-affinity binding of cisapride to HERG channels. Mol Pharmacol. 2005 Sep;68(3):855-65. Epub 2005 Jun 20. [PubMed:15967876 ]
  4. Perrio M, Voss S, Shakir SA: Application of the bradford hill criteria to assess the causality of cisapride-induced arrhythmia: a model for assessing causal association in pharmacovigilance. Drug Saf. 2007;30(4):333-46. [PubMed:17408310 ]
  5. Mohammad S, Zhou Z, Gong Q, January CT: Blockage of the HERG human cardiac K+ channel by the gastrointestinal prokinetic agent cisapride. Am J Physiol. 1997 Nov;273(5 Pt 2):H2534-8. [PubMed:9374794 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Pearce RE, Gotschall RR, Kearns GL, Leeder JS: Cytochrome P450 Involvement in the biotransformation of cisapride and racemic norcisapride in vitro: differential activity of individual human CYP3A isoforms. Drug Metab Dispos. 2001 Dec;29(12):1548-54. [PubMed:11717173 ]
  3. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxygen binding
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23