Cisapride

Identification

Summary

Cisapride is a medication used to treat heartburn associated with GERD.

Generic Name

Cisapride

DrugBank Accession Number

DB00604

Background

In many countries (including Canada) cisapride has been either withdrawn or has had its indications limited due to reports about long QT syndrome due to cisapride, which predisposes to arrhythmias.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.

Type

Small Molecule

Groups

Approved, Investigational, Withdrawn

Structure

Similar Structures

Weight: Average: 465.945
Monoisotopic: 465.183062343
Chemical Formula: C₂₃H₂₉ClFN₃O₄

Synonyms

Cisaprid
Cisaprida
Cisapride
Cisapridum

External IDs

R 51619
R-51,619
R-51619

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Pharmacology

Indication

For the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Treatment of	Gastrointestinal disorder		••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Cisapride is a parasympathomimetic which acts as a serotonin 5-HT₄ agonist; upon activation of the receptor signaling pathway, cisapride promotes the release of acetylcholine neurotransmitters in the enteric nervous system. Cisapride stimulates motility of the upper gastrointestinal tract without stimulating gastric, biliary, or pancreatic secretions. Cisapride increases the tone and amplitude of gastric (especially antral) contractions, relaxes the pyloric sphincter and the duodenal bulb, and increases peristalsis of the duodenum and jejunum resulting in accelerated gastric emptying and intestinal transit. It increases the resting tone of the lower esophageal sphincter. It has little, if any, effect on the motility of the colon or gallbladder. Cisapride does not induce muscarinic or nicotinic receptor stimulation, nor does it inhibit acetylcholinesterase activity.

Mechanism of action

Cisapride acts through the stimulation of the serotonin 5-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.

Target	Actions	Organism
A5-hydroxytryptamine receptor 4	agonist	Humans
A5-hydroxytryptamine receptor 3A	agonist	Humans
A5-hydroxytryptamine receptor 2A	agonist	Humans
UPotassium voltage-gated channel subfamily H member 2	inhibitor	Humans

Absorption

Cisapride is rapidly absorbed after oral administration, with an absolute bioavailability of 35-40%.

Volume of distribution

Not Available

Protein binding

97.5%

Metabolism

Hepatic. Extensively metabolized via cytochrome P450 3A4 enzyme.

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Cisapride

Route of elimination

Not Available

Half-life

6-12 hours

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of CNS depression can be increased when Cisapride is combined with 1,2-Benzodiazepine.
Abametapir	The serum concentration of Cisapride can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Cisapride can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be decreased when combined with Cisapride.
Abiraterone	The metabolism of Cisapride can be decreased when combined with Abiraterone.

Food Interactions

Avoid grapefruit products.
Exercise caution with St. John's Wort.
Take before a meal. Take at least 15 minutes before meals.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Cisapride monohydrate	VZV0A4I38W	260779-88-2	QBYYXIDJOFZORM-LBPAWUGGSA-N

International/Other Brands

Enteropride / Kinestase / Prepulsid (Janssen-Ortho) / Pridesia / Propulsid Quicksolv (Janssen-Ortho)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Prepulsid Sus 1mg/ml	Suspension	1 mg / mL	Oral	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1992-12-31	2000-08-25
Prepulsid Tab 10mg	Tablet	10 mg / tab	Oral	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1990-12-31	2000-08-25
Prepulsid Tab 20mg	Tablet	20 mg / tab	Oral	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1993-12-31	2000-08-25
Prepulsid Tab 5mg	Tablet	5 mg / tab	Oral	Janssen Pharmaceutica, Division Of Janssen Ortho Inc.	1990-12-31	2000-08-25
Propulsid	Tablet	10 mg/1	Oral	Ortho-McNeil-Janssen Pharmaceuticals, Inc.	1993-07-01	2000-07-01

Chemical Identifiers

UNII: UVL329170W
CAS number: 81098-60-4
InChI Key: DCSUBABJRXZOMT-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[C@H]1CN(CCCOC2=CC=C(F)C=C2)CC[C@H]1NC(=O)C1=CC(Cl)=C(N)C=C1OC

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

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. [Article]

External Links

Human Metabolome Database: HMDB0014742
KEGG Drug: D00274
KEGG Compound: C06910
PubChem Compound: 6917698
PubChem Substance: 46504980
ChemSpider: 5292927
BindingDB: 50462032
RxNav: 35255
ChEBI: 3720
ChEMBL: CHEMBL560739
ZINC: ZINC000003775140
Therapeutic Targets Database: DAP000222
PharmGKB: PA449011
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Cisapride

MSDS

Download (74.5 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Terminated	Treatment	Diabetes Mellitus / Gastroparesis	1
4	Terminated	Treatment	Gastroesophageal Reflux	1
4	Terminated	Treatment	Gastroparesis	1
4	Terminated	Treatment	Infants, Premature / Newborn Infants	1

Pharmacoeconomics

Manufacturers

Ortho mcneil janssen pharmaceuticals inc
Janssen pharmaceutica products lp

Packagers

Janssen-Ortho Inc.
Neuman Distributors Inc.
Ortho Mcneil Janssen Pharmaceutical Inc.
PD-Rx Pharmaceuticals Inc.
Pharmaceutical Utilization Management Program VA Inc.
Sandhills Packaging Inc.

Dosage Forms

Form	Route	Strength
Tablet	Oral
Granule, effervescent
Suspension	Oral
Tablet, orally disintegrating
Tablet, delayed release	Oral	10 mg
Suspension	Oral	0.1 g
Tablet	Oral	5 MG
Capsule, coated	Oral
Suspension	Oral	1 mg / mL
Tablet	Oral	10 mg / tab
Tablet	Oral	20 mg / tab
Tablet	Oral	5 mg / tab
Suspension	Oral	1 mg/1mL
Tablet	Oral	10 mg/1
Tablet	Oral	20 mg/1
Suspension	Oral	100 mg
Tablet	Oral	10 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US5648093	No	1997-07-15	2014-07-15

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	110 °C	Not Available
water solubility	2.71 mg/L	Not Available
logP	3.3	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.012 mg/mL	ALOGPS
logP	2.95	ALOGPS
logP	2.49	Chemaxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.58	Chemaxon
pKa (Strongest Basic)	8.24	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	86.05 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	122.93 m³·mol^-1	Chemaxon
Polarizability	49.11 Å³	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9666
Blood Brain Barrier	+	0.9383
Caco-2 permeable	+	0.5835
P-glycoprotein substrate	Substrate	0.8103
P-glycoprotein inhibitor I	Inhibitor	0.5422
P-glycoprotein inhibitor II	Inhibitor	0.5
Renal organic cation transporter	Non-inhibitor	0.5978
CYP450 2C9 substrate	Non-substrate	0.8718
CYP450 2D6 substrate	Substrate	0.8918
CYP450 3A4 substrate	Substrate	0.7375
CYP450 1A2 substrate	Non-inhibitor	0.6912
CYP450 2C9 inhibitor	Non-inhibitor	0.8868
CYP450 2D6 inhibitor	Inhibitor	0.8933
CYP450 2C19 inhibitor	Non-inhibitor	0.8269
CYP450 3A4 inhibitor	Inhibitor	0.7959
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.524
Ames test	Non AMES toxic	0.6505
Carcinogenicity	Non-carcinogens	0.8915
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.0806 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.8918
hERG inhibition (predictor II)	Inhibitor	0.8616

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001i-2922000000-0772f474daac82b426ee
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-001i-0980000000-a0df861122e90da3494b
MS/MS Spectrum - , positive	LC-MS/MS	splash10-001i-0980000000-a0df861122e90da3494b
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0159-0710900000-262b97df953edaab4cfa
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-014i-0000900000-85054d507294174b3bfd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0159-0112900000-945edc67b96fb94ff1eb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03di-0000900000-0ac547ef429c39b3512c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-02u9-1913300000-15624ce8328f4233c984
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03e9-2212900000-81aa834cf4012bfdbdb6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-01q9-7727900000-5d3408124dbe15ed51e7
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	212.8542501	predicted	DarkChem Lite v0.1.0
[M-H]-	216.5452501	predicted	DarkChem Lite v0.1.0
[M-H]-	202.1925	predicted	DeepCCS 1.0 (2019)
[M+H]+	211.8588501	predicted	DarkChem Lite v0.1.0
[M+H]+	217.1472501	predicted	DarkChem Lite v0.1.0
[M+H]+	204.55049	predicted	DeepCCS 1.0 (2019)
[M+Na]+	212.3624501	predicted	DarkChem Lite v0.1.0
[M+Na]+	216.6602501	predicted	DarkChem Lite v0.1.0
[M+Na]+	210.64363	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	14.3	N/A	N/A	A7835
Ki (nM)	29	N/A	N/A	A27846

Details1. 5-hydroxytryptamine receptor 4

Kind: Protein
Organism: Humans
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 ...
Gene Name: HTR4
Uniprot ID: Q13639
Uniprot Name: 5-hydroxytryptamine receptor 4
Molecular Weight: 43760.975 Da

References

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	152	N/A	N/A	A28656

Details2. 5-hydroxytryptamine receptor 3A

Kind: Protein
Organism: Humans
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-gate...
Gene Name: HTR3A
Uniprot ID: P46098
Uniprot Name: 5-hydroxytryptamine receptor 3A
Molecular Weight: 55279.835 Da

References

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. [Article]
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. [Article]
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. [Article]
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. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	10.2	N/A	N/A	A27825

Details3. 5-hydroxytryptamine receptor 2A

Kind: Protein
Organism: Humans
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-iodop...
Gene Name: HTR2A
Uniprot ID: P28223
Uniprot Name: 5-hydroxytryptamine receptor 2A
Molecular Weight: 52602.58 Da

References

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. [Article]
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. [Article]
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. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	6.5	N/A	N/A	A27426 / A27847
IC 50 (nM)	45	N/A	N/A	A27427
IC 50 (nM)	47	N/A	N/A	A27846
IC 50 (nM)	40	N/A	N/A	A18337
IC 50 (nM)	39.81	N/A	N/A	A27428 / A27431
IC 50 (nM)	6.46	N/A	N/A	A27432
IC 50 (nM)	10	N/A	N/A	A27850
IC 50 (nM)	6.7	N/A	N/A	A27851
IC 50 (nM)	6.76	N/A	N/A	A27558

Details4. Potassium voltage-gated channel subfamily H member 2

Kind: Protein
Organism: Humans
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 ...
Gene Name: KCNH2
Uniprot ID: Q12809
Uniprot Name: Potassium voltage-gated channel subfamily H member 2
Molecular Weight: 126653.52 Da

References

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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]

Enzymes

Details1. Cytochrome P450 2A6

Kind: Protein
Organism: Humans
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. Const...
Gene Name: CYP2A6
Uniprot ID: P11509
Uniprot Name: Cytochrome P450 2A6
Molecular Weight: 56501.005 Da

References

Bohets H, Lavrijsen K, Hendrickx J, van Houdt J, van Genechten V, Verboven P, Meuldermans W, Heykants J: Identification of the cytochrome P450 enzymes involved in the metabolism of cisapride: in vitro studies of potential co-medication interactions. Br J Pharmacol. 2000 Apr;129(8):1655-67. doi: 10.1038/sj.bjp.0703246. [Article]
Di YM, Chow VD, Yang LP, Zhou SF: Structure, function, regulation and polymorphism of human cytochrome P450 2A6. Curr Drug Metab. 2009 Sep;10(7):754-80. [Article]

Details2. Cytochrome P450 2B6

Kind: Protein
Organism: Humans
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 un...
Gene Name: CYP2B6
Uniprot ID: P20813
Uniprot Name: Cytochrome P450 2B6
Molecular Weight: 56277.81 Da

References

Desta Z, Soukhova N, Mahal SK, Flockhart DA: Interaction of cisapride with the human cytochrome P450 system: metabolism and inhibition studies. Drug Metab Dispos. 2000 Jul;28(7):789-800. [Article]

Details3. Cytochrome P450 2C19

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

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 im...
Gene Name: CYP2C19
Uniprot ID: P33261
Uniprot Name: Cytochrome P450 2C19
Molecular Weight: 55930.545 Da

References

Bohets H, Lavrijsen K, Hendrickx J, van Houdt J, van Genechten V, Verboven P, Meuldermans W, Heykants J: Identification of the cytochrome P450 enzymes involved in the metabolism of cisapride: in vitro studies of potential co-medication interactions. Br J Pharmacol. 2000 Apr;129(8):1655-67. doi: 10.1038/sj.bjp.0703246. [Article]
Desta Z, Soukhova N, Mahal SK, Flockhart DA: Interaction of cisapride with the human cytochrome P450 system: metabolism and inhibition studies. Drug Metab Dispos. 2000 Jul;28(7):789-800. [Article]
Andersson T, Hassan-Alin M, Hasselgren G, Rohss K: Drug interaction studies with esomeprazole, the (S)-isomer of omeprazole. Clin Pharmacokinet. 2001;40(7):523-37. doi: 10.2165/00003088-200140070-00004. [Article]

Details4. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
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 un...
Gene Name: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

References

Desta Z, Soukhova N, Mahal SK, Flockhart DA: Interaction of cisapride with the human cytochrome P450 system: metabolism and inhibition studies. Drug Metab Dispos. 2000 Jul;28(7):789-800. [Article]

Details5. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor
Curator comments: This enzyme inhibition is weak and unlikely to cause clinically significant changes.

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 un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Bohets H, Lavrijsen K, Hendrickx J, van Houdt J, van Genechten V, Verboven P, Meuldermans W, Heykants J: Identification of the cytochrome P450 enzymes involved in the metabolism of cisapride: in vitro studies of potential co-medication interactions. Br J Pharmacol. 2000 Apr;129(8):1655-67. doi: 10.1038/sj.bjp.0703246. [Article]

Details6. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
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...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Desta Z, Soukhova N, Mahal SK, Flockhart DA: Interaction of cisapride with the human cytochrome P450 system: metabolism and inhibition studies. Drug Metab Dispos. 2000 Jul;28(7):789-800. [Article]

Details7. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

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 react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

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. [Article]
Michalets EL, Williams CR: Drug interactions with cisapride: clinical implications. Clin Pharmacokinet. 2000 Jul;39(1):49-75. doi: 10.2165/00003088-200039010-00004. [Article]
Lowry JA, Kearns GL, Abdel-Rahman SM, Nafziger AN, Khan IS, Kashuba AD, Schuetz EG, Bertino JS Jr, van den Anker JN, Leeder JS: Cisapride: a potential model substrate to assess cytochrome P4503A4 activity in vivo. Clin Pharmacol Ther. 2003 Mar;73(3):209-22. doi: 10.1067/mcp.2003.29. [Article]
Zhou S, Yung Chan S, Cher Goh B, Chan E, Duan W, Huang M, McLeod HL: Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin Pharmacokinet. 2005;44(3):279-304. doi: 10.2165/00003088-200544030-00005. [Article]
Flockhart Table of Drug Interactions [Link]

Details8. Cytochrome P450 3A5

Kind: Protein
Organism: Humans
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 un...
Gene Name: CYP3A5
Uniprot ID: P20815
Uniprot Name: Cytochrome P450 3A5
Molecular Weight: 57108.065 Da

References

Desta Z, Soukhova N, Mahal SK, Flockhart DA: Interaction of cisapride with the human cytochrome P450 system: metabolism and inhibition studies. Drug Metab Dispos. 2000 Jul;28(7):789-800. [Article]
Flockhart Table of Drug Interactions [Link]

Details9. Cytochrome P450 3A7

Kind: Protein
Organism: Humans
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 un...
Gene Name: CYP3A7
Uniprot ID: P24462
Uniprot Name: Cytochrome P450 3A7
Molecular Weight: 57525.03 Da

References

Desta Z, Soukhova N, Mahal SK, Flockhart DA: Interaction of cisapride with the human cytochrome P450 system: metabolism and inhibition studies. Drug Metab Dispos. 2000 Jul;28(7):789-800. [Article]
Flockhart Table of Drug Interactions [Link]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 07:00

Cisapride

Identification

Structure for Cisapride (DB00604)

Pharmacology

Interactions

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

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Enzymes

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