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In many countries (including Canada) cisapride has been either withdrawn or has had its indications limited due to reports about long QT syndrome due to cisapride, which predisposes to arrhythmias.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Approved, Investigational, Withdrawn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
Weight
Average: 465.945
Monoisotopic: 465.183062343
Chemical Formula
C23H29ClFN3O4
Synonyms
  • Cisaprid
  • Cisaprida
  • Cisapride
  • Cisapridum
External IDs
  • R 51619
  • R-51,619
  • R-51619

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofGastrointestinal 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.

TargetActionsOrganism
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.

Hover over products below to view reaction partners

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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Cisapride is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Cisapride can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Cisapride can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Cisapride.
AbirateroneThe 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
IngredientUNIICASInChI Key
Cisapride monohydrateVZV0A4I38W260779-88-2QBYYXIDJOFZORM-LBPAWUGGSA-N
International/Other Brands
Enteropride / Kinestase / Prepulsid (Janssen-Ortho) / Pridesia / Propulsid Quicksolv (Janssen-Ortho)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Prepulsid Sus 1mg/mlSuspension1 mg / mLOralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1992-12-312000-08-25Canada flag
Prepulsid Tab 10mgTablet10 mg / tabOralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1990-12-312000-08-25Canada flag
Prepulsid Tab 20mgTablet20 mg / tabOralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1993-12-312000-08-25Canada flag
Prepulsid Tab 5mgTablet5 mg / tabOralJanssen Pharmaceutica, Division Of Janssen Ortho Inc.1990-12-312000-08-25Canada flag
PropulsidTablet10 mg/1OralOrtho-McNeil-Janssen Pharmaceuticals, Inc.1993-07-012000-07-01US flag

Categories

ATC Codes
A03FA02 — Cisapride
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Aminobenzamides
Alternative Parents
3-halobenzoic acids and derivatives / Aminophenyl ethers / Benzamides / Methoxyanilines / Anisoles / Phenoxy compounds / Benzoyl derivatives / Methoxybenzenes / Alkyl aryl ethers / Chlorobenzenes
show 15 more
Substituents
3-halobenzoic acid or derivatives / Alkyl aryl ether / Amine / Amino acid or derivatives / Aminobenzamide / Aminophenyl ether / Aniline or substituted anilines / Anisole / Aromatic heteromonocyclic compound / Aryl chloride
show 33 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, organofluorine compound, aromatic ether, substituted aniline, benzamides, monochlorobenzenes (CHEBI:3720)
Affected organisms
  • Humans and other mammals

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
  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. [Article]
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);">
PhaseStatusPurposeConditionsCount
4TerminatedTreatmentDiabetes Mellitus / Gastroparesis1
4TerminatedTreatmentGastroesophageal Reflux1
4TerminatedTreatmentGastroparesis1
4TerminatedTreatmentInfants, Premature / Newborn Infants1

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
FormRouteStrength
TabletOral
Granule, effervescent
SuspensionOral
Tablet, orally disintegrating
Tablet, delayed releaseOral10 mg
SuspensionOral0.1 g
TabletOral5 MG
Capsule, coatedOral
SuspensionOral1 mg / mL
TabletOral10 mg / tab
TabletOral20 mg / tab
TabletOral5 mg / tab
SuspensionOral1 mg/1mL
TabletOral10 mg/1
TabletOral20 mg/1
SuspensionOral100 mg
TabletOral10 mg
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5648093No1997-07-152014-07-15US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)110 °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 RuleNoChemaxon
MDDR-like RuleYesChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001i-2922000000-0772f474daac82b426ee
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-001i-0980000000-a0df861122e90da3494b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0980000000-a0df861122e90da3494b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0159-0710900000-262b97df953edaab4cfa
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-85054d507294174b3bfd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0159-0112900000-945edc67b96fb94ff1eb
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0000900000-0ac547ef429c39b3512c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02u9-1913300000-15624ce8328f4233c984
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03e9-2212900000-81aa834cf4012bfdbdb6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-7727900000-5d3408124dbe15ed51e7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[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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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
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
  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. [Article]
  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. [Article]
  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. [Article]
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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Enzymes

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
  1. 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]
  2. 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]
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
  1. 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]
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
  1. 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]
  2. 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]
  3. 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]
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
  1. 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]
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
  1. 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]
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
  1. 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]
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
  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. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. Flockhart Table of Drug Interactions [Link]
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
  1. 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]
  2. Flockhart Table of Drug Interactions [Link]
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
  1. 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]
  2. Flockhart Table of Drug Interactions [Link]

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