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Identification
NameCisapride
Accession NumberDB00604  (APRD00454)
TypeSmall Molecule
GroupsApproved, Investigational, Withdrawn
Description

In many countries (including Canada) cisapride has been either withdrawn or has had its indications limited due to reports about long QT syndrome due to cisapride, which predisposes to arrhythmias.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

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 KeyInChIKey=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[[email protected]]1CN(CCCOC2=CC=C(F)C=C2)CC[[email protected]]1NC(=O)C1=CC(Cl)=C(N)C=C1OC
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
Pharmacology
IndicationFor the symptomatic treatment of adult patients with nocturnal heartburn due to gastroesophageal reflux disease.
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.
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
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
SpectraNot Available
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)
Interactions
Drug Interactions
Drug
AmitriptylineAmitriptyline may increase the arrhythmogenic activities of Cisapride.
AprepitantThe serum concentration of Cisapride can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Cisapride can be increased when it is combined with Atazanavir.
BatimastatThe serum concentration of Cisapride can be increased when it is combined with Batimastat.
BepridilCisapride may increase the QTc-prolonging activities of Bepridil.
BicalutamideThe serum concentration of Cisapride can be increased when it is combined with Bicalutamide.
BoceprevirThe serum concentration of Cisapride can be increased when it is combined with Boceprevir.
CimetidineThe serum concentration of Cisapride can be increased when it is combined with Cimetidine.
CitalopramCitalopram may increase the QTc-prolonging activities of Cisapride.
ClarithromycinThe metabolism of Cisapride can be decreased when combined with Clarithromycin.
CobicistatThe serum concentration of Cisapride can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Cisapride can be increased when it is combined with Conivaptan.
DarunavirThe serum concentration of Cisapride can be increased when it is combined with Darunavir.
DofetilideDofetilide may increase the QTc-prolonging activities of Cisapride.
ErythromycinThe metabolism of Cisapride can be decreased when combined with Erythromycin.
EthanolThe risk or severity of adverse effects can be increased when Cisapride is combined with Ethanol.
FluconazoleThe serum concentration of Cisapride can be increased when it is combined with Fluconazole.
FosamprenavirThe serum concentration of Cisapride can be increased when it is combined with Fosamprenavir.
FosaprepitantThe serum concentration of Cisapride can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Cisapride can be increased when it is combined with Fusidic Acid.
GoserelinGoserelin may increase the QTc-prolonging activities of Cisapride.
IdelalisibThe serum concentration of Cisapride can be increased when it is combined with Idelalisib.
IndinavirThe serum concentration of Cisapride can be increased when it is combined with Indinavir.
IsoflurophateThe serum concentration of Cisapride can be increased when it is combined with Isoflurophate.
ItraconazoleThe serum concentration of Cisapride can be increased when it is combined with Itraconazole.
IvabradineIvabradine may increase the QTc-prolonging activities of Cisapride.
IvacaftorThe serum concentration of Cisapride can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Cisapride can be increased when it is combined with Ketoconazole.
LeuprolideLeuprolide may increase the QTc-prolonging activities of Cisapride.
LuliconazoleThe serum concentration of Cisapride can be increased when it is combined with Luliconazole.
MifepristoneMifepristone may increase the QTc-prolonging activities of Cisapride.
NefazodoneThe serum concentration of Cisapride can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Cisapride can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of Cisapride can be increased when it is combined with Netupitant.
NifedipineThe serum concentration of Nifedipine can be increased when it is combined with Cisapride.
OctreotideOctreotide may increase the QTc-prolonging activities of Cisapride.
PalbociclibThe serum concentration of Cisapride can be increased when it is combined with Palbociclib.
PosaconazoleThe serum concentration of Cisapride can be increased when it is combined with Posaconazole.
ProcyclidineThe therapeutic efficacy of Cisapride can be decreased when used in combination with Procyclidine.
ProtriptylineProtriptyline may increase the arrhythmogenic activities of Cisapride.
RitonavirThe serum concentration of Cisapride can be increased when it is combined with Ritonavir.
SaquinavirThe serum concentration of Cisapride can be increased when it is combined with Saquinavir.
SimeprevirThe serum concentration of Cisapride can be increased when it is combined with Simeprevir.
StiripentolThe serum concentration of Cisapride can be increased when it is combined with Stiripentol.
TelaprevirThe serum concentration of Cisapride can be increased when it is combined with Telaprevir.
TelithromycinThe metabolism of Cisapride can be decreased when combined with Telithromycin.
TipranavirThe serum concentration of Cisapride can be increased when it is combined with Tipranavir.
VoriconazoleThe serum concentration of Cisapride can be increased when it is combined with Voriconazole.
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.

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 January 20, 2014 13:45