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Identification
NameMephenytoin
Accession NumberDB00532  (APRD00512)
TypeSmall Molecule
GroupsInvestigational, Withdrawn
DescriptionMephenytoin is used for the treatment of refractory partial epilepsy. Mephenytoin is a solid. This compound belongs to the phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Mephenytoin is known to target sodium channel protein type 5 subunit alpha. Cytochrome P450 2C19, Cytochrome P450 2C8, Cytochrome P450 2C9, Cytochrome P450 2B6, Cytochrome P450 1A2, and Cytochrome P450 2D6 are known to metabolize mephenytoin. Mephenytoin is a hydantoin-derivative anticonvulsant used to control various partial seizures. Mephenytoin and oxazolidinedione derivatives are associated with higher incidences of blood dyscrasias compared to other anticonvulsants. It is still studied largely because of its interesting hydroxylation polymorphism.
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MesantoinNovartis
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIR420KW629U
CAS number50-12-4
WeightAverage: 218.2518
Monoisotopic: 218.105527702
Chemical FormulaC12H14N2O2
InChI KeyGMHKMTDVRCWUDX-UHFFFAOYSA-N
InChI
InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16)
IUPAC Name
5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
SMILES
CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1
Pharmacology
IndicationFor the treatment of refractory partial epilepsy.
Structured Indications Not Available
PharmacodynamicsMephenytoin is an antiepileptic drug which can be useful in the treatment of epilepsy. The primary site of action appears to be the motor cortex where spread of seizure activity is inhibited. Possibly by promoting sodium efflux from neurons, mephenytoin tends to stabilize the threshold against hyperexcitability caused by excessive stimulation or environmental changes capable of reducing membrane sodium gradient. This includes the reduction of posttetanic potentiation at synapses. Loss of posttetanic potentiation prevents cortical seizure foci from detonating adjacent cortical areas. Mephenytoin reduces the maximal activity of brain stem centers responsible for the tonic phase of tonic-clonic (grand mal) seizures.
Mechanism of actionThe mechanism of action of mephenytoin is not definitely known, but extensive research strongly suggests that its main mechanism is to block frequency-, use- and voltage-dependent neuronal sodium channels, and therefore limit repetitive firing of action potentials.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sodium channel protein type 5 subunit alphaProteinyes
inhibitor
HumanQ14524 details
Related Articles
AbsorptionNot Available
Volume of distribution
  • 1.4 L/kg
Protein bindingNot Available
Metabolism
SubstrateEnzymesProduct
Mephenytoin
NirvanolDetails
Mephenytoin
S-4-HydroxymephenytoinDetails
Mephenytoin
S-NirvanolDetails
Route of eliminationNot Available
Half lifeApproximately 7 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated Effects
Interacting Gene/EnzymeSNP RS IDAllele nameDefining changeEffectReference(s)
Cytochrome P450 2C19
Gene symbol: CYP2C19
UniProt: P33261
rs4986893 CYP2C19*3A Allele, homozygotePoor metabolizer, lower dose requirement7969038
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Mephenytoin can be increased when it is combined with Abiraterone.Approved
AmiodaroneThe metabolism of Mephenytoin can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe metabolism of Mephenytoin can be increased when combined with Aprepitant.Approved, Investigational
ArmodafinilThe metabolism of Mephenytoin can be decreased when combined with Armodafinil.Approved, Investigational
ArtemetherThe metabolism of Mephenytoin can be decreased when combined with Artemether.Approved
AtomoxetineThe metabolism of Mephenytoin can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Mephenytoin can be decreased when combined with Azithromycin.Approved
BetaxololThe metabolism of Mephenytoin can be decreased when combined with Betaxolol.Approved
BortezomibThe metabolism of Mephenytoin can be decreased when combined with Bortezomib.Approved, Investigational
BupropionThe metabolism of Mephenytoin can be decreased when combined with Bupropion.Approved
CaffeineThe metabolism of Mephenytoin can be decreased when combined with Caffeine.Approved
CapecitabineThe metabolism of Mephenytoin can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Mephenytoin can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Mephenytoin can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Mephenytoin can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Mephenytoin can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineThe metabolism of Mephenytoin can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Mephenytoin can be decreased when combined with Chlorpromazine.Approved, Vet Approved
CholecalciferolThe metabolism of Mephenytoin can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Mephenytoin.Approved
CimetidineThe metabolism of Mephenytoin can be decreased when combined with Cimetidine.Approved
CinacalcetThe metabolism of Mephenytoin can be decreased when combined with Cinacalcet.Approved
CitalopramThe metabolism of Mephenytoin can be decreased when combined with Citalopram.Approved
ClemastineThe metabolism of Mephenytoin can be decreased when combined with Clemastine.Approved
ClobazamThe metabolism of Mephenytoin can be decreased when combined with Clobazam.Approved, Illicit
ClomipramineThe metabolism of Mephenytoin can be decreased when combined with Clomipramine.Approved, Vet Approved
ClopidogrelThe metabolism of Mephenytoin can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Mephenytoin can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Mephenytoin can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Mephenytoin can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Mephenytoin can be decreased when combined with Cocaine.Approved, Illicit
CrizotinibThe metabolism of Mephenytoin can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Mephenytoin can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Mephenytoin can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Mephenytoin can be decreased when it is combined with Dabrafenib.Approved
DarifenacinThe metabolism of Mephenytoin can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Mephenytoin can be increased when it is combined with Darunavir.Approved
DeferasiroxThe serum concentration of Mephenytoin can be increased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Mephenytoin can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Mephenytoin can be decreased when combined with Desipramine.Approved
DiphenhydramineThe metabolism of Mephenytoin can be decreased when combined with Diphenhydramine.Approved
DoxorubicinThe metabolism of Mephenytoin can be decreased when combined with Doxorubicin.Approved, Investigational
DronedaroneThe metabolism of Mephenytoin can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Mephenytoin can be decreased when combined with Duloxetine.Approved
EfavirenzThe metabolism of Mephenytoin can be decreased when combined with Efavirenz.Approved, Investigational
EliglustatThe metabolism of Mephenytoin can be decreased when combined with Eliglustat.Approved
Eslicarbazepine acetateThe metabolism of Mephenytoin can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Mephenytoin can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe metabolism of Mephenytoin can be decreased when combined with Etravirine.Approved
FelodipineThe metabolism of Mephenytoin can be decreased when combined with Felodipine.Approved, Investigational
FloxuridineThe metabolism of Mephenytoin can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Mephenytoin can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Mephenytoin can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Mephenytoin can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe metabolism of Mephenytoin can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Mephenytoin can be decreased when combined with Fluvoxamine.Approved, Investigational
FosphenytoinThe metabolism of Mephenytoin can be increased when combined with Fosphenytoin.Approved
GemfibrozilThe metabolism of Mephenytoin can be decreased when combined with Gemfibrozil.Approved
HaloperidolThe metabolism of Mephenytoin can be decreased when combined with Haloperidol.Approved
ImipramineThe metabolism of Mephenytoin can be decreased when combined with Imipramine.Approved
IndinavirThe metabolism of Mephenytoin can be decreased when combined with Indinavir.Approved
IrbesartanThe metabolism of Mephenytoin can be decreased when combined with Irbesartan.Approved, Investigational
IsoniazidThe metabolism of Mephenytoin can be decreased when combined with Isoniazid.Approved
KetoconazoleThe metabolism of Mephenytoin can be decreased when combined with Ketoconazole.Approved, Investigational
LapatinibThe metabolism of Mephenytoin can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideThe metabolism of Mephenytoin can be decreased when combined with Leflunomide.Approved, Investigational
LidocaineThe metabolism of Mephenytoin can be decreased when combined with Lidocaine.Approved, Vet Approved
LopinavirThe metabolism of Mephenytoin can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Mephenytoin can be decreased when combined with Lorcaserin.Approved
LosartanThe metabolism of Mephenytoin can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Mephenytoin can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Mephenytoin can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Mephenytoin can be increased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Mephenytoin can be decreased when combined with Lumefantrine.Approved
MefloquineThe therapeutic efficacy of Mephenytoin can be decreased when used in combination with Mefloquine.Approved
MethadoneThe metabolism of Mephenytoin can be decreased when combined with Methadone.Approved
MethotrimeprazineThe metabolism of Mephenytoin can be decreased when combined with Methotrimeprazine.Approved
MetoprololThe metabolism of Mephenytoin can be decreased when combined with Metoprolol.Approved, Investigational
MexiletineThe metabolism of Mephenytoin can be decreased when combined with Mexiletine.Approved
MianserinThe therapeutic efficacy of Mephenytoin can be decreased when used in combination with Mianserin.Approved
MifepristoneThe serum concentration of Mephenytoin can be increased when it is combined with Mifepristone.Approved, Investigational
MirabegronThe metabolism of Mephenytoin can be decreased when combined with Mirabegron.Approved
MoclobemideThe metabolism of Mephenytoin can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Mephenytoin can be decreased when combined with Modafinil.Approved, Investigational
NelfinavirThe metabolism of Mephenytoin can be decreased when combined with Nelfinavir.Approved
NevirapineThe metabolism of Mephenytoin can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Mephenytoin can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Mephenytoin can be decreased when combined with Nilotinib.Approved, Investigational
OmeprazoleThe metabolism of Mephenytoin can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OrlistatThe serum concentration of Mephenytoin can be decreased when it is combined with Orlistat.Approved, Investigational
OsimertinibThe serum concentration of Mephenytoin can be decreased when it is combined with Osimertinib.Approved
PanobinostatThe serum concentration of Mephenytoin can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Mephenytoin can be decreased when combined with Pantoprazole.Approved
ParoxetineThe metabolism of Mephenytoin can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Mephenytoin can be decreased when it is combined with Peginterferon alfa-2b.Approved
PhenobarbitalThe metabolism of Mephenytoin can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Mephenytoin can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe metabolism of Mephenytoin can be decreased when combined with Pioglitazone.Approved, Investigational
PrimidoneThe metabolism of Mephenytoin can be increased when combined with Primidone.Approved, Vet Approved
PromazineThe metabolism of Mephenytoin can be decreased when combined with Promazine.Approved, Vet Approved
PyrimethamineThe metabolism of Mephenytoin can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe serum concentration of Mephenytoin can be increased when it is combined with Quazepam.Approved, Illicit
QuinidineThe metabolism of Mephenytoin can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Mephenytoin can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Mephenytoin can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe metabolism of Mephenytoin can be decreased when combined with Ranolazine.Approved, Investigational
RifampicinThe metabolism of Mephenytoin can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Mephenytoin can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Mephenytoin can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe metabolism of Mephenytoin can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Mephenytoin can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneThe metabolism of Mephenytoin can be decreased when combined with Rosiglitazone.Approved, Investigational
SecobarbitalThe metabolism of Mephenytoin can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Mephenytoin can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Mephenytoin can be decreased when combined with Sildenafil.Approved, Investigational
SimeprevirThe metabolism of Mephenytoin can be decreased when combined with Simeprevir.Approved
SorafenibThe metabolism of Mephenytoin can be decreased when combined with Sorafenib.Approved, Investigational
StiripentolThe metabolism of Mephenytoin can be decreased when combined with Stiripentol.Approved
SulfadiazineThe metabolism of Mephenytoin can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Mephenytoin can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Mephenytoin can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TamoxifenThe metabolism of Mephenytoin can be decreased when combined with Tamoxifen.Approved
TenofovirThe metabolism of Mephenytoin can be decreased when combined with Tenofovir.Approved, Investigational
TerbinafineThe metabolism of Mephenytoin can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TeriflunomideThe serum concentration of Mephenytoin can be decreased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Mephenytoin can be decreased when combined with Theophylline.Approved
ThioridazineThe metabolism of Mephenytoin can be decreased when combined with Thioridazine.Approved
ThiotepaThe metabolism of Mephenytoin can be decreased when combined with Thiotepa.Approved
TicagrelorThe metabolism of Mephenytoin can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Mephenytoin can be decreased when combined with Ticlopidine.Approved
TipranavirThe metabolism of Mephenytoin can be decreased when combined with Tipranavir.Approved, Investigational
TolbutamideThe metabolism of Mephenytoin can be decreased when combined with Tolbutamide.Approved
TopiramateThe metabolism of Mephenytoin can be decreased when combined with Topiramate.Approved
TranylcypromineThe metabolism of Mephenytoin can be decreased when combined with Tranylcypromine.Approved
TrimethoprimThe metabolism of Mephenytoin can be decreased when combined with Trimethoprim.Approved, Vet Approved
Valproic AcidThe metabolism of Mephenytoin can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Mephenytoin can be decreased when combined with Valsartan.Approved, Investigational
VemurafenibThe serum concentration of Mephenytoin can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Mephenytoin can be decreased when combined with Venlafaxine.Approved
VoriconazoleThe metabolism of Mephenytoin can be decreased when combined with Voriconazole.Approved, Investigational
ZafirlukastThe metabolism of Mephenytoin can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Mephenytoin can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesN03AB04N03AB54
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.1 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9771
Caco-2 permeable+0.6007
P-glycoprotein substrateNon-substrate0.5353
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8593
Renal organic cation transporterNon-inhibitor0.9017
CYP450 2C9 substrateNon-substrate0.7827
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.6645
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8812
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9185
Ames testNon AMES toxic0.8301
CarcinogenicityNon-carcinogens0.7739
BiodegradationNot ready biodegradable0.9654
Rat acute toxicity2.3788 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9518
hERG inhibition (predictor II)Non-inhibitor0.8827
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point135 °CPhysProp
water solubility1270 mg/LNot Available
logP1.69SANGSTER (1994)
pKa8.51TOMLINSON,E & HAFKENSCHEID,TL (1986)
Predicted Properties
PropertyValueSource
Water Solubility0.97 mg/mLALOGPS
logP1.64ALOGPS
logP1.67ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)11.18ChemAxon
pKa (Strongest Basic)-8.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.54 m3·mol-1ChemAxon
Polarizability22.67 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.17 KB)
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 phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentPhenylhydantoins
Alternative Parents
Substituents
  • 5-phenylhydantoin
  • Phenylimidazolidine
  • Ureide
  • Benzenoid
  • Monocyclic benzene moiety
  • Urea
  • Tertiary amine
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Voltage-gated sodium channel activity involved in sa node cell action potential
Specific Function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is respon...
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
References
  1. Lenkowski PW, Ko SH, Anderson JD, Brown ML, Patel MK: Block of human NaV1.5 sodium channels by novel alpha-hydroxyphenylamide analogues of phenytoin. Eur J Pharm Sci. 2004 Apr;21(5):635-44. [PubMed:15066664 ]
  2. Swadron SP, Rudis MI, Azimian K, Beringer P, Fort D, Orlinsky M: A comparison of phenytoin-loading techniques in the emergency department. Acad Emerg Med. 2004 Mar;11(3):244-52. [PubMed:15001403 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. 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 ]
  3. Zhang T, Zhu Y, Gunaratna C: Rapid and quantitative determination of metabolites from multiple cytochrome P450 probe substrates by gradient liquid chromatography-electrospray ionization-ion trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 25;780(2):371-9. [PubMed:12401364 ]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
  2. Lewis DF, Modi S, Dickins M: Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82. [PubMed:11996013 ]
  3. Heyn H, White RB, Stevens JC: Catalytic role of cytochrome P4502B6 in the N-demethylation of S-mephenytoin. Drug Metab Dispos. 1996 Sep;24(9):948-54. [PubMed:8886603 ]
  4. Source [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. Coller JK, Somogyi AA, Bochner F: Comparison of (S)-mephenytoin and proguanil oxidation in vitro: contribution of several CYP isoforms. Br J Clin Pharmacol. 1999 Aug;48(2):158-67. [PubMed:10417492 ]
  2. Koyama E, Chiba K, Tani M, Ishizaki T: Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210. [PubMed:9190854 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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. Koyama E, Chiba K, Tani M, Ishizaki T: Reappraisal of human CYP isoforms involved in imipramine N-demethylation and 2-hydroxylation: a study using microsomes obtained from putative extensive and poor metabolizers of S-mephenytoin and eleven recombinant human CYPs. J Pharmacol Exp Ther. 1997 Jun;281(3):1199-210. [PubMed:9190854 ]
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23