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Identification
NameEzetimibe
Accession NumberDB00973  (APRD00619)
TypeSmall Molecule
GroupsApproved
DescriptionEzetimibe is an anti-hyperlipidemic medication which is used to lower cholesterol levels. Specifically, it appears to bind to a critical mediator of cholesterol absorption, the Niemann-Pick C1-Like 1 (NPC1L1) protein on the gastrointestinal tract epithelial cells as well as in hepatocytes.
Structure
Thumb
Synonyms
Ezedoc
Ezetimiba
Ezetimibum
Ezetrol
Zetia
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ach-ezetimibeTablet10 mgOralAccord Healthcare Inc2014-09-17Not applicableCanada
Act EzetimibeTablet10 mgOralActavis Pharma Company2014-09-15Not applicableCanada
Bio-ezetimibeTablet10 mgOralBiomed Pharma2014-10-08Not applicableCanada
EzetimibeTablet10 mgOralSivem Pharmaceuticals Ulc2014-09-16Not applicableCanada
EzetimibeTablet10 mgOralSanis Health Inc2014-10-08Not applicableCanada
EzetimibeTablet10 mgOralPro Doc Limitee2014-09-17Not applicableCanada
EzetrolTablet10 mgOralMerck Canada Inc2003-06-15Not applicableCanada
Ipg-ezetimibeTablet10 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-ezetimibeTablet10 mgOralJamp Pharma Corporation2014-09-15Not applicableCanada
Mar-ezetimibeTablet10 mgOralMarcan Pharmaceuticals Inc2014-09-15Not applicableCanada
Mint-ezetimibeTablet10 mgOralMint Pharmaceuticals Inc2014-09-15Not applicableCanada
Mylan-ezetimibeTablet10 mgOralMylan Pharmaceuticals Ulc2014-09-15Not applicableCanada
PMS-ezetimibeTablet10 mgOralPharmascience Inc2014-09-15Not applicableCanada
Priva-ezetimibeTablet10 mgOralPharmapar Inc2014-09-15Not applicableCanada
Ran-ezetimibeTablet10 mgOralRanbaxy Pharmaceuticals Canada Inc.2014-09-15Not applicableCanada
Riva-ezetimibeTablet10 mgOralLaboratoire Riva Inc2014-09-15Not applicableCanada
Sandoz EzetimibeTablet10 mgOralSandoz Canada Incorporated2014-09-15Not applicableCanada
Teva-ezetimibeTablet10 mgOralTeva Canada Limited2014-09-15Not applicableCanada
ZetiaTablet10 mg/1OralMerck Sharp & Dohme Corp.2002-10-25Not applicableUs
ZetiaTablet10 mg/1OralRebel Distributors Corp2009-07-27Not applicableUs
ZetiaTablet10 mg/1OralPhysicians Total Care, Inc.2002-12-26Not applicableUs
ZetiaTablet10 mg/1OralAvera Mc Kennan Hospital2015-07-09Not applicableUs
ZetiaTablet10 mg/1OralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-19Not applicableUs
ZetiaTablet10 mg/1OralCardinal Health2009-07-27Not applicableUs
ZetiaTablet10 mg/1OralCardinal Health2011-07-29Not applicableUs
ZetiaTablet10 mg/1OralREMEDYREPACK INC.2013-10-04Not applicableUs
ZetiaTablet10 mg/1OralA S Medication Solutions2002-10-25Not applicableUs
ZetiaTablet10 mg/1OralCardinal Health2002-10-25Not applicableUs
ZetiaTablet10 mg/1OralA S Medication Solutions Llc2009-07-27Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ezetimibeTablet10 mgOralApotex Inc2014-09-23Not applicableCanada
EzetimibeTablet10 mg/1OralGlenmark Pharmaceuticals Inc., Usa2011-12-31Not applicableUs
EzetimibeTablet10 mg/1OralPar Pharmaceutical Inc2015-06-26Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EzedocNot Available
EzetibNot Available
ZientNot Available
Brand mixtures
NameLabellerIngredients
LiptruzetMerck Sharp & Dohme Corp.
VytorinRebel Distributors Corp
SaltsNot Available
Categories
UNIIEOR26LQQ24
CAS number163222-33-1
WeightAverage: 409.4252
Monoisotopic: 409.148949953
Chemical FormulaC24H21F2NO3
InChI KeyOLNTVTPDXPETLC-XPWALMASSA-N
InChI
InChI=1S/C24H21F2NO3/c25-17-5-1-15(2-6-17)22(29)14-13-21-23(16-3-11-20(28)12-4-16)27(24(21)30)19-9-7-18(26)8-10-19/h1-12,21-23,28-29H,13-14H2/t21-,22+,23-/m1/s1
IUPAC Name
(3R,4S)-1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-hydroxyphenyl)azetidin-2-one
SMILES
O[C@@H](CC[C@@H]1[[email protected]](N(C1=O)C1=CC=C(F)C=C1)C1=CC=C(O)C=C1)C1=CC=C(F)C=C1
Pharmacology
IndicationFor use as adjunctive therapy to diet for the reduction of elevated total-C, LDL-C, and Apo B in patients with primary (heterozygous familial and non-familial) hypercholesterolemia.
Structured Indications
PharmacodynamicsEzetimibe is in a class of lipid-lowering compounds that selectively inhibits the intestinal absorption of cholesterol and related phytosterols. Ezetimibe, administered alone is indicated as adjunctive therapy to diet for the reduction of elevated total-C, LDL-C, and Apo B in patients with primary (heterozygous familial and non-familial) hypercholesterolemia. It is also used in combination therapy with HMG-CoA reductase inhibitors. Ezetimibe has a mechanism of action that differs from those of other classes of cholesterol-reducing compounds (HMG-CoA reductase inhibitors, bile acid sequestrants, fibric acid derivatives, and plant stanols). Ezetimibe does not inhibit cholesterol synthesis in the liver, or increase bile acid excretion but instead localizes and appears to act at the brush border of the small intestine and inhibits the absorption of cholesterol, leading to a decrease in the delivery of intestinal cholesterol to the liver. This causes a reduction of hepatic cholesterol stores and an increase in clearance of cholesterol from the blood; this distinct mechanism is complementary to that of HMG-CoA reductase inhibitors.
Mechanism of actionEzetimibe localizes and appears to act at the brush border of the small intestine and inhibits the absorption of cholesterol. This leads to a decrease in the delivery of intestinal cholesterol to the liver.
TargetKindPharmacological actionActionsOrganismUniProt ID
Sterol O-acyltransferase 1Proteinyes
inhibitor
HumanP35610 details
Niemann-Pick C1-like protein 1Proteinyes
inhibitor
HumanQ9UHC9 details
Aminopeptidase NProteinunknown
other
HumanP15144 details
Related Articles
AbsorptionAfter oral administration, ezetimibe is absorbed and extensively conjugated to a pharmacologically active phenolic glucuronide (ezetimibe-glucuronide). When a single 10 mg dose of ezetimibe is given to a fasted, male, adult subject, the pharmacokinetic parameters are as follows: Cmax = 3.5 - 5.5 ng/mL; Tmax = 4- 12 hours. The pharmacokinetic parameters for ezetimibe-glucuronide are as follows: Cmax = 45 - 71 ng/mL; Tmax = 1-2 hours. Food has not impact on the extent of absorption of ezetimibe. However, Cmax increases by 38% with a high-fat meal.
Volume of distributionNot Available
Protein binding>90% bound to human plasma protein
Metabolism

Ezetimibe is primarily metabolized in the small intestine and liver via glucuronide conjugation (a phase II reaction) with subsequent biliary and renal excretion. In humans, ezetimibe is rapidly metabolized to ezetimibe-glucuronide.

Route of elimination78% of the dose is excreted into feces. 11% of the dose is excreted into urine. Ezetimibe was the major component in feces and accounted for 69% of the administered dose, while ezetimibe-glucuronide was the major component in urine and accounted for 9% of the administered dose.
Half life22 hours (both ezetimibe and ezetimibe-glucuronide).
ClearanceNot Available
ToxicityThe most common adverse reactions in the group of patients treated with ezetimibe that led to treatment discontinuation and occurred at a rate greater than placebo were, arthralgia (0.3%), dizziness (0.2%), and gamma-glutamyltransferase increase (0.2%).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetaminophenThe serum concentration of Ezetimibe can be increased when it is combined with Acetaminophen.Approved
AfatinibThe serum concentration of Ezetimibe can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Ezetimibe can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Ezetimibe can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Ezetimibe can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Ezetimibe can be increased when it is combined with Alfentanil.Approved, Illicit
AmantadineThe serum concentration of Ezetimibe can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Ezetimibe can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe serum concentration of Ezetimibe can be decreased when it is combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Ezetimibe can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Ezetimibe can be increased when it is combined with Amlodipine.Approved
AmprenavirThe serum concentration of Ezetimibe can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Ezetimibe can be increased when it is combined with Amsacrine.Approved
AstemizoleThe serum concentration of Ezetimibe can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe serum concentration of Ezetimibe can be increased when it is combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Ezetimibe can be increased when it is combined with Atenolol.Approved
AtorvastatinThe serum concentration of Ezetimibe can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Ezetimibe can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Ezetimibe can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Ezetimibe can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Ezetimibe can be increased when it is combined with Bepridil.Approved, Withdrawn
BezafibrateThe risk or severity of adverse effects can be increased when Bezafibrate is combined with Ezetimibe.Approved
BiperidenThe serum concentration of Ezetimibe can be increased when it is combined with Biperiden.Approved
BosutinibThe serum concentration of Ezetimibe can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Ezetimibe can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Ezetimibe can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Ezetimibe can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe serum concentration of Ezetimibe can be increased when it is combined with Cabazitaxel.Approved
CaffeineThe serum concentration of Ezetimibe can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Ezetimibe can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Ezetimibe can be increased when it is combined with Candesartan.Approved
CaptoprilThe serum concentration of Ezetimibe can be increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Ezetimibe can be decreased when it is combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Ezetimibe can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Ezetimibe can be increased when it is combined with Caspofungin.Approved
ChloroquineThe serum concentration of Ezetimibe can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Ezetimibe can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Ezetimibe can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Ezetimibe can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
CholesterolThe serum concentration of Ezetimibe can be increased when it is combined with Cholesterol.Experimental
CholestyramineCholestyramine can cause a decrease in the absorption of Ezetimibe resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Cholic AcidThe serum concentration of Ezetimibe can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Ezetimibe can be increased when it is combined with Cilazapril.Approved
CimetidineThe serum concentration of Ezetimibe can be decreased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Ezetimibe can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Ezetimibe can be increased when it is combined with Citalopram.Approved
ClarithromycinThe serum concentration of Ezetimibe can be increased when it is combined with Clarithromycin.Approved
ClofazimineThe serum concentration of Ezetimibe can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Ezetimibe can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe serum concentration of Ezetimibe can be decreased when it is combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Ezetimibe can be increased when it is combined with Cobicistat.Approved
ColchicineThe serum concentration of Ezetimibe can be increased when it is combined with Colchicine.Approved
ColesevelamColesevelam can cause a decrease in the absorption of Ezetimibe resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColestipolColestipol can cause a decrease in the absorption of Ezetimibe resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
ColforsinThe serum concentration of Ezetimibe can be increased when it is combined with Colforsin.Experimental
CrizotinibThe serum concentration of Ezetimibe can be increased when it is combined with Crizotinib.Approved
CyclophosphamideThe serum concentration of Ezetimibe can be increased when it is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Ezetimibe.Approved, Investigational, Vet Approved
CyclosporineThe serum concentration of Ezetimibe can be decreased when it is combined with Cyclosporine.Approved, Investigational, Vet Approved
DaclatasvirThe serum concentration of Ezetimibe can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Ezetimibe can be increased when it is combined with Dactinomycin.Approved
DasatinibThe serum concentration of Ezetimibe can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Ezetimibe can be decreased when it is combined with Daunorubicin.Approved
DesipramineThe serum concentration of Ezetimibe can be increased when it is combined with Desipramine.Approved
DesloratadineThe serum concentration of Ezetimibe can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Ezetimibe can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Ezetimibe can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Ezetimibe can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigoxinThe serum concentration of Ezetimibe can be decreased when it is combined with Digoxin.Approved
DihydroergotamineThe serum concentration of Ezetimibe can be increased when it is combined with Dihydroergotamine.Approved
DiltiazemThe serum concentration of Ezetimibe can be increased when it is combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Ezetimibe can be increased when it is combined with Dipyridamole.Approved
DoxazosinThe serum concentration of Ezetimibe can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Ezetimibe can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Ezetimibe can be decreased when it is combined with Doxorubicin.Approved, Investigational
DronabinolThe serum concentration of Ezetimibe can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe serum concentration of Ezetimibe can be increased when it is combined with Dronedarone.Approved
ElbasvirThe serum concentration of Ezetimibe can be increased when it is combined with Elbasvir.Approved
EltrombopagThe serum concentration of Ezetimibe can be increased when it is combined with Eltrombopag.Approved
EnalaprilThe serum concentration of Ezetimibe can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Ezetimibe can be increased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Ezetimibe can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Ezetimibe can be increased when it is combined with Ergotamine.Approved
ErythromycinThe serum concentration of Ezetimibe can be decreased when it is combined with Erythromycin.Approved, Vet Approved
EstramustineThe serum concentration of Ezetimibe can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Ezetimibe can be decreased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Ezetimibe can be decreased when it is combined with Estrone.Approved
EtoposideThe serum concentration of Ezetimibe can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Ezetimibe can be increased when it is combined with Etravirine.Approved
FelodipineThe serum concentration of Ezetimibe can be increased when it is combined with Felodipine.Approved, Investigational
FenofibrateThe risk or severity of adverse effects can be increased when Fenofibrate is combined with Ezetimibe.Approved
FentanylThe serum concentration of Ezetimibe can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Ezetimibe can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Ezetimibe can be increased when it is combined with Fidaxomicin.Approved
FluconazoleThe serum concentration of Ezetimibe can be increased when it is combined with Fluconazole.Approved
FluoxetineThe serum concentration of Ezetimibe can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Ezetimibe can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Ezetimibe can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Ezetimibe can be increased when it is combined with Flurazepam.Approved, Illicit
FluvoxamineThe serum concentration of Ezetimibe can be increased when it is combined with Fluvoxamine.Approved, Investigational
GefitinibThe serum concentration of Ezetimibe can be increased when it is combined with Gefitinib.Approved, Investigational
GemfibrozilThe risk or severity of adverse effects can be increased when Gemfibrozil is combined with Ezetimibe.Approved
GenisteinThe serum concentration of Ezetimibe can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Ezetimibe can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Ezetimibe can be increased when it is combined with Glycerol.Experimental
Gramicidin DThe serum concentration of Ezetimibe can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Ezetimibe can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolThe serum concentration of Ezetimibe can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Ezetimibe can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Ezetimibe can be increased when it is combined with Idelalisib.Approved
ImatinibThe serum concentration of Ezetimibe can be increased when it is combined with Imatinib.Approved
ImipramineThe serum concentration of Ezetimibe can be increased when it is combined with Imipramine.Approved
IndinavirThe serum concentration of Ezetimibe can be decreased when it is combined with Indinavir.Approved
IndomethacinThe serum concentration of Ezetimibe can be increased when it is combined with Indomethacin.Approved, Investigational
IsavuconazoniumThe serum concentration of Ezetimibe can be increased when it is combined with Isavuconazonium.Approved, Investigational
ItraconazoleThe serum concentration of Ezetimibe can be increased when it is combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Ezetimibe can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Ezetimibe can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Ezetimibe can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe serum concentration of Ezetimibe can be increased when it is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Ezetimibe can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Ezetimibe can be increased when it is combined with Lapatinib.Approved, Investigational
LevofloxacinThe serum concentration of Ezetimibe can be increased when it is combined with Levofloxacin.Approved, Investigational
LevothyroxineThe serum concentration of Ezetimibe can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Ezetimibe can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Ezetimibe can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Ezetimibe can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Ezetimibe can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Ezetimibe can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Ezetimibe can be increased when it is combined with Loperamide.Approved
LopinavirThe serum concentration of Ezetimibe can be increased when it is combined with Lopinavir.Approved
LoratadineThe serum concentration of Ezetimibe can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Ezetimibe can be increased when it is combined with Losartan.Approved
LovastatinThe serum concentration of Ezetimibe can be increased when it is combined with Lovastatin.Approved, Investigational
LumacaftorThe serum concentration of Ezetimibe can be decreased when it is combined with Lumacaftor.Approved
MaprotilineThe serum concentration of Ezetimibe can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Ezetimibe can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Ezetimibe can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Ezetimibe can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Ezetimibe can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Ezetimibe can be increased when it is combined with Methadone.Approved
MetoprololThe serum concentration of Ezetimibe can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Ezetimibe can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Ezetimibe can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Ezetimibe can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Ezetimibe can be decreased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Ezetimibe can be increased when it is combined with Mitomycin.Approved
MitoxantroneThe serum concentration of Ezetimibe can be decreased when it is combined with Mitoxantrone.Approved, Investigational
MorphineThe serum concentration of Ezetimibe can be increased when it is combined with Morphine.Approved, Investigational
NaltrexoneThe serum concentration of Ezetimibe can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Ezetimibe can be increased when it is combined with Naringenin.Experimental
NefazodoneThe serum concentration of Ezetimibe can be decreased when it is combined with Nefazodone.Approved, Withdrawn
NelfinavirThe serum concentration of Ezetimibe can be decreased when it is combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Ezetimibe can be increased when it is combined with Neostigmine.Approved, Vet Approved
NicardipineThe serum concentration of Ezetimibe can be increased when it is combined with Nicardipine.Approved
NifedipineThe serum concentration of Ezetimibe can be decreased when it is combined with Nifedipine.Approved
NilotinibThe serum concentration of Ezetimibe can be increased when it is combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Ezetimibe can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Ezetimibe can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Ezetimibe can be increased when it is combined with Nitrendipine.Approved
NorethisteroneThe serum concentration of Ezetimibe can be decreased when it is combined with Norethisterone.Approved
OmeprazoleThe serum concentration of Ezetimibe can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
P-NitrophenolThe serum concentration of Ezetimibe can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe serum concentration of Ezetimibe can be increased when it is combined with Paclitaxel.Approved, Vet Approved
Palmitic AcidThe serum concentration of Ezetimibe can be increased when it is combined with Palmitic Acid.Experimental
PantoprazoleThe serum concentration of Ezetimibe can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Ezetimibe can be increased when it is combined with Paroxetine.Approved, Investigational
PerindoprilThe serum concentration of Ezetimibe can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe serum concentration of Ezetimibe can be decreased when it is combined with Phenobarbital.Approved
PimozideThe serum concentration of Ezetimibe can be increased when it is combined with Pimozide.Approved
Platelet Activating FactorThe serum concentration of Ezetimibe can be decreased when it is combined with Platelet Activating Factor.Experimental
PonatinibThe serum concentration of Ezetimibe can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe serum concentration of Ezetimibe can be increased when it is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Ezetimibe can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Ezetimibe can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Ezetimibe can be increased when it is combined with Prednisone.Approved, Vet Approved
ProbenecidThe serum concentration of Ezetimibe can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Ezetimibe can be decreased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Ezetimibe can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Ezetimibe can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Ezetimibe can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Ezetimibe can be increased when it is combined with Protriptyline.Approved
QuercetinThe serum concentration of Ezetimibe can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Ezetimibe can be increased when it is combined with Quinacrine.Approved
QuinidineThe serum concentration of Ezetimibe can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Ezetimibe can be increased when it is combined with Quinine.Approved
RanitidineThe serum concentration of Ezetimibe can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Ezetimibe can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Ezetimibe can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Ezetimibe can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Ezetimibe can be decreased when it is combined with Reserpine.Approved
RifampicinThe serum concentration of Ezetimibe can be decreased when it is combined with Rifampicin.Approved
RilpivirineThe serum concentration of Ezetimibe can be increased when it is combined with Rilpivirine.Approved
RitonavirThe serum concentration of Ezetimibe can be decreased when it is combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Ezetimibe can be increased when it is combined with Rolapitant.Approved
SaquinavirThe serum concentration of Ezetimibe can be decreased when it is combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Ezetimibe can be increased when it is combined with Scopolamine.Approved
SelegilineThe serum concentration of Ezetimibe can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Ezetimibe can be increased when it is combined with Sertraline.Approved
SimeprevirThe serum concentration of Ezetimibe can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Ezetimibe can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Ezetimibe can be decreased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Ezetimibe can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Ezetimibe can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Ezetimibe can be decreased when it is combined with St. John's Wort.Nutraceutical
StaurosporineThe serum concentration of Ezetimibe can be increased when it is combined with Staurosporine.Experimental
StreptozocinThe serum concentration of Ezetimibe can be decreased when it is combined with Streptozocin.Approved
SulfinpyrazoneThe serum concentration of Ezetimibe can be increased when it is combined with Sulfinpyrazone.Approved
SumatriptanThe serum concentration of Ezetimibe can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Ezetimibe can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Ezetimibe can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Ezetimibe can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Ezetimibe can be decreased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Ezetimibe can be increased when it is combined with Taurocholic Acid.Experimental
TelmisartanThe serum concentration of Ezetimibe can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Ezetimibe can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Ezetimibe can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Ezetimibe can be increased when it is combined with Terfenadine.Withdrawn
TeriflunomideThe serum concentration of Ezetimibe can be increased when it is combined with Teriflunomide.Approved
TesmilifeneThe serum concentration of Ezetimibe can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Ezetimibe can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Ezetimibe can be increased when it is combined with Ticagrelor.Approved
TolvaptanThe serum concentration of Ezetimibe can be increased when it is combined with Tolvaptan.Approved
TrazodoneThe serum concentration of Ezetimibe can be decreased when it is combined with Trazodone.Approved, Investigational
TrifluoperazineThe serum concentration of Ezetimibe can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Ezetimibe can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Ezetimibe can be decreased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Ezetimibe can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Ezetimibe can be increased when it is combined with Troleandomycin.Approved
VenlafaxineThe serum concentration of Ezetimibe can be increased when it is combined with Venlafaxine.Approved
VerapamilThe serum concentration of Ezetimibe can be decreased when it is combined with Verapamil.Approved
VinblastineThe serum concentration of Ezetimibe can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Ezetimibe can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Ezetimibe can be increased when it is combined with Vinorelbine.Approved, Investigational
ZimelidineThe serum concentration of Ezetimibe can be increased when it is combined with Zimelidine.Withdrawn
Food Interactions
  • Take without regard to meals.
References
Synthesis Reference

Venkataraman Sundaram, Srinivasam Rajan, Vaddadi Ramayya, Sunkara Vardhan, Bulusu Subrahmanyam, Cheemalapati Sasikala, “Polymorphs of ezetimibe and process for preparation thereof.” U.S. Patent US20050171080, issued August 04, 2005.

US20050171080
General References
  1. Garcia-Calvo M, Lisnock J, Bull HG, Hawes BE, Burnett DA, Braun MP, Crona JH, Davis HR Jr, Dean DC, Detmers PA, Graziano MP, Hughes M, Macintyre DE, Ogawa A, O'neill KA, Iyer SP, Shevell DE, Smith MM, Tang YS, Makarewicz AM, Ujjainwalla F, Altmann SW, Chapman KT, Thornberry NA: The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1). Proc Natl Acad Sci U S A. 2005 Jun 7;102(23):8132-7. Epub 2005 May 31. [PubMed:15928087 ]
External Links
ATC CodesC10BA02C10BA05C10BA06C10AX09
AHFS Codes
  • 24:06.05
PDB EntriesNot Available
FDA labelDownload (321 KB)
MSDSDownload (281 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9899
Blood Brain Barrier+0.9074
Caco-2 permeable-0.5225
P-glycoprotein substrateNon-substrate0.6918
P-glycoprotein inhibitor INon-inhibitor0.6026
P-glycoprotein inhibitor IIInhibitor0.5306
Renal organic cation transporterNon-inhibitor0.8659
CYP450 2C9 substrateNon-substrate0.8244
CYP450 2D6 substrateNon-substrate0.7505
CYP450 3A4 substrateSubstrate0.5341
CYP450 1A2 substrateNon-inhibitor0.7013
CYP450 2C9 inhibitorNon-inhibitor0.6125
CYP450 2D6 inhibitorNon-inhibitor0.8442
CYP450 2C19 inhibitorNon-inhibitor0.5807
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5289
Ames testNon AMES toxic0.7476
CarcinogenicityNon-carcinogens0.8328
BiodegradationNot ready biodegradable0.9853
Rat acute toxicity2.4979 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9767
hERG inhibition (predictor II)Inhibitor0.5455
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Msp singapore co llc
Packagers
Dosage forms
FormRouteStrength
TabletOral10 mg
Tablet, film coatedOral
TabletOral
TabletOral10 mg/1
Prices
Unit descriptionCostUnit
Zetia 10 mg tablet5.15USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2172149 No2000-11-282014-09-14Canada
US5846966 No1993-09-212013-09-21Us
US5969156 Yes1997-01-082017-01-08Us
US7030106 Yes2002-07-252022-07-25Us
US7612058 Yes2006-04-302026-04-30Us
USRE37721 Yes1997-04-252017-04-25Us
USRE42461 Yes1997-04-252017-04-25Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point163°C FDA label
water solubilityInsoluble FDA label
logP4.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00846 mg/mLALOGPS
logP4.14ALOGPS
logP4.56ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area60.77 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity108.86 m3·mol-1ChemAxon
Polarizability41.64 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monobactams. These are compounds comprising beta-lactam ring is alone and not fused to another ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentMonobactams
Alternative Parents
Substituents
  • Monobactam
  • 2-phenylazetidine
  • 1-phenylazetidine
  • Phenol
  • Halobenzene
  • Fluorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl fluoride
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary alcohol
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Sterol o-acyltransferase activity
Specific Function:
Catalyzes the formation of fatty acid-cholesterol esters, which are less soluble in membranes than cholesterol. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:
SOAT1
Uniprot ID:
P35610
Molecular Weight:
64733.975 Da
References
  1. Singh A, Basit A, Banerjee UC: Burkholderia cenocepacia: a new biocatalyst for efficient bioreduction of ezetimibe intermediate. J Ind Microbiol Biotechnol. 2009 Nov;36(11):1369-74. doi: 10.1007/s10295-009-0622-z. Epub 2009 Aug 8. [PubMed:19669185 ]
  2. Costet P: Molecular pathways and agents for lowering LDL-cholesterol in addition to statins. Pharmacol Ther. 2010 Jun;126(3):263-78. doi: 10.1016/j.pharmthera.2010.02.006. Epub 2010 Mar 19. [PubMed:20227438 ]
  3. Wang HH, Portincasa P, Mendez-Sanchez N, Uribe M, Wang DQ: Effect of ezetimibe on the prevention and dissolution of cholesterol gallstones. Gastroenterology. 2008 Jun;134(7):2101-10. doi: 10.1053/j.gastro.2008.03.011. Epub 2008 Mar 10. [PubMed:18442485 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Rab gtpase binding
Specific Function:
Plays a major role in cholesterol homeostasis. Is critical for the uptake of cholesterol across the plasma membrane of the intestinal enterocyte. Is the direct molecular target of ezetimibe, a drug that inhibits cholesterol absorption. Lack of activity leads to multiple lipid transport defects. The protein may have a function in the transport of multiple lipids and their homeostasis, and may pl...
Gene Name:
NPC1L1
Uniprot ID:
Q9UHC9
Molecular Weight:
148726.52 Da
References
  1. Altmann SW, Davis HR Jr, Zhu LJ, Yao X, Hoos LM, Tetzloff G, Iyer SP, Maguire M, Golovko A, Zeng M, Wang L, Murgolo N, Graziano MP: Niemann-Pick C1 Like 1 protein is critical for intestinal cholesterol absorption. Science. 2004 Feb 20;303(5661):1201-4. [PubMed:14976318 ]
  2. Wang J, Williams CM, Hegele RA: Compound heterozygosity for two non-synonymous polymorphisms in NPC1L1 in a non-responder to ezetimibe. Clin Genet. 2005 Feb;67(2):175-7. [PubMed:15679830 ]
  3. Sudhop T, Lutjohann D, von Bergmann K: Sterol transporters: targets of natural sterols and new lipid lowering drugs. Pharmacol Ther. 2005 Mar;105(3):333-41. Epub 2004 Dec 9. [PubMed:15737409 ]
  4. Garcia-Calvo M, Lisnock J, Bull HG, Hawes BE, Burnett DA, Braun MP, Crona JH, Davis HR Jr, Dean DC, Detmers PA, Graziano MP, Hughes M, Macintyre DE, Ogawa A, O'neill KA, Iyer SP, Shevell DE, Smith MM, Tang YS, Makarewicz AM, Ujjainwalla F, Altmann SW, Chapman KT, Thornberry NA: The target of ezetimibe is Niemann-Pick C1-Like 1 (NPC1L1). Proc Natl Acad Sci U S A. 2005 Jun 7;102(23):8132-7. Epub 2005 May 31. [PubMed:15928087 ]
  5. von Bergmann K, Sudhop T, Lutjohann D: Cholesterol and plant sterol absorption: recent insights. Am J Cardiol. 2005 Jul 4;96(1A):10D-14D. [PubMed:15992510 ]
  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
unknown
Actions
other
General Function:
Zinc ion binding
Specific Function:
Broad specificity aminopeptidase. Plays a role in the final digestion of peptides generated from hydrolysis of proteins by gastric and pancreatic proteases. May play a critical role in the pathogenesis of cholesterol gallstone disease. May be involved in the metabolism of regulatory peptides of diverse cell types, responsible for the processing of peptide hormones, such as angiotensin III and I...
Gene Name:
ANPEP
Uniprot ID:
P15144
Molecular Weight:
109538.68 Da
References
  1. Kramer W, Girbig F, Corsiero D, Pfenninger A, Frick W, Jahne G, Rhein M, Wendler W, Lottspeich F, Hochleitner EO, Orso E, Schmitz G: Aminopeptidase N (CD13) is a molecular target of the cholesterol absorption inhibitor ezetimibe in the enterocyte brush border membrane. J Biol Chem. 2005 Jan 14;280(2):1306-20. Epub 2004 Oct 19. [PubMed:15494415 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naph...
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular Weight:
59590.91 Da
References
  1. Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]
  2. Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular Weight:
60337.835 Da
References
  1. Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]
  2. Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
Specific Function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidatio...
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular Weight:
61035.815 Da
References
  1. Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of ezetimibe (Zetia). Drug Metab Dispos. 2004 Mar;32(3):314-20. [PubMed:14977865 ]
  2. Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 Da
References
  1. Ghosal A, Hapangama N, Yuan Y, Achanfuo-Yeboah J, Iannucci R, Chowdhury S, Alton K, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of ezetimibe (Zetia). Drug Metab Dispos. 2004 Mar;32(3):314-20. [PubMed:14977865 ]
  2. Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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. Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94. [PubMed:15871634 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
References
  1. Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Organic anion transmembrane transporter activity
Specific Function:
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name:
ABCC2
Uniprot ID:
Q92887
Molecular Weight:
174205.64 Da
References
  1. Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]
  2. de Waart DR, Vlaming ML, Kunne C, Schinkel AH, Oude Elferink RP: Complex pharmacokinetic behavior of ezetimibe depends on abcc2, abcc3, and abcg2. Drug Metab Dispos. 2009 Aug;37(8):1698-702. doi: 10.1124/dmd.108.026146. Epub 2009 May 14. [PubMed:19443695 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. Oswald S, Nassif A, Modess C, Keiser M, Ulrich A, Runge D, Hanke U, Lutjohann D, Engel A, Weitschies W, Siegmund W: Drug interactions between the immunosuppressant tacrolimus and the cholesterol absorption inhibitor ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2011 Apr;89(4):524-8. doi: 10.1038/clpt.2011.4. Epub 2011 Mar 2. [PubMed:21368751 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein heterodimerization activity
Specific Function:
Transporter that appears to play an indispensable role in the selective transport of the dietary cholesterol in and out of the enterocytes and in the selective sterol excretion by the liver into bile.
Gene Name:
ABCG5
Uniprot ID:
Q9H222
Molecular Weight:
72503.02 Da
References
  1. Couture P, Lamarche B: Ezetimibe and bile acid sequestrants: impact on lipoprotein metabolism and beyond. Curr Opin Lipidol. 2013 Jun;24(3):227-32. doi: 10.1097/MOL.0b013e3283613a55. [PubMed:23571732 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Organic anion transmembrane transporter activity
Specific Function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes (By similarity).
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular Weight:
169341.14 Da
References
  1. de Waart DR, Vlaming ML, Kunne C, Schinkel AH, Oude Elferink RP: Complex pharmacokinetic behavior of ezetimibe depends on abcc2, abcc3, and abcg2. Drug Metab Dispos. 2009 Aug;37(8):1698-702. doi: 10.1124/dmd.108.026146. Epub 2009 May 14. [PubMed:19443695 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular Weight:
72313.47 Da
References
  1. de Waart DR, Vlaming ML, Kunne C, Schinkel AH, Oude Elferink RP: Complex pharmacokinetic behavior of ezetimibe depends on abcc2, abcc3, and abcg2. Drug Metab Dispos. 2009 Aug;37(8):1698-702. doi: 10.1124/dmd.108.026146. Epub 2009 May 14. [PubMed:19443695 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Sterol transporter activity
Specific Function:
Transporter that appears to play an indispensable role in the selective transport of the dietary cholesterol in and out of the enterocytes and in the selective sterol excretion by the liver into bile.
Gene Name:
ABCG8
Uniprot ID:
Q9H221
Molecular Weight:
75678.03 Da
References
  1. Couture P, Lamarche B: Ezetimibe and bile acid sequestrants: impact on lipoprotein metabolism and beyond. Curr Opin Lipidol. 2013 Jun;24(3):227-32. doi: 10.1097/MOL.0b013e3283613a55. [PubMed:23571732 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 09, 2016 03:54