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Identification
NameEzetimibe
Accession NumberDB00973  (APRD00619)
TypeSmall Molecule
GroupsApproved
Description

Ezetimibe 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
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 mgoralPro Doc Limitee2014-09-17Not applicableCanada
Ezetimibetablet10 mgoralSanis Health Inc2014-10-08Not applicableCanada
Ezetimibetablet10 mgoralSivem Pharmaceuticals Ulc2014-09-16Not 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.2002-10-252016-04-05Us
Zetiatablet10 mg/1oralRebel Distributors Corp2009-07-272016-04-05Us
Zetiatablet10 mg/1oralCardinal Health2002-10-252016-04-05Us
Zetiatablet10 mg/1oralCardinal Health2009-07-272016-04-05Us
Zetiatablet10 mg/1oralCardinal Health2011-07-292016-04-05Us
Zetiatablet10 mg/1oralPhysicians Total Care, Inc.2002-12-262016-04-05Us
Zetiatablet10 mg/1oralA S Medication Solutions Llc2009-07-272016-04-05Us
Zetiatablet10 mg/1oralREMEDYREPACK INC.2013-10-042016-04-05Us
Zetiatablet10 mg/1oralAvera Mc Kennan Hospital2015-07-092016-04-05Us
Zetiatablet10 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2012-03-192016-04-05Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-ezetimibetablet10 mgoralApotex Inc2014-09-23Not applicableCanada
Ezetimibetablet10 mg/1oralGlenmark Pharmaceuticals Inc., Usa2011-12-312016-04-05Us
Over the Counter ProductsNot 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 KeyInChIKey=OLNTVTPDXPETLC-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
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
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.
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.
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
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
SpectraNot Available
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 CodesC10AX09C10BA02C10BA05C10BA06
AHFS Codes
  • 24:06.05
PDB EntriesNot Available
FDA labelDownload (321 KB)
MSDSDownload (281 KB)
Interactions
Drug Interactions
Drug
BezafibrateThe risk or severity of adverse effects can be increased when Bezafibrate is combined with Ezetimibe.
CholestyramineCholestyramine can cause a decrease in the absorption of Ezetimibe resulting in a reduced serum concentration and potentially a decrease in efficacy.
Choline fenofibrateThe risk or severity of adverse effects can be increased when Choline fenofibrate is combined with Ezetimibe.
ColesevelamColesevelam can cause a decrease in the absorption of Ezetimibe resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Ezetimibe resulting in a reduced serum concentration and potentially a decrease in efficacy.
CyclosporineThe serum concentration of Cyclosporine can be increased when it is combined with Ezetimibe.
EltrombopagThe serum concentration of Ezetimibe can be increased when it is combined with Eltrombopag.
FenofibrateThe risk or severity of adverse effects can be increased when Fenofibrate is combined with Ezetimibe.
GemfibrozilThe risk or severity of adverse effects can be increased when Gemfibrozil is combined with Ezetimibe.
TeriflunomideThe serum concentration of Ezetimibe can be increased when it is combined with Teriflunomide.
Food Interactions
  • Take without regard to meals.

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 ]
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Drug created on June 13, 2005 07:24 / Updated on May 05, 2016 03:15