Page last updated: 2024-11-11

sch 60663

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

SCH 60663: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9894653
CHEMBL ID321017
SCHEMBL ID10027374
MeSH IDM0364951

Synonyms (35)

Synonym
(2s,3s,4s,5r,6s)-6-(4-{(2s,3r)-1-(4-fluoro-phenyl)-3-[3-((s)-4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
bdbm50240720
(2s,3s,4s,5r,6s)-6-(4-{(2s,3r)-1-(4-fluoro-phenyl)-3-[(s)-3-(4-fluoro-phenyl)-3-hydroxy-propyl]-4-oxo-azetidin-2-yl}-phenoxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid
(2s,3s,4s,5r,6s)-6-(4-((2s,3r)-1-(4-fluorophenyl)-3-((s)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxy-tetrahydro-2h-pyran-2-carboxylic acid
CHEMBL321017 ,
ezetimibe-glucuronide
sch 60663
190448-57-8
ezetimibe phenoxy glucuronide
sch-58235 glucuronide
SCHEMBL10027374
ezetimibe b-d-glucuronide
W-201700
ezetimibe glucuronide
sch-60663
DTXSID10432454
b-d-glucopyranosiduronic acid,4-[(2s,3r)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl
mfcd08063721
ezetimibe phenoxy-beta-d-glucuronide
(2s,3s,4s,5r,6s)-6-[4-[(2s,3r)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
AKOS030241675
HY-135391
CS-0112345
v7fa38e13k ,
unii-v7fa38e13k
beta-d-glucopyranosiduronic acid, 4-((2s,3r)-1-(4-fluorophenyl)-3-((3s)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxo-2-azetidinyl)phenyl
.beta.-d-glucopyranosiduronic acid, 4-((2s,3r)-1-(4-fluorophenyl)-3-((3s)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxo-2-azetidinyl)phenyl
beta-d-glucopyranosiduronic acid, 4-[(2s,3r)-1-(4-fluorophenyl)-3-[(3s)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxo-2-azetidinyl]phenyl
F82539
MS-30471
(2s,3s,4s,5r,6s)-6-(4-((2s,3r)-1-(4-fluorophenyl)-3-((s)-3-(4-fluorophenyl)-3-hydroxypropyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2h-pyran-2-carboxylic acid
ezetimibe phenoxy beta-d-glucuronide
ezetimibe phenoxy ?-d-glucuronide
ezetimibe beta -d-glucuronide
ezetimibe glucuronide;ezetimibe -d-glucuronide

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"This study was conducted to evaluate the potential for pharmacokinetic interaction between fenofibrate and ezetimibe in healthy subjects."( Evaluation of the potential for pharmacokinetic interaction between fenofibrate and ezetimibe: A phase I, open-label, multiple-dose, three-period crossover study in healthy subjects.
Achari, R; Burt, DA; Chira, T; Edeki, T; Gustavson, LE; Kelly, MT; Rieser, MJ; Schweitzer, SM; Yannicelli, HD, 2006
)
0.33
" Forty-three subjects among them participated in a pharmacokinetic study of ezetimibe."( Effects of UDP-glucuronosyltransferase polymorphisms on the pharmacokinetics of ezetimibe in healthy subjects.
Bae, JW; Choi, CI; Chung, MW; Jang, CG; Lee, JH; Lee, SY, 2011
)
0.37
" Besides the C(max) of unchanged ezetimibe, no significant difference was found in any other pharmacokinetic parameter of unchanged ezetimibe or ezetimibe-glucuronide in the three groups."( Effects of UDP-glucuronosyltransferase polymorphisms on the pharmacokinetics of ezetimibe in healthy subjects.
Bae, JW; Choi, CI; Chung, MW; Jang, CG; Lee, JH; Lee, SY, 2011
)
0.37
" Both drugs exhibit complex pharmacokinetic profiles attributed mainly to repetitive enterohepatic kinetics."( Development of a joint population pharmacokinetic model of ezetimibe and its conjugated metabolite.
Karalis, V; Soulele, K, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Blood samples were collected for up to 24 hours after dosing on study day 1 and up to 120 hours after dosing on study day 10 for determination of plasma concentrations of fenofibric acid, unconjugated (free) ezetimibe, and total (conjugated and unconjugated) ezetimibe using validated high-performance liquid chromatography methods with mass-spectrometric detection."( Evaluation of the potential for pharmacokinetic interaction between fenofibrate and ezetimibe: A phase I, open-label, multiple-dose, three-period crossover study in healthy subjects.
Achari, R; Burt, DA; Chira, T; Edeki, T; Gustavson, LE; Kelly, MT; Rieser, MJ; Schweitzer, SM; Yannicelli, HD, 2006
)
0.33
" The sinusoidal transporter Abcc3 was induced in MCD rats, which correlated with increased plasma concentrations of EZE-GLUC, regardless of dosing method."( Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
Canet, MJ; Cherrington, NJ; Fisher, CD; Hardwick, RN; Street, SM, 2012
)
0.38
" No difference between 20-mg and 10-mg dosing was seen among patients not receiving statins."( Incremental lowering of low-density lipoprotein cholesterol with ezetimibe 20 mg vs 10 mg daily in patients receiving concomitant statin therapy.
Ban, MR; DeGorter, MK; Hegele, RA; Kim, RB; Schwarz, UI; Tirona, RG; Ziada, A, 2013
)
0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Niemann-Pick C1-like 1 proteinCanis lupus familiaris (dog)IC50 (µMol)0.06000.06000.06000.0600AID352736
Niemann-Pick C1-like 1 proteinMacaca mulatta (Rhesus monkey)IC50 (µMol)0.03000.03000.03000.0300AID352737
NPC1-like intracellular cholesterol transporter 1Rattus norvegicus (Norway rat)IC50 (µMol)0.58000.58000.58000.5800AID352733
NPC1-like intracellular cholesterol transporter 1Rattus norvegicus (Norway rat)Ki0.18000.18000.19000.2000AID315718
NPC1-like intracellular cholesterol transporter 1Homo sapiens (human)IC50 (µMol)0.30000.30000.32330.3700AID352731; AID352732
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
cholesterol biosynthetic processNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
intestinal cholesterol absorptionNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cholesterol transportNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
lipoprotein metabolic processNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
vitamin E metabolic processNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
vitamin transportNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cellular response to sterol depletionNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cholesterol homeostasisNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (7)

Processvia Protein(s)Taxonomy
cholesterol transfer activityNiemann-Pick C1-like 1 proteinCanis lupus familiaris (dog)
protein bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
vitamin E bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cholesterol bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
small GTPase bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
myosin V bindingNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
protein homodimerization activityNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
plasma membraneNiemann-Pick C1-like 1 proteinCanis lupus familiaris (dog)
plasma membraneNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
apical plasma membraneNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
cytoplasmic vesicle membraneNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
plasma membraneNPC1-like intracellular cholesterol transporter 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID315721Metabolic stability assessed as half life in rat liver microsomes2008Bioorganic & medicinal chemistry letters, Jan-15, Volume: 18, Issue:2
Substituted oxazolidinones as novel NPC1L1 ligands for the inhibition of cholesterol absorption.
AID352732Displacement of [35S](2S,3S,4S,5R,6S)-6-(4-((2S,3R)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-(3-(methylsulfonamido)prop-1-ynyl)phenyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid from NPC1L1 in human enterocyte2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Spiroimidazolidinone NPC1L1 inhibitors. 1: Discovery by 3D-similarity-based virtual screening.
AID352735Displacement of [35S](2S,3S,4S,5R,6S)-6-(4-((2S,3R)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-(3-(methylsulfonamido)prop-1-ynyl)phenyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid from NPC1L1 in guinea pig enter2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Spiroimidazolidinone NPC1L1 inhibitors. 1: Discovery by 3D-similarity-based virtual screening.
AID1211344Drug level in methionine and choline deficient fed Sprague-Dawley rat bile treated with ezetimibe at 10 mg/kg, po after 120 mins by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 40, Issue:3
Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
AID315718Displacement of [3H]ezetimibe-glucuronide from NPC1L1 in Sprague-Dawley rat brush border membrane2008Bioorganic & medicinal chemistry letters, Jan-15, Volume: 18, Issue:2
Substituted oxazolidinones as novel NPC1L1 ligands for the inhibition of cholesterol absorption.
AID352737Displacement of [35S](2S,3S,4S,5R,6S)-6-(4-((2S,3R)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-(3-(methylsulfonamido)prop-1-ynyl)phenyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid from NPC1L1 in rhesus monkey en2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Spiroimidazolidinone NPC1L1 inhibitors. 1: Discovery by 3D-similarity-based virtual screening.
AID1211338Drug level in methionine and choline deficient fed Sprague-Dawley rat plasma treated with ezetimibe at 10 mg/kg, iv after 40 mins by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 40, Issue:3
Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
AID352736Displacement of [35S](2S,3S,4S,5R,6S)-6-(4-((2S,3R)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-(3-(methylsulfonamido)prop-1-ynyl)phenyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid from NPC1L1 in dog enterocyte b2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Spiroimidazolidinone NPC1L1 inhibitors. 1: Discovery by 3D-similarity-based virtual screening.
AID1211332Drug level in methionine and choline deficient fed Sprague-Dawley rat plasma treated with ezetimibe at 10 mg/kg, po after 40 mins by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 40, Issue:3
Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
AID1211335Drug level in methionine and choline deficient fed Sprague-Dawley rat plasma treated with ezetimibe at 10 mg/kg, po after 120 mins by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 40, Issue:3
Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
AID1211327Drug level in methionine and choline deficient fed Sprague-Dawley rat urine treated with ezetimibe at 10 mg/kg, iv after 120 mins by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 40, Issue:3
Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
AID352738Displacement of [35S](2S,3S,4S,5R,6S)-6-(4-((2S,3R)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-(3-(methylsulfonamido)prop-1-ynyl)phenyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid from NPC1L1 in pig enterocyte b2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Spiroimidazolidinone NPC1L1 inhibitors. 1: Discovery by 3D-similarity-based virtual screening.
AID352731Displacement of [35S](2S,3S,4S,5R,6S)-6-(4-((2S,3R)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-(3-(methylsulfonamido)prop-1-ynyl)phenyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid from human recombinant NPC1L1 e2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Spiroimidazolidinone NPC1L1 inhibitors. 1: Discovery by 3D-similarity-based virtual screening.
AID181919Percent inhibition of 14C]cholesterol absorption into plasma using cholesterol absorption assay in rats at the dose of 10 ug/Kg2002Bioorganic & medicinal chemistry letters, Feb-11, Volume: 12, Issue:3
Synthesis of fluorescent biochemical tools related to the 2-azetidinone class of cholesterol absorption inhibitors.
AID352734Displacement of [35S](2S,3S,4S,5R,6S)-6-(4-((2S,3R)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-(3-(methylsulfonamido)prop-1-ynyl)phenyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid from NPC1L1 in hamster enterocy2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Spiroimidazolidinone NPC1L1 inhibitors. 1: Discovery by 3D-similarity-based virtual screening.
AID86018Compound was tested for percent reduction of liver cholesterol esters absorption in cholesterol fed hamster model at a dose of 3 mg/kg/day1998Bioorganic & medicinal chemistry letters, Feb-03, Volume: 8, Issue:3
Sugar-substituted 2-azetidinone cholesterol absorption inhibitors: enhanced potency by modification of the sugar.
AID1211341Drug level in methionine and choline deficient fed Sprague-Dawley rat plasma treated with ezetimibe at 10 mg/kg, iv after 120 mins by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 40, Issue:3
Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
AID352733Displacement of [35S](2S,3S,4S,5R,6S)-6-(4-((2S,3R)-3-((S)-3-(4-fluorophenyl)-3-hydroxypropyl)-1-(4-(3-(methylsulfonamido)prop-1-ynyl)phenyl)-4-oxoazetidin-2-yl)phenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid from NPC1L1 in rat enterocyte b2009Bioorganic & medicinal chemistry letters, Jun-01, Volume: 19, Issue:11
Spiroimidazolidinone NPC1L1 inhibitors. 1: Discovery by 3D-similarity-based virtual screening.
AID86158Compound was tested for percent reduction of serum cholesterol absorption in cholesterol fed hamster model at a dose of 3 mg/kg/day1998Bioorganic & medicinal chemistry letters, Feb-03, Volume: 8, Issue:3
Sugar-substituted 2-azetidinone cholesterol absorption inhibitors: enhanced potency by modification of the sugar.
AID84707Dose required to inhibit cholesterol absorption in cholesterol fed hamster model1998Bioorganic & medicinal chemistry letters, Feb-03, Volume: 8, Issue:3
Sugar-substituted 2-azetidinone cholesterol absorption inhibitors: enhanced potency by modification of the sugar.
AID1211324Drug level in methionine and choline deficient fed Sprague-Dawley rat urine treated with ezetimibe at 10 mg/kg, po after 120 mins by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 40, Issue:3
Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
AID1211321Drug level in methionine and choline deficient fed Sprague-Dawley rat bile treated with ezetimibe at 10 mg/kg, iv after 30 to 90 mins by LC-MS/MS method2012Drug metabolism and disposition: the biological fate of chemicals, Mar, Volume: 40, Issue:3
Molecular mechanism of altered ezetimibe disposition in nonalcoholic steatohepatitis.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (4.35)18.2507
2000's10 (43.48)29.6817
2010's11 (47.83)24.3611
2020's1 (4.35)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.71

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.71 (24.57)
Research Supply Index3.33 (2.92)
Research Growth Index5.05 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.71)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials4 (17.39%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (82.61%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]