Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H25F10NO3 |
Molecular Weight | 637.5084 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(F)=C(C=C1C2=C(CN3[C@@H](C)[C@H](OC3=O)C4=CC(=CC(=C4)C(F)(F)F)C(F)(F)F)C=C(C=C2)C(F)(F)F)C(C)C
InChI
InChIKey=MZZLGJHLQGUVPN-HAWMADMCSA-N
InChI=1S/C30H25F10NO3/c1-14(2)22-11-23(25(43-4)12-24(22)31)21-6-5-18(28(32,33)34)9-17(21)13-41-15(3)26(44-27(41)42)16-7-19(29(35,36)37)10-20(8-16)30(38,39)40/h5-12,14-15,26H,13H2,1-4H3/t15-,26-/m0/s1
DescriptionCurator's Comment: Description was created based on several sources, including
http://www.selleckchem.com/products/anacetrapib-mk-0859.html
Curator's Comment: Description was created based on several sources, including
http://www.selleckchem.com/products/anacetrapib-mk-0859.html
Anacetrapib is a CETP inhibitor being developed by Merck to treat hypercholesterolemia (elevated cholesterol levels) and prevent cardiovascular disease. Anacetrapib is a cholesterol ester transfer protein (CETP) inhibitor that blocks the transfer of cholesterol from highdensity lipoprotein to other lipoproteins. This results in an increase in high-density lipoprotein cholesterol (HDL-C) and a decrease in lowdensity lipoprotein cholesterol (LDL-C), which may reduce the development of atherosclerosis. Anacetrapib has not been approved for sale in Canada or the United States. Clinical evidence to support the use of anacetrapib for dyslipidemia has been reported in two clinical trials. REVEAL is an ongoing, large-scale phase 3 trial evaluating the effectiveness of anacetrapib with a statin for the secondary prevention of major coronary events in patients who have a history of cardiovascular disease. Results are anticipated in January 2017.
Originator
Sources: http://adisinsight.springer.com/drugs/800024490
Curator's Comment: # Merck & Co
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.45 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23958252 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ANACETRAPIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
4460 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27432781 |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
9140 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19843057 |
800 mg 1 times / day single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
889 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19843057 |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
34.95 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23958252 |
300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ANACETRAPIB plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
109000 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27432781 |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
117.4 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19843057 |
800 mg 1 times / day single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
13.6 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19843057 |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
371 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27432781 |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
82.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19843057 |
800 mg 1 times / day single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT |
|
61.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19843057 |
1000 mg single, oral dose: 1000 mg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.98% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27432781 |
10 mg/kg single, oral dose: 10 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
ANACETRAPIB plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1000 mg single, oral Highest studied dose Dose: 1000 mg Route: oral Route: single Dose: 1000 mg Sources: Page: p.544 |
healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Population Size: 6 Sources: Page: p.544 |
|
300 mg 1 times / day multiple, oral (total daily dose) Studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: Page: p.57, 58 |
unhealthy, ADULT n = 41 Health Status: unhealthy Condition: dyslipidemia Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 41 Sources: Page: p.57, 58 |
PubMed
Title | Date | PubMed |
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Effect of the cholesteryl ester transfer protein inhibitor, anacetrapib, on lipoproteins in patients with dyslipidaemia and on 24-h ambulatory blood pressure in healthy individuals: two double-blind, randomised placebo-controlled phase I studies. | 2007 Dec 8 |
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Cholesteryl ester transfer protein inhibition and HDL increase: has the dream ended? | 2008 Apr |
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Torcetrapib-induced blood pressure elevation is independent of CETP inhibition and is accompanied by increased circulating levels of aldosterone. | 2008 Aug |
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The failure of torcetrapib: what have we learned? | 2008 Aug |
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Multiple-dose pharmacodynamics and pharmacokinetics of anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects. | 2008 Dec |
|
Treating high-density lipoprotein cholesterol: a return to inhibition of cholesteryl ester transfer protein? | 2008 Jun |
|
Anacetrapib: new hope for cholesteryl ester transfer protein inhibitors in the treatment of dyslipidemia. | 2008 Jun |
|
Gateways to clinical trials. | 2008 Mar |
|
HDL metabolism and CETP inhibition. | 2008 May-Jun |
|
JTT-705: is there still future for a CETP inhibitor after torcetrapib? | 2008 Oct |
|
Gateways to clinical trials. | 2009 Apr |
|
Efficacy and safety of the cholesteryl ester transfer protein inhibitor anacetrapib as monotherapy and coadministered with atorvastatin in dyslipidemic patients. | 2009 Feb |
|
Assessment of the CYP3A-mediated drug interaction potential of anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy volunteers. | 2009 Jan |
|
Effect of cholesteryl ester transfer protein inhibitor on vitamin E transport should be studied. | 2009 Jul |
|
The end of the road for CETP inhibitors after torcetrapib? | 2009 Jul |
|
Assessment of a pharmacokinetic and pharmacodynamic interaction between simvastatin and anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects. | 2009 May |
|
Drug discovery using chemical systems biology: identification of the protein-ligand binding network to explain the side effects of CETP inhibitors. | 2009 May |
|
Triglycerides and HDL cholesterol: stars or second leads in diabetes? | 2009 Nov |
|
Single-dose pharmacokinetics and pharmacodynamics of anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects. | 2009 Oct |
|
High-density lipoprotein cholesterol: current perspective for clinicians. | 2009 Oct-Nov |
|
Anacetrapib, a cholesterol ester transfer protein (CETP) inhibitor for the treatment of atherosclerosis. | 2009 Sep |
|
Cholesteryl ester transfer protein inhibitors as high-density lipoprotein raising agents. | 2009 Sep |
|
Anacetrapib. | 2010 |
|
Raising HDL cholesterol in women. | 2010 Aug 9 |
|
Modulating cholesteryl ester transfer protein activity maintains efficient pre-β-HDL formation and increases reverse cholesterol transport. | 2010 Dec |
|
Safety of anacetrapib in patients with or at high risk for coronary heart disease. | 2010 Dec 16 |
|
Treatment of dyslipidemia in patients with type 2 diabetes. | 2010 Dec 20 |
|
Cholesteryl ester transfer protein: at the heart of the action of lipid-modulating therapy with statins, fibrates, niacin, and cholesteryl ester transfer protein inhibitors. | 2010 Jan |
|
Gateways to clinical trials. | 2010 Jan-Feb |
|
High density lipoproteins-based therapies for cardiovascular disease. | 2010 Jul |
|
Cholesterol efflux potential and antiinflammatory properties of high-density lipoprotein after treatment with niacin or anacetrapib. | 2010 Jul |
|
Dissociating HDL cholesterol from cardiovascular risk. | 2010 Jul 31 |
|
[Recent advances in the research on HDL subfraction]. | 2010 Jun |
|
Dalcetrapib: a review of Phase II data. | 2010 Jun |
|
Pharmacokinetics, metabolism, and excretion of anacetrapib, a novel inhibitor of the cholesteryl ester transfer protein, in rats and rhesus monkeys. | 2010 Mar |
|
Current status and future directions in lipid management: emphasizing low-density lipoproteins, high-density lipoproteins, and triglycerides as targets for therapy. | 2010 Mar 3 |
|
High-density lipoprotein-mediated anti-atherosclerotic and endothelial-protective effects: a potential novel therapeutic target in cardiovascular disease. | 2010 May |
|
Good news for 'good' cholesterol. | 2010 Nov 18 |
|
Effects of fenofibrate on lipid profiles, cholesterol ester transfer activity, and in-stent intimal hyperplasia in patients after elective coronary stenting. | 2010 Oct 25 |
|
Biochemical characterization of cholesteryl ester transfer protein inhibitors. | 2010 Sep |
|
Emerging drugs for hyperlipidemia. | 2010 Sep |
|
Drug off-target effects predicted using structural analysis in the context of a metabolic network model. | 2010 Sep 23 |
|
Update on CETP inhibition. | 2010 Sep-Oct |
|
Cholesteryl ester transfer protein inhibition in cardiovascular risk management: ongoing trials will end the confusion. | 2011 Dec |
|
Biphenyl-substituted oxazolidinones as cholesteryl ester transfer protein inhibitors: modifications of the oxazolidinone ring leading to the discovery of anacetrapib. | 2011 Jul 14 |
|
Anacetrapib lowers LDL by increasing ApoB clearance in mildly hypercholesterolemic subjects. | 2015 Jun |
|
Anacetrapib as lipid-modifying therapy in patients with heterozygous familial hypercholesterolaemia (REALIZE): a randomised, double-blind, placebo-controlled, phase 3 study. | 2015 May 30 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01252953
tablet, 100mg daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20861162
Anacetrapib (0.1 to 10 uM) dose-dependently inhibited pre-β-HDL formation in vitro in human plasma
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NCI_THESAURUS |
C471
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C29703
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C75251
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100000128110
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DTXSID90236452
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SUB34824
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ANACETRAPIB
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C530884
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DB06630
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875446-37-0
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CHEMBL1800807
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m1885
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ACTIVE MOIETY