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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
Structure of ANACETRAPIB

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

HIDE SMILES / InChI

Molecular Formula C30H25F10NO3
Molecular Weight 637.5084
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment: # Merck & Co

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.45 μM
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
34.95 μM × h
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
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
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
371 min
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
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
8.98%
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

Doses

DosePopulationAdverse 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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Cholesteryl ester transfer protein inhibition and HDL increase: has the dream ended?
2008 Apr
The failure of torcetrapib: what have we learned?
2008 Aug
HDL metabolism and CETP inhibition.
2008 May-Jun
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
Assessment of a pharmacokinetic and pharmacodynamic interaction between simvastatin and anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects.
2009 May
The pharmacology and off-target effects of some cholesterol ester transfer protein inhibitors.
2009 Nov 16
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
Raising HDL cholesterol in women.
2010 Aug 9
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
Cholesterol efflux potential and antiinflammatory properties of high-density lipoprotein after treatment with niacin or anacetrapib.
2010 Jul
[Recent advances in the research on HDL subfraction].
2010 Jun
Update on CETP inhibition.
2010 Sep-Oct
Biphenyl-substituted oxazolidinones as cholesteryl ester transfer protein inhibitors: modifications of the oxazolidinone ring leading to the discovery of anacetrapib.
2011 Jul 14
Patents

Sample Use Guides

tablet, 100mg daily
Route of Administration: Oral
Anacetrapib (0.1 to 10 uM) dose-dependently inhibited pre-β-HDL formation in vitro in human plasma
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:48:46 UTC 2023
Edited
by admin
on Wed Jul 05 23:48:46 UTC 2023
Record UNII
P7T269PR6S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ANACETRAPIB
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
MK0859
Code English
anacetrapib [INN]
Common Name English
2-OXAZOLIDINONE, 5-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-3-((4'-FLUORO-2'-METHOXY-5'-(1-METHYLETHYL)-4-(TRIFLUOROMETHYL)(1,1'-BIPHENYL)-2-YL)METHYL)-4-METHYL-, (4S,5R)-
Common Name English
ANACETRAPIB [USAN]
Common Name English
(4S,5R)-5-(3,5-BIS(TRIFLUOROMETHYL)PHENYL)-3-((4'-FLUORO-2'-METHOXY-5'-(PROPAN-2-YL)-4-(TRIFLUOROMETHYL)(1,1'-BIPHENYL)-2-YL)METHYL)-4-METHYL-1,3-OXAZOLIDIN-2-ONE
Common Name English
ANACETRAPIB [MART.]
Common Name English
Anacetrapib [WHO-DD]
Common Name English
MK-0859
Code English
ANACETRAPIB [JAN]
Common Name English
ANACETRAPIB [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C471
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
NCI_THESAURUS C29703
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C75251
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
SMS_ID
100000128110
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID90236452
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
EVMPD
SUB34824
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
WIKIPEDIA
ANACETRAPIB
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
MESH
C530884
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
DRUG BANK
DB06630
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
PUBCHEM
11556427
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
INN
8926
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
CAS
875446-37-0
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
ChEMBL
CHEMBL1800807
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
USAN
TT-18
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
MERCK INDEX
M1885
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY Merck Index
FDA UNII
P7T269PR6S
Created by admin on Wed Jul 05 23:48:46 UTC 2023 , Edited by admin on Wed Jul 05 23:48:46 UTC 2023
PRIMARY
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Name Property Type Amount Referenced Substance Defining Parameters References
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