ANACETRAPIB

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 Search

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
Sources: https://www.cadth.ca/media/pdf/EH0007-000_Anacetrapib_draft_e.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cholesteryl ester transfer protein 15 Target ID: CHEMBL3572 Sources: https://www.cadth.ca/media/pdf/EH0007-000_Anacetrapib_draft_e.pdf https://www.ncbi.nlm.nih.gov/pubmed/20861162	Inhibitor 8297		17.2 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypercholesterolemia 47 Sources: https://clinicaltrials.gov/ct2/show/NCT01252953	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	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	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

T_1/2

Value	Dose	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

F_unbound

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: https://pubmed.ncbi.nlm.nih.gov/19843057 Page: p.544	healthy, ADULT n = 6 Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/19843057 Page: p.544	Sources: https://pubmed.ncbi.nlm.nih.gov/19843057 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: https://pubmed.ncbi.nlm.nih.gov/23958252 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: https://pubmed.ncbi.nlm.nih.gov/23958252 Page: p.57, 58	Sources: https://pubmed.ncbi.nlm.nih.gov/23958252 Page: p.57, 58

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY10537	https://www.001chemical.com/chem/search?q=DY10537
1PlusChem LLC	1P0039O1	https://www.1pchem.com/search?query=1P0039O1
A2B Chem	AB51697	http://a2bchem.com/prod/AB51697
AA Blocks	AA00394L	http://aablocks.com/goods/Goods/detail?id=AA00394L
AChemBlock	C-3348	http://www.achemblock.com/catalogsearch/result/?q=C-3348
AK Scientific	Y0279	https://aksci.com/item_detail.php?cat=Y0279
AOBIOUS INC	AOB87304	http://aobious.com/aobious/search?search_query=AOB87304
Alfa Chemistry	33894	http://www.alfa-chemistry.com/search.aspx?q=33894
Alfa Chemistry	ACM1061715909	http://www.alfa-chemistry.com/search.aspx?q=ACM1061715909
Ambeed	A293882	http://www.ambeed.com/search/Search.html?keyword=A293882
Angene	AGN-PC-0VENDU	http://www.angenechemical.com/productshow/AGN-PC-0VENDU.html
ApexBio Technology	A4375	https://www.apexbt.com/catalogsearch/result/?q=A4375
AstaTech	41214	http://astatechinc.com/CPSResult.php?CRNO=41214
BOC Sciences	875446-37-0	http://www.bocsci.com/description.asp?cas=875446-37-0
BioSynth	J-501484	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501484
BoronPharm	BP22252	https://www.boronpharm.com/boron/search.do?q=BP22252
Capot Chemical	29380	https://www.capotchem.com/search.do?q=29380
Cayman Chemical	21558	http://www.caymanchem.com/app/template/Product.vm/catalog/21558
ChemShuttle	104914	https://www.chemshuttle.com/catalogsearch/result/?q=104914
Combi-Blocks	QE-9719	http://www.combi-blocks.com/cgi-bin/find.cgi?QE-9719
Coresyn	CM14263	http://www.coresyn.com/search.do?q=CM14263
Excenen	EX-A420	http://www.excenen.com/searchresultlist.php?id=EX-A420
Hairui	ANSA064	http://www.hairuichem.com/en/product/search.do?q=ANSA064
KeyOrganics	AS-19552	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-19552
Lab Seeker	SC-50566	http://www.labseeker.com/search.php?keywords=SC-50566&category=0
LabSeeker	SC-50566	http://www.labseeker.com/search.php?keywords=SC-50566&category=0
Matrix Scientific	112674	http://www.matrixscientific.com/112674.html
MedChem Express	HY-12090	https://www.medchemexpress.com/search.html?q=HY-12090&ft=&fa=&fp=
MolPort	MolPort-021-804-915	https://www.molport.com/shop/molecule-link/MolPort-021-804-915
Molcore	MC10537	http://www.molcore.com/CatMC10537.html
Molnova	M16362	https://www.molnova.com/en/serch-list.html?keywords=M16362
MuseChem	R052759	https://www.musechem.com/product/R052759.html
Ryan Scientific	Pseudolaric_Acid_B	https://ryansci.com/products?q=Pseudolaric_Acid_B&list_q=&search_type=exact
ShangHai Biochempartner	BCP000329	http://www.biochempartner.com/search_BCP000329
ShangHai Biochempartner	BCP02374	http://www.biochempartner.com/search_BCP02374
Synovel	SN-0280	http://www.synovellab.com/?s=SN-0280&submit=Search
TargetMol	T1928	https://www.targetmol.com/search?keyword=T1928
Tetrahedron	TS87152	http://www.thsci.com/search.do?q=TS87152
Toronto Research Chemicals	A637200	https://www.trc-canada.com/product-detail/?CatNum=A637200
eMolecules	108761774	https://orderbb.emolecules.com/search/#?query=108761774
eMolecules	300515794	https://orderbb.emolecules.com/search/#?query=300515794
eMolecules	36096531	https://orderbb.emolecules.com/search/#?query=36096531
eNovation Chemicals	D496738	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D496738&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-4574141932	https://mcule.com/MCULE-4574141932/
mcule	MCULE-7871861095	https://mcule.com/MCULE-7871861095/

PubMed

Title	Date	PubMed
		25824513
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	18068514
Torcetrapib-induced blood pressure elevation is independent of CETP inhibition and is accompanied by increased circulating levels of aldosterone.	2008 Aug	18536749
The failure of torcetrapib: what have we learned?	2008 Aug	18536741
Treating high-density lipoprotein cholesterol: a return to inhibition of cholesteryl ester transfer protein?	2008 Jun	18489843
HDL metabolism and CETP inhibition.	2008 May-Jun	18414186
Gateways to clinical trials.	2009 Apr	19536362
Efficacy and safety of the cholesteryl ester transfer protein inhibitor anacetrapib as monotherapy and coadministered with atorvastatin in dyslipidemic patients.	2009 Feb	19185645
Effect of cholesteryl ester transfer protein inhibitor on vitamin E transport should be studied.	2009 Jul	19540377
Assessment of a pharmacokinetic and pharmacodynamic interaction between simvastatin and anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects.	2009 May	19552746
Single-dose pharmacokinetics and pharmacodynamics of anacetrapib, a potent cholesteryl ester transfer protein (CETP) inhibitor, in healthy subjects.	2009 Oct	19843057
Anacetrapib, a cholesterol ester transfer protein (CETP) inhibitor for the treatment of atherosclerosis.	2009 Sep	19705341
Raising HDL cholesterol in women.	2010 Aug 9	21072287
Safety of anacetrapib in patients with or at high risk for coronary heart disease.	2010 Dec 16	21082868
Treatment of dyslipidemia in patients with type 2 diabetes.	2010 Dec 20	21172030
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	19825813
Gateways to clinical trials.	2010 Jan-Feb	20383346
Dissociating HDL cholesterol from cardiovascular risk.	2010 Jul 31	20655104
Pharmacokinetics, metabolism, and excretion of anacetrapib, a novel inhibitor of the cholesteryl ester transfer protein, in rats and rhesus monkeys.	2010 Mar	20016052
High-density lipoprotein-mediated anti-atherosclerotic and endothelial-protective effects: a potential novel therapeutic target in cardiovascular disease.	2010 May	20196740
Emerging drugs for hyperlipidemia.	2010 Sep	20423271
Biphenyl-substituted oxazolidinones as cholesteryl ester transfer protein inhibitors: modifications of the oxazolidinone ring leading to the discovery of anacetrapib.	2011 Jul 14	21682257

Patents

Sample Use Guides

In Vivo Use Guide

tablet, 100mg daily

Route of Administration: Oral

In Vitro Use Guide

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 `Fri Dec 15 16:22:20 GMT 2023` Edited by `admin` on `Fri Dec 15 16:22:20 GMT 2023`
Record UNII	P7T269PR6S
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ANACETRAPIB

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