anacetrapib   Click here for help

GtoPdb Ligand ID: 8400

Synonyms: MK-0859
Compound class: Synthetic organic
Comment: Anacetrapib is a small molecule that inhibits cholesterylester transfer protein (CETP; P11597) [3,10]. CETP was considered as a target for prevention of dyslipidemia and reducing cardiovascular mortality, with CETP inhibitors proposed as a direct route to raise HDL.
Clinical trial results for a number of CETP inhibitors have failed to show clinical benefit. Failed candidates include evacetrapib, anacetrapib, torcetrapib, and dalcetrapib [8]. Anacetrapib was discovered to have unfavourable pharmacokinetics, including a very extended terminal half-life (3-4 weeks) [1] and accumulation in adipose tissue (due to slow elimination from this tissue) [5,9].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 38.77
Molecular weight 637.17
XLogP 9.78
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES COc1cc(F)c(cc1c1ccc(cc1CN1C(=O)OC(C1C)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C(F)(F)F)C(C)C
Isomeric SMILES COc1cc(F)c(cc1c1ccc(cc1CN1C(=O)O[C@@H]([C@@H]1C)c1cc(cc(c1)C(F)(F)F)C(F)(F)F)C(F)(F)F)C(C)C
InChI 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
InChI Key MZZLGJHLQGUVPN-HAWMADMCSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[[2-(4-fluoro-2-methoxy-5-propan-2-ylphenyl)-5-(trifluoromethyl)phenyl]methyl]-4-methyl-1,3-oxazolidin-2-one
International Nonproprietary Names Click here for help
INN number INN
8926 anacetrapib
Synonyms Click here for help
MK-0859
Database Links Click here for help
CAS Registry No. 875446-37-0
ChEMBL Ligand CHEMBL1800807
GtoPdb PubChem SID 252166610
PubChem CID 11556427
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Wikipedia Anacetrapib