ETC-588

Status : investigational

Description

ETC-588, or LUV (large unilamellar vesicles), is made of naturally occurring lipids that circulate through arteries to facilitate the role of high-density lipoprotein (HDL) in removing accumulated cholesterol and other lipids from cells including those in the arterial wall. LUV are capable of transporting excess cholesterol from the vasculature to the liver for eventual elimination as part of the reverse lipid transport (RLT) pathway. It is believed that the removal of cholesterol by ETC-588 through this pathway may result in the reversal of atherosclerosis. Esperion is currently developing ETC-588 as a treatment for patients with acute coronary syndromes.

Used

Investigated for use/treatment in atherosclerosis, coronary artery disease, and vascular diseases.

Mechanism Of Action

ETC-588 is a phospholipid bilayer that can sequester cholesterol. Once the HDL particle, which is small enough to enter the arterial wall, pulls the cholesterol out of the plaque, it readily hands the cholesterol over to the LUV. The LUV then transports the cholesterol to the liver for processing.

Pharmacodynamics

ETC-588, or LUV (large unilamellar vesicles), is made of naturally occurring lipids that circulate through arteries to facilitate the role of high-density lipoprotein (HDL) in removing accumulated cholesterol and other lipids from cells including those in the arterial wall. LUV are capable of transporting excess cholesterol from the vasculature to the liver for eventual elimination as part of the reverse lipid transport (RLT) pathway.

Chemical Classification

This compound belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Phosphatidylcholines

Organic compounds

Lipids and lipid-like molecules

Glycerophospholipids

Glycerophosphocholines

Calculated Property

kind Value Source
logP 5.59 ALOGPS
logS -7.6 ALOGPS
Water Solubility 2.06e-05 g/l ALOGPS
logP 8.64 ChemAxon
IUPAC Name (2-{[2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium ChemAxon
Traditional IUPAC Name 1-oleoyl-2-palmitoyl lecithin ChemAxon
Molecular Weight 760.0761 ChemAxon
Monoisotopic Weight 759.577805117 ChemAxon
SMILES CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCCC=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C ChemAxon
Molecular Formula C42H82NO8P ChemAxon
InChI InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20- ChemAxon
InChIKey InChIKey=RRVPPYNAZJRZFR-MRCUWXFGSA-N ChemAxon
Polar Surface Area (PSA) 111.19 ChemAxon
Refractivity 226.18 ChemAxon
Polarizability 93.43 ChemAxon
Rotatable Bond Count 41 ChemAxon
H Bond Acceptor Count 4 ChemAxon
H Bond Donor Count 0 ChemAxon
pKa (strongest acidic) 1.86 ChemAxon
pKa (strongest basic) -6.7 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 0 ChemAxon
Bioavailability 0 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon