ETC-588

Identification

Generic Name
ETC-588
DrugBank Accession Number
DB05456
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 760.0761
Monoisotopic: 759.577805117
Chemical Formula
C42H82NO8P
Synonyms
Not Available

Pharmacology

Indication

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

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
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.

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.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
RRVPPYNAZJRZFR-MRCUWXFGSA-N
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-
IUPAC Name
(2-{[2-(hexadecanoyloxy)-3-[(9Z)-octadec-9-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium
SMILES
CCCCCCCCCCCCCCCC(=O)OC(COC(=O)CCCCCCC\C=C/CCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

References

General References
  1. Martin K, Brownfield D, Karmonik C, Sanford L, Torres L, Insull W, Morrisett J: Short-term tracking of atherosclerosis in operated and unoperated human carotid arteries by high resolution magnetic resonance imaging. World J Surg. 2007 Apr;31(4):723-32. [Article]
  2. Doggrell SA: ETC-588 (Pfizer). Curr Opin Investig Drugs. 2004 Sep;5(9):993-9. [Article]
PubChem Compound
6449792
PubChem Substance
175427008
ChemSpider
4952476

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.06e-05 mg/mLALOGPS
logP5.59ALOGPS
logP8.64ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area111.19 Å2ChemAxon
Rotatable Bond Count41ChemAxon
Refractivity226.18 m3·mol-1ChemAxon
Polarizability93.43 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.97
Blood Brain Barrier+0.874
Caco-2 permeable-0.5297
P-glycoprotein substrateSubstrate0.5826
P-glycoprotein inhibitor INon-inhibitor0.6467
P-glycoprotein inhibitor IINon-inhibitor0.795
Renal organic cation transporterNon-inhibitor0.844
CYP450 2C9 substrateNon-substrate0.881
CYP450 2D6 substrateNon-substrate0.8149
CYP450 3A4 substrateSubstrate0.5665
CYP450 1A2 substrateNon-inhibitor0.859
CYP450 2C9 inhibitorNon-inhibitor0.8809
CYP450 2D6 inhibitorNon-inhibitor0.8972
CYP450 2C19 inhibitorNon-inhibitor0.8148
CYP450 3A4 inhibitorNon-inhibitor0.7487
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9548
Ames testNon AMES toxic0.6786
CarcinogenicityCarcinogens 0.6137
BiodegradationReady biodegradable0.9351
Rat acute toxicity2.8765 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5766
hERG inhibition (predictor II)Non-inhibitor0.7096
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Drug created on November 18, 2007 18:25 / Updated on June 12, 2020 16:52