Succinobucol

Identification

Name
Succinobucol
Accession Number
DB05399
Type
Small Molecule
Groups
Investigational
Description

AGI-1067, is a novel small molecule with anti-oxidant and anti-inflammatory properties that was discovered by AtheroGenics and designed to treat atherosclerosis of the blood vessels of the heart, or coronary artery disease.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
J1J54V24R4
CAS number
216167-82-7
Weight
Average: 616.914
Monoisotopic: 616.325616154
Chemical Formula
C35H52O5S2
InChI Key
RKSMVPNZHBRNNS-UHFFFAOYSA-N
InChI
InChI=1S/C35H52O5S2/c1-31(2,3)23-17-21(18-24(29(23)39)32(4,5)6)41-35(13,14)42-22-19-25(33(7,8)9)30(26(20-22)34(10,11)12)40-28(38)16-15-27(36)37/h17-20,39H,15-16H2,1-14H3,(H,36,37)
IUPAC Name
4-[2,6-di-tert-butyl-4-({2-[(3,5-di-tert-butyl-4-hydroxyphenyl)sulfanyl]propan-2-yl}sulfanyl)phenoxy]-4-oxobutanoic acid
SMILES
CC(C)(C)C1=CC(SC(C)(C)SC2=CC(=C(OC(=O)CCC(O)=O)C(=C2)C(C)(C)C)C(C)(C)C)=CC(=C1O)C(C)(C)C

Pharmacology

Indication

Investigated for use/treatment in atherosclerosis, coronary artery disease, diabetes mellitus type 2, and in-stent restenosis.

Pharmacodynamics
Not Available
Mechanism of action

AGI-1067 works by inhibiting key oxidant signals within cells of blood vessel walls that generate inflammatory processes that are key to the pathogenesis of atherosclerosis. This includes inhibition of inflammatory cytokines, chemokines and vascular adhesion molecules that participate in the initiation, growth and eventual destabilization of the plaque. Its anti-oxidant properties also play a role in its ability to inhibit the formation of oxidized LDL, a critical component in the formation of atherosclerotic plaque.

TargetActionsOrganism
UVascular cell adhesion protein 1Not AvailableHumans
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
Toxicity
Not Available
Affected organisms
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

References

General References
  1. Serebruany VL, Malinin A, Eisert C, Ong S: AGI-1067, a novel vascular protectant, anti-inflammatory drug and mild antiplatelet agent for treatment of atherosclerosis. Expert Rev Cardiovasc Ther. 2007 Jul;5(4):635-41. [PubMed:17605642]
  2. Serebruany V, Malinin A, Scott R: The in vitro effects of a novel vascular protectant, AGI-1067, on platelet aggregation and major receptor expression in subjects with multiple risk factors for vascular disease. J Cardiovasc Pharmacol Ther. 2006 Sep;11(3):191-6. [PubMed:17056832]
External Links
PubChem Compound
216325
PubChem Substance
175426994
ChemSpider
187514
BindingDB
50117525
ChEMBL
CHEMBL83626
ZINC
ZINC000003937467

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3Unknown StatusTreatmentDiabetes1

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 Solubility3.09e-05 mg/mLALOGPS
logP8.18ALOGPS
logP10.31ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)4.33ChemAxon
pKa (Strongest Basic)-5.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity179.3 m3·mol-1ChemAxon
Polarizability71.4 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8205
Blood Brain Barrier+0.5662
Caco-2 permeable-0.5317
P-glycoprotein substrateSubstrate0.591
P-glycoprotein inhibitor INon-inhibitor0.7001
P-glycoprotein inhibitor IIInhibitor0.701
Renal organic cation transporterNon-inhibitor0.8961
CYP450 2C9 substrateNon-substrate0.6952
CYP450 2D6 substrateNon-substrate0.8408
CYP450 3A4 substrateSubstrate0.5831
CYP450 1A2 substrateNon-inhibitor0.7413
CYP450 2C9 inhibitorNon-inhibitor0.6781
CYP450 2D6 inhibitorNon-inhibitor0.8996
CYP450 2C19 inhibitorNon-inhibitor0.729
CYP450 3A4 inhibitorNon-inhibitor0.8024
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6932
Ames testNon AMES toxic0.7639
CarcinogenicityNon-carcinogens0.8257
BiodegradationNot ready biodegradable0.9887
Rat acute toxicity2.5346 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9885
hERG inhibition (predictor II)Non-inhibitor0.783
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol esters
Sub Class
Not Available
Direct Parent
Phenol esters
Alternative Parents
Phenylpropanes / Thiophenol ethers / Phenoxy compounds / Phenols / Fatty acid esters / Dithioketals / Alkylarylthioethers / Dicarboxylic acids and derivatives / Carboxylic acid esters / Sulfenyl compounds
show 4 more
Substituents
Phenol ester / Phenylpropane / Phenoxy compound / Aryl thioether / Thiophenol ether / Dithioketal / Fatty acid ester / Phenol / Alkylarylthioether / Monocyclic benzene moiety
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Primary amine oxidase activity
Specific Function
Important in cell-cell recognition. Appears to function in leukocyte-endothelial cell adhesion. Interacts with integrin alpha-4/beta-1 (ITGA4/ITGB1) on leukocytes, and mediates both adhesion and si...
Gene Name
VCAM1
Uniprot ID
P19320
Uniprot Name
Vascular cell adhesion protein 1
Molecular Weight
81275.43 Da

Drug created on November 18, 2007 11:24 / Updated on March 01, 2020 19:32

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