Identification
- Generic Name
- Succinobucol
- DrugBank Accession Number
- DB05399
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Succinobucol (DB05399)
- Weight
- Average: 616.914
Monoisotopic: 616.325616154 - Chemical Formula
- C35H52O5S2
- Synonyms
- Succinobucol
Pharmacology
- Indication
Investigated for use/treatment in atherosclerosis, coronary artery disease, diabetes mellitus type 2, and in-stent restenosis.
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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.
Target Actions Organism UVascular cell adhesion protein 1 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
- Chemical TaxonomyProvided by Classyfire
- 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
- Alkylarylthioether / Aromatic homomonocyclic compound / Aryl thioether / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid ester / Dicarboxylic acid or derivatives / Dithioketal / Fatty acid ester show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- J1J54V24R4
- CAS number
- 216167-82-7
- 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
References
- General References
- 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. [Article]
- 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. [Article]
- External Links
- PubChem Compound
- 216325
- PubChem Substance
- 175426994
- ChemSpider
- 187514
- BindingDB
- 50117525
- ChEMBL
- CHEMBL83626
- ZINC
- ZINC000003937467
Clinical Trials
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
Property Value Source Water Solubility 3.09e-05 mg/mL ALOGPS logP 8.18 ALOGPS logP 10.31 Chemaxon logS -7.3 ALOGPS pKa (Strongest Acidic) 4.33 Chemaxon pKa (Strongest Basic) -5.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 83.83 Å2 Chemaxon Rotatable Bond Count 13 Chemaxon Refractivity 179.3 m3·mol-1 Chemaxon Polarizability 71.27 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8205 Blood Brain Barrier + 0.5662 Caco-2 permeable - 0.5317 P-glycoprotein substrate Substrate 0.591 P-glycoprotein inhibitor I Non-inhibitor 0.7001 P-glycoprotein inhibitor II Inhibitor 0.701 Renal organic cation transporter Non-inhibitor 0.8961 CYP450 2C9 substrate Non-substrate 0.6952 CYP450 2D6 substrate Non-substrate 0.8408 CYP450 3A4 substrate Substrate 0.5831 CYP450 1A2 substrate Non-inhibitor 0.7413 CYP450 2C9 inhibitor Non-inhibitor 0.6781 CYP450 2D6 inhibitor Non-inhibitor 0.8996 CYP450 2C19 inhibitor Non-inhibitor 0.729 CYP450 3A4 inhibitor Non-inhibitor 0.8024 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6932 Ames test Non AMES toxic 0.7639 Carcinogenicity Non-carcinogens 0.8257 Biodegradation Not ready biodegradable 0.9887 Rat acute toxicity 2.5346 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9885 hERG inhibition (predictor II) Non-inhibitor 0.783
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 281.233866 predictedDarkChem Lite v0.1.0 [M-H]- 249.20253 predictedDeepCCS 1.0 (2019) [M+H]+ 281.457166 predictedDarkChem Lite v0.1.0 [M+H]+ 251.02742 predictedDeepCCS 1.0 (2019) [M+Na]+ 280.133166 predictedDarkChem Lite v0.1.0 [M+Na]+ 256.63327 predictedDeepCCS 1.0 (2019)
Targets
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- 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 at November 18, 2007 18:24 / Updated at February 21, 2021 18:51