U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C35H52O5S2
Molecular Weight 616.914
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SUCCINOBUCOL

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

InChI

InChIKey=RKSMVPNZHBRNNS-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C35H52O5S2
Molecular Weight 616.914
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Succinobucol (also known as AGI-1067) is a probucol derivative patented by American pharmaceutical company Atherogenics, Inc as vascular protectant with antioxidant, anti-inflammatory and antiplatelet activities. In vitro, succinobucol inhibits the TNF-α induced expression of VCAM-1 and MCP-1 with little effect on intercellular adhesion molecule (ICAM)-1. In addition, succinobucol inhibits lipopolysaccharide (LPS)-induced expression of tissue factor in human monocytic cells and endothelial cells, an effect thought to be mediated independently from the nuclear factor κB pathway. Preclinical studies have shown reduced total cholesterol and low-density lipoprotein cholesterol concentrations, increased high-density lipoprotein cholesterol concentrations, decreased levels of inflammatory mediators, and reduced atheroma area with Succinobucol treatment in animal models. Unfortunately, in clinical trials, Succinobucol failed to demonstrate a strong cardioprotective effect. Undesired metabolic effects including high-density lipoprotein cholesterol-lowering have been consistently reported, and diarrhea appears to be an expected adverse effect.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Drug reverses coronary atherosclerosis.
2002 Jan 1
Pharmacologic prevention of both restenosis and atherosclerosis progression: AGI-1067, probucol, statins, folic acid and other therapies.
2003 Dec
Effects of AGI-1067 and probucol after percutaneous coronary interventions.
2003 Feb 4
Clinical results with AGI-1067: a novel antioxidant vascular protectant.
2003 Feb 6
Chemistry and pharmacology of vascular protectants: a novel approach to the treatment of atherosclerosis and coronary artery disease.
2003 Feb 6
Signal jammer. An academic experiment leads to a new class of drug for attacking heart disease.
2003 Jul
AGI-1067: a multifunctional phenolic antioxidant, lipid modulator, anti-inflammatory and antiatherosclerotic agent.
2003 Jun
Experimental and clinical studies show that the probucol derivative AGI-1067 prevents vascular growth.
2003 Nov
Vascular protectants for the treatment of atherosclerosis.
2003 Sep
Inhibition of lipoprotein lipid oxidation.
2005
Antioxidants and atherosclerosis: emerging drug therapies.
2005 Feb
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.
2006 Sep
[Research and developmental strategy of anti-dyslipidemic agents].
2007 Apr
Assessment of lipoprotein profiles study (ALPS) and antioxidant activity in healthy subjects treated with AGI-1067.
2007 Aug
A novel class of antioxidants inhibit LPS induction of tissue factor by selective inhibition of the activation of ASK1 and MAP kinases.
2007 Aug
Clinical trials update from the European Society of Cardiology Congress in Vienna, 2007: PROSPECT, EVEREST, ARISE, ALOFT, FINESSE, Prague-8, CARESS in MI and ACUITY.
2007 Dec
American Heart Association - Scientific Sessions 2006. Cell therapies for ischemic tissues and treatments for lipid metabolism disorders.
2007 Jan
AGI-1067, a novel vascular protectant, anti-inflammatory drug and mild antiplatelet agent for treatment of atherosclerosis.
2007 Jul
Follicular development and expression of the messenger ribonucleic acid for the inhibin/activin subunits in two genetic lines of turkey hens that differ in total egg production.
2007 May
Gateways to clinical trials. July-August 2008.
2008 Jul-Aug
Succinobucol: review of the metabolic, antiplatelet and cardiovascular effects.
2009 Apr
Molecular mechanisms underlying the antiatherosclerotic and antidiabetic effects of probucol, succinobucol, and other probucol analogues.
2009 Jun
Selective thromboxane inhibition after vascular protectant AGI-1067: results of assessment of lipoprotein profiles (ALPS) biomarkers in vitro and in vivo substudy.
2009 May
Heme oxygenase-1 increases endothelial progenitor cells.
2009 Oct
Malformed mdx myofibers have normal cytoskeletal architecture yet altered EC coupling and stress-induced Ca2+ signaling.
2009 Sep
Impact of medical therapy on atheroma volume measured by different cardiovascular imaging modalities.
2010
AGI-1067, a novel antioxidant and anti-inflammatory agent, enhances insulin release and protects mouse islets.
2010 Jul 29
Analyses of copy number variation of GK rat reveal new putative type 2 diabetes susceptibility loci.
2010 Nov 23
Probucol and succinobucol in atrial fibrillation: pros and cons.
2010 Oct 8
Emerging drugs for hyperlipidemia.
2010 Sep
Patents

Patents

Sample Use Guides

two 150 mg tablets daily with a meal
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:24:28 UTC 2023
Edited
by admin
on Sat Dec 16 17:24:28 UTC 2023
Record UNII
J1J54V24R4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SUCCINOBUCOL
INN   MI   USAN  
INN   USAN  
Official Name English
succinobucol [INN]
Common Name English
SUCCINOBUCOL [MI]
Common Name English
SUCCINOBUCOL [USAN]
Common Name English
AGI-1067
Code English
Classification Tree Code System Code
NCI_THESAURUS C275
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
Code System Code Type Description
MERCK INDEX
m10272
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY Merck Index
FDA UNII
J1J54V24R4
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
USAN
PP-56
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID10176003
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
EVMPD
SUB128140
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
PUBCHEM
216325
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
CAS
216167-82-7
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
SMS_ID
100000153841
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
DRUG BANK
DB05399
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL83626
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
NCI_THESAURUS
C75299
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
INN
8496
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
MESH
C471047
Created by admin on Sat Dec 16 17:24:28 UTC 2023 , Edited by admin on Sat Dec 16 17:24:28 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> DERIVATIVE
Related Record Type Details
ACTIVE MOIETY