ELSIBUCOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C35H54O4S2
Molecular Weight	602.931
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)C1=CC(SC(C)(C)SC2=CC(=C(OCCCC(O)=O)C(=C2)C(C)(C)C)C(C)(C)C)=CC(=C1O)C(C)(C)C

InChI

InChIKey=YHFUPQNXMNMQAK-UHFFFAOYSA-N

InChI=1S/C35H54O4S2/c1-31(2,3)24-18-22(19-25(29(24)38)32(4,5)6)40-35(13,14)41-23-20-26(33(7,8)9)30(27(21-23)34(10,11)12)39-17-15-16-28(36)37/h18-21,38H,15-17H2,1-14H3,(H,36,37)

HIDE SMILES / InChI

Molecular Formula	C35H54O4S2
Molecular Weight	602.931
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://adisinsight.springer.com/drugs/800016776 | https://www.ncbi.nlm.nih.gov/pubmed/15201693 | https://www.ncbi.nlm.nih.gov/pubmed/15239610 | https://www.ncbi.nlm.nih.gov/pubmed/25244503

Elsibucol (AGI-1096) is a phenolic intracellular antioxidant with anti-inflammatory and antiproliferative properties. In vitro, elsibucol inhibited the inducible expression of vascular cell adhesion molecule (VCAM)-1, E-selectin, and monocyte chemoattractant protein (MCP)-1 in endothelial cells and tumor necrosis factor (TNF)-alpha and interleukin (IL)-1beta secretion from lipopolysaccharide (LPS)-stimulated peripheral blood mononuclear cells. It also inhibited serum-stimulated proliferation of aortic smooth-muscle cells. In vivo, elsibucol demonstrated anti-inflammatory properties in a murine delayed-type hypersensitivity model. In hypercholesterolemic animals, elsibucol inhibits atherosclerosis and preserves endothelial healing following arterial injury. Elsibucol development for the prevention of transplant rejection has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Discovery of novel phenolic antioxidants as inhibitors of vascular cell adhesion molecule-1 expression for use in chronic inflammatory diseases.	2004 Dec 2	15566311
Effects of AGI-1096, a novel antioxidant compound with anti-inflammatory and antiproliferative properties, on rodent allograft arteriosclerosis.	2004 May 27	15239610
Helicobacter pylori seroprevalence in patients with chronic obstructive pulmonary disease and its relation to pulmonary function tests.	2007	16369121
Lead acetate induces EGFR activation upstream of SFK and PKCalpha linkage to the Ras/Raf-1/ERK signaling.	2009 Mar 1	19133285

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:10 UTC 2023` Edited by `admin` on `Fri Dec 15 15:37:10 UTC 2023`
Record UNII	O7T92N1Y8T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELSIBUCOL

Official Name

English

ELSIBUCOL [USAN]

Common Name

English

4-[4-[[1-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]sulfanyl]-1-methylethyl]sulfanyl]-2,6-bis(1,1-dimethylethyl)phenoxy]butanoic acid

Systematic Name

English

AGI-1096

Code

English

BUTANOIC ACID, 4-(4-((1-((3,5-BIS(1,1-DIMETHYLETHYL)-4-HYDROXYPHENYL)THIO)-1-METHYLETHYL)THIO)-2,6-BIS(1,1-DIMETHYLETHYL)PHENOXY)-

Common Name

English

elsibucol [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C275