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Details

Stereochemistry ACHIRAL
Molecular Formula C17H17Cl2FN4O4S
Molecular Weight 463.311
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELUBRIXIN

SMILES

OC1=C(C(Cl)=CC=C1NC(=O)NC2=CC=CC(F)=C2Cl)S(=O)(=O)N3CCNCC3

InChI

InChIKey=YQYFEGTYCUQBEI-UHFFFAOYSA-N
InChI=1S/C17H17Cl2FN4O4S/c18-10-4-5-13(23-17(26)22-12-3-1-2-11(20)14(12)19)15(25)16(10)29(27,28)24-8-6-21-7-9-24/h1-5,21,25H,6-9H2,(H2,22,23,26)

HIDE SMILES / InChI

Molecular Formula C17H17Cl2FN4O4S
Molecular Weight 463.311
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Elubrixin (SB-656933) is a CXCR2 antagonist that demonstrates dose-dependent effects on neutrophil activation and recruitment. In preclinical studies, the compound was shown to inhibit CXCL1-induced CD11b up-regulation on PMNs in an in vitro whole blood assay and to be active in in vivo rodent inhalation challenge models of airway inflammation that used endotoxin and ozone to induce airway neutrophilia. Elubrixin was being developed by GlaxoSmithKline for the treatment of chronic obstructive pulmonary disease, cystic fibrosis and ulcerative colitis. Elubrixin was withdrawn from the Phase II trial due to the lack of efficacy.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
CF patients were randomized to receive either placebo or SB-656933 20mg or 50mg once daily for 28days.
Route of Administration: Oral
Substance Class Chemical
Record UNII
MW2AIJ8USP
Record Status Validated (UNII)
Record Version