ELUBRIXIN TOSYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H17Cl2FN4O4S.C7H8O3S
Molecular Weight	635.512
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.OC2=C(C(Cl)=CC=C2NC(=O)NC3=CC=CC(F)=C3Cl)S(=O)(=O)N4CCNCC4

InChI

InChIKey=CJAUWWGOABMMJX-UHFFFAOYSA-N

InChI=1S/C17H17Cl2FN4O4S.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h1-5,21,25H,6-9H2,(H2,22,23,26);2-5H,1H3,(H,8,9,10)

HIDE SMILES / InChI

Molecular Formula	C7H8O3S
Molecular Weight	172.202
Charge	0
Count

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

Molecular Formula	C17H17Cl2FN4O4S
Molecular Weight	463.311
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25861835 | https://adisinsight.springer.com/drugs/800009746 | https://www.ncbi.nlm.nih.gov/pubmed/21426372

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 Elubrixin was withdrawn from the Phase II trial due to the lack of efficacy.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

Title	Date	PubMed
SB-656933, a novel CXCR2 selective antagonist, inhibits ex vivo neutrophil activation and ozone-induced airway inflammation in humans.	2011 Aug	21426372
Safety and early treatment effects of the CXCR2 antagonist SB-656933 in patients with cystic fibrosis.	2013 May	22995323
International Union of Basic and Clinical Pharmacology. [corrected]. LXXXIX. Update on the extended family of chemokine receptors and introducing a new nomenclature for atypical chemokine receptors.	2014	24218476
Inflammatory bowel disease therapies discontinued between 2009 and 2014.	2015	25861835

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 Created by `admin` on `Sat Dec 16 01:36:22 GMT 2023` Edited by `admin` on `Sat Dec 16 01:36:22 GMT 2023`
Record UNII	13FVR7WD4P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELUBRIXIN TOSYLATE

Official Name

English

ELUBRIXIN TOSILATE

Common Name

English

Elubrixin tosilate [WHO-DD]

Common Name

English

UREA, N-(2-CHLORO-3-FLUOROPHENYL)-N'-(4-CHLORO-2-HYDROXY-3-(1- PIPERAZINYLSULFONYL)PHENYL)-, 4-METHYLBENZENESULFONATE (1:1)

Systematic Name

English

ELUBRIXIN TOSYLATE [USAN]

Common Name

English

SB-656933-AAA

Code

English

Code System Code Type Description

ChEMBL

CHEMBL2178579