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Key Documents

SML0201

Sigma-Aldrich

SB 297006

≥98% (HPLC)

Synonym(s):

N-Benzoyl-4-nitro-L-phenylalanine ethyl ester

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About This Item

Empirical Formula (Hill Notation):
C18H18N2O5
CAS Number:
Molecular Weight:
342.35
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

assay

≥98% (HPLC)

optical activity

[α]/D -60 to -78° in ethanol (c=1)

color

white to tan

solubility

DMSO: ≥15 mg/mL

storage temp.

2-8°C

SMILES string

CCOC(=O)[C@H](Cc1ccc(cc1)[N+]([O-])=O)NC(=O)c2ccccc2

InChI

1S/C18H18N2O5/c1-2-25-18(22)16(19-17(21)14-6-4-3-5-7-14)12-13-8-10-15(11-9-13)20(23)24/h3-11,16H,2,12H2,1H3,(H,19,21)/t16-/m0/s1

InChI key

BEZXGSZPWXRHIN-INIZCTEOSA-N

Application

SB 297006 may be used to study CCR3-mediated cell signaling in asthma models.

Biochem/physiol Actions

CCR3 Antagonist
SB 297006 inhibits the recruitment and migration of eosinophils in allergen models of models. It suppresses the Th2-mediated eosinophil infiltration in the airways.[1][2]
SB-297006 is a potent, selective CCR-3 antagonist (IC50 = 60 nM). The compound blocked CCR3 agonist-induced calcium mobilization in CCR3 expressing cells with the following IC50 values: eotaxin, 210 nM; eotaxin-2, 90 nM and MCP4, 80 nM.

Features and Benefits

This compound is featured on the Chemokine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation markEnvironment

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Peter J Barnes
Annual review of pharmacology and toxicology, 42, 81-98 (2002-01-25)
Cytokines play a critical role in orchestrating and perpetuating inflammation in asthmatic airways and several specific cytokine and chemokine inhibitors are now in development for the treatment of asthma. Inhibition of IL-4 with soluble IL-4 receptors has shown promising early
Leyi Gong et al.
Expert opinion on therapeutic patents, 19(8), 1109-1132 (2009-07-30)
Since the mid-1990s, there has been significant effort invested in the discovery and clinical development of CC chemokine receptor-3 (CCR3) antagonists as potential therapeutics for airway disease. A patent literature review is presented of small molecule CCR3 antagonists comprising the

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