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Merck
CN

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:
58816-69-6
Molecular Weight:
342.35
MDL number:
MFCD19690954
UNSPSC Code:
51111800
PubChem Substance ID:
329825225
NACRES:
NA.77

Key Documents

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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.
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
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H400

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
111M4606V

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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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