SB 328437 (DMSO solution), CCR3 antagonist

Key facts

CAS number

247580-43-4

Form

Liquid

form

Molecular weight

378.4 Da

Molecular formula

C₂₁H₁₈N₂O₅

PubChem

10474776

Nature

Synthetic

Biochemical name

methyl (2S)-2-(naphthalene-2-carbonylamino)-3-(4-nitrophenyl)propanoate

Biological description

A highly potent and selective CC chemokine receptor-3 (CCR3) antagonist (IC₅₀ = 4 nM). Shows >2500-fold selectivity over CCR7, CXCR1, CXCR2, C4aR and LTD₄ receptors. Inhibits Ca²⁺ mobilization induced by eotaxin, eotaxin-2 and MCP-4 (IC₅₀ values are 38, 35, and 20 nM, respectively). Also inhibits eosinophil chemotaxis.

Canonical smiles

COC(=O)C(CC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)C2=CC=CC3=CC=CC=C32

Isomeric smiles

COC(=O)[C@H](CC1=CC=C(C=C1)[N+](=O)[O-])NC(=O)C2=CC=CC3=CC=CC=C32

InChi

InChI=1S/C21H18N2O5/c1-28-21(25)19(13-14-9-11-16(12-10-14)23(26)27)22-20(24)18-8-4-6-15-5-2-3-7-17(15)18/h2-12,19H,13H2,1H3,(H,22,24)/t19-/m0/s1

InChiKey

VMFGCGRAIBLAFY-IBGZPJMESA-N

IUPAC Name

methyl (2S)-2-(naphthalene-1-carbonylamino)-3-(4-nitrophenyl)propanoate