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Merck
CN

SML4039

SCH-527123

≥98% (HPLC)

Synonym(s):

2-Hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]benzamide, 2-Hydroxy-N,N-dimethyl-3-[[2-[[(1R)-1-(5-methylfuran-2-yl)propyl]amino]-3,4-dioxocyclobuten-1-yl]amino]benzamide, 3-[[3-[(Dimethylamino)carbonyl]-2-hydroxyphenyl]amino]-4-[[(R)-1-(5-methylfuran-2-yl)propyl]amino]cyclobut-3-ene-1,2-dione, CXCR2 Antagonist IV, MK 7123, MK-7123, MK7123, Navarixin, PS 291822, PS-291822, PS291822, SCH 527123, SCH527123

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About This Item

Empirical Formula (Hill Notation):
C21H23N3O5
CAS Number:
473727-83-2
Molecular Weight:
397.42
MDL number:
MFCD16628072

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

N([C@H](CC)c3[o]c(cc3)C)c1[c]([c](c1Nc2c(c(ccc2)C(=O)N(C)C)O)=O)=O

InChI key

RXIUEIPPLAFSDF-CYBMUJFWSA-N

Biochem/physiol Actions

Orally active, high-affinity, potent and selective allosteric CXCR2 antagonist.

SCH-527123 is an orally active, high-affinity, potent and selective allosteric CXCR2 antagonist (IC50 = 2.6 nM) with much reduced CXCR1 potency (IC50 = 36 nM) and little activity against a large panel of enzymes, channels, and GPCRs (IC50 >10 µM). SCH-527123 blocks CXCL8- and CXCL1-induced human neutrophil (hPMN) chemotaxis in cultures (IC50 = 16 & <1 nM, respectively) and pulmonary neutrophilia in vivo (ED50 = 1.2 mg/kg mouse, 1.8 mg/kg rat p.o.) following intranasal LPS administration.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000404697
0000404698
0000392723
0000404698
0000404697

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Michael P Dwyer et al.
Journal of medicinal chemistry, 49(26), 7603-7606 (2006-12-22)
Structure-activity studies on lead cyclobutenedione 3 led to the discovery of 4 (SCH 527123), a potent, orally bioavailable CXCR2/CXCR1 receptor antagonist with excellent cell-based activity. Compound 4 displayed good oral bioavailability in rat and may be a potential therapeutic agent
Richard W Chapman et al.
The Journal of pharmacology and experimental therapeutics, 322(2), 486-493 (2007-05-15)
Sch527123 [2-hydroxy-N,N-dimethyl-3-[[2-[[1(R)-(5-methyl-2-furanyl)propyl]amino]-3,4-dioxo-1-cyclobuten-1-yl]amino]ben-zamide] is a potent, selective antagonist of the human CXCR1 and CXCR2 receptors (Gonsiorek et al., 2007). Here we describe its pharmacologic properties at rodent CXCR2 and at the CXCR1 and CXCR2 receptors in the cynomolgus monkey, as well
Waldemar Gonsiorek et al.
The Journal of pharmacology and experimental therapeutics, 322(2), 477-485 (2007-05-15)
In neutrophils, growth-related protein-alpha (CXCL1) and interleukin-8 (CXCL8), are potent chemoattractants (Cytokine 14:27-36, 2001; Biochemistry 42:2874-2886, 2003) and can stimulate myeloperoxidase release via activation of the G protein-coupled receptors CXCR1 and CXCR2. The role of CXCR1 and CXCR2 in the

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