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SML2655

Sigma-Aldrich

Reparixin

≥98% (HPLC)

Synonym(e):

αR-methyl-4-(2-methylpropyl)-N-(methylsulfonyl)-benzeneacetamide, (R)-(-)-N-2-[(4-Isobutylphenyl)propionyl]methanesulfonamide, DF 1681Y, Repertaxin

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About This Item

Empirische Formel (Hill-System):
C14H21NO3S
CAS-Nummer:
266359-83-5
Molekulargewicht:
283.39
MDL-Nummer:
MFCD18633292
UNSPSC-Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

Form

powder

Optische Aktivität

[α]/D -80 to -90°, c = 1.0 in ethanol

Farbe

white to beige

Löslichkeit

DMSO: 2 mg/mL, clear

Lagertemp.

−20°C

InChI

1S/C14H21NO3S/c1-10(2)9-12-5-7-13(8-6-12)11(3)14(16)15-19(4,17)18/h5-8,10-11H,9H2,1-4H3,(H,15,16)

InChIKey

KQDRVXQXKZXMHP-UHFFFAOYSA-N

Biochem./physiol. Wirkung

Reparixin is a noncompetitive allosteric inhibitor of the inflammatory CXCL8 (IL-8) chemokine receptors CXCR1 and CXCR2 with IC50 values of 1 nM for CXCR1 and 100 nM for CXCR2. It is believed to prevent receptor signaling by locking CXCR1/R2 in an inactive conformation. Reparixin has been studied to prevent ischaemia-reperfusion injury and inflammation and is clinical trials for triple negative breast cancer and to prevent injury occurring after pancreatic islet transplantation.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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N C Bergenhem et al.
Biochemical genetics, 30(5-6), 279-287 (1992-06-01)
Two, electrophoretically distinct, forms of carbonic anhydrase I (CA Ia and CA Ib) are found at high polymorphic frequencies in red cells of natural populations of pigtail macaques, Macaca nemestrina, from southeast Asia. By use of the polymerase chain reaction
Anne F Schott et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 23(18), 5358-5365 (2017-05-26)
Purpose: Chemokine receptor 1 (CXCR1) is recognized as an actionable receptor selectively expressed by breast cancer stem cells (BCSCs). Reparixin is an investigational allosteric inhibitor of chemokine receptors 1 and 2 (CXCR1/2), and demonstrates activity against BCSCs in human breast
P Opfermann et al.
Clinical and experimental immunology, 180(1), 131-142 (2014-11-18)
Reparixin, a CXCR 1/2 antagonist, has been shown to mitigate ischaemia-reperfusion injury (IRI) in various organ systems in animals, but data in humans are scarce. The aim of this double-blinded, placebo-controlled pilot study was to evaluate the safety and efficacy

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