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SML2655

Sigma-Aldrich

Reparixin

≥98% (HPLC)

Synonym(s):

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

Empirical Formula (Hill Notation):
C14H21NO3S
CAS Number:
266359-83-5
Molecular Weight:
283.39
MDL number:
MFCD18633292
UNSPSC Code:
51111800
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -80 to -90°, c = 1.0 in ethanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−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)

InChI key

KQDRVXQXKZXMHP-UHFFFAOYSA-N

Biochem/physiol Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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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