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SML2655

Sigma-Aldrich

Reparixin

≥98% (HPLC)

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Synonym(s):
αR-methyl-4-(2-methylpropyl)-N-(methylsulfonyl)-benzeneacetamide, (R)-(-)-N-2-[(4-Isobutylphenyl)propionyl]methanesulfonamide, DF 1681Y, Repertaxin
Empirical Formula (Hill Notation):
C14H21NO3S
CAS Number:
Molecular Weight:
283.39
MDL number:

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

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Reparixin ≥98% (HPLC)

Sigma-Aldrich

SML2655

Reparixin

KPR-2579 ≥98% (HPLC)

Sigma-Aldrich

SML2411

KPR-2579

Bepristat 1a ≥98% (HPLC)

Sigma-Aldrich

SML2164

Bepristat 1a

BAY-1797 ≥98% (HPLC)

Sigma-Aldrich

SML2817

BAY-1797

form

powder

form

powder

form

powder

form

powder

color

white to beige

color

white to beige

color

white to light brown

color

white to beige

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

optical activity

[α]/D -80 to -90°, c = 1.0 in ethanol

optical activity

[α]/D +124 to +136°, c = c=1 in chloroform-d

optical activity

-

optical activity

-

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


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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
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

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