| Identification | Back Directory | [Name]
Repertaxin | [CAS]
266359-83-5 | [Synonyms]
CS-2395
DF 1681Y
Reparixin
Reparaxin
Repertaxin
REPARIXIN;DF 1681Y
DF 1681Y;REPERTAXIN
Reparixin (Repertaxin
REPERTAXIN;DF 1681Y;REPARAXIN
Repertaxin(R-configuration, free base form)
(R)-(-)-N-2-[(4-Isobutylphenyl)propionyl]methanesulfonamide
Benzeneacetamide, α-methyl-4-(2-methylpropyl)-N-(methylsulfonyl)-, (αR)- | [Molecular Formula]
C14H21NO3S | [MDL Number]
MFCD18633292 | [MOL File]
266359-83-5.mol | [Molecular Weight]
283.39 |
| Chemical Properties | Back Directory | [Melting point ]
103-105℃ | [density ]
1.137±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Soluble in DMSO (up to 100 mg/ml) or in Ethanol (up to 25 mg/ml) | [form ]
solid | [pka]
4.28±0.40(Predicted) | [color ]
White | [Optical Rotation]
[α]/D -80 to -90°, c =1.0 in ethanol | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months. | [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 | [SMILES]
[S](=O)(=O)(NC(=O)C(C)c1ccc(cc1)CC(C)C)C |
| Hazard Information | Back Directory | [Description]
Reparixin (CAS 266359-83-5) is a noncompetitive allosteric inhibitor of IL-8 (CXCL8) activation of CXCR1 and CXCR2 chemokine receptors (IC50?= 1 and 100 nM, respectively). It blocks a number of activities related to IL-8 signaling, including leukocyte recruitment (IC50?= 1 nM) without affecting receptor activation induced by other CXCR1 and CXCR2 agonists.1?In spontaneously hypertensive rats, 5 mg/kg reparixin administered daily for three weeks was shown to reduce blood pressure by inhibiting hypertension-related mediators.2?It attenuates inflammatory responses and promotes recovery of function after traumatic lesion to the spinal cord.3?Reparixin blockade (100 nM) of CXCR1 has also been used to deplete a cancer stem cell population in human breast cancer cell lines?in vitro.4 | [Uses]
Prevention of delayed graft function in solid organ transplant (CXCL8 inhibitor). | [Definition]
ChEBI: Reparixin is a monoterpenoid. | [in vivo]
Reparixin is an inhibitor of CXCL8 receptor CXCR1 and CXCR2 activation, has been shown to attenuate inflammatory responses in various injury models. Spontaneously hypertensive rats (SHR) are administered a subcutaneous injection of Reparixin (5 mg/kg) daily for 3 weeks. Reparixin effectively decreases systolic blood pressure and increased the blood flow[3]. Reparixin reduces the levels of IL-1β in the brain after middle cerebral artery occlusion/reperfusion (MCAo) in mice. Bars represent levels of IL-1β (pg/100 mg) measured by ELISA in the brain tissues of mice subjected or not (SHAM) to MCAo and pretreated with vehicle or Reparixin (30 mg/kg, s.c.)[4]. | [IC 50]
CXCR1wt: 5.6 nM (IC50, in L1.2 cells); CXCR1Ile43Val: 80 nM (IC50, in L1.2 cells); CXCR1: 1 nM (IC50, in cells); CXCR2: ～100 nM (IC50, in cells) | [References]
1) Bertini?et al.?(2004),?Non-competitive allosteric inhibitors of the inflammatory cytokine receptors CXCR1 and CXCR2: prevention of reperfusion injury; Proc. Natl. Acad. Sci. USA,?101?11791
2) Kim?et al. (2011),?Reparixin, an inhibitor of CXCR1 and CXCR2 receptor activation, attenuates blood pressure and hypertension-related mediators expression in spontaneously hypertensive rats; Biol. Pharm. Bull.,?34?120
3) Gorio?et al.?(2007),?Reparixin, an inhibitor of CXCR2 function, attenuates inflammatory responses and promotes recovery of function after traumatic lesion to the spinal cord; J. Pharmacol. Exp. Ther.,?322?973
4) Ginestier?et al.?(2010),?CXCR1 blockade selectively targets human breast cancer stem cells in vitro and in xenografts; J. Clin. Invest.,?120?485 |
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