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266359-83-5

266359-83-5 Structure

266359-83-5 Structure
IdentificationBack 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 PropertiesBack 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 activity]

[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.
Hazard InformationBack 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.
[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
Spectrum DetailBack Directory
[Spectrum Detail]

Repertaxin(266359-83-5)1HNMR
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