Repertaxin Chemical Properties

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)

pka

4.28±0.40(Predicted)

form 

solid

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.

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

Safety Information

WGK Germany 

WGK 3

Storage Class

11 - Combustible Solids

Repertaxin Usage And Synthesis

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).

Uses

Reparixin is an inhibitor of CXCR1 and CXCR2 chemokine receptors. Functions as an agent that blocks a range of activities including leukocyte recruitment and IL-8 signaling.

Definition

ChEBI: Reparixin is a monoterpenoid.

in vivo

IC 50

CXCR1^wt: 5.6 nM (IC₅₀, in L1.2 cells); CXCR1^Ile43Val: 80 nM (IC₅₀, in L1.2 cells); CXCR1: 1 nM (IC₅₀, in cells); CXCR2: ～100 nM (IC₅₀, in cells)

References

[1] Non-competitive allosteric inhibitors of the inflammatory cytokine receptors CXCR1 and CXCR2: prevention of reperfusion injury
[2] HYE YOUNG KIM. Reparixin, an inhibitor of CXCR1 and CXCR2 receptor activation, attenuates blood pressure and hypertension-related mediators expression in spontaneously hypertensive rats.[J]. Biological & pharmaceutical bulletin, 2011, 34 1: 120-127. DOI:10.1248/bpb.34.120
[3] ALFREDO GORIO. Reparixin, an inhibitor of CXCR2 function, attenuates inflammatory responses and promotes recovery of function after traumatic lesion to the spinal cord.[J]. Journal of Pharmacology and Experimental Therapeutics, 2007, 322 3: 973-981. DOI:10.1124/jpet.107.123679
[4] CHRISTOPHE GINESTIER. CXCR1 blockade selectively targets human breast cancer stem cells in vitro and in xenografts.[J]. Journal of Clinical Investigation, 2010, 120 2: 485-497. DOI:10.1172/jci39397

Repertaxin(266359-83-5)Related Product Information

• TCPOBOP
• Imatinib mesylate
• ZM 336372
• SU 4312
• R-(-)-2-(4-ISOBUTYLPHENYL)PROPIONYL METHANSULPHONAMIDE, LYSINE SALT