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Repertaxin

CAS No.:
266359-83-5
Catalog Number:
AG00BEB1
Molecular Formula:
C14H21NO3S
Molecular Weight:
283.3864
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
2mg
99%
1 week
United States
$182
- +
5mg
99%
1 week
United States
$265
- +
10mg
99%
1 week
United States
$404
- +
25mg
99%
1 week
United States
$751
- +
100mg
95%
1 week
United States
$798
- +
Product Description
Catalog Number:
AG00BEB1
Chemical Name:
Repertaxin
CAS Number:
266359-83-5
Molecular Formula:
C14H21NO3S
Molecular Weight:
283.3864
MDL Number:
MFCD18633292
IUPAC Name:
(2R)-2-[4-(2-methylpropyl)phenyl]-N-methylsulfonylpropanamide
InChI:
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)/t11-/m1/s1
InChI Key:
KQDRVXQXKZXMHP-LLVKDONJSA-N
SMILES:
CC(Cc1ccc(cc1)[C@H](C(=O)NS(=O)(=O)C)C)C
UNII:
U604E1NB3K
Properties
Complexity:
389  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
283.124g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
283.386g/mol
Monoisotopic Mass:
283.124g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
71.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.9  
Literature
Title Journal
Chemokine receptor antagonists. Journal of medicinal chemistry 20121126
CXCR1/2 inhibition enhances pancreatic islet survival after transplantation. The Journal of clinical investigation 20121001
Elevated interleukin-8 enhances prefrontal synaptic transmission in mice with persistent inflammatory pain. Molecular pain 20120101
Changes in expression of mRNA for interleukin-8 and effects of interleukin-8 receptor inhibitor in the spinal dorsal horn in a rat model of lumbar disc herniation. Spine 20111201
Progress in structure based drug design for G protein-coupled receptors. Journal of medicinal chemistry 20110714
Inhibition of CXCR1 and CXCR2 chemokine receptors attenuates acute inflammation, preserves gray matter and diminishes autonomic dysreflexia after spinal cord injury. Spinal cord 20110301
Reparixin, an inhibitor of CXCR1 and CXCR2 receptor activation, attenuates blood pressure and hypertension-related mediators expression in spontaneously hypertensive rats. Biological & pharmaceutical bulletin 20110101
CXC chemokine receptor-1 is expressed by hepatocytes and regulates liver recovery after hepatic ischemia/reperfusion injury. Hepatology (Baltimore, Md.) 20110101
CXCR1 blockade selectively targets human breast cancer stem cells in vitro and in xenografts. The Journal of clinical investigation 20100201
Interfering with inflammation: a new strategy to block breast cancer self-renewal and progression? Breast cancer research : BCR 20100101
A crucial role for TNF-alpha in mediating neutrophil influx induced by endogenously generated or exogenous chemokines, KC/CXCL1 and LIX/CXCL5. British journal of pharmacology 20091001
Development and validation of an LC-MS/MS method for determination of methanesulfonamide in human urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090715
Novel role of CXCR2 in regulation of gamma-secretase activity. ACS chemical biology 20081219
Therapeutic inhibition of CXCR2 by Reparixin attenuates acute lung injury in mice. British journal of pharmacology 20081001
The chemokine receptors CXCR1/CXCR2 modulate antigen-induced arthritis by regulating adhesion of neutrophils to the synovial microvasculature. Arthritis and rheumatism 20080801
Platelet activating factor receptors drive CXC chemokine production, neutrophil influx and edema formation in the lungs of mice injected with Tityus serrulatus venom. Toxicon : official journal of the International Society on Toxinology 20070901
Reparixin, an inhibitor of CXCR2 function, attenuates inflammatory responses and promotes recovery of function after traumatic lesion to the spinal cord. The Journal of pharmacology and experimental therapeutics 20070901
Design of noncompetitive interleukin-8 inhibitors acting on CXCR1 and CXCR2. Journal of medicinal chemistry 20070823
Down-regulation of CXCR2 on neutrophils in severe sepsis is mediated by inducible nitric oxide synthase-derived nitric oxide. American journal of respiratory and critical care medicine 20070301
Reparixin, a specific interleukin-8 inhibitor, has no effects on inflammation during endotoxemia. International journal of immunopathology and pharmacology 20070101
The interleukin-8 (IL-8/CXCL8) receptor inhibitor reparixin improves neurological deficits and reduces long-term inflammation in permanent and transient cerebral ischemia in rats. Molecular medicine (Cambridge, Mass.) 20070101
Chemokine MIP-2/CXCL2, acting on CXCR2, induces motor neuron death in primary cultures. Neuroimmunomodulation 20070101
Species differences in the pharmacokinetics and metabolism of reparixin in rat and dog. Xenobiotica; the fate of foreign compounds in biological systems 20060501
2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors. Journal of medicinal chemistry 20050630
Neuroprotection with the CXCL8 inhibitor repertaxin in transient brain ischemia. Cytokine 20050507
Inhibition of the chemokine receptor CXCR2 prevents kidney graft function deterioration due to ischemia/reperfusion. Kidney international 20050501
Predicting human serum albumin affinity of interleukin-8 (CXCL8) inhibitors by 3D-QSPR approach. Journal of medicinal chemistry 20050407
Inhibition of interleukin-8 (CXCL8/IL-8) responses by repertaxin, a new inhibitor of the chemokine receptors CXCR1 and CXCR2. Biochemical pharmacology 20050201
Neutrophil recruitment in the reperfused-injured rat liver was effectively attenuated by repertaxin, a novel allosteric noncompetitive inhibitor of CXCL8 receptors: a therapeutic approach for the treatment of post-ischemic hepatic syndromes. International journal of immunopathology and pharmacology 20050101
Repertaxin, a novel inhibitor of rat CXCR2 function, inhibits inflammatory responses that follow intestinal ischaemia and reperfusion injury. British journal of pharmacology 20040901
Noncompetitive allosteric inhibitors of the inflammatory chemokine receptors CXCR1 and CXCR2: prevention of reperfusion injury. Proceedings of the National Academy of Sciences of the United States of America 20040810
Properties