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266359-83-5,MFCD18633292
Catalog No.:AA00BE89

266359-83-5 | Repertaxin

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1mg
98%
in stock  
$22.00   $15.00
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5mg
≥95%
in stock  
$73.00   $51.00
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10mg
≥95%
in stock  
$129.00   $90.00
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25mg
98%
in stock  
$240.00   $168.00
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50mg
98%
in stock  
$454.00   $318.00
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100mg
95%
in stock  
$808.00   $565.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00BE89
Chemical Name:
Repertaxin
CAS Number:
266359-83-5
Molecular Formula:
C14H21NO3S
Molecular Weight:
283.3864
MDL Number:
MFCD18633292
SMILES:
CC(Cc1ccc(cc1)[C@H](C(=O)NS(=O)(=O)C)C)C
Properties
Computed Properties
 
Complexity:
389  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
5  
XLogP3:
2.9  

Downstream Synthesis Route
3144-09-0    51146-57-7   
repertaxin 

[1]JournalofMedicinalChemistry,2005,vol.48,p.4312-4331

[2]JournalofMedicinalChemistry,2005,vol.48,p.2469-2479

Literature

Title: Chemokine receptor antagonists.

Journal: Journal of medicinal chemistry 20121126

Title: CXCR1/2 inhibition enhances pancreatic islet survival after transplantation.

Journal: The Journal of clinical investigation 20121001

Title: Elevated interleukin-8 enhances prefrontal synaptic transmission in mice with persistent inflammatory pain.

Journal: Molecular pain 20120101

Title: 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.

Journal: Spine 20111201

Title: Progress in structure based drug design for G protein-coupled receptors.

Journal: Journal of medicinal chemistry 20110714

Title: Inhibition of CXCR1 and CXCR2 chemokine receptors attenuates acute inflammation, preserves gray matter and diminishes autonomic dysreflexia after spinal cord injury.

Journal: Spinal cord 20110301

Title: Reparixin, an inhibitor of CXCR1 and CXCR2 receptor activation, attenuates blood pressure and hypertension-related mediators expression in spontaneously hypertensive rats.

Journal: Biological & pharmaceutical bulletin 20110101

Title: CXC chemokine receptor-1 is expressed by hepatocytes and regulates liver recovery after hepatic ischemia/reperfusion injury.

Journal: Hepatology (Baltimore, Md.) 20110101

Title: CXCR1 blockade selectively targets human breast cancer stem cells in vitro and in xenografts.

Journal: The Journal of clinical investigation 20100201

Title: Interfering with inflammation: a new strategy to block breast cancer self-renewal and progression?

Journal: Breast cancer research : BCR 20100101

Title: A crucial role for TNF-alpha in mediating neutrophil influx induced by endogenously generated or exogenous chemokines, KC/CXCL1 and LIX/CXCL5.

Journal: British journal of pharmacology 20091001

Title: Development and validation of an LC-MS/MS method for determination of methanesulfonamide in human urine.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20090715

Title: Novel role of CXCR2 in regulation of gamma-secretase activity.

Journal: ACS chemical biology 20081219

Title: Therapeutic inhibition of CXCR2 by Reparixin attenuates acute lung injury in mice.

Journal: British journal of pharmacology 20081001

Title: The chemokine receptors CXCR1/CXCR2 modulate antigen-induced arthritis by regulating adhesion of neutrophils to the synovial microvasculature.

Journal: Arthritis and rheumatism 20080801

Title: Platelet activating factor receptors drive CXC chemokine production, neutrophil influx and edema formation in the lungs of mice injected with Tityus serrulatus venom.

Journal: Toxicon : official journal of the International Society on Toxinology 20070901

Title: Reparixin, an inhibitor of CXCR2 function, attenuates inflammatory responses and promotes recovery of function after traumatic lesion to the spinal cord.

Journal: The Journal of pharmacology and experimental therapeutics 20070901

Title: Design of noncompetitive interleukin-8 inhibitors acting on CXCR1 and CXCR2.

Journal: Journal of medicinal chemistry 20070823

Title: Down-regulation of CXCR2 on neutrophils in severe sepsis is mediated by inducible nitric oxide synthase-derived nitric oxide.

Journal: American journal of respiratory and critical care medicine 20070301

Title: Reparixin, a specific interleukin-8 inhibitor, has no effects on inflammation during endotoxemia.

Journal: International journal of immunopathology and pharmacology 20070101

Title: 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.

Journal: Molecular medicine (Cambridge, Mass.) 20070101

Title: Chemokine MIP-2/CXCL2, acting on CXCR2, induces motor neuron death in primary cultures.

Journal: Neuroimmunomodulation 20070101

Title: Species differences in the pharmacokinetics and metabolism of reparixin in rat and dog.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20060501

Title: 2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors.

Journal: Journal of medicinal chemistry 20050630

Title: Neuroprotection with the CXCL8 inhibitor repertaxin in transient brain ischemia.

Journal: Cytokine 20050507

Title: Inhibition of the chemokine receptor CXCR2 prevents kidney graft function deterioration due to ischemia/reperfusion.

Journal: Kidney international 20050501

Title: Predicting human serum albumin affinity of interleukin-8 (CXCL8) inhibitors by 3D-QSPR approach.

Journal: Journal of medicinal chemistry 20050407

Title: Inhibition of interleukin-8 (CXCL8/IL-8) responses by repertaxin, a new inhibitor of the chemokine receptors CXCR1 and CXCR2.

Journal: Biochemical pharmacology 20050201

Title: 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.

Journal: International journal of immunopathology and pharmacology 20050101

Title: Repertaxin, a novel inhibitor of rat CXCR2 function, inhibits inflammatory responses that follow intestinal ischaemia and reperfusion injury.

Journal: British journal of pharmacology 20040901

Title: Noncompetitive allosteric inhibitors of the inflammatory chemokine receptors CXCR1 and CXCR2: prevention of reperfusion injury.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20040810

Title: Moriconi A, et al. Design of noncompetitive interleukin-8 inhibitors acting on CXCR1 and CXCR2. J Med Chem. 2007 Aug 23;50(17):3984-4002.

Title: Bertini R, et al. Receptor binding mode and pharmacological characterization of a potent and selective dual CXCR1/CXCR2non-competitive allosteric inhibitor. Br J Pharmacol. 2012 Jan;165(2):436-54.

Title: Kim HY, et al. Reparixin, an inhibitor of CXCR1 and CXCR2 receptor activation, attenuates blood pressure and hypertension-related mediators expression in spontaneously hypertensive rats. Biol Pharm Bull. 2011;34(1):120-7.

Title: Sousa LF, et al. Blockade of CXCR1/2 chemokine receptors protects against brain damage in ischemic stroke in mice. Clinics (Sao Paulo). 2013;68(3):391-4.

Title: Bertini R, et al. Noncompetitive allosteric inhibitors of the inflammatory chemokine receptors CXCR1 and CXCR2: prevention of reperfusion injury. Proc Natl Acad Sci U S A. 2004 Aug 10;101(32):11791-6.

Title: Krishnamurthy A, et al. Identification of a novel chemokine-dependent molecular mechanism underlying rheumatoid arthritis-associated autoantibody-mediated bone loss. Ann Rheum Dis. 2016 Apr;75(4):721-9.

Title: Crespo J, et al. Human Naive T Cells Express Functional CXCL8 and Promote Tumorigenesis. J Immunol. 2018 Jul 15;201(2):814-820.

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