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MedKoo Cat#: 574076 | Name: Reparixin L-lysine salt
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Reparixin L-lysine salt is a potent and noncompetitive CXCR1 and CXCR2 allosteric antagonist that inhibits migration of neutrophils induced by CXCL1, CXCL2, CXCL8 and CINC-1. This product also inhibits vascular permeability and neutrophil recruitment in in vivo models of mild and severe ischemia/reperfusion injury. Also selectively depletes cancer stem cells in human breast cancer cell lines and xenograft models.

Chemical Structure

Reparixin L-lysine salt
Reparixin L-lysine salt
CAS#266359-93-7

Theoretical Analysis

MedKoo Cat#: 574076

Name: Reparixin L-lysine salt

CAS#: 266359-93-7

Chemical Formula: C22H39N3O7S

Exact Mass: 489.2509

Molecular Weight: 489.63

Elemental Analysis: C, 53.97; H, 8.03; N, 8.58; O, 22.87; S, 6.55

Price and Availability

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10mg USD 500.00
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Related CAS #
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Synonym
Reparixin L-lysine salt, Repertaxin L-lysine salt
IUPAC/Chemical Name
(αR)-α-Methyl-4-(2-methylpropyl)-N-(methylsulfonyl)benzeneacetamide L-Lysine salt
InChi Key
KQHPMRNHRQKRBO-NXAOXGSFSA-N
InChi Code
InChI=1S/C14H21NO3S.C6H14N2O2.C2H4O2/c1-10(2)9-12-5-7-13(8-6-12)11(3)14(16)15-19(4,17)18;7-4-2-1-3-5(8)6(9)10;1-2(3)4/h5-8,10-11H,9H2,1-4H3,(H,15,16);5H,1-4,7-8H2,(H,9,10);1H3,(H,3,4)/t;5-;/m.0./s1
SMILES Code
O=C(O)C.[NH3+][C@@H](CCCCN)C(O)=O.O=C([N-]S(=O)(C)=O)C(C)C1=CC=C(CC(C)C)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Reparixin is a non-competitive allosteric inhibitor of the activation of CXCR1 and CXCR2 chemokine receptors by IL-8 (IC50s = 1 and 100 nM, respectively). It blocks a range of activities related to IL-8 signaling, including leukocyte recruitment (IC50 = 1 nM) and other inflammatory responses, without affecting receptor activation induced by other CXCR1 and CXCR2 agonists.
In vitro activity:
Pretreatment and treatment of endothelial cells with reparixin demonstrated a protective effect on cell viability after simulated ischemia-reperfusion. Reference: Int J Health Sci (Qassim). 2022 May-Jun;16(3):20-24. https://pubmed.ncbi.nlm.nih.gov/35599941/
In vivo activity:
This meta-analysis found that reparixin improved survival in critically ill or transplant patients (including both COVID-19 and non-COVID-19 patients) without increasing the risk of infection. Reference: Eur J Clin Invest. 2023 May 9:e14015. https://pubmed.ncbi.nlm.nih.gov/37161521/
Solvent mg/mL mM
Solubility
DMSO 10.0 20.42
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 489.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Thitiwuthikiat P, Ta-Uea T, Ponghan T, Meebua S, Siriwittayawan D, Nuamchit T. The protective effects of reparixin against endothelial ischemia-reperfusion injury. Int J Health Sci (Qassim). 2022 May-Jun;16(3):20-24. PMID: 35599941; PMCID: PMC9092537. 2. Liotti F, De Pizzol M, Allegretti M, Prevete N, Melillo RM. Multiple anti-tumor effects of Reparixin on thyroid cancer. Oncotarget. 2017 May 30;8(22):35946-35961. doi: 10.18632/oncotarget.16412. PMID: 28415590; PMCID: PMC5482629. 3. Piersanti G, Landoni G, Scquizzato T, Zangrillo A, Piemonti L. Reparixin improves survival in critically ill and transplant patients: A meta-analysis. Eur J Clin Invest. 2023 May 9:e14015. doi: 10.1111/eci.14015. Epub ahead of print. PMID: 37161521. 4. Zarbock A, Allegretti M, Ley K. Therapeutic inhibition of CXCR2 by Reparixin attenuates acute lung injury in mice. Br J Pharmacol. 2008 Oct;155(3):357-64. doi: 10.1038/bjp.2008.270. Epub 2008 Jun 30. PMID: 18587419; PMCID: PMC2567887.
In vitro protocol:
1. Thitiwuthikiat P, Ta-Uea T, Ponghan T, Meebua S, Siriwittayawan D, Nuamchit T. The protective effects of reparixin against endothelial ischemia-reperfusion injury. Int J Health Sci (Qassim). 2022 May-Jun;16(3):20-24. PMID: 35599941; PMCID: PMC9092537. 2. Liotti F, De Pizzol M, Allegretti M, Prevete N, Melillo RM. Multiple anti-tumor effects of Reparixin on thyroid cancer. Oncotarget. 2017 May 30;8(22):35946-35961. doi: 10.18632/oncotarget.16412. PMID: 28415590; PMCID: PMC5482629.
In vivo protocol:
1. Piersanti G, Landoni G, Scquizzato T, Zangrillo A, Piemonti L. Reparixin improves survival in critically ill and transplant patients: A meta-analysis. Eur J Clin Invest. 2023 May 9:e14015. doi: 10.1111/eci.14015. Epub ahead of print. PMID: 37161521. 2. Zarbock A, Allegretti M, Ley K. Therapeutic inhibition of CXCR2 by Reparixin attenuates acute lung injury in mice. Br J Pharmacol. 2008 Oct;155(3):357-64. doi: 10.1038/bjp.2008.270. Epub 2008 Jun 30. PMID: 18587419; PMCID: PMC2567887.
Bertini et al (2004) Noncompetitive allosteric inhibitors of the inflammatory chemokine receptors CXCR1 and CXCR2: prevention of reperfusion injury. Proc.Natl.Acad.Sci.U.S.A. 101 11791 PMID: 15282370 Souza et al (2004) Repertaxin, a novel inhibitor of rat CXCR2 function, inhibits inflammatory responses that follow intestinal ischaemia and reperfusion injury. Br.J.Pharmacol. 143 132 PMID: 15302676 Ginestier et al (2010) CXCR1 blockade selectively targets human breast cancer stem cells in vitro and in xenografts. J.Clin.Invest. 120 485 PMID: 20051626