Reparixin

Base Information

• Chemical Name: Reparixin
• CAS No.: 266359-83-5
• Molecular Formula: C₁₄H₂₁NO₃S
• Molecular Weight: 283.392
• European Community (EC) Number: 691-864-3
• UNII: U604E1NB3K
• DSSTox Substance ID: DTXSID6046509
• Nikkaji Number: J2.853.672K
• Wikidata: Q27088533
• NCI Thesaurus Code: C66515
• Pharos Ligand ID: GV767X8CASCU
• Metabolomics Workbench ID: 144345
• ChEMBL ID: CHEMBL191413
• Mol file: 266359-83-5.mol

Synonyms:(R)-2-(4-isobutylphenyl)propionylmethanesulfonamide;2-(4-isobutylphenyl)propionylmethanesulfonamide;DF 1681Y;DF-1681Y;DF1681Y;reparixin;reparixin lysine;reparixin lysine salt;repertaxin

Chemical Property of Reparixin

Chemical Property:

• Melting Point: 103-105℃
• PKA: 4.28±0.40(Predicted)
• PSA: 75.11000
• Density: 1.137g/cm³
• LogP: 3.98550
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in DMSO (up to 100 mg/ml) or in Ethanol (up to 25 mg/ml)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 283.12421471
• Heavy Atom Count: 19
• Complexity: 389

Purity/Quality:

99% ^*data from raw suppliers

Reparixin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1=CC=C(C=C1)C(C)C(=O)NS(=O)(=O)C
• Isomeric SMILES: C[C@H](C1=CC=C(C=C1)CC(C)C)C(=O)NS(=O)(=O)C
• Recent ClinicalTrials: Reparixin as add-on Therapy to Standard of Care to Limit Disease Progression in Adult Patients With COVID-19 and Other Community-Acquired Pneumonia.
• Recent EU Clinical Trials: Reparixin 1200 mg three times a day as add-on therapy to standard of care to limit disease progression in hospitalised adult patients with COVID-19
• 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). 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.

Technology Process of Reparixin

There total 3 articles about Reparixin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

methanesulfonamide (3144-09-0) + (R)-ibuprofene (51146-57-7,58560-75-1) → repertaxin (266359-83-5)

Guidance literature:

(R)-ibuprofene; With 1,1'-carbonyldiimidazole; In dichloromethane; at 0 - 5 ℃; for 2h;

methanesulfonamide; With 1,2-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4h;

DOI:10.1021/jm049082i

Reference yield: 82.0%

methanesulfonamide (3144-09-0) + ibuprofen (15687-27-1,58560-75-1) → 2-[4-(2-methylpropyl)phenyl]-N-(methylsulfonyl)propanamide (266359-83-5)

Guidance literature:

With benzoic acid anhydride; zinc(II) chloride; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2007.08.048

Reference yield: 80.0%

methanesulfonamide (3144-09-0) + (S)-ibuprofen (51146-56-6,58560-75-1) → reparixin (266359-83-5)

Guidance literature:

(S)-ibuprofen; With 1,1'-carbonyldiimidazole; In dichloromethane; at 0 - 5 ℃; for 2h;

methanesulfonamide; With 1,2-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4h;

DOI:10.1021/jm049082i

upstream raw materials:

methanesulfonamide

(R)-ibuprofene

(S)-ibuprofen

ibuprofen

Refernces

• 1、 Raji Reddy, Chada,Mahipal, Bodugam,Yaragorla, Srinivasa Rao. "A new and efficient method for the facile synthesis of N-acyl sulfonamides under Lewis acid catalysis". . p. 7528 - 7532. Retrieved 2008/03/14.
• 2、 Aureli, Loretta,Cruciani, Gabriele,Cesta, Maria Candida,Anacardio, Roberto,De Simone, Lucio,Moriconi, Alessio. "Predicting human serum albumin affinity of interleukin-8 (CXCL8) inhibitors by 3D-QSPR approach". . p. 2469 - 2479. Retrieved 2007/10/03.