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    Technical details about Reparixin, learn more about the structure, uses, toxicity, action, side effects and more

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    Reparixin

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    DIGITAL CONTENT

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    2D Structure
    1. Also known as: Repertaxin, 266359-83-5, Df 1681y, Df1681y, Reparixin (repertaxin), (r)-2-(4-isobutylphenyl)-n-(methylsulfonyl)propanamide
    Molecular Formula
    C14H21NO3S
    Molecular Weight
    283.39  g/mol
    InChI Key
    KQDRVXQXKZXMHP-LLVKDONJSA-N
    FDA UNII
    U604E1NB3K
    Reparixin is an orally available inhibitor of CXC chemokine receptor types 1 (CXCR1) and 2 (CXCR2), with potential antineoplastic activity. Upon administration, reparixin allosterically binds to CXCR1 and prevents CXCR1 activation by its ligand interleukin 8 (IL-8 or CXCL8). This may cause cancer stem cell (CSC) apoptosis and may inhibit tumor cell progression and metastasis. CXCR1, overexpressed on CSCs, plays a key role in CSC survival and the ability of CSC to self-renew; it is also linked to tumor resistance to chemotherapy. Inhibition of the IL-8/CXCR1 interaction also potentiates the cytotoxic effect of chemotherapeutic agents. In addition, reparixin inhibits CXCR2 activation and may reduce both neutrophil recruitment and vascular permeability during inflammation or injury.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2R)-2-[4-(2-methylpropyl)phenyl]-N-methylsulfonylpropanamide
    2.1.2 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
    2.1.3 InChI Key
    KQDRVXQXKZXMHP-LLVKDONJSA-N
    2.1.4 Canonical SMILES
    CC(C)CC1=CC=C(C=C1)C(C)C(=O)NS(=O)(=O)C
    2.1.5 Isomeric SMILES
    C[C@H](C1=CC=C(C=C1)CC(C)C)C(=O)NS(=O)(=O)C
    2.2 Other Identifiers
    2.2.1 UNII
    U604E1NB3K
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (r)-2-(4-isobutylphenyl)propionylmethanesulfonamide

    2. 2-(4-isobutylphenyl)propionylmethanesulfonamide

    3. Df 1681y

    4. Df-1681y

    5. Df1681y

    6. Reparixin Lysine

    7. Reparixin Lysine Salt

    8. Repertaxin

    2.3.2 Depositor-Supplied Synonyms

    1. Repertaxin

    2. 266359-83-5

    3. Df 1681y

    4. Df1681y

    5. Reparixin (repertaxin)

    6. (r)-2-(4-isobutylphenyl)-n-(methylsulfonyl)propanamide

    7. Df-1681y

    8. Chembl191413

    9. U604e1nb3k

    10. 266359-83-5 (free Base)

    11. Reparixin [inn]

    12. (2r)-2-[4-(2-methylpropyl)phenyl]-n-methylsulfonylpropanamide

    13. Reparixin [usan:inn]

    14. Unii-u604e1nb3k

    15. (2r)-2-(4-(2-methylpropyl)phenyl)-n-methylsulfonylpropanamide

    16. 2-(4-isobutylphenyl)propionylmethanesulfonamide

    17. Reparixin (usan/inn)

    18. Reparixin [usan]

    19. Reparixin [mart.]

    20. Reparixin [who-dd]

    21. Dsstox_cid_26509

    22. Dsstox_rid_81678

    23. Dsstox_gsid_46509

    24. Gtpl8498

    25. Schembl1884299

    26. Zinc8717

    27. Dtxsid6046509

    28. Chebi:177765

    29. Bcp10635

    30. Ex-a2461

    31. Tox21_112272

    32. Bdbm50169045

    33. Mfcd18633292

    34. S8640

    35. Ccg-267282

    36. Cs-1379

    37. Db12614

    38. Benzeneacetamide, Alpha-methyl-4-(2-methylpropyl)-n-(methylsulfonyl)-, (alphar)-

    39. Ac-32023

    40. Bs-16754

    41. Hy-15251

    42. Cas-266359-83-5

    43. D08984

    44. Q27088533

    45. (2r)-2-[4-(2-methylpropyl)phenyl]-n-methylsulonylpropanamide

    46. N-[(r)-2-(4-isobutyl-phenyl)-propionyl]-methanesulfonamide

    47. Benzeneacetamide, Alpha-methyl-4-(2-methylpropyl)-n-(methylsulfonyl)- (alphar)-

    48. Benzeneacetamide, .alpha.-methyl-4-(2-methylpropyl)-n-(methylsulfonyl)-, (.alpha.r)-

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 283.39 g/mol
    Molecular Formula C14H21NO3S
    XLogP32.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass283.12421471 g/mol
    Monoisotopic Mass283.12421471 g/mol
    Topological Polar Surface Area71.6 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity389
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Prevention of graft rejection

    Treatment of coronavirus disease 2019 (COVID-2019)

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