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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

Reparixin

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 Formula	C₁₄H₂₁NO₃S
Molecular Weight	283.39 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	283.12421471 g/mol
Monoisotopic Mass	283.12421471 g/mol
Topological Polar Surface Area	71.6 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	389
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Prevention of graft rejection

Treatment of coronavirus disease 2019 (COVID-2019)

Drugs in Development

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