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    Sparsentan

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    2D Structure
    Also known as: 254740-64-2, Sparsentan (re-021), Re-021, Sparsentan [usan], Ps433540, Ps-433540
    Molecular Formula
    C32H40N4O5S
    Molecular Weight
    592.8  g/mol
    InChI Key
    WRFHGDPIDHPWIQ-UHFFFAOYSA-N
    FDA UNII
    9242RO5URM
    Sparsentan has been used in trials studying the treatment of Focal Segmental Glomerulosclerosis. Sparsentan is the first and only dual-acting angiotensin and endothelin receptor antagonist (DARA) in development.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-(ethoxymethyl)phenyl]-N-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide
    2.1.2 InChI
    InChI=1S/C32H40N4O5S/c1-5-7-14-29-33-32(17-10-11-18-32)31(37)36(29)20-24-15-16-26(25(19-24)21-40-6-2)27-12-8-9-13-28(27)42(38,39)35-30-22(3)23(4)41-34-30/h8-9,12-13,15-16,19H,5-7,10-11,14,17-18,20-21H2,1-4H3,(H,34,35)
    2.1.3 InChI Key
    WRFHGDPIDHPWIQ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCC1=NC2(CCCC2)C(=O)N1CC3=CC(=C(C=C3)C4=CC=CC=C4S(=O)(=O)NC5=NOC(=C5C)C)COCC
    2.2 Other Identifiers
    2.2.1 UNII
    9242RO5URM
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (1,1'-biphenyl)-2-sulfonamide, 4'-((2-butyl-4-oxo-1,3-diazaspiro(4.4)non-1-en-3-yl)methyl)-n-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-

    2. 4'-((2-butyl-4-oxo-1,3-diazaspiro(4.4)non-1-en-3-yl)methyl)-n-(4,5-dimethyl-1,2-oxazol-3-yl)-2'-(ethoxymethyl)-2-biphenylsulfonamide

    3. 4'-((2-butyl-4-oxo-1,3-diazaspiro(4.4)non-1-en-3-yl)methyl)-n-(4,5-dimethyl-1,2-oxazol-3-yl)-2'-(ethoxymethyl)biphenyl-2-sulfonamide

    4. Re-021

    2.3.2 Depositor-Supplied Synonyms

    1. 254740-64-2

    2. Sparsentan (re-021)

    3. Re-021

    4. Sparsentan [usan]

    5. Ps433540

    6. Ps-433540

    7. 9242ro5urm

    8. Chembl539423

    9. 2-[4-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-2-(ethoxymethyl)phenyl]-n-(4,5-dimethyl-1,2-oxazol-3-yl)benzenesulfonamide

    10. 4'-((2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-n-(4,5-dimethylisoxazol-3-yl)-2'-(ethoxymethyl)-[1,1'-biphenyl]-2-sulfonamide

    11. Retrophin

    12. (1,1'-biphenyl)-2-sulfonamide, 4'-((2-butyl-4-oxo-1,3-diazaspiro(4.4)non-1-en-3-yl)methyl)-n-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-

    13. [1,1'-biphenyl]-2-sulfonamide, 4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-n-(4,5-dimethyl-3-isoxazolyl)-2'-(ethoxymethyl)-

    14. Unii-9242ro5urm

    15. Dara

    16. Compound 7 [pmid 15634011]

    17. Dara-a

    18. Ps 33540

    19. Sparsentan [inn]

    20. Sparsentan (usan/inn)

    21. Sparsentan(ps433540)

    22. Sparsentan [who-dd]

    23. Schembl535109

    24. Gtpl8448

    25. Amy38147

    26. Bcp23969

    27. Ex-a3048

    28. Bdbm50175523

    29. S6665

    30. Cs-7947

    31. Db12548

    32. Sb16876

    33. Dara-a (dual Acting Receptor Antagonist Of Angiotension And Endothelin Receptors)

    34. Ps-433540;re-021;dara

    35. Ac-35179

    36. Hy-17621

    37. Sparsentan (ps-433540,re-021,dara)

    38. D11776

    39. F77045

    40. A858308

    41. L023324

    42. Q27088845

    43. 4''''-(2-butyl-4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-ylmethyl)-2''''-ethoxymethyl-biphenyl-2-sulfonic Acid (4,5-dimethyl-isoxazol-3-yl)-amide

    44. 4''-(2-butyl-4-oxo-1,3-diaza-spiro[4.4]non-1-en-3-ylmethyl)-2''-ethoxymethyl-biphenyl-2-sulfonic Acid (4,5-dimethyl-isoxazol-3-yl)-amide

    45. 4'-((2-butyl-4-oxo-1,3-diazaspiro(4.4)non-1-en-3-yl)methyi)-n-(4,5- Dimethylisoxazol-3-yl)-2'-(ethoxymethyl)biphenyl-2-sulfonamide

    46. 4'-((2-butyl-4-oxo-1,3-diazaspiro(4.4)non-1-en-3-yl)methyl)-n-(4,5-dimethyl-1,2-oxazol-3-yl)-2'-(ethoxymethyl)-2-biphenylsulfonamide

    47. 4'-((2-butyl-4-oxo-1,3-diazaspiro(4.4)non-1-en-3-yl)methyl)-n-(4,5-dimethyl-1,2-oxazol-3-yl)-2'-(ethoxymethyl)biphenyl-2-sulfonamide

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 592.8 g/mol
    Molecular Formula C32H40N4O5S
    XLogP35
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count12
    Exact Mass592.27194156 g/mol
    Monoisotopic Mass592.27194156 g/mol
    Topological Polar Surface Area123 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity1060
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    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

    Treatment of focal segmental glomerulosclerosis

    Treatment of primary IgA nephropathy

    5 Pharmacology and Biochemistry
    5.1 Mechanism of Action

    Sparsentan, which possesses two clinically validated mechanisms of action in a single molecule, works by selectively blocking the action of two potent vasoconstrictor and mitogenic agents, angiotensin II (AII) and endothelin 1 (ET1), at their respective receptors. Sparsentan is highly selective (10,000-fold) for the AII receptor sub-type 1 and the ET receptor sub-type A. As such, Sparsentan combines the properties of an angiotensin receptor blocker (ARB) and an endothelin receptor antagonist (ERA) in the same molecule.