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    L-Prolinamide, N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-N-((2R,3S)-2-ethoxytetrahydro-5-oxo-3-furanyl)-

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    2D Structure
    Also known as: Vx-765, 273404-37-8, Vx765, Belnacasan (vx-765), Belnacasan [usan], Belnacasan (vx765)
    Molecular Formula
    C24H33ClN4O6
    Molecular Weight
    509.0  g/mol
    InChI Key
    SJDDOCKBXFJEJB-MOKWFATOSA-N
    FDA UNII
    00OLE78529
    VX-765 is the orally available prodrug of a potent and selective competitive inhibitor of ICE/caspase-1 (VRT-043198). VX-765 is currently under clinical development for the treatment of inflammatory and autoimmune conditions, as it blocks the hypersensitive response to an inflammatory stimulus.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-1-[(2S)-2-[(4-amino-3-chlorobenzoyl)amino]-3,3-dimethylbutanoyl]-N-[(2R,3S)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide
    2.1.2 InChI
    InChI=1S/C24H33ClN4O6/c1-5-34-23-16(12-18(30)35-23)27-21(32)17-7-6-10-29(17)22(33)19(24(2,3)4)28-20(31)13-8-9-15(26)14(25)11-13/h8-9,11,16-17,19,23H,5-7,10,12,26H2,1-4H3,(H,27,32)(H,28,31)/t16-,17-,19+,23+/m0/s1
    2.1.3 InChI Key
    SJDDOCKBXFJEJB-MOKWFATOSA-N
    2.1.4 Canonical SMILES
    CCOC1C(CC(=O)O1)NC(=O)C2CCCN2C(=O)C(C(C)(C)C)NC(=O)C3=CC(=C(C=C3)N)Cl
    2.1.5 Isomeric SMILES
    CCO[C@H]1[C@H](CC(=O)O1)NC(=O)[C@@H]2CCCN2C(=O)[C@H](C(C)(C)C)NC(=O)C3=CC(=C(C=C3)N)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    00OLE78529
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (s)-1-((s)-2-1((-(4-amino-3-chloro-phenyl)-methanoyl)-amino)-3,3-dimethyl-butanoyl)-pyrrolidine-2-carboxylic Acid ((2r,3s)-2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

    2. (s)-3-((1-((s)-1-((s)-2-((1-(4-amino-3-chlorophenyl)methanoyl)amino)-3,3-dimethyl-butanoyl)pyrrolidin-2yl)methanoyl)amino)-4-oxo-butyric Acid

    3. 1-((2s)-2-((4-amino-3-chlorobenzoyl)amino)-3,3-dimethylbutanoyl)-n-((2r,3s)-2- Ethoxy-5-oxo-tetrahydrofuran-3-yl)-l-prolinamide

    4. L-prolinamide, N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-n-((1s)-2-carboxy-1-formylethyl)-

    5. N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-n-((1s)-2-carboxy-1-formylethyl)-l-prolinamide

    6. O-desethyl-belnacasan

    7. Vrt 043198

    8. Vrt-043198

    9. Vx 765

    10. Vx-765

    11. Vx-765 Hemiketal

    12. Vx765

    2.3.2 Depositor-Supplied Synonyms

    1. Vx-765

    2. 273404-37-8

    3. Vx765

    4. Belnacasan (vx-765)

    5. Belnacasan [usan]

    6. Belnacasan (vx765)

    7. Belnacasan (usan)

    8. (s)-1-((s)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-n-((2r,3s)-2-ethoxy-5-oxotetrahydrofuran-3-yl)pyrrolidine-2-carboxamide

    9. 851091-96-8

    10. Unii-00ole78529

    11. Belnacasan(vx-765)

    12. Vx-765 (belnacasan)

    13. (2s)-1-[(2s)-2-[(4-amino-3-chlorobenzoyl)amino]-3,3-dimethylbutanoyl]-n-[(2r,3s)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide

    14. 00ole78529

    15. (2s)-1-[(2s)-2-[(4-amino-3-chlorophenyl)formamido]-3,3-dimethylbutanoyl]-n-[(2r,3s)-2-ethoxy-5-oxooxolan-3-yl]pyrrolidine-2-carboxamide

    16. 1-((2s)-2-((4-amino-3-chlorobenzoyl)amino)-3,3-dimethylbutanoyl)-n-((2r,3s)-2- Ethoxy-5-oxo-tetrahydrofuran-3-yl)-l-prolinamide

    17. L-prolinamide, N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-n-((2r,3s)-2-ethoxytetrahydro-5-oxo-3-furanyl)-

    18. N-(4-amino-3-chlorobenzoyl)-3-methyl-l-valyl-n-[(2r,3s)-2-ethoxytetrahydro-5-oxo-3-furanyl]-l-prolinamide

    19. Vx 765

    20. Belnacasan [usan:inn]

    21. Belnacasan [inn]

    22. Belnacasan [who-dd]

    23. Gtpl9035

    24. Schembl3393597

    25. Chembl2107819

    26. Chebi:188567

    27. Dtxsid901017651

    28. Hms3884b11

    29. Amy24224

    30. Zinc3963010

    31. Mfcd11100350

    32. S2228

    33. Akos024464751

    34. Ccg-269769

    35. Ncgc00183682-09

    36. Ncgc00183682-10

    37. Ncgc00183682-13

    38. (s)-1-((s)-2-{[1-(4-amino-3-chloro-phenyl)-methanoyl]-amino}-3,3-dimethyl-butanoyl)-pyrrolidine-2-carboxylic Acid ((2r,3s)-2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide

    39. As-35159

    40. Bcp0726000319

    41. Ft-0774330

    42. V0176

    43. D10416

    44. A857663

    45. J-523035

    46. Q27075000

    47. (s)-1-((s)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-n-((2r,3s)-2-ethoxy-5-oxo-tetrahydrofuran-3-yl)pyrrolidine-2-carboxamide;vx-765

    48. 1-((2s)-2-(4-amino-3-chlorobenzamido)-3,3-dimethylbutanoyl)-n-((2r,3s)-2-ethoxy-5-oxooxolan-3-yl)-l-prolinamide

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 509.0 g/mol
    Molecular Formula C24H33ClN4O6
    XLogP32.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count8
    Exact Mass508.2088625 g/mol
    Monoisotopic Mass508.2088625 g/mol
    Topological Polar Surface Area140 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity818
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    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

    Investigated for use/treatment in inflammatory disorders (unspecified) and psoriasis and psoriatic disorders.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    VX-765 is an orally-absorbed pro-drug of VRT-043198, a potent and selective inhibitor of ICE/caspase-1 sub-family caspases. It has been shown to reduce disease severity and the expression of inflammatory mediators in models of rheumatoid arthritis and skin inflammation, suggesting that it may be useful for treatment of inflammatory diseases.

    5.2 Mechanism of Action

    VX-765 is a potent and selective inhibitor of ICE/caspase-1 sub-family caspases. In preclinical trials, VX-765 was efficiently converted to VRT-043198 when administered orally to mice and inhibited LPS-induced cytokine secretion. The result was a blocking of IL-1beta and IL-18 secretion, with out much effect on the release of several other cytokines, including IL-1{alpha}, tumor necrosis factor-{alpha}, IL-6 and IL-8. There was also no demonstrable activity in cellular models of apoptosis and it did not affect the proliferation of activated primary T-cells or T-cell lines.