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    Navitoclax

    DEVELOPMENTS

    DIGITAL CONTENT

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    2D Structure
    Also known as: 923564-51-6, Abt-263, Abt 263, Abt263, Abt-263 (navitoclax), Navitoclax (abt-263)
    Molecular Formula
    C47H55ClF3N5O6S3
    Molecular Weight
    974.6  g/mol
    InChI Key
    JLYAXFNOILIKPP-KXQOOQHDSA-N
    FDA UNII
    XKJ5VVK2WD
    Navitoclax is an orally active, synthetic small molecule and an antagonist of a subset of the B-cell leukemia 2 (Bcl-2) family of proteins with potential antineoplastic activity. Navitoclax selectively binds to apoptosis suppressor proteins Bcl-2, Bcl-XL, and Bcl-w, which are frequently overexpressed in a wide variety of cancers, including those of the lymph, breast, lung, prostate, and colon, and are linked to tumor drug resistance. Inhibition of these apoptosis suppressors prevents their binding to the apoptotic effectors Bax and Bak proteins, thereby triggering apoptotic processes in cells overexpressing Bcl-2, Bcl-XL, and Bcl-w. This eventually reduces tumor cell proliferation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[4-[[2-(4-chlorophenyl)-5,5-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-N-[4-[[(2R)-4-morpholin-4-yl-1-phenylsulfanylbutan-2-yl]amino]-3-(trifluoromethylsulfonyl)phenyl]sulfonylbenzamide
    2.1.2 InChI
    InChI=1S/C47H55ClF3N5O6S3/c1-46(2)20-18-42(34-8-12-37(48)13-9-34)36(31-46)32-55-22-24-56(25-23-55)39-14-10-35(11-15-39)45(57)53-65(60,61)41-16-17-43(44(30-41)64(58,59)47(49,50)51)52-38(19-21-54-26-28-62-29-27-54)33-63-40-6-4-3-5-7-40/h3-17,30,38,52H,18-29,31-33H2,1-2H3,(H,53,57)/t38-/m1/s1
    2.1.3 InChI Key
    JLYAXFNOILIKPP-KXQOOQHDSA-N
    2.1.4 Canonical SMILES
    CC1(CCC(=C(C1)CN2CCN(CC2)C3=CC=C(C=C3)C(=O)NS(=O)(=O)C4=CC(=C(C=C4)NC(CCN5CCOCC5)CSC6=CC=CC=C6)S(=O)(=O)C(F)(F)F)C7=CC=C(C=C7)Cl)C
    2.1.5 Isomeric SMILES
    CC1(CCC(=C(C1)CN2CCN(CC2)C3=CC=C(C=C3)C(=O)NS(=O)(=O)C4=CC(=C(C=C4)N[C@H](CCN5CCOCC5)CSC6=CC=CC=C6)S(=O)(=O)C(F)(F)F)C7=CC=C(C=C7)Cl)C
    2.2 Other Identifiers
    2.2.1 UNII
    XKJ5VVK2WD
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Abt 263

    2. Abt-263

    3. Abt263

    2.3.2 Depositor-Supplied Synonyms

    1. 923564-51-6

    2. Abt-263

    3. Abt 263

    4. Abt263

    5. Abt-263 (navitoclax)

    6. Navitoclax (abt-263)

    7. Unii-xkj5vvk2wd

    8. Xkj5vvk2wd

    9. A-855071.0

    10. Chembl443684

    11. (r)-4-(4-((4'-chloro-4,4-dimethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)methyl)piperazin-1-yl)-n-((4-((4-morpholino-1-(phenylthio)butan-2-yl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide

    12. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[4-[[(1r)-3-(4-morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]phenyl]sulfonyl]benzamide

    13. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethylcyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[(2r)-4-morpholin-4-yl-1-phenylsulfanylbutan-2-yl]amino]-3-(trifluoromethylsulfonyl)phenyl]sulfonylbenzamide

    14. (r)-4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-n-(4-(4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)p

    15. (r)-4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-enyl)methyl)piperazin-1-yl)-n-(4-(4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonyl)benzamide

    16. 4-(4-{[2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-n-({4-({(1r)-3-morpholin-4-yl-1-[(phenylsulfanyl)methyl]propyl}amino)-3-[(trifluoromethyl)sulfonyl]phenyl}sulfonyl)benzamide

    17. 4-(4-{[2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl]methyl}piperazin-1-yl)-n-[(4-{[(2r)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl]amino}-3-[(trifluoromethyl)sulfonyl]phenyl)sulfonyl]benzamide

    18. Navitoclax [usan]

    19. Navitoclax [usan:inn]

    20. Navitoclaxum

    21. C47h55clf3n5o6s3

    22. 4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-((4-(((2r)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide

    23. Abt-263,navitoclax

    24. Navitoclax [mi]

    25. Abt-263 In Bulk

    26. Navitoclax, Abt-263

    27. Navitoclax; Abt-263

    28. Navitoclax [inn]

    29. Navitoclax [jan]

    30. Navitoclax (usan/inn)

    31. Abt-263 - Navitoclax

    32. Navitoclax [who-dd]

    33. Mls006011021

    34. Schembl522847

    35. Gtpl8319

    36. Dtxsid2042640

    37. Chebi:94128

    38. Ex-a055

    39. Chebi:131174

    40. Bdbm50270877

    41. Mfcd12756219

    42. Nsc759659

    43. S1001

    44. Akos015896297

    45. Zinc150338726

    46. Db12340

    47. Nsc-759659

    48. Rg-7433

    49. Ncgc00188344-01

    50. Ncgc00188344-02

    51. Ncgc00188344-03

    52. Ncgc00188344-05

    53. Ncgc00188344-08

    54. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[4-[[(1r)-3-(4-mo

    55. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethyl-cyclohexen-1-yl]methyl]piperazin-1-yl]-n-[4-[[(1r)-3-morpholino-1-(phenylsulfanylmethyl)propyl]amino]-3-(trifluoromethylsulfonyl)phenyl]sulfonyl-benzamide

    56. Ac-31055

    57. As-16690

    58. Hy-10087

    59. Smr004702817

    60. 4-[4-[[2-(4-chlorophenyl)-5,5-dimet

    61. Sw218055-2

    62. D09935

    63. 564a516

    64. J-519525

    65. Brd-k82746043-001-01-1

    66. Brd-k82746043-001-02-9

    67. Brd-k82746043-001-03-7

    68. Brd-k82746043-001-04-5

    69. Q18002993

    70. (r)-4-(4-((4-chloro-4,4-dimethyl-3,4,5,6-tetrahydro-[1,1-biphenyl]-2-yl)methyl)piperazin-1-yl)-n-((4-((4-morpholino-1-(phenylthio)butan-2-yl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide

    71. 4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-((4-(((1r)-3-(morpholin-4-yl)-1-((phenylsulfanyl)methyl)propyl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)benzamide

    72. 4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)-n-(4-(((2r)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl)amino)-3-(trifluoromethanesulfonyl)benzenesulfonyl)benzamide

    73. 4-[4-[[2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl]methyl]-1-piperazinyl]-n-[[4-[[(1r)-3-(4-morpholinyl)-1-[(phenylthio)methyl]propyl]amino]-3-[(trifluoromethyl)sulfonyl]phenyl]sulfonyl]benzamide;abt 263;benzamide, 4-(4-((2-(4-chlorophenyl)-5,5-dime

    74. 4-{4-[(4'-chloro-4,4-dimethyl-3,4,5,6-tetrahydro[biphenyl]-2-yl)methyl]piperazin-1-yl}-n-[(4-{[(2r)-4-(morpholin-4-yl)-1-(phenylsulfanyl)butan-2-yl]amino}-3-[(trifluoromethyl)sulfonyl]phenyl)sulfonyl]benzamide

    75. Benzamide, 4-(4-((2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl)methyl)-1- Piperazinyl)-n-((4-(((1r)-3-(4-morpholinyl)-1-((phenylthio)methyl)propyl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)-

    76. Benzamide, 4-(4-((2-(4-chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-yl)methyl)-1-piperazinyl)-n-((4-(((1r)-3-(4-morpholinyl)-1-((phenylthio)methyl)propyl)amino)-3-((trifluoromethyl)sulfonyl)phenyl)sulfonyl)-

    77. N-(4-{4-[2-(4-chlorophenyl)-5,5-dimethyl-cyclohex-1-enylmethyl]-piperazin-1-yl}-benzoyl)-4-((r)-3-morpholin-4-yl-1-phenylsulfanylmethyl-propylamino)-3-trifluoromethanesulfonyl-benzenesulfonamide

    2.4 Create Date
    2008-10-27
    3 Chemical and Physical Properties
    Molecular Weight 974.6 g/mol
    Molecular Formula C47H55ClF3N5O6S3
    XLogP39.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count16
    Exact Mass973.2955102 g/mol
    Monoisotopic Mass973.2955102 g/mol
    Topological Polar Surface Area170 Ų
    Heavy Atom Count65
    Formal Charge0
    Complexity1800
    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

    Treatment of myelofibrosis

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

    5.2 Mechanism of Action

    Navitoclax targets the Bcl-2 family of proteins, the major negative regulators of apoptosis. The Bcl-2 proteins, including Bcl-2, Bcl-xL, and Bcl-w, work by binding to two other groups of proteins-the executioners (Bax, Bak) that actually start the destruction pathway, and the sentinel proteins. Cancer cells frequently overexpress the Bcl-2-like proteins, and thus, when they sustain DNA damage-from radiation, for example-they continue growing. Preventing the Bcl-2-like proteins from binding to the executioners might be able to trigger cell death in the tumor.