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    AS1413, Xanafide, Quinamed, 69408-81-7

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: 69408-81-7, Nafidimide, Quinamed, Benzisoquinolinedione, Xanafide, 5-aminomitonafide
    Molecular Formula
    C16H17N3O2
    Molecular Weight
    283.32  g/mol
    InChI Key
    UPALIKSFLSVKIS-UHFFFAOYSA-N
    FDA UNII
    1Q8D39N37L
    Amonafide is an imide derivative of naphthalic acid. Amonafide intercalates into DNA and inhibits topoisomerase II, resulting in protein-associated strand breaks and impaired DNA and RNA synthesis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-amino-2-[2-(dimethylamino)ethyl]benzo[de]isoquinoline-1,3-dione
    2.1.2 InChI
    InChI=1S/C16H17N3O2/c1-18(2)6-7-19-15(20)12-5-3-4-10-8-11(17)9-13(14(10)12)16(19)21/h3-5,8-9H,6-7,17H2,1-2H3
    2.1.3 InChI Key
    UPALIKSFLSVKIS-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C)CCN1C(=O)C2=CC=CC3=CC(=CC(=C32)C1=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    1Q8D39N37L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-amino-2-(2-(dimethylamino)ethyl)-1h-benz(de)isoquinoline-1,3(2h)-dione

    2. 5-amino-2-(2-dimethylaminoethyl)benzo(de)isoquinolin-1,3-dione

    3. Benzisoquinolinedione

    4. Fa 142

    5. M-fa 142

    6. M-fa-142

    7. Mfa 142

    8. Mfa-142

    9. Nafidimide

    10. Nsc 308847

    11. Nsc-308847

    2.3.2 Depositor-Supplied Synonyms

    1. 69408-81-7

    2. Nafidimide

    3. Quinamed

    4. Benzisoquinolinedione

    5. Xanafide

    6. 5-aminomitonafide

    7. Nsc-308847

    8. As1413

    9. M-fa 142

    10. Fa 142

    11. Nsc308847

    12. As-1413

    13. 3-amino-n-(2-(dimethylamino)ethyl)naphthalimide

    14. 5-amino-2-[2-(dimethylamino)ethyl]benzo[de]isoquinoline-1,3-dione

    15. Mls000757039

    16. Chembl428676

    17. Amonifide

    18. 1q8d39n37l

    19. Amonafide (usan)

    20. 1h-benz(de)isoquinoline-1,3(2h)-dione, 5-amino-2-(2-(dimethylamino)ethyl)-

    21. Naphthalimide, 3-amino-n-(2-(dimethylamino)ethyl)-

    22. Amonafide [usan]

    23. 5-amino-2-(2-(dimethylamino)ethyl)-1h-benzo[de]isoquinoline-1,3(2h)-dione

    24. Amonafide [inn]

    25. Amonafidum [latin]

    26. Amonafida [spanish]

    27. Amonafidum

    28. Amonafida

    29. Smr000528907

    30. Amonafide [usan:inn]

    31. As-1413(amonafide)

    32. Nsc 308847

    33. Brn 5344673

    34. Amonofide

    35. Unii-1q8d39n37l

    36. 5-amino-2-[2-(dimethylamino)ethyl]-1h-benzo[de]isoquinoline-1,3(2h)-dione

    37. Amonafide-[d6]

    38. M-fa-142

    39. Bida

    40. 3-amino-n-(2-(dimethylamino)ethyl)-1,8-naphthalindicarboximid

    41. Amonafide [mart.]

    42. 1h-benz(de)isoquinoline-1,3(2h)-dione, 5-amino-2-(dimethylamino)ethyl-

    43. Ncimech_000383

    44. Amonafide [who-dd]

    45. Schembl27226

    46. Mls006010419

    47. Mls006011267

    48. Chebi:94661

    49. Cgx-571

    50. Dtxsid30219562

    51. Hms3654h19

    52. 5-amino-2-(2-dimethylaminoethyl)benzo[de]isoquinoline-1,3-dione

    53. Zinc4214836

    54. Bdbm50033894

    55. Ccg-35694

    56. Nsc758251

    57. S1367

    58. Akos015850731

    59. Bcp9000321

    60. Cs-0496

    61. Db05022

    62. Nci-308847

    63. Nsc-758251

    64. Nsc308847,as1413

    65. Ncgc00346513-01

    66. Ac-22581

    67. As-56124

    68. Hy-10982

    69. Nci60_002643

    70. Ft-0662118

    71. Sw219946-1

    72. A24926

    73. D10090

    74. 408a817

    75. Q4747531

    76. Brd-k56334280-001-02-8

    77. Brd-k56334280-001-03-6

    78. 1h-benz[de]isoquinoline-1, 5-amino-2-[2-(dimethylamino)ethyl]-

    79. 5-amino-2-(2-dimethylamino-ethyl)-benzo[de]isoquinoline-1,3-dione

    80. 1h-benz[de]isoquinoline-1,3(2h)-dione,5-amino-2-[2-(dimethylamino)ethyl]-

    81. 5-amino-2-(2-dimethylamino-ethyl)-benzo[de]isoquinoline-1,3-dione (amonafide)

    82. 5-amino-2-(2-dimethylamino-ethyl)-benzo[de]isoquinoline-1,3-dione(amonafide)

    83. 5-amino-2-[2-(dimethylamino)ethyl]-1h-benz[de]isoquinoline-1,3(2h)-dione;amonafide.

    84. 5-amino-2-[2-(dimethylamino)ethyl]-1h-benzo[de]isoquinoline-1,3(2h)-dione #

    85. 11-amino-3-[2-(dimethylamino)ethyl]-3-azatricyclo[7.3.1.0?,??]trideca-1(13),5,7,9,11-pentaene-2,4-dione

    86. Amonafidedihydrochloride,1h-benz[de]isoquinoline-1,3(2h)-dione,5-amino-2-[2-(dimethylamino)ethyl]-

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 283.32 g/mol
    Molecular Formula C16H17N3O2
    XLogP31.5
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass283.132076794 g/mol
    Monoisotopic Mass283.132076794 g/mol
    Topological Polar Surface Area66.6 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity437
    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

    Investigated for use/treatment in breast cancer, ovarian cancer, and prostate cancer.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antiviral Agents

    Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

    Antineoplastic Agents

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

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Intercalating Agents

    Agents that are capable of inserting themselves between the successive bases in DNA, thus kinking, uncoiling or otherwise deforming it and therefore preventing its proper functioning. They are used in the study of DNA. (See all compounds classified as Intercalating Agents.)

    5.2 Mechanism of Action

    Amonafide is a DNA intercalating agent and inhibitor of topoisomerase II that has been extensively studied in patients with malignant solid tumors. Amonafide has also been studied in patients with AML.