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    Apaziquone

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    PharmaCompass
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    2D Structure
    Also known as: 114560-48-4, Eoquin, Qapzola, Eo-9, Nor-701, Nsc-382459
    Molecular Formula
    C15H16N2O4
    Molecular Weight
    288.30  g/mol
    InChI Key
    MXPOCMVWFLDDLZ-NSCUHMNNSA-N
    FDA UNII
    H464ZO600O
    Apaziquone is an indolequinone bioreductive prodrug and analog of mitomycin C with potential antineoplastic and radiosensitization activities. Apaziquone is converted to active metabolites in hypoxic cells by intracellular reductases, which are present in greater amounts in hypoxic tumor cells. The active metabolites alkylate DNA, resulting in apoptotic cell death. This agent displays selectivity activity towards both hypoxic solid tumors, which exhibits higher expression of cytochrome P450 reductase, and well-oxygenated malignant cells that overexpress the bioreductive enzyme NQO1 (NAD(P)H: quinone oxidoreductase). Apaziquone may selectively sensitize hypoxic tumor cells to radiocytotoxicity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-(aziridin-1-yl)-3-(hydroxymethyl)-2-[(E)-3-hydroxyprop-1-enyl]-1-methylindole-4,7-dione
    2.1.2 InChI
    InChI=1S/C15H16N2O4/c1-16-10(3-2-6-18)9(8-19)13-14(16)12(20)7-11(15(13)21)17-4-5-17/h2-3,7,18-19H,4-6,8H2,1H3/b3-2+
    2.1.3 InChI Key
    MXPOCMVWFLDDLZ-NSCUHMNNSA-N
    2.1.4 Canonical SMILES
    CN1C(=C(C2=C1C(=O)C=C(C2=O)N3CC3)CO)C=CCO
    2.1.5 Isomeric SMILES
    CN1C(=C(C2=C1C(=O)C=C(C2=O)N3CC3)CO)/C=C/CO
    2.2 Other Identifiers
    2.2.1 UNII
    H464ZO600O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-hydroxymethyl-5-aziridinyl-1-methyl-2-(1h-indole-4,7-dione)prop-beta-en-alpha-ol

    2. 5-(azridin-1-yl)-3-(hydroxymethyl)-2-((1e)-3-hydroxyprop-1-enyl)-methyl-1h-indole-4,7-dione

    3. E 09

    4. E-09

    5. Eo 9

    6. Eo-9

    7. Eo9

    8. Nsc 382,459

    9. Nsc 382459

    10. Nsc-382459

    11. Qapzola

    2.3.2 Depositor-Supplied Synonyms

    1. 114560-48-4

    2. Eoquin

    3. Qapzola

    4. Eo-9

    5. Nor-701

    6. Nsc-382459

    7. 5-(aziridin-1-yl)-3-(hydroxymethyl)-2-[(e)-3-hydroxyprop-1-enyl]-1-methylindole-4,7-dione

    8. E-85/053

    9. Eo9

    10. 141304-51-0

    11. 5-(azridin-1-yl)-3-(hydroxymethyl)-2-((1e)-3-hydroxyprop-1-enyl)-methyl-1h-indole-4,7-dione

    12. Apaziquonum

    13. H464zo600o

    14. Nsc-382456

    15. Neoquin

    16. Eo 9 (pharmaceutical)

    17. Apaziquone [usan:inn]

    18. Apaziquonum [inn-latin]

    19. 1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-((1e)-3-hydroxy-1-propenyl)-1-methyl-

    20. E09

    21. E 09

    22. 5-aziridin-1-yl-3-hydroxymethyl-2-((e)-3-hydroxy-propenyl)-1-methyl-1h-indole-4,7-dione

    23. Nsc 382459

    24. Eoquin (tn)

    25. E-09

    26. Apaziquone (usan/inn)

    27. Nsc 382456

    28. Unii-h464zo600o

    29. 1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl-

    30. Apaziquone [usan]

    31. (e)-5-(1-azirinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1h-indole-4,7-dione

    32. Apaziquone [mi]

    33. Apaziquone [inn]

    34. 1h-indole-4,7-dione, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-, (e)-

    35. Chembl73822

    36. Schembl367964

    37. Schembl367965

    38. E-85/050

    39. Antineoplastic-382459

    40. Dtxsid90869587

    41. Chebi:177558

    42. Zinc1536777

    43. N1,n6-diethyl-3-methylhexanediamide

    44. Nsc382459

    45. Bcp9000309

    46. Db12593

    47. Cs-0006128

    48. D02965

    49. Q4779259

    50. 1h-indole-4, 5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-

    51. 5-(aziridin-1-yl)-3-(hydroxymethyl)-2-(3-hydroxyprop-1-enyl)-1-methylindole-4,7-dione

    52. (e)-5-(1-aziridinyl)-3-(hydroxymethyl)-2-(3-hydroxy-1-propenyl)-1-methyl-1h-indole-4,7-dione

    53. 5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl-1h-indole-4,7-dione

    54. 5-(1-aziridinyl)-3-(hydroxymethyl)-2-[(1e)-3-hydroxy-1-propen-1-yl]-1-methyl-1h-indole-4,7-dione;

    2.4 Create Date
    2005-09-08
    3 Chemical and Physical Properties
    Molecular Weight 288.30 g/mol
    Molecular Formula C15H16N2O4
    XLogP3-0.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass288.11100700 g/mol
    Monoisotopic Mass288.11100700 g/mol
    Topological Polar Surface Area82.5 Ų
    Heavy Atom Count21
    Formal Charge0
    Complexity524
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Antineoplastic Agents

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