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    Sobuzoxane

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: 98631-95-9, Mst 16, Mst-16, [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-dioxopiperazin-1-yl]ethyl]-2,6-dioxopiperazin-1-yl]methyl 2-methylpropyl carbonate, Perazolin, R1308vh37p
    Molecular Formula
    C22H34N4O10
    Molecular Weight
    514.5  g/mol
    InChI Key
    OCOKWVBYZHBHLU-UHFFFAOYSA-N
    FDA UNII
    R1308VH37P
    Sobuzoxane is the orally available active prodrug of ICRF-154, a bisdioxopiperazine derivative, with cardioprotective and antineoplastic activities. Like other ICRF compounds, sobuzoxane and its active metabolite ICRF-154 interfere with topoisomerase II activity prior to the formation of intermediate cleavable DNA-enzyme complexes during the catalytic cycle resulting in tumor cell growth inhibition. Furthermore, sobuzoxane chelates metal cations thereby limiting the formation of free radical-generating anthracycline-metal complexes and may prevent anthracycline-induced oxidative damage to cardiac and soft tissues.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-dioxopiperazin-1-yl]ethyl]-2,6-dioxopiperazin-1-yl]methyl 2-methylpropyl carbonate
    2.1.2 InChI
    InChI=1S/C22H34N4O10/c1-15(2)11-33-21(31)35-13-25-17(27)7-23(8-18(25)28)5-6-24-9-19(29)26(20(30)10-24)14-36-22(32)34-12-16(3)4/h15-16H,5-14H2,1-4H3
    2.1.3 InChI Key
    OCOKWVBYZHBHLU-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(C)COC(=O)OCN1C(=O)CN(CC1=O)CCN2CC(=O)N(C(=O)C2)COC(=O)OCC(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    R1308VH37P
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1,2-bis(4-isobutoxycarbonyloxymethyl-3,5-dioxopiperazin-1-yl)ethane

    2. Mst 16

    3. Mst-16

    2.3.2 Depositor-Supplied Synonyms

    1. 98631-95-9

    2. Mst 16

    3. Mst-16

    4. [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-dioxopiperazin-1-yl]ethyl]-2,6-dioxopiperazin-1-yl]methyl 2-methylpropyl Carbonate

    5. Perazolin

    6. R1308vh37p

    7. Sobuzoxane (jan)

    8. Ncgc00015954-02

    9. Sobuzoxane [jan]

    10. Sobuzoxano

    11. Sobuzoxanum

    12. Sobuzoxane [inn:jan]

    13. Sobuzoxanum [inn-latin]

    14. 4,4'-(1,2-ethanediyl)bis(1-iso-butoxycarbonyloxmethyl-2,6-piperazinedione)

    15. Sobuzoxano [inn-spanish]

    16. Brn 6031322

    17. Unii-r1308vh37p

    18. Perazolin (tn)

    19. Sobuzoxane [mi]

    20. Sobuzoxane [inn]

    21. Lopac-s-4692

    22. 1,2-bis(4-isobutoxycarbonyloxymethyl-3,5-dioxo-piperazin-1-yl)ethane

    23. Sobuzoxane [mart.]

    24. 4,4'-ethylenebis(1-(hydroxymethyl)-2,6-piperazinedione) Bis(isobutyl Carbonate) (ester)

    25. Dsstox_cid_25203

    26. Dsstox_rid_80747

    27. Sobuzoxane [who-dd]

    28. Dsstox_gsid_45203

    29. Lopac0_001094

    30. Schembl18416

    31. Mls002153414

    32. Chembl1256871

    33. Dtxsid5045203

    34. Chebi:32136

    35. Hms2230c04

    36. Hms3263k10

    37. Hms3369l07

    38. Tox21_110265

    39. Tox21_501094

    40. Mfcd00866498

    41. Zinc22032147

    42. Sobuzoxane, >=99% (hplc), Solid

    43. Ccg-205171

    44. Lp01094

    45. Sdccgsbi-0051064.p002

    46. Ncgc00015954-01

    47. Ncgc00015954-03

    48. Ncgc00015954-04

    49. Ncgc00094367-01

    50. Ncgc00094367-02

    51. Ncgc00261779-01

    52. Carbonic Acid, 1,2-ethanediylbis((2,6-dioxo-4,1-piperazinediyl)methylene)bis(2-methylpropyl) Ester

    53. Smr001230790

    54. Cas-98631-95-9

    55. Eu-0101094

    56. 1-n-trityl-imidazole-2-ylpropionicacid

    57. D01404

    58. F52515

    59. S 4692

    60. 631s959

    61. A839107

    62. Sr-01000075401

    63. Sr-01000075401-2

    64. Q27287640

    65. 4,4'-(1,2-ethanediyl)bis(1-isobutoxycarbonyloxmethyl-2,6-piperazinedione)

    66. 4,4'-(1,2-ethanediyl)bis(1-isobutoxycarbonyloxymethyl-2,6-piperazinedione)

    67. (4,4'-(ethane-1,2-diyl)bis(2,6-dioxopiperazine-4,1-diyl))bis(methylene) Isobutyl Dicarbonate

    68. [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-bis(oxidanylidene)piperazin-1-yl]ethyl]-2,6-bis(oxidanylidene)piperazin-1-yl]methyl 2-methylpropyl Carbonate

    69. [4-[2-[4-(2-methylpropoxycarbonyloxymethyl)-3,5-dioxo-piperazin-1-yl]ethyl]-2,6-dioxo-piperazin-1-yl]methyl 2-methylpropyl Carbonate

    70. Carbonic Acid [4-[2-[4-[[2-methylpropoxy(oxo)methoxy]methyl]-3,5-dioxo-1-piperazinyl]ethyl]-2,6-dioxo-1-piperazinyl]methyl 2-methylpropyl Ester

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 514.5 g/mol
    Molecular Formula C22H34N4O10
    XLogP32
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count15
    Exact Mass514.22749329 g/mol
    Monoisotopic Mass514.22749329 g/mol
    Topological Polar Surface Area152 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity743
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    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.)

    Topoisomerase II Inhibitors

    Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)