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    Vosaroxin

    PharmaCompass
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    2D Structure
    Also known as: Vosaroxin, 175414-77-4, Sns-595, Ag-7352, Ag 7352, Spc-595
    Molecular Formula
    C18H19N5O4S
    Molecular Weight
    401.4  g/mol
    InChI Key
    XZAFZXJXZHRNAQ-STQMWFEESA-N
    FDA UNII
    K6A90IIZ19
    Vosaroxin is a small molecule and a naphthyridine analogue with antineoplastic activity. Vosaroxin intercalates into DNA in a site-specific manner and blocks the re-ligation process carried out by topoisomerase II during DNA replication. As a result, inhibition of DNA replication, RNA and protein synthesis occurs, followed by cell cycle arrest at G2 phase and induced p53-independent apoptosis. This agent shows a favorable toxicity profile in several aspects: it does not generate reactive oxygen species, as do anthracyclines, hence reducing the risk of cardiotoxicity; it is not a P-glycoprotein (P-gp) substrate, and thereby evades the common mechanism for multidrug resistance; and it has limited distribution to normal tissues and a more chemically stable molecular structure.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    7-[(3S,4S)-3-methoxy-4-(methylamino)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic acid
    2.1.2 InChI
    InChI=1S/C18H19N5O4S/c1-19-12-8-22(9-13(12)27-2)14-4-3-10-15(24)11(17(25)26)7-23(16(10)21-14)18-20-5-6-28-18/h3-7,12-13,19H,8-9H2,1-2H3,(H,25,26)/t12-,13-/m0/s1
    2.1.3 InChI Key
    XZAFZXJXZHRNAQ-STQMWFEESA-N
    2.1.4 Canonical SMILES
    CNC1CN(CC1OC)C2=NC3=C(C=C2)C(=O)C(=CN3C4=NC=CS4)C(=O)O
    2.1.5 Isomeric SMILES
    CN[C@H]1CN(C[C@@H]1OC)C2=NC3=C(C=C2)C(=O)C(=CN3C4=NC=CS4)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    K6A90IIZ19
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1,4-dihydro-7-(3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acid

    2. Ag 7352

    3. Ag-7352

    4. Ag7352

    5. Sns-595

    6. Vosaroxin

    2.3.2 Depositor-Supplied Synonyms

    1. Vosaroxin

    2. 175414-77-4

    3. Sns-595

    4. Ag-7352

    5. Ag 7352

    6. Spc-595

    7. Vosaroxin (usan)

    8. Vosaroxin [usan]

    9. K6a90iiz19

    10. 7-((3s,4s)-3-methoxy-4-(methylamino)pyrrolidin-1-yl)-4-oxo-1-(thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

    11. Quinprezo

    12. 174726-60-4

    13. 7-((3s,4s)-3-methoxy-4-(methylamino)pyrrolidin-1-yl)-4-oxo-1-(thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid.

    14. Trans-7-(3-methoxy-4-(methylamino)pyrrolidin-1-yl)-4-oxo-1-(thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

    15. Sns 595

    16. Spc 595

    17. Vosaroxin [usan:inn]

    18. Unii-k6a90iiz19

    19. 7-[(3s,4s)-3-methoxy-4-(methylamino)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,8-naphthyridine-3-carboxylic Acid

    20. Ag7352

    21. 1,4-dihydro-7-(3-methoxy-4-methylamino-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-1,8-naphthyridine-3-carboxylic Acid

    22. Vosaroxin [inn]

    23. (+)-ag-7352

    24. Vosaroxin [mart.]

    25. Vosaroxin [who-dd]

    26. Chembl68117

    27. Schembl674441

    28. Dtxsid50938662

    29. Ex-a847

    30. Voreloxin;sns-595;ag 7352

    31. Mfcd13185156

    32. Nsc760764

    33. Zinc26186622

    34. Akos030526660

    35. Cs-0790

    36. Db11999

    37. Nsc-760764

    38. Ac-36005

    39. Hy-10534

    40. Vosaroxin Hydrochloride, >=98% (hplc)

    41. Sw219924-1

    42. D08024

    43. A911613

    44. J-690243

    45. Q18395775

    46. (+)-7-((3s,4s)-3-methoxy-4-(methylamino)pyrrolidin-1-yl)-4-oxo-1-(thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

    47. (+)-7-[3(s)-methoxy-4(s)-(methylamino)pyrrolidin-1-yl]-4-oxo-1-(2-thiazolyl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

    48. 1,8-naphthyridine-3-carboxylic Acid, 1,4-dihydro-7-((3s,4s)-3-methoxy-4-(methylamino)-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-

    49. 1,8-naphthyridine-3-carboxylic Acid, 1,4-dihydro-7-(3-methoxy-4-(methylamino)-1-pyrrolidinyl)-4-oxo-1-(2-thiazolyl)-, (3s-trans)-

    50. 7-[(3s,4s)-3-methoxy-4-(methylamino)pyrrolidin-1-yl]-4-oxo-1-(1,3-thiazol-2-yl)-1,4-dihydro-1,8-naphthyridine-3-carboxylic Acid

    51. 960398-99-6

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 401.4 g/mol
    Molecular Formula C18H19N5O4S
    XLogP3-0.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count5
    Exact Mass401.11577528 g/mol
    Monoisotopic Mass401.11577528 g/mol
    Topological Polar Surface Area136 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity662
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    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 acute myeloid leukaemia

    5 Pharmacology and Biochemistry
    5.1 ATC Code

    L - Antineoplastic and immunomodulating agents

    L01 - Antineoplastic agents

    L01X - Other antineoplastic agents

    L01XX - Other antineoplastic agents

    L01XX53 - Vosaroxin