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    Ropidoxuridine

    DEVELOPMENTS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 93265-81-7, Ipdr, 5-iodo-2-pyrimidinone-2'-deoxyribose, Ipd-r, 3hx21a3sqf, 1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone
    Molecular Formula
    C9H11IN2O4
    Molecular Weight
    338.10  g/mol
    InChI Key
    XIJXHOVKJAXCGJ-XLPZGREQSA-N
    FDA UNII
    3HX21A3SQF
    Ropidoxuridine is an orally available 5-substituted 2-pyrimidinone-2'-deoxyribonucleoside analogue and prodrug of 5-iododeoxyuridine (IUdR), an iodinated analogue of deoxyuridine, with radiosensitizing activity. Upon oral administration, ropidoxuridine (IPdR) is efficiently converted to idoxuridine (IUdR) by a hepatic aldehyde oxidase. In turn, IUdR is incorporated into DNA during replication, thereby sensitizing cells to ionizing radiation by increasing DNA strand breaks. Compared to IUdR, ropidoxuridine is associated with a lower toxicity profile and improved anti-tumor activity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one
    2.1.2 InChI
    InChI=1S/C9H11IN2O4/c10-5-2-11-9(15)12(3-5)8-1-6(14)7(4-13)16-8/h2-3,6-8,13-14H,1,4H2/t6-,7+,8+/m0/s1
    2.1.3 InChI Key
    XIJXHOVKJAXCGJ-XLPZGREQSA-N
    2.1.4 Canonical SMILES
    C1C(C(OC1N2C=C(C=NC2=O)I)CO)O
    2.1.5 Isomeric SMILES
    C1[C@@H]([C@H](O[C@H]1N2C=C(C=NC2=O)I)CO)O
    2.2 Other Identifiers
    2.2.1 UNII
    3HX21A3SQF
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone

    2. 5-iodo-2-pyrimidinone 2' Deoxyribonucleoside

    3. 5-iodo-2-pyrimidinone-2'-deoxyribose

    4. Ipdr

    2.3.2 Depositor-Supplied Synonyms

    1. 93265-81-7

    2. Ipdr

    3. 5-iodo-2-pyrimidinone-2'-deoxyribose

    4. Ipd-r

    5. 3hx21a3sqf

    6. 1-(2-deoxy-beta-ribofuranosyl)-5-iodo-2-pyrimidinone

    7. Nsc-726188

    8. 2(1h)-pyrimidinone, 1-(2-deoxy-beta-d-erythro-pentofuranosyl)-5-iodo-

    9. 1-((2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-iodopyrimidin-2(1h)-one

    10. Ropidoxuridine [usan]

    11. Unii-3hx21a3sqf

    12. Ropidoxuridine (inn/usan)

    13. Ropidoxuridine [usan:inn]

    14. 5-iodo-2-pyrimidinone 2' Deoxyribonucleoside

    15. Ropidoxuridine [inn]

    16. Schembl8602575

    17. Chembl2103821

    18. Dtxsid00239353

    19. Zinc6091380

    20. 5-iodo-2-pyrimidinone-2-deoxyribose

    21. Db06485

    22. 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidin-2-one

    23. Hy-13742

    24. Cs-0007768

    25. D08992

    26. D96122

    27. 265i817

    28. A901121

    29. Q27257237

    30. 5-iodo-1-(2-deoxy-beta-d-ribofuranosyl)pyrimidin-2(1h)-one

    31. 1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-5-iodopyrimidin-2(1h)-one

    32. 2(1h)-pyrimidinone, 1-(2-deoxy-.beta.-d-erythro-pentofuranosyl)-5-iodo-

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 338.10 g/mol
    Molecular Formula C9H11IN2O4
    XLogP3-0.5
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass337.97635 g/mol
    Monoisotopic Mass337.97635 g/mol
    Topological Polar Surface Area82.4 Ų
    Heavy Atom Count16
    Formal Charge0
    Complexity357
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    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 cancer/tumors (unspecified).

    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.)