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    Eniluracil

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: 59989-18-3, 5-ethynyluracil, 5-ethynylpyrimidine-2,4(1h,3h)-dione, 5-ethynyl-1h-pyrimidine-2,4-dione, Gw776c85, 776c85
    Molecular Formula
    C6H4N2O2
    Molecular Weight
    136.11  g/mol
    InChI Key
    JOZGNYDSEBIJDH-UHFFFAOYSA-N
    FDA UNII
    2E2W0W5XIU
    Eniluracil is an orally-active fluoropyrimidine analogue. Eniluracil inhibits dihydropyrimidine dehydrogenase, the rate-limiting enzyme that catabolizes and inactivates 5-fluorouracil (5-FU) in the liver. Co-administration of ethynyluracil permits the oral administration of 5-FU.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-ethynyl-1H-pyrimidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C6H4N2O2/c1-2-4-3-7-6(10)8-5(4)9/h1,3H,(H2,7,8,9,10)
    2.1.3 InChI Key
    JOZGNYDSEBIJDH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C#CC1=CNC(=O)NC1=O
    2.2 Other Identifiers
    2.2.1 UNII
    2E2W0W5XIU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-ethynyluracil

    2. 776c85

    3. Compound 776c

    4. Gw776c85

    2.3.2 Depositor-Supplied Synonyms

    1. 59989-18-3

    2. 5-ethynyluracil

    3. 5-ethynylpyrimidine-2,4(1h,3h)-dione

    4. 5-ethynyl-1h-pyrimidine-2,4-dione

    5. Gw776c85

    6. 776c85

    7. 5-ethynyl-2,4(1h,3h)-pyrimidinedione

    8. 5-ethynyl-2-hydroxypyrimidin-4(1h)-one

    9. 5-ethynyl-6-hydroxypyrimidin-2(1h)-one

    10. 5-ethynyl-2,4(1h,3h)pyrimidinedione

    11. 2e2w0w5xiu

    12. Chembl355200

    13. Compound 776c

    14. 5-ethynylpyrimidine-2,4(1h,3h)-dione.

    15. 776-c-85

    16. Eniluracil [usan]

    17. 5-ethynylpyrimidine-2,4-diol

    18. Unii-2e2w0w5xiu

    19. 5-ethynyl-2-hydroxypyrimidin-4(3h)-one

    20. 5-ethynyl-4-hydroxypyrimidin-2(1h)-one

    21. Eniluracil [usan:inn:ban]

    22. 2,4(1h,3h)-pyrimidinedione, 5-ethynyl-

    23. 5-ethynyl-uracil

    24. Y3g

    25. Eniluracil [mi]

    26. Eniluracil [inn]

    27. Eniluracil (usan/inn)

    28. Eniluracil [mart.]

    29. Eniluracil [who-dd]

    30. Schembl37817

    31. Zinc5467

    32. Dtxsid10208696

    33. Chebi:177783

    34. Hms3745i03

    35. Bdbm50124202

    36. Geo-02731

    37. Gw-776

    38. Mfcd00871973

    39. Nsc687296

    40. Zb1821

    41. Akos006240058

    42. Akos016009479

    43. Adh-300004

    44. Db03516

    45. Nsc-687296

    46. As-66226

    47. Hy-10533

    48. Cs-0002630

    49. E1096

    50. Ft-0667865

    51. D03998

    52. T72682

    53. A857850

    54. Q27094456

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 136.11 g/mol
    Molecular Formula C6H4N2O2
    XLogP3-0.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count1
    Exact Mass136.027277375 g/mol
    Monoisotopic Mass136.027277375 g/mol
    Topological Polar Surface Area58.2 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity269
    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

    For the treatment of cancer in combination with 5-fluorouracil.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Eniluracil is an orally active dihydropyrimidine dehydrogenase (DPD) inhibitor, designed to enhance activity of chemotaxic agents. It is under investigation by Adherex, under license from GlaxoSmithKline, for the treatment of cancer in combination with 5-fluorouracil (5-FU).

    5.2 MeSH Pharmacological Classification

    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.)

    5.3 Mechanism of Action

    Normally, 5-FU is rapidly broken down in the body by an enzyme known as dihydropyrimidine dehydrogenase (DPD). Eniluracil irreversibly inhibits DPD, thereby substantially slowing the breakdown of 5-FU and prolonging exposure of the tumor cells to the drug.