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    Oteracil

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    2D Structure
    Also known as: Oteracil, 937-13-3, 5-azaorotic acid, Allantoxanic acid, 4,6-dioxo-1,4,5,6-tetrahydro-1,3,5-triazine-2-carboxylic acid, Oteracil [inn]
    Molecular Formula
    C4H3N3O4
    Molecular Weight
    157.08  g/mol
    InChI Key
    RYYCJUAHISIHTL-UHFFFAOYSA-N
    FDA UNII
    5VT6420TIG
    Antagonist of urate oxidase.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4,6-dioxo-1H-1,3,5-triazine-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C4H3N3O4/c8-2(9)1-5-3(10)7-4(11)6-1/h(H,8,9)(H2,5,6,7,10,11)
    2.1.3 InChI Key
    RYYCJUAHISIHTL-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1(=NC(=O)NC(=O)N1)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    5VT6420TIG
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Oteracil

    2.3.2 Depositor-Supplied Synonyms

    1. Oteracil

    2. 937-13-3

    3. 5-azaorotic Acid

    4. Allantoxanic Acid

    5. 4,6-dioxo-1,4,5,6-tetrahydro-1,3,5-triazine-2-carboxylic Acid

    6. Oteracil [inn]

    7. Oxonate

    8. 1,4,5,6-tetrahydro-4,6-dioxo-1,3,5-triazine-2-carboxylic Acid

    9. 4,6-dioxo-1h-1,3,5-triazine-2-carboxylic Acid

    10. 5vt6420tig

    11. Chebi:30863

    12. 1,4,5,6-tetrahydro-4,6-dioxo-s-triazine-2-carboxylic Acid

    13. Oxc

    14. Unii-5vt6420tig

    15. Oxonsaure

    16. Oxonic-acid

    17. 1,3,5-triazine-2-carboxylic Acid, 1,4,5,6-tetrahydro-4,6-dioxo-

    18. Oxonic Acid [mi]

    19. Oteracil [who-dd]

    20. Nciopen2_000442

    21. Oteracil [ema Epar]

    22. Schembl464773

    23. Chembl181932

    24. Dtxsid9048358

    25. Bcp32168

    26. Zinc13514753

    27. Akos006272679

    28. Am84784

    29. Db03209

    30. Sb73387

    31. Db-079670

    32. Dihydroxy-1,3,5-triazine-2-carboxylic Acid

    33. Ft-0707227

    34. S-triazine-2,4-dione-6-carboxylic Acid

    35. Q22075725

    36. 1,3,5-triazine-2-carboxylicacid,1,4,5,6-tetrahydro-4,6-dioxo-

    37. 4,6-dioxo-1,4,5,6-tetrahydro-1,3,5-triazine-2-carboxylicacid

    38. Oteracil Pound>>5-azaorotic Acid Pound>>4,6-dioxo-1,4,5,6-tetrahydro-1,3,5-triazine-2-carboxylic Acid

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 157.08 g/mol
    Molecular Formula C4H3N3O4
    XLogP3-1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count1
    Exact Mass157.01235559 g/mol
    Monoisotopic Mass157.01235559 g/mol
    Topological Polar Surface Area108 Ų
    Heavy Atom Count11
    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

    Oteracil is used as an adjunct to antineoplastic therapy. When used within the product Teysuno, oteracil is indicated for the treatment of adults with advanced gastric (stomach) cancer when given in combination with cisplatin.

    5 Pharmacology and Biochemistry
    5.1 Absorption, Distribution and Excretion

    Absorption

    After administration of a single dose of 50 mg Teysuno (expressed as tegafur content), median Tmax for Teysuno components tegafur, gimeracil, and oteracil was 0.5, 1.0, and 2.0 hours, respectively.

    Route of Elimination

    Following a single dose of Teysuno, approximately 3.8% to 4.2% of administered tegafur, 65% to 72% of administered gimeracil, and 3.5% to 3.9% of administered oteracil were excreted unchanged in the urine.

    Volume of Distribution

    Although no intravenous data are available for Teysuno in humans, the volume of distribution could be roughly estimated from the apparent volume of distribution and urinary excretion data as 16 l/m2, 17 l/m2, and 23 l/m2 for tegafur, gimeracil and oteracil, respectively.

    5.2 Metabolism/Metabolites

    Based on the results of in vitro studies, a part of oteracil is non-enzymatically degraded to 5-azauracil (5-AZU) by gastric fluid, and is then converted to cyanuric acid (CA) in the digestive tract. Only a small amount of oteracil is metabolised in the liver because of its low permeability.

    5.3 Biological Half-Life

    Following a single dose of Teysuno, T1/2 values ranged from 6.7 to 11.3 hours for tegafur, from 3.1 to 4.1 hours for gimeracil, and from 1.8 to 9.5 hours for oteracil.

    5.4 Mechanism of Action

    Oteracil's main role within Teysuno is to reduce the activity of 5-FU within normal gastrointestinal mucosa, and therefore reduce's gastrointestinal toxicity. It functions by blocking the enzyme orotate phosphoribosyltransferase (OPRT), which is involved in the production of 5-FU.