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    Chemistry

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    Also known as: 626-48-2, 2,4-dihydroxy-6-methylpyrimidine, 6-methylpyrimidine-2,4(1h,3h)-dione, Pseudothymine, 4-methyluracil, 6-methyl-1h-pyrimidine-2,4-dione
    Molecular Formula
    C5H6N2O2
    Molecular Weight
    126.11  g/mol
    InChI Key
    SHVCSCWHWMSGTE-UHFFFAOYSA-N
    FDA UNII
    5O052W0G6I
    6-Methyluracil
    1 2D Structure

    6-Methyluracil

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-methyl-1H-pyrimidine-2,4-dione
    2.1.2 InChI
    InChI=1S/C5H6N2O2/c1-3-2-4(8)7-5(9)6-3/h2H,1H3,(H2,6,7,8,9)
    2.1.3 InChI Key
    SHVCSCWHWMSGTE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=O)NC(=O)N1
    2.2 Other Identifiers
    2.2.1 UNII
    5O052W0G6I
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-methyluracil, 14c-labeled

    2. Awd 23-15

    3. Awd-23-15

    4. Methacil

    5. Methyluracil

    6. Pseudothymine

    2.3.2 Depositor-Supplied Synonyms

    1. 626-48-2

    2. 2,4-dihydroxy-6-methylpyrimidine

    3. 6-methylpyrimidine-2,4(1h,3h)-dione

    4. Pseudothymine

    5. 4-methyluracil

    6. 6-methyl-1h-pyrimidine-2,4-dione

    7. 6-methyl-2,4(1h,3h)-pyrimidinedione

    8. 6-methylpyrimidine-2,4-diol

    9. 2,4(1h,3h)-pyrimidinedione, 6-methyl-

    10. Uracil, 6-methyl-

    11. 2,4-pyrimidinediol, 6-methyl-

    12. 2(1h)-pyrimidinone, 4-hydroxy-6-methyl-

    13. Nsc 9456

    14. Awd 23-15

    15. Mfcd00006028

    16. Chebi:74733

    17. Chembl1650614

    18. 5o052w0g6i

    19. Nsc-9456

    20. 6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

    21. Pseudothymine (van)

    22. Hsdb 5508

    23. Einecs 210-949-4

    24. 24pyrimidinedione6methyl

    25. Metacyl

    26. Methacyl

    27. Unii-5o052w0g6i

    28. Ai3-25472

    29. 4-(6)-methyluracil

    30. Methyluracil, 4-

    31. Wln: T6mvmvj F1

    32. Dsstox_cid_30880

    33. Dsstox_gsid_52308

    34. Schembl60308

    35. 6-methyluracil [mi]

    36. 4-methyl-2.6-dioxypyrimidin

    37. Methyluracil [who-dd]

    38. 6-methylpyrimidine-2,4-dione

    39. 6-methyluracil [hsdb]

    40. Dtxsid8052308

    41. Schembl21990343

    42. 6-methyluracil, 97% (hplc)

    43. Nsc9456

    44. Hms1762e01

    45. Zinc162484

    46. 2,4-dihydroxy-6-methyl-pyrimidine

    47. Act07641

    48. Albb-022469

    49. Bcp26951

    50. Hy-y1125

    51. Str00504

    52. 2,3h)-pyrimidinedione, 6-methyl-

    53. 2,4-dihydroxyl-6-methyl Pyrimidine

    54. Tox21_304049

    55. Bdbm50106396

    56. Stl283926

    57. Stl426163

    58. 6-methyl-2,4(1h,3h)pyrimidinedione

    59. Akos000120980

    60. Akos002303990

    61. Ac-2536

    62. Am81337

    63. Sb57748

    64. Ncgc00357256-01

    65. Bp-12331

    66. Cas-626-48-2

    67. Sy001859

    68. 6-methyl-2,4(1h,3h)-pyrimidinedione #

    69. Db-016105

    70. Bb 0256780

    71. Cs-0017143

    72. Ft-0610121

    73. M0454

    74. A15712

    75. D70607

    76. 4-hydroxy-6-methyl-1,2-dihydro-pyrimidin-2-one

    77. Ab-323/25048156

    78. 1-boc-3-(2-fluoro-benzylamino)-piperidine

    79. Q-200556

    80. Q4161980

    81. Z56871945

    82. F0322-0043

    83. 6mu

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 126.11 g/mol
    Molecular Formula C5H6N2O2
    XLogP3-0.8
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count0
    Exact Mass126.042927438 g/mol
    Monoisotopic Mass126.042927438 g/mol
    Topological Polar Surface Area58.2 Ų
    Heavy Atom Count9
    Formal Charge0
    Complexity195
    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 Therapeutic Uses

    Anti-ulcer Agents; Radiation-protective Agents; Adjuvants, Immunologic

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999

    EXPTL USE: 4-METHYLURACIL (50 MG/KG/DAY) SHOWED SIGNIFICANT ANTIMETASTATIC EFFECTS WHEN ADMIN ORALLY TO RATS WITH LYMPHO- OR LYMPHOHEMATOGENIC METASTASES OF PLISS LYMPHOSARCOMA OR WALKER CARCINOSARCOMA FOR 3 DAYS BEFORE & AFTER LAPAROTOMY.

    YAREMENKO KV; PREVENTION OF THE METASTATIC SPREAD OF TRANSPLANTED TUMORS BY PREPARATIONS WITH ANABOLIC PROPERTIES UNDER SURGICAL STRESS CONDITIONS; ONKOLOGIYA (KIEV) 4: 20 (1973)

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Ulcer Agents

    Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

    Radiation-Protective Agents

    Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military. (See all compounds classified as Radiation-Protective Agents.)

    Adjuvants, Immunologic

    Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)

    5.2 Metabolism/Metabolites

    UNCHANGED 6-METHYL-2-THIOURACIL (46% OF DOSE), 6-METHYLURACIL (9%), 6-METHYL-2-METHYLTHIOURACIL (2%), 6-METHYL-4-OXOPYRIMIDINE (2%), 2-AMINO-6-METHYL-4-OXOPYRIMIDINE (0.2%), & UREA (1%) WERE EXCRETED IN URINE OF RATS THAT HAD BEEN TREATED ORALLY WITH 6-METHYL-2-THIOURACIL.

    The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 4: A Review of the Literature Published during 1974 and 1975. London: The Chemical Society, 1977., p. 153

    ...STUDIES INDICATED THE FORMATION OF FOUR VOLATILE SUBSTANCES AFTER IRRADIATION OF A 10 PPM AQ BROMACIL SOLN FOR 6 DAYS. THE MAJOR PRODUCT (37%) WAS 6-METHYLURACIL.

    Menzie, C.M. Metabolism of Pesticides, Update II. U.S. Department of the Interior, Fish Wildlife Service, Special Scientific Report - Wildlife No. 2l2. Washington, DC: U.S. Government Printing Office, 1978., p. 288

    A MIXED CULTURE OF PSEUDOMONAS SPECIES & PROACTINOMYCES RUBER UTILIZED 6-METHYLURACIL AS THE SOLE SOURCE OF CARBON & NITROGEN. 6-METHYLURACIL WAS OXIDATIVELY CONVERTED TO URACIL WHICH WAS SUBSEQUENTLY METABOLIZED TO BARBITURIC ACID & UREA.

    ZVYAGINTSEVA IS, MAMULINA NS; OXIDATIVE METABOLISM OF 4 6-METHYLURACIL; IZV AKAD NAUK USSR, SER BIOL (6) 929 (1969)

    API Reference Price

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