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2 API Suppliers, 1 EU WC, 2 Listed Suppliers, $ API Reference Price

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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

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 Formula	C₅H₆N₂O₂
Molecular Weight	126.11 g/mol
XLogP3	-0.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	126.042927438 g/mol
Monoisotopic Mass	126.042927438 g/mol
Topological Polar Surface Area	58.2 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	195
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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)

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API Reference Price

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