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Eniluracil

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Chemistry

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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

Eniluracil

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 Formula	C₆H₄N₂O₂
Molecular Weight	136.11 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	136.027277375 g/mol
Monoisotopic Mass	136.027277375 g/mol
Topological Polar Surface Area	58.2 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	269
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 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.

Drugs in Development