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Chemistry

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Also known as: 103766-25-2, Gimestat, 5-chloro-2,4-dihydroxypyridine, 5-chloropyridine-2,4-diol, 5-chloro-4-hydroxy-2(1h)-pyridone, 5-chloro-4-hydroxy-2(1h)-pyridinone

Molecular Formula

C₅H₄ClNO₂

Molecular Weight

145.54 g/mol

InChI Key

ZPLQIPFOCGIIHV-UHFFFAOYSA-N

FDA UNII

UA8SE1325T

Gimeracil is a pyridine derivative with antitumor activity. Gimeracil enhances the antitumor activity of fluoropyrimidines by competitively and reversibly inhibiting the enzyme dihydropyrimidine dehydrogenase causing decreased degradation of the fluoropyrimidines.

1 2D Structure

Gimeracil

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-chloro-4-hydroxy-1H-pyridin-2-one

2.1.2 InChI

InChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)

2.1.3 InChI Key

ZPLQIPFOCGIIHV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=C(C(=CNC1=O)Cl)O

2.2 Other Identifiers

2.2.1 UNII

UA8SE1325T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-chloro-2,4-dihydroxypyridine

2. 5-chloro-4-hydroxy-2(1h)-pyridinone

2.3.2 Depositor-Supplied Synonyms

1. 103766-25-2

2. Gimestat

3. 5-chloro-2,4-dihydroxypyridine

4. 5-chloropyridine-2,4-diol

5. 5-chloro-4-hydroxy-2(1h)-pyridone

6. 5-chloro-4-hydroxy-2(1h)-pyridinone

7. Gimeracil [inn]

8. 5-chloro-4-hydroxy-1h-pyridin-2-one

9. 5-chloro-2,4-pyridinediol

10. 5-chloro-2-hydroxypyridin-4(1h)-one

11. 2(1h)-pyridinone, 5-chloro-4-hydroxy-

12. 5-chloro-4-hydroxy-2-pyridone

13. Ua8se1325t

14. 5-chloro-4-hydroxypyridin-2(1h)-one

15. Mfcd08458352

16. 1349387-07-0

17. Ncgc00181011-01

18. Dsstox_cid_26799

19. Dsstox_rid_81914

20. Dsstox_gsid_46799

21. Cdhp Compound

22. Cas-103766-25-2

23. Unii-ua8se1325t

24. Gimeracil (cdhp)

25. Gimeracil (jan/inn)

26. Gimeracil [jan]

27. Gimeracil [mi]

28. Gimeracil [who-dd]

29. Gimeracil Impurity 1

30. Gimeracil [ema Epar]

31. Schembl124438

32. Ts-1 (tn)

33. Chembl1730601

34. Dtxsid8046799

35. Gimeracil, >=98% (hplc)

36. Chebi:31652

37. Amy2406

38. Teysuno Component Gimeracil

39. Hms3655b15

40. Act04735

41. Bcp05824

42. Tox21_112661

43. Ac-475

44. Stl452964

45. Zinc13831809

46. Gimeracil Component Of Teysuno

47. Akos006346735

48. Akos015891515

49. Akos026749993

50. Tox21_112661_1

51. Bcp9000727

52. Ccg-266172

53. Cs-1822

54. Db09257

55. Ks-5133

56. Ncgc00181011-02

57. Hy-17469

58. Sy029154

59. Ft-0645353

60. S2055

61. Sw219483-1

62. D01846

63. Ab01566858_01

64. 766g252

65. A800802

66. A935098

67. Sr-01000945072

68. Q-100034

69. Sr-01000945072-1

70. Q22075887

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₅H₄ClNO₂
Molecular Weight	145.54 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	144.9930561 g/mol
Monoisotopic Mass	144.9930561 g/mol
Topological Polar Surface Area	49.3 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	207
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

Gimeracil is used as an adjunct to antineoplastic therapy. When used within the product Teysuno, gimeracil 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

Mean 5-FU maximum plasma concentration (Cmax) and area under the concentration-time curve (AUC) values were approximately 3-fold higher after Teysuno administration than after administration of tegafur alone, despite a 16-fold lower Teysuno dose (50 mg of tegafur) compared to tegafur alone (800 mg), and are attributed to inhibition of DPD by gimeracil. Maximum plasma uracil concentration was observed at 4 hours, with a return to baseline levels within approximately 48 hours after dosing, indicating the reversibility of the DPD inhibition by gimeracil. 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 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.

5.3 Mechanism of Action

Gimeracil's main role within Teysuno is to prevent the breakdown of [DB00544] (5-FU), which helps to maintin high enough concentrations for sustained effect against cancer cells. It functions by reversibly blocking the enzyme dihydropyrimidine dehydrogenase (DPD), which is involved in the degradation of 5-FU.

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