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Chemistry

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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

Oteracil

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 Formula	C₄H₃N₃O₄
Molecular Weight	157.08 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	157.01235559 g/mol
Monoisotopic Mass	157.01235559 g/mol
Topological Polar Surface Area	108 Å²
Heavy Atom Count	11
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

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.

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