6-Azauridine, 6-氮杂尿苷

6-Azauridine is a synthetic triazine analogue of uridine with antimetabolite activity. 6-azauridine inhibits de novo pyrimidine synthesis and DNA synthesis and is converted intracellularly into mono, di, and triphosphate derivatives, which incorporate into RNA and inhibit protein synthesis.

6-azauridine is a N-glycosyl-1,2,4-triazine. It has a role as an antineoplastic agent, an antimetabolite and a drug metabolite.

A triazine nucleoside used as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis thereby preventing formation of cellular nucleic acids. As the triacetate, it is also effective as an antipsoriatic.

Title: 6-Azauridine

CAS Registry Number: 54-25-1

CAS Name: 2-b-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione

Additional Names: 6-azauracil riboside; 3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine riboside; AzUR

Molecular Formula: C8H11N3O6

Molecular Weight: 245.19

Percent Composition: C 39.19%, H 4.52%, N 17.14%, O 39.15%

Literature References: Cytostatic nucleoside analog; inhibits orotidyl decarboxylase and blocks de novo pyrimidine biosynthesis. Production by E. coli in the presence of 6-azauracil: J. Skoda et al., Experientia 13, 150 (1957). Chemical synthesis: M. Prystas et al., Chem. Ind. (London) 1961, 947. Crystal structure and conformation: C. H. Schwalbe et al., Biochem. Biophys. Res. Commun. 44, 57 (1971). Degradation kinetics: C. M. Riley et al., Pharm. Res. 12, 1361 (1995). Clinical evaluation in recalcitrant psoriasis: J. C. Alper et al., J. Am. Acad. Dermatol. 13, 567 (1985). Toxicity study: J. Plevova et al., Toxicol. Appl. Pharmacol. 17, 511 (1970). Review of effect on vitamin B6 and homocystinemia: W. Drell, A. D. Welch, Pharmacol. Ther. 41, 195-206 (1989).

Properties: Crystals from ethanol, ether, mp 160-161°. [a]D24 -132° (pyridine). uv max (water): 262 nm (e 6100). pK 6.70.

Melting point: mp 160-161°

pKa: pK 6.70

Optical Rotation: [a]D24 -132° (pyridine)

Absorption maximum: uv max (water): 262 nm (e 6100)

Derivative Type: 2',3',5'-Triacetate

CAS Registry Number: 2169-64-4

Additional Names: Azaribine; 2-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)-as-triazine-3,5(2H,4H)-dione

Manufacturers' Codes: CB-304

Trademarks: Triazure (Calbiochem)

Molecular Formula: C14H17N3O9

Molecular Weight: 371.30

Percent Composition: C 45.29%, H 4.61%, N 11.32%, O 38.78%

Properties: pKa (25°): 6.42. LD50 in mice, rats (g/kg): 7.8, 12.0 orally (Plevova).

pKa: pKa (25°): 6.42

Toxicity data: LD50 in mice, rats (g/kg): 7.8, 12.0 orally (Plevova)

Therap-Cat: Antipsoriatic.

Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs; Antipsoriatic.