6-Azauridine
Structural Formula Vector Image
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.

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