4112. Floxuridine
Nomenclature
CAS number: 50-91-9
2′-Deoxy-5-fluorouridine; 1-(2-deoxy-β-d-ribofuranosyl)-5-fluorouracil; 5-fluoro-2′-deoxy-β-uridine; NSC-27640; FUDR (Roche). C9H11FN2O5; mol wt 246.19.
C 43.91%, H 4.50%, F 7.72%, N 11.38%, O 32.49%.
Description and references
Prepn: Hoffer et al., J. Am. Chem. Soc. 81, 4112 (1959); Heidelberger, Duschinsky, US 2885396 (1959); Duschinsky et al., US 2970139 (1961); Hoffer, US 2949451; idem, US 3041335 (1960, 1962 both to Hoffmann-La Roche). Structure: Lemieux, Hoffer, Can. J. Chem. 39, 110 (1961). Crystal and molecular structure: Harris, Diss. Abstr. 24, 4425 (1964); Harris, McIntyre, Biophys. J. 4, 203 (1964). Conformation of furanose ring in molecule: Sundaralingam, J. Am. Chem. Soc. 87, 599 (1965).
Properties
Crystals from butyl acetate, mp 150-151° (Hoffer, 1959); also reported as mp 145° (US 3041335). [α]D +37° (water), +48.6° (DMF). uv max (pH 7.2): 268 nm (ε 7570); (pH 14): 270 nm (ε 6480).Derivative
α-Anomer.Nomenclature
1-(2-Deoxy-α-d-erythro-pentofuranosyl)-5-fluorouracil.Properties
Crystals from butyl acetate, mp 150-151°. [α]D25 21° (c = 2 in water).Therapeutic Category
Antiviral; antineoplastic.
Keywords
Antineoplastic; Antimetabolites; Pyrimidine Analogs; Antiviral; Nucleosides/Nucleotides