Title: Floxuridine
CAS Registry Number: 50-91-9
CAS Name: 2¢-Deoxy-5-fluorouridine
Additional Names: 1-(2-deoxy-b-D-ribofuranosyl)-5-fluorouracil; 5-fluoro-2¢-deoxy-b-uridine
Manufacturers' Codes: NSC-27640
Trademarks: FUDR (Roche)
Molecular Formula: C9H11FN2O5
Molecular Weight: 246.19
Percent Composition: C 43.91%, H 4.50%, F 7.72%, N 11.38%, O 32.49%
Literature 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; 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). [a]D +37° (water), +48.6° (DMF). uv max (pH 7.2): 268 nm (e 7570); (pH 14): 270 nm (e 6480).
Melting point: mp 150-151° (Hoffer, 1959); mp 145° (US 3041335)
Optical Rotation: [a]D +37° (water), +48.6° (DMF)
Absorption maximum: uv max (pH 7.2): 268 nm (e 7570); (pH 14): 270 nm (e 6480)
Derivative Type: a-Anomer
Additional Names: 1-(2-Deoxy-a-D-erythro-pentofuranosyl)-5-fluorouracil
Properties: Crystals from butyl acetate, mp 150-151°. [a]D25 -21° (c = 2 in water).
Melting point: mp 150-151°
Optical Rotation: [a]D25 -21° (c = 2 in water)
Therap-Cat: Antiviral; antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs; Antiviral; Purines/Pyrimidinones. |