Floxuridine

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.
Fluacizine Fluanisone Fluazacort Fluazifop-butyl Fluazinam

Floxuridine
Floxuridine.png
Systematic (IUPAC) name
5-Fluoro-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1H-pyrimidine-2,4-dione
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a682006
Legal status  ?
Identifiers
CAS number 50-91-9 YesY
ATC code None
PubChem CID 5790
DrugBank DB00322
ChemSpider 5586 YesY
UNII 039LU44I5M YesY
KEGG D04197 YesY
ChEBI CHEBI:60761 YesY
ChEMBL CHEMBL917 YesY
Chemical data
Formula C9H11FN2O5 
Mol. mass 246.192 g/mol
 YesY (what is this?)  (verify)

Floxuridine (also 5-fluorodeoxyuridine) is an oncology drug that belongs to the class known as antimetabolites. The drug is most often used in the treatment of colorectal cancer.