Fluorouracil

Title: Fluorouracil
CAS Registry Number: 51-21-8
CAS Name: 5-Fluoro-2,4(1H,3H)-pyrimidinedione
Additional Names: 2,4-dioxo-5-fluoropyrimidine; 5-FU
Manufacturers' Codes: Ro-2-9757; NSC-19893
Trademarks: Adrucil (Adria); Arumel (SS Pharm.); Efudex (Roche); Efudix (Roche); Fluril; Fluracil; Fluoroplex (Allergan); Fluroblastin (Farmitalia); Fluro Uracil; Timazin (Torii)
Molecular Formula: C4H3FN2O2
Molecular Weight: 130.08
Percent Composition: C 36.93%, H 2.32%, F 14.61%, N 21.54%, O 24.60%
Literature References: Prepn: Duschinsky et al., J. Am. Chem. Soc. 79, 4559 (1957); Heidelberger, Duschinsky, US 2802005 (1957); US 2885396 (1959); Barton et al., J. Org. Chem. 37, 329 (1972); O. Miyashita et al., Chem. Pharm. Bull. 29, 3181 (1981). Pharmacokinetics: W. Sadee, C. G. Wong, Clin. Pharmacokinet. 2, 437 (1977). Site of action: F. Maley, G. F. Maley, FEBS Symp. 57, 21 (1979). Comprehensive description: B. C. Rudy, B. Z. Senkowski, Anal. Profiles Drug Subs. 2, 221-244 (1973); S. M. Bayomi, A. A. Al-Badr, ibid. 18, 599-639 (1989). Review of clinical trials: R. M. Hansen, Cancer Invest. 9, 637-642 (1991).
Properties: Crystals from water or methanol-ether, dec 282-283°. Sublimes (0.1 mm) 190-200°. uv max (0.1N HCl): 265-266 nm (e 7070).
Absorption maximum: uv max (0.1N HCl): 265-266 nm (e 7070)
Derivative Type: Sodium salt
Trademarks: Effluderm (Allergan)
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.
Fluosilicic Acid Fluosol DA Fluoxastrobin Fluoxetine Fluoxymesterone

Fluorouracil
Systematic (IUPAC) name
5-fluoro-1H,3H-pyrimidine-2,4-dione
Clinical data
Trade names Adrucil, Carac, Efudex
AHFS/Drugs.com monograph
MedlinePlus a682708
Licence data US FDA:link
Pregnancy cat. D (AU)
D (IV), X (topical) (US)
Legal status Prescription Only (S4) (AU) -only (CA) POM (UK) -only (US)
Routes IV (infusion or bolus) and topical
Pharmacokinetic data
Bioavailability 28 to 100%
Protein binding 8 to 12%
Metabolism Intracellular and hepatic (CYP-mediated)
Half-life 16 minutes
Excretion Renal
Identifiers
CAS number 51-21-8 YesY
ATC code L01BC02
PubChem CID 3385
DrugBank DB00544
ChemSpider 3268 YesY
UNII U3P01618RT YesY
KEGG D00584 YesY
ChEBI CHEBI:46345 YesY
ChEMBL CHEMBL185 YesY
Chemical data
Formula C4H3FN2O2 
Mol. mass 130.077 g/mol
Physical data
Melt. point 282 - 283 °C (-195 °F)
 YesY (what is this?)  (verify)

Fluorouracil (pronounced flu-row-u-ra-sil) or 5-FU (trademarked as Adrucil (IV), Carac (topical), Efudex (topical)) is a drug that is a pyrimidine analog which is used in the treatment of cancer. It is a suicide inhibitor and works through irreversible inhibition of thymidylate synthase. It belongs to the family of drugs called antimetabolites.