Fluorouracil

Fluorouracil (5-FU, 5-fluorouracil), sold under the brand name Adrucil among others, is a cytotoxic chemotherapy medication used to treat cancer. By intravenous injection it is used for treatment of colorectal cancer, oesophageal cancer, stomach cancer, pancreatic cancer, breast cancer, and cervical cancer. As a cream it is used for actinic keratosis, basal cell carcinoma, and skin warts.

Fluorouracil
Clinical data
Pronunciation/ˌflʊəroʊˈjʊərəsɪl/
Trade namesAdrucil, Carac, Efudex, others
AHFS/Drugs.comMonograph
MedlinePlusa682708
License data
Pregnancy
category
  • AU: D
Routes of
administration		Intravenous, topical
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability28 to 100%
Protein binding8 to 12%
MetabolismIntracellular and liver (CYP-mediated)
Elimination half-life16 minutes
ExcretionKidney
Identifiers
  • 5-Fluoro-1H,3H-pyrimidine-2,4-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.078
Chemical and physical data
FormulaC4H3FN2O2
Molar mass130.078 g·mol−1
3D model (JSmol)
Melting point282–283 °C (540–541 °F)
SMILES
  • O=C1NC(=O)NC=C1F
  • InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) Y
  • Key:GHASVSINZRGABV-UHFFFAOYSA-N Y
  (verify)

Side effects of use by injection are common. They may include inflammation of the mouth, loss of appetite, low blood cell counts, hair loss, and inflammation of the skin. When used as a cream, irritation at the site of application usually occurs. Use of either form in pregnancy may harm the fetus. Fluorouracil is in the antimetabolite and pyrimidine analog families of medications. How it works is not entirely clear, but it is believed to involve blocking the action of thymidylate synthase and thus stopping the production of DNA.

Fluorouracil was patented in 1956 and came into medical use in 1962. It is on the World Health Organization's List of Essential Medicines. In 2021, it was the 281st most commonly prescribed medication in the United States, with more than 800,000 prescriptions.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.