5-fluorouracil

Fluorouracil

Clinical data
Pronunciation	/ˌflʊroʊˈjʊrəˌsɪl/
Trade names	Adrucil, Carac, Efudex, Efudix, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682708
License data	US FDA: Fluorouracil
Pregnancy category	AU: D D (IV), X (topical) (US)
Routes of administration	IV (infusion or ) and topical
ATC code	L01BC02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	28 to 100%
Protein binding	8 to 12%
Metabolism	Intracellular and liver (-mediated)
Biological half-life	16 minutes
Excretion	kidney
Identifiers
IUPAC name 5-Fluoro-1H,3H-pyrimidine-2,4-dione
CAS Number	51-21-8 Y
PubChem CID	3385
IUPHAR/BPS	4789
DrugBank	DB00544 Y
ChemSpider	3268 Y
UNII	U3P01618RT
KEGG	D00584 Y
ChEBI	CHEBI:46345 Y
ChEMBL	CHEMBL185 Y
ECHA InfoCard	100.000.078
Chemical and physical data
Formula	C4H3FN2O2
Molar mass	130.077 g/mol
3D model (Jmol)	Interactive image
Melting point	282–283 °C (540–541 °F)
SMILES c1c(c(=O)[nH]c(=O)[nH]1)F
InChI 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

Fluorouracil (5-FU), sold under the brand name Adrucil among others, is a medication used to treat cancer. By injection into a vein it is used for colon cancer, esophageal cancer, stomach cancer, pancreatic cancer, breast cancer, and cervical cancer. As a cream it is used for actinic keratosis and basal cell carcinoma.

When used by injection most people develop side effects. Common side effects 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 may occur. Use of either form in pregnancy may harm the baby. Fluorouracil is in the antimetabolite and pyrimidine analog families of medications. How it works is not entirely clear but 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, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 1.18 to 3.40 USD per 500 mg vial. In the United Kingdom this amount costs the NHS about 6.40 pounds.

Fluorouracil has been given systemically for anal, breast, colorectal, oesophageal, stomach, pancreatic and skin cancers (especially head and neck cancers). It has also been given topically (on the skin) for actinic keratoses, skin cancers and Bowen's disease and as eye drops for treatment of ocular surface squamous neoplasia.