Structure via PubChem · Public domain (PubChem)
fluorouracil
Sign in to saveAlso known as Efudex, Tolak, fluoro uracil, 5-FU, topical 5-fluorouracil, fluorouracilum, 5-fluorouracil, Timazin
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.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 456480929
- Drug.image
- Fluorouracil2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 80
- Drug.image2
- Fluorouracil-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 100
- Drug.tradename
- Adrucil, others
- Drug.MedlinePlus
- a682708
- Drug.DailyMedID
- Fluorouracil
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- Intravenous, topical
- Drug.ATC_prefix
- L01
- Drug.ATC_suffix
- BC02
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_UK
- POM
via Wikipedia infobox
Chemical data
- Formula
- C4H3FN2O2
- Molecular weight
- 130.08 g/mol
- IUPAC name
- 5-fluoro-1H-pyrimidine-2,4-dione
- SMILES
- C1=C(C(=O)NC(=O)N1)F
- InChIKey
- GHASVSINZRGABV-UHFFFAOYSA-N
- XLogP
- -0.9
- Polar surface area
- 58.2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
71,124 papers- Clinical pharmacology of 5-fluorouracil.Clinical pharmacokinetics · 1989
- 5-Fluorouracil in the treatment of gastrointestinal neoplasia.The New England journal of medicine · 1973
- The metabolism and pharmacology of 5-fluorouracil.Journal of surgical oncology · 1971
- 5-fluorouracil and beyond.The British journal of ophthalmology · 1991
- [5-fluorouracil therapeutic drug monitoring: Update and recommendations of the STP-PT group of the SFPT and the GPCO-Unicancer].Bulletin du cancer · 2018
via PubMed
Wikidata facts
- Mass
- 130.018
Show 5 more facts
- MCN code
- 2933.59.23
- chemical formula
- C₄H₃FN₂O₂
- Commons category
- 5-Fluorouracil
- canonical SMILES
- C1=C(C(=O)NC(=O)N1)F
- World Health Organisation international non-proprietary name
- fluorouracil
Sources (6)
via Wikidata · CC0
~10 min read
Article
19 sectionsContents
- Medical uses
- Contraindications
- Adverse effects
- During systemic use
- During topical use
- Neurological damage
- Potential overdose
- Dangers to pets
- Interactions
- Pharmacology
- Pharmacogenetics
- Mechanism of action
- History
- Natural analogues
- Interactive pathway map
- Names
- References
- Further reading
- External links
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.
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.