Back فلورويوراسيل Arabic فلوروراسیل AZB Fluorouracil Catalan Fflworowracil Welsh 5-Fluoruracil German Φθοριοουρακίλη Greek 5-fluorouracilo Spanish فلوروراسیل Persian Fluorourasiili Finnish Fluorouracile French

Fluorouracil

Fluorouracil
Clinical data
Pronunciation/ˌflʊəroʊˈjʊərəsɪl/[1]
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
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 Edit this at Wikidata
Chemical and physical data
FormulaC4H3FN2O2
Molar mass130.078 g·mol−1
3D model (JSmol)
Melting point282–283 °C (540–541 °F)
  • O=C1NC(=O)NC=C1F
  • InChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9) checkY
  • Key:GHASVSINZRGABV-UHFFFAOYSA-N checkY
  (verify)

Fluorouracil (5-FU, 5-fluorouracil), sold under the brand name Adrucil among others, is a cytotoxic chemotherapy medication used to treat cancer.[3] By intravenous injection it is used for treatment of colorectal cancer, oesophageal cancer, stomach cancer, pancreatic cancer, breast cancer, and cervical cancer.[3] As a cream it is used for actinic keratosis, basal cell carcinoma, and skin warts.[4][5]

Side effects of use by injection are common.[3] They may include inflammation of the mouth, loss of appetite, low blood cell counts, hair loss, and inflammation of the skin.[3] When used as a cream, irritation at the site of application usually occurs.[4] Use of either form in pregnancy may harm the fetus.[3] Fluorouracil is in the antimetabolite and pyrimidine analog families of medications.[6][7] 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.[3]

Fluorouracil was patented in 1956 and came into medical use in 1962.[8] It is on the World Health Organization's List of Essential Medicines.[9] In 2021, it was the 281st most commonly prescribed medication in the United States, with more than 800,000 prescriptions.[10][11]

  1. ^ "Fluorouracil – Definition and More from the Free Merriam-Webster Dictionary". Archived from the original on 29 November 2014. Retrieved 19 November 2014.
  2. ^ "TOLAK : Fluorouracil Cream : 4% (w/w) fluorouracil (as fluorouracil sodium)" (PDF). Pdf.hres.ca. Archived (PDF) from the original on 10 June 2022. Retrieved 8 June 2022.
  3. ^ a b c d e f "Fluorouracil". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  4. ^ a b "Fluorouracil topical". The American Society of Health-System Pharmacists. Archived from the original on 26 December 2016. Retrieved 8 December 2016.
  5. ^ Moore AY (2009). "Clinical applications for topical 5-fluorouracil in the treatment of dermatological disorders". The Journal of Dermatological Treatment. 20 (6): 328–335. doi:10.3109/09546630902789326. PMID 19954388. S2CID 218896998.
  6. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 590. ISBN 9780857111562.
  7. ^ Airley R (2009). Cancer Chemotherapy: Basic Science to the Clinic. John Wiley & Sons. p. 76. ISBN 9780470092569. Archived from the original on 5 November 2017.
  8. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 511. ISBN 9783527607495. Archived from the original on 11 September 2017.
  9. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  10. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  11. ^ "Fluorouracil - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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