Flucytosine

Flucytosine
Clinical data
Trade namesAncobon, Ancotil, others
AHFS/Drugs.comMonograph
MedlinePlusa601132
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability75 to 90% (by mouth)
Protein binding2.9 to 4%
Metabolismminimal, in the GI tract
Elimination half-life2.4 to 4.8 hours
Excretionkidney (90%)
Identifiers
  • 4-amino-5-fluoro-1,2-dihydropyrimidin-2-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.016.336 Edit this at Wikidata
Chemical and physical data
FormulaC4H4FN3O
Molar mass129.094 g·mol−1
3D model (JSmol)
Melting point295 to 297 °C (563 to 567 °F) (dec.)
  • Nc1[nH]c(=O)ncc1F
  • InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9) checkY
  • Key:XRECTZIEBJDKEO-UHFFFAOYSA-N checkY
  (verify)

Flucytosine, also known as 5-fluorocytosine (5-FC), is an antifungal medication.[2] It is specifically used, together with amphotericin B, for serious Candida infections and cryptococcosis.[2] It may be used by itself or with other antifungals for chromomycosis.[2] Flucytosine is used by mouth and by injection into a vein.[2][3]

Common side effects include bone marrow suppression, loss of appetite, diarrhea, vomiting, and psychosis.[2] Anaphylaxis and other allergic reactions occasionally occur.[2] It is unclear if use in pregnancy is safe for the baby.[4] Flucytosine is in the fluorinated pyrimidine analogue family of medications.[2] It works by being converted into fluorouracil inside the fungus, which impairs its ability to make protein.[2]

Flucytosine was first made in 1957.[5] It is on the World Health Organization's List of Essential Medicines.[6] As of 2016, in the United States the medication cost about US$2,000 per day while in the United Kingdom it is about US$22 per day.[7] It is not available in much of the developing world.[8]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ a b c d e f g h "Flucytosine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  3. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 147. hdl:10665/44053. ISBN 9789241547659.
  4. ^ "Flucytosine (Ancobon) Use During Pregnancy". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 11 December 2016.
  5. ^ Northern Neonatal Network (2008). "Drug Monographs: Flucytosine". Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (5th ed.). John Wiley & Sons. p. 108. ISBN 9780470750353. Archived from the original on 2016-12-20.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^ Merry M, Boulware DR (June 2016). "Cryptococcal Meningitis Treatment Strategies Affected by the Explosive Cost of Flucytosine in the United States: A Cost-effectiveness Analysis". Clinical Infectious Diseases. 62 (12): 1564–1568. doi:10.1093/cid/ciw151. PMC 4885648. PMID 27009249.
  8. ^ Brew BJ, Laffan A (2016). "Opportunistic infections in HIV-positive subjects and AIDS patients". In Lisak RP, Truong DD, Carroll WM, Bhidayasiri R (eds.). International Neurology (2nd ed.). John Wiley & Sons. p. 343. ISBN 9781118777350. Archived from the original on 2016-12-20.