Structure via PubChem · Public domain (PubChem)
5-fluorocytosine
Sign in to saveAlso known as fluorcytosine, flucytosine
Flucytosine, also known as 5-fluorocytosine (5-FC), is an antifungal medication. It is specifically used, together with amphotericin B, for serious Candida infections and cryptococcosis. It may be used by itself or with other antifungals for chromomycosis. Flucytosine is used by mouth and by injection into a vein.
Chemical data
- Formula
- C4H4FN3O
- Molecular weight
- 129.09 g/mol
- IUPAC name
- 6-amino-5-fluoro-1H-pyrimidin-2-one
- SMILES
- C1=NC(=O)NC(=C1F)N
- InChIKey
- XRECTZIEBJDKEO-UHFFFAOYSA-N
- XLogP
- -0.9
- Polar surface area
- 67.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1971
- Admin. routes
- oral
- Indications
- hepatocellular carcinoma, infection, anaplastic astrocytoma, anaplastic oligodendroglioma
via ChEMBL · EBI
Research
5,199 papers- Flucytosine (5-fluorocytosine).Clinics in laboratory medicine · 1987
- 5-fluorocytosine: a brief review.Clinical pediatrics · 1977
- 5-Fluorocytosine therapy.Annals of internal medicine · 1972
- [5-Fluorocytosine and combinations].Annales de biologie clinique · 1987
- Experimental intravitreal 5-fluorocytosine.Annals of ophthalmology · 1985
via PubMed
Wikidata facts
- Subclass of
- nucleoside analogue
- Mass
- 129.034
- Has use
- medication
Show 8 more facts
- chemical formula
- C₄H₄FN₃O
- subject has role
- essential medicine
- canonical SMILES
- C1=NC(=O)NC(=C1F)N
- World Health Organisation international non-proprietary name
- flucytosine
- Commons category
- 5-Fluorocytosine
- found in taxon
- Garcinia dulcis
- legal status (medicine)
- boxed warning
- significant drug interaction
- zidovudine
Sources (8)
via Wikidata · CC0
~8 min read
Encyclopedic overview
14 sectionsContents
- Medical uses
- Pregnancy and breastfeeding
- Children
- Side effects
- Interactions
- Overdose
- Pharmacology
- Mechanisms of action
- Spectrum of susceptible fungi and resistance
- Pharmacokinetic data
- Economics
- Other animals
- References
- External links
Flucytosine, also known as 5-fluorocytosine (5-FC), is an antifungal medication. It is specifically used, together with amphotericin B, for serious Candida infections and cryptococcosis. It may be used by itself or with other antifungals for chromomycosis. Flucytosine is used by mouth and by injection into a vein.
Common side effects include bone marrow suppression, loss of appetite, diarrhea, vomiting, and psychosis. Anaphylaxis and other allergic reactions occasionally occur. It is unclear if use in pregnancy is safe for the baby. Flucytosine is in the fluorinated pyrimidine analogue family of medications. It works by being converted into fluorouracil inside the fungus, which impairs its ability to make protein.
Excerpted from Wikipedia’s “5-fluorocytosine” article, available under the CC BY-SA 4.0 licence.