Flucytosine

Flucytosine
Clinical data
Trade names	Ancobon, Ancotil, Cytoflu, others
AHFS/Drugs.com	Monograph
MedlinePlus	a601132
Pregnancy; category	AU: B3;
Routes of; administration	By mouth, intravenous
ATC code	D01AE21 (WHO) J02AX01 (WHO);
Legal status
Legal status	UK: POM (Prescription only); US: WARNINGRx-only;
Pharmacokinetic data
Bioavailability	75 to 90% (by mouth)
Protein binding	2.9 to 4%
Metabolism	minimal, in the GI tract
Elimination half-life	2.4 to 4.8 hours
Excretion	kidney (90%)
Identifiers
	IUPAC name 4-amino-5-fluoro-1,2-dihydropyrimidin-2-one;
CAS Number	2022-85-7 ;
PubChem CID	3366;
DrugBank	DB01099 ;
ChemSpider	3249 ;
UNII	D83282DT06;
KEGG	D00323 ;
ChEBI	CHEBI:5100 ;
ChEMBL	ChEMBL1463 ;
CompTox Dashboard (EPA)	DTXSID3023059 ;
ECHA InfoCard	100.016.336
Chemical and physical data
Formula	C4H4FN3O
Molar mass	129.094 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	295 to 297 °C (563 to 567 °F) (dec.)
	SMILES Nc1[nH]c(=O)ncc1F;
	InChI InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9) ; Key:XRECTZIEBJDKEO-UHFFFAOYSA-N ;
	(verify)

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.

Flucytosine was first made in 1957. It is on the World Health Organization's List of Essential Medicines. 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. It is not available in much of the developing world.

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