Flucytosine

Flucytosine
Clinical data
Trade names	Ancobon, Ancotil, 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: ℞-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.^[1] It is specifically used, together with amphotericin B, for serious Candida infections and cryptococcosis.^[1] It may be used by itself or with other antifungals for chromomycosis.^[1] Flucytosine is used by mouth and by injection into a vein.^[1]^[2]

Common side effects include bone marrow suppression, loss of appetite, diarrhea, vomiting, and psychosis.^[1] Anaphylaxis and other allergic reactions occasionally occur.^[1] It is unclear if use in pregnancy is safe for the baby.^[3] Flucytosine is in the fluorinated pyrimidine analogue family of medications.^[1] It works by being converted into fluorouracil inside the fungus, which impairs its ability to make protein.^[1]

Flucytosine was first made in 1957.^[4] It is on the World Health Organization's List of Essential Medicines.^[5] It is not available in much of the developing world.^[6]

^ ^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.
^ 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.
^ "Flucytosine (Ancobon) Use During Pregnancy". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 11 December 2016.
^ 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.
^ 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.
^ 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.

[AHFS2016-1] ^ ^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.

[WHO2008-2] 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.

[3] "Flucytosine (Ancobon) Use During Pregnancy". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 11 December 2016.

[4] 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.

[WHO21st-5] 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.

[6] 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.

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