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	129.09 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 used, together with amphotericin B, for serious Candida infections and cryptococcosis. It may be used by itself or with other antifungals. Flucytosine is taken by mouth and by injection into a vein.

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. It works by being converted into fluorouracil inside the fungus, which stops its ability to make protein.

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

Mechanisms of action

Two major mechanisms of action have been elucidated:

Flucytosine is intrafungally converted into the cytostatic fluorouracil which undergoes further steps of activation and finally interacts as 5-fluorouridinetriphosphate with RNA biosynthesis thus disturbing the building of certain essential proteins.
Flucytosine also undergoes conversion into fluorodeoxyuridylate which inhibits fungal DNA synthesis.

References

1 2 3 4 5 6 7 "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.
↑ Vermes A, Guchelaar HJ, Dankert J (August 2000). "Flucytosine: a review of its pharmacology, clinical indications, pharmacokinetics, toxicity and drug interactions". The Journal of Antimicrobial Chemotherapy. 46 (2): 171–179. doi:10.1093/jac/46.2.171. PMID 10933638.

External links

"Flucytosine". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on January 20, 2017.

[AHFS2016-1] 1 2 3 4 5 6 7 "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.

[pmid10933638-7] Vermes A, Guchelaar HJ, Dankert J (August 2000). "Flucytosine: a review of its pharmacology, clinical indications, pharmacokinetics, toxicity and drug interactions". The Journal of Antimicrobial Chemotherapy. 46 (2): 171–179. doi:10.1093/jac/46.2.171. PMID 10933638.