Metabolites-BOC Sciences

5-Fluorocytosine

5-Fluorocytosine - CAS 2022-85-7

Catalog number: BBF-04516

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Catalog Number BBF-04516
CAS 2022-85-7
Description 5-Fluorocytosine, a fluorinated pyrimidine analogue, is a synthetic antifungal medication.
Molecular Formula C4H4FN3O
Molecular Weight 129.09
Antibiotic Activity Spectrum Fungi
Synonyms Flucytosine; Flucytosin; Ancobon; Ancotil; 4-Amino-5-fluoro-2(1H)-pyrimidine; 5-FC; NSC 103805; 6-Amino-5-fluoro-2(1H)-pyrimidinone
IUPAC Name 6-amino-5-fluoro-1H-pyrimidin-2-one
Canonical SMILES C1=NC(=O)NC(=C1F)N
InChI InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
InChI Key XRECTZIEBJDKEO-UHFFFAOYSA-N
Melting Point 295-297°C (dec.)
Purity >98%
Density 1.73 g/cm3
Solubility Slightly soluble in Aqueous Base, DMSO (Heated), Methanol (Heated)
Appearance White Solid
Storage Store at 2-8°C protect from light
1.Favorable Evolution of Cryptococcal Meningitis in the Context of Flucytosine Resistance.
Claustre J1, Brion JP, Quétant S, Bedouch P, Pison C, Camara B. Exp Clin Transplant. 2016 Apr 26. doi: 10.6002/ect.2015.0217. [Epub ahead of print]
Cryptococcal meningitis is a critical illness affecting 0.2% to 5% solid-organ transplant recipients with a 40% to 50% mortality. We report the case of a 48-year-old lung transplant recipient, who, 15 months after a right lung graft, kept parakeets and developed meningitis due to Cryptococcus neoformans. Immunosuppressive treatment was based on a quadruple sequential immunosuppressive therapy that included induction therapy with thymoglobulin, followed by corticosteroids, calcineurin inhibitors, and mycophenolate mofetil. Antifungal susceptibility testing of Cryptococcus neoformans showed resistance to flucytosine and intermediate sensitivity to fluconazole. Initial treatment adhered to international guidelines; however, the patient could not tolerate an effective double-antifungal therapy during the first 2 months of treatment. Despite this delayed treatment for an aggressive infection in an immunocompromised patient, the patient survived without relapse and received maintenance treatment with fluconazole during the course of 3 years.
2.Cryptococcal Meningitis Treatment Strategies Affected by the Explosive Cost of Flucytosine in the United States: A Cost-effectiveness Analysis.
Merry M1, Boulware DR1. Clin Infect Dis. 2016 Mar 23. pii: ciw151. [Epub ahead of print]
BACKGROUND:  In the United States, cryptococcal meningitis causes approximately 3400 hospitalizations and approximately 330 deaths annually. The US guidelines recommend treatment with amphotericin B plus flucytosine for at least 2 weeks, followed by fluconazole for a minimum of 8 weeks. Due to generic drug manufacturer monopolization, flucytosine currently costs approximately $2000 per day in the United States, with a 2-week flucytosine treatment course costing approximately $28 000. The daily flucytosine treatment cost in the United Kingdom is approximately $22. Cost-effectiveness analysis was performed to determine the value of flucytosine relative to alternative regimens.
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