Fluorocytosine
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04516 |
| CAS | 2022-85-7 |
| Molecular Weight | 129.09 |
| Molecular Formula | C4H4FN3O |
| Purity | >98% |
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Description
5-Fluorocytosine, a fluorinated pyrimidine analogue, is a synthetic antifungal medication.
Specification
| Synonyms | Flucytosine; Flucytosin; Ancobon; Ancotil; 4-Amino-5-fluoro-2(1H)-pyrimidine; 5-FC; NSC 103805; 6-Amino-5-fluoro-2(1H)-pyrimidinone |
| Storage | Store at 2-8°C protect from light |
| 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 |
| Source | Synthetic |
Properties
| Appearance | White Solid |
| Application | Antifungal agents; antimetabolites |
| Antibiotic Activity Spectrum | Fungi |
| Melting Point | 295-297°C (dec.) |
| Density | 1.73 g/cm3 |
| Solubility | Slightly soluble in Aqueous Base, DMSO (Heated), Methanol (Heated) |
| LogP | -1.1 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Although the exact mode of action is unknown, it has been proposed that Fluorocytosine acts directly on fungal organisms by competitive inhibition of purine and pyrimidine uptake and indirectly by intracellular metabolism to 5-fluorouracil. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and RNA. The result is unbalanced growth and death of the fungal organism. It also appears to be an inhibitor of fungal thymidylate synthase. |
| Toxicity | LD50: 15 gm/kg (Oral, Rat). |
Reference Reading
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.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C4H4FN3O
Molecular Weight (Monoisotopic Mass): 129.0338 Da
Molecular Weight (Avergae Mass): 129.0925 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C4H4FN3O
Molecular Weight (Monoisotopic Mass): 129.0338 Da
Molecular Weight (Avergae Mass): 129.0925 Da
LC-MS/MS Spectrum - LC-ESI-QFT , negative
Experimental Conditions
Instrument Type: LC-ESI-QFT
Ionization Mode: negative
Ionization Mode: negative
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C4H4FN3O
Molecular Weight (Monoisotopic Mass): 129.0338 Da
Molecular Weight (Avergae Mass): 129.0925 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C4H4FN3O
Molecular Weight (Monoisotopic Mass): 129.0338 Da
Molecular Weight (Avergae Mass): 129.0925 Da
13C NMR Spectrum
Experimental Conditions
Solvent: D2O
Nucleus: 13C
Frequency: 100
Nucleus: 13C
Frequency: 100
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
