6-amino-5-fluoro-1,2-dihydropyrimidin-2-one

• ChemBase编号: 970
• 分子式: C4H4FN3O
• 平均质量: 129.0924632
• 单一同位素质量: 129.03383998
• SMILES: Fc1c([nH]c(=O)nc1)N
• Canonical SMILES: Nc1c(F)cnc(=O)[nH]1
• InChI: InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
• InChIKey: XRECTZIEBJDKEO-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-amino-5-fluoro-1,2-dihydropyrimidin-2-one
• IUPAC传统名: flucytosine
• 商标名: Ancobon; Ancotil
• 别名: 5-FC; 5-Fluorocystosine; 5-Fluorocytosin; 5-Fluorocytosine; 5-Flurocytosine; Flucytosin; Fluocytosine; Fluorcytosine; Flucytosine; 5-Fluoro cytosine; 6-amino-5-fluoro-1,2-dihydropyrimidin-2-one; 5-Fluorocytosine

登记号

• CAS号: 2022-85-7
• MDL号: MFCD00006035
• PubChem SID: 46504735; 160964433
• PubChem CID: 3366

理论计算性质

JChem

• Acid pKa: 8.163184
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -0.9489975
• LogD (pH = 7.4): -1.0088187
• Log P: -0.94816285
• 摩尔折射率: 38.2177 cm^3
• 极化性: 10.144018 Å^3
• 极化表面积: 67.48 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.24
• LOG S: -1.83
• 溶解度: 1.92e+00 g/l

分子性质

理化性质

• 溶解度: 10.5 g/L
• 外观: white crystalline powder
• 熔点: 295 - 297°C
• 疏水性(logP): -1.1; -1.772

产品相关信息

• 纯度: 95%; 98%; 99%

详细说明

DrugBank - DB01099

• Drug Groups: approved
• Description: A fluorinated cytosine analog that is used as an antifungal agent. [PubChem]
• Indication: For the treatment (in combination with amphotericin B) of serious infections caused by susceptible strains of Candida (septicemia, endocarditis and urinary system infections) and/or Cryptococcus (meningitis and pulmonary infections).
• Pharmacology: Flucytosine is an antimetabolite that acts as an antifungal agent with in vitro and in vivo activity against Candida and Cryptococcus. Flucytosine enters the fungal cell via cytosine permease; thus, flucytosine is metabolized to 5-fluorouracil within fungal organisms. 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. Antifungal synergism between Ancobon and polyene antibiotics, particularly amphotericin B, has been reported.
• Toxicity: Oral, rat: LD₅₀ = >15 gm/kg.
• Affected Organisms: Yeast and other fungi
• Biotransformation: Flucytosine is deaminated, possibly by gut bacteria or by the fungal targets, to 5-fluorouracil, the active metabolite.
• Absorption: Rapidly and virtually completely absorbed following oral administration. Bioavailability 78% to 89%.
• Half Life: 2.4 to 4.8 hours.
• Protein Binding: 28-31%
• Elimination: Flucytosine is excreted via the kidneys by means of glomerular filtration without significant tubular reabsorption.; A small portion of the dose is excreted in the feces.
• External Links: Wikipedia; RxList; Drugs.com