2022-85-7

• 常用中文名：5-氟胞嘧啶
• 常用英文名：5-Flucytosine
• CAS号：2022-85-7
• 分子式：C₄H₄FN₃O
• 分子量：129.092
• 相关类别： 原料药 人工合成抗感染类药 抗真菌类药
• 发布时间：2018-02-06 08:00:00
• 更新时间：2024-01-01 18:57:34
• Flucytosine(5-Fluorocytosine, 5-FC, Ancobon)是抗真菌化合物。

名称

• 中文名: 5-氟胞嘧啶
• 英文名: flucytosine
• 中文别名: 4-氨基-5-氟-2(1H)-嘧啶酮氟胞嘧啶安拉喷5-氟氧胺嘧啶5-氟胞嗪4-氨基-5-氟嘧啶酮-2(1H); 5-氟氧胺嘧啶; 氟胞嘧啶; 4-氨基-5-氟-2(1H)-嘧啶酮; 安拉喷; 5-氟胞嗪; 4-氨基-5-氟嘧啶酮-2(1H)
• 英文别名: 4-amino-5-fluoro-1,2-dihydropyrimidin-2-one; 4-Amino-5-fluoro-2(1H)-pyrimidinone; 5-Fluorocytosine; Fluocytosine; 6-amino-5-fluoro-1H-pyrimidin-2-one; Flucytosin; Ancotil; 4-amino-5-fluoro-2(1H)-pyrimidinone,5-Fluorocytosine,Flucytosine; 5-Fluorocytosin; 4-amino-5-fluoro-2(1H)-pyrimidinone,Flucytosine; MFCD00006035; 4-Amino-5-fluoro-2-hydroxypyrimidine; EINECS 217-968-7; Fluorcytosine; Flucytosine; Ancobon; 5-Fluorocystosine; 4-amino-5-fluoro-2-pyrimidone; Fluorocytosine

物化性质

• 密度: 1.7±0.1 g/cm3
• 沸点: 298ºC
• 熔点: 298-300 °C (dec.)(lit.)
• 分子式: C₄H₄FN₃O
• 分子量: 129.092
• 精确质量: 129.033844
• PSA: 71.77000
• LogP: -2.36
• 外观性状: 白色结晶固体
• 蒸汽压: 0.0492mmHg at 25°C
• 折射率: 1.649
• 储存条件:

  保持贮藏器密封、储存在阴凉、干燥的地方，确保工作间有良好的通风或排气装置

• 稳定性:

  如果遵照规格使用和储存则不会分解，未有已知危险反应，避免氧化物

• 水溶解性: 1.5g/100mL (25 ºC)
• 计算化学:

  1.疏水参数计算参考值（XlogP）:-0.9

  2.氢键供体数量:2

  3.氢键受体数量:3

  4.可旋转化学键数量:0

  5.互变异构体数量:9

  6.拓扑分子极性表面积67.5

  7.重原子数量:9

  8.表面电荷:0

  9.复杂度:208

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1. 性状：晶体状粉末

  2. 密度（g/mL,25ºC）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：297

  5. 沸点（ºC）：未确定

  6. 沸点（ºC，2mmHg）：未确定

  7. 折射率：未确定

  8. 闪点（°F）：未确定

  9. 比旋光度（ºF）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,20ºC）：未确定

  12. 饱和蒸气压（kPa,25ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：能溶解于水的,在乙醇中微溶；在氯仿、乙醚中几乎不溶；在稀盐酸或稀氢氧化钠溶液中易溶。

生物活性

• 描述: Flucytosine(5-Fluorocytosine, 5-FC, Ancobon)是抗真菌化合物。
• 相关类别:
  信号通路 >> 抗感染 >> 真菌
  研究领域 >> 感染
• 参考文献:

  [1]. Vermes A, et al. Flucytosine: a review of its pharmacology, clinical indications, pharmacokinetics, toxicity and drug interactions. J Antimicrob Chemother. 2000 Aug;46(2):171-9.

  [2]. Te Dorsthorst DT, et al. In vitro interaction of flucytosine combined with amphotericin B or fluconazole against thirty-five yeast isolates determined by both the fractional inhibitory concentration index and the response surface approach. Antimicrob Agen

MSDS

Name: 5-Fluorocytosine 98% Material Safety Data Sheet Synonym: CAS: 2022-85-7 Section 1 - Chemical Product MSDS Name:5-Fluorocytosine 98% Material Safety Data Sheet Synonym: Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 2022-85-7 5-Fluorocytosine 217-968-7 Hazard Symbols: XN Risk Phrases: 40 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Limited evidence of a carcinogenic effect.Light sensitive. Potential Health Effects Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: No hazard expected in normal industrial use. Inhalation: May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Chronic: Prolonged or repeated exposure may cause adverse reproductive effects. Section 4 - FIRST AID MEASURES Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. Skin: Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Ingestion: Get medical aid. Wash mouth out with water. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Notes to Physician: Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Section 7 - HANDLING and STORAGE Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Store protected from light. Storage: Store in a cool, dry place. Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.) Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 2022-85-7: Personal Protective Equipment Eyes: Not available. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Solid Color: white Odor: odorless pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: 296 deg C dec Autoignition Temperature: Not available. Flash Point: 296 deg C ( 564.80 deg F) Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: 296 deg C Solubility in water: IN WATER: 1.5 G/100 ML (25C) Specific Gravity/Density: Molecular Formula: Molecular Weight: 129.09 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Not available. Conditions to Avoid: Incompatible materials, light, excess heat, exposure to flame. Incompatibilities with Other Materials: Oxidizing agents. Hazardous Decomposition Products: Hydrogen cyanide, carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen fluoride gas. Hazardous Polymerization: Has not been reported Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 2022-85-7: HA6040000 LD50/LC50: CAS# 2022-85-7: Oral, rat: LD50 = >15 gm/kg. Carcinogenicity: 5-Fluorocytosine - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA No information available. IMO No information available. RID/ADR No information available. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: XN Risk Phrases: R 40 Limited evidence of a carcinogenic effect. Safety Phrases: S 36/37 Wear suitable protective clothing and gloves. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 2022-85-7: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 2022-85-7 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 2022-85-7 is not listed on the TSCA inventory. It is for research and development use only. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 1、急性毒性：女人经口TDLo：1080mg/kg/10D-I；大鼠经口LD50：>15mg/kg；大鼠经腹腔LD50：3811mg/kg；大鼠经皮下LD50：3336mg/kg；大鼠经静脉LD50：>600mg/kg；小鼠经口LC50：>15mg/kg；小鼠经腹腔LC50：1190mg/kg；小鼠经皮下LC50：1mg/kg；小鼠经静脉LC50：500mg/kg； 2、致突变性 微生物的DNA抑制：100mg/L； 微生物突变：100mg/L； 酿酒酵母突变：8mg/L。 生态学数据: 对水是稍微有危害的不要让未稀释或大量的产品接触地下水、水道或者污水系统，若无政府许可，勿将材料排入周围环境。 CHEMICAL IDENTIFICATION RTECS NUMBER : HA6040000 CHEMICAL NAME : Cytosine, 5-fluoro- CAS REGISTRY NUMBER : 2022-85-7 LAST UPDATED : 199801 DATA ITEMS CITED : 14 MOLECULAR FORMULA : C4-H4-F-N3-O MOLECULAR WEIGHT : 129.11 WISWESSER LINE NOTATION : T6MVNJ DZ EF HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Human - woman DOSE/DURATION : 1080 mg/kg/10D-I TOXIC EFFECTS : Brain and Coverings - other degenerative changes Behavioral - changes in motor activity (specific assay) Behavioral - ataxia TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >15 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3811 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3336 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >600 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >15 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1190 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 500 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value MUTATION DATA TYPE OF TEST : Mutation in microorganisms TEST SYSTEM : Yeast - Saccharomyces cerevisiae DOSE/DURATION : 8 mg/L REFERENCE : MGGEAE Molecular and General Genetics. (Springer-Verlag, Heidelberger Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.99- 1967- Volume(issue)/page/year: 146,253,1976 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6122 No. of Facilities: 53 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1033 (estimated) No. of Female Employees: 480 (estimated)

安全

• 符号: GHS08
• 信号词: Warning
• 危害声明: H361
• 警示性声明: P280
• 个人防护装备: Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
• 危害码 (欧洲): Xn:Harmful
• 风险声明 (欧洲): R40
• 安全声明 (欧洲): S22-S24/25-S45-S36/37
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 2
• RTECS号: HA6040000
• 海关编码: 2933599090

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制备

1.由5-氟尿嘧啶经氯化、氨化、水解而得。1.氯化将5-氟尿嘧啶和三氯氧磷加入氯化锅，搅拌，控制在20℃以下滴加N,N-二甲基苯胺。滴加完毕，升温到110℃左右反应2h。冷至室温，放至冰盐水中冰解，维持15℃搅拌1h。过滤，水洗，得2,4-二氯-5-氟嘧啶。2.氨化将2,4-二氯-5-氟嘧啶溶解在乙醇中，搅拌，控制在35℃以下滴加氨水。滴毕，降温至25℃反应3h，减压回收乙醇至干，加水搅拌升温到20℃。过滤，用水洗涤结晶，干燥，得出4-氨基-2-氯-5-氟嘧啶。3.水解将4-氨基-2-氯-5-氟嘧啶和盐酸混合，搅拌升温至90-95℃,反应2h后，减压浓缩至干，加水溶解结晶，加活性炭脱色。过滤，滤液用氨水调pH至7-8，放置过夜。甩滤，用水洗涤结晶，经精制即得氟胞密啶。总收率50%。该法的起始原料为抗癌药氟尿嘧啶[51-21-8]，也可以采用氟尿嘧啶的前体，即2-甲氧基-4-羟基-5-氟嘧啶为原料，经氯化，氨化，水解制备氟胞嘧啶，收率70%。将上述前体加入甲苯中，再加入二甲基苯胺，加热至50-60℃，滴加三氯氧磷。然后105-110℃反应3h。冷却至室温，将反应液加入甲苯和水的混合液中，在25-40℃搅拌。分出甲苯层，水层用甲苯提出取，将提出取液与甲苯层合并，先减压回收甲苯，再收集86-90℃（2.66kPa）馏分即得2-甲氧基-4-氯-5-氟嘧啶。将上步氯化产物与无水甲醇加入压力釜中，在室温下通氨至饱和，缓缓升温使压力达到0.5MPa，搅拌反应过夜。冷到室温出料，经处理得2-甲氧基-4-氨基-5-氟嘧啶，熔点189-191℃。将其与30%盐酸在100-105℃反应3h。水解物减压蒸干，用水溶解残留物，加氨水碱化到pH8.5，冷却至5℃以下，过滤，得氟胞嘧啶粗品，用水重结晶即得成品。

海关

海关编码	2933599090
中文概述	2933599090. 其他结构上有嘧啶环的化合物(包括其他结构上有哌嗪环的化合物. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:20.0%
申报要素	品名, 成分含量, 用途, 乌洛托品请注明外观, 6－己内酰胺请注明外观, 签约日期
Summary	2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%