5-Fluoro-5'-deoxyuridine 5'-脱氧-5-氟尿苷

CAS 3094-09-5 MFCD00866530

化学结构图

3094-09-5
SMILES: C[C@H]1O[C@@H](n2cc(F)c(=O)[nH]c2=O)[C@H](O)[C@@H]1O

化学属性

Mol. FormulaC9H11FN2O5
Mol. Weight246.19
Melting Point187-189
Refractive index20 ° (C=1, H2O)
Appearance Solid powder
SolubilitySoluble in DMSO, not in water

别名和识别编码

Chemical Name5-Fluoro-5'-deoxyuridine
CAS Number3094-09-5
Alfabeta NameFLUORODEOXYURIDINE 55---'
MDL NumberMFCD00866530
Synonym Doxifluridine {LY} Doxifluridine {} {LY} Doxifluridine {} {} {LY} Doxifluridine {} {} {} {LY} Doxifluridine {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Doxifluridine {} {} {} {} {} {}
PubChem Substance ID18343
EC Number221-440-1
Chemical Name Translation5'-脱氧-5-氟尿苷
Reaxys-RN890191
Merck Number3437
Wiswesser Line NotationT6NVMVJ EF A- BT5OTJ CQ DQ E1
LabNetwork Molecule IDLN01343007
FormulaC9H11FN2O5
IUPAC Name1-((2R,3R,4S,5R)-3,4-dihydroxy-5-methyltetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
InChIKeyZWAOHEXOSAUJHY-ZIYNGMLESA-N
InChIInChI=1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1
Canonical SMILESO=C(N1)N([C@H]2[C@H](O)[C@H](O)[C@@H](C)O2)C=C(F)C1=O
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分类

  • {Chemicalbook} 药物: 抗肿瘤药: 抗代谢物抗肿瘤药物
  • {SNA} Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, DNA Synthesis Inhibitors, DNA metabolism, F, 抗肿瘤药物, 生物活性小分子, 癌症研究, 细胞信号转导和神经科学, 细胞生物学
  • {SNA} Antitumor Agents, Apoptosis and Cell Cycle, Bioactive Small Molecules, Cancer Research, Cell Biology, Cell Signaling and Neuroscience, DNA Synthesis Inhibitors, DNA metabolism, F
  • {SNA} Antitumor Agents, Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, DNA Synthesis Inhibitors, DNA metabolism, F,

产品应用

  • Doxifluridine, also known as 5'-Deoxy-5-fluorouridine, is a fluoropyrimidine derivative and oral prodrug of the antineoplastic agent 5-fluorouracil (5-FU) with antitumor activity. Doxifluridine, designed to circumvent the rapid degradation of 5-FU by dihydropyrimidine dehydrogenase in the gut wall, is converted into 5-FU in the presence of pyrimidine nucleoside phosphorylase.

安全信息

Warnings IRRITANT, IRRITANT-HARMFUL
WGK Germany2
RTECSYU7526000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Signal word
Hazard statements
  • H226 Flammable liquid and vapour 易燃液体和蒸气
  • H303 May be harmfully swallowed 吞食可能有害
  • H315 Causes skin irritation 会刺激皮肤
  • H317 May cause an allergic skin reaction 可能导致皮肤过敏
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H332 Harmful if inhaled 吸入有害
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H340 May cause genetic defects 可能导致遗传性缺陷
  • H350 May cause cancer 可能致癌
  • H351 Suspected of causing cancer 怀疑致癌
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
  • H411 Toxictoaquaticlifewithlonglastingeffects 对水生生物有毒性并具有长期影响。
Precautionary statements
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前,切勿操作。
  • P203
  • P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking. 远离热源/火花/明火/热的表面。——禁止吸烟。
  • P233 Keep container tightly closed. ?保持容器密闭。
  • P240 Ground/bond container and receiving equipment. 与地面接触/连接集装箱和接受设备。
  • P241 Use explosion-proof electrical/ventilating/lighting/…/equipment. 使用防爆电气/通风/照明/ .../设备。
  • P242 Use only non-sparking tools. 只能使用无火花工具。
  • P243 Take precautionary measures against static discharge. 采取预防措施,防止静电放电。
  • P260 Do not breathe dust/fume/gas/mist/vapours/spray. 不要吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P262 Do not get in eyes, on skin, or on clothing. 不要接触眼睛,皮肤或衣服。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P264+P265
  • P271 Use only outdoors or in a well-ventilated area.? 只能在室外或通风良好的地方使用。
  • P272 Contaminated work clothing should not be allowed out of the workplace. 污染的工作服不得带出工作场所。
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P302+P350
  • P302+P352
  • P302+P352+P333+P313+P362+P364
  • P303+P361+P353
  • P304+P312
  • P304+P340
  • P305+P351+P338
  • P308+P313
  • P312 Call a POISON CENTER or doctor/physician if you feel unwell. 如果你感觉不适,呼叫解毒中心或医生/医师。
  • P314 Get medical advice/attention if you feel unwell. 获取医疗咨询/就医,如果你觉得不舒服
  • P317
  • P318
  • P319
  • P321 Specific treatment (see … on this label). 具体治疗(见本标签上的)。
  • P332+P313
  • P332+P317
  • P333+P313
  • P337+P313
  • P337+P317
  • P362 Take off contaminated clothing and wash before reuse. 脱掉污染的衣服,清洗后方可重新使用
  • P362+P364
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P370+P378
  • P391 Collect spillage. Hazardous to the aquatic environment 收集对水环境有危害的泄漏物。
  • P403+P233
  • P403+P235
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
GHS Symbol
Safety Statements
Hazard Codes Xi
Risk Statements
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 3390 mg/kg
TOXIC EFFECTS :
   Behavioral - somnolence (general depressed activity)
   Skin and Appendages - hair
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-
   Volume(issue)/page/year: 13(Suppl 2),209,1985

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >2 gm/kg
TOXIC EFFECTS :
   Skin and Appendages - hair
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-
   Volume(issue)/page/year: 13(Suppl 2),209,1985

TYPE OF TEST            : LDLo - Lowest published lethal dose
ROUTE OF EXP

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-
   Volume(issue)/page/year: 13(Suppl 2),209,1985

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : >1 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-
   Volume

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - mouse Leukocyte
DOSE/DURATION           : 615 umol/L
REFERENCE :
   CCCCAK Collection of Czechoslovak Chemical Communications.  (Academic Press
   Inc. Ltd., 24-28 Oval Rd., London NW1 7DX, UK)  V.1-    1929-
   Volume(issue)/page/year: 49,2551,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 5950 mg/kg
SEX/DURATION            : male 14 week(s) pre-mating
                          female 2 week(s) pre-mating  - 7 day(s) after
                          conception
TOXIC EFFECTS :
   Reproductive - Fertility - post-implantation mortality (e.g. dead and/or
   resorbed implants per total number of implants)
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-
   Volume(issue)/page/year: 13(Suppl 2),469,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 1100 mg/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured
   before birth)
   Reproductive - Effects on Newborn - live birth index (measured after birth)
   Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight
   gain)
REFERENCE :
   YACHDS Yakuri to Chiryo.

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 550 mg/kg
SEX/DURATION            : female 7-17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death,
   e.g., stunted fetus)
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   YACHDS Yakuri to Chiryo.  Pharmacology and Therapeutics.  (Raifu Saiensu
   Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan)  V.1-    1972-

Storage condition 2-8°C {LY} 2-8°C Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). {} {LY} 2-8°C {} {} {LY} 2-8°C {} {} {} {LY} 2-8°C {} {} {} {} {LY} 2-8°C {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C

其他信息

  • 用途一:氟尿嘧啶类抗肿瘤药,为氟尿嘧啶的前体药物。在肿瘤组织内存在着的胸腺嘲嚏核苷磷酸化酶,对其进行作用而使其在肿瘤内转化为氟尿嘧啶,从而发挥抗肿瘤的作用。其抗肿瘤的专一性较强,毒性较低。临床用于胃癌、结肠直肠癌、乳腺癌,缓解率可达30%以上。
  • MOL 文件:3094-09-5.mol
  • 方法一:50g(191mmo1)的5-氟尿嘧啶核苷和39.3g对甲苯磺酸单水合物悬浮于750ml丙酮和94m12,2-二甲氧基丙烷中,在室温下搅拌50min至澄清,加入过量的碳酸氢钠固体,继续搅拌至中性。过滤,滤饼用丙酮洗,洗液和滤液一起蒸发至干,剩余物用2L醋酸乙酯重结晶,得48g 5-氟尿嘧啶核苷的缩酮化物,收率83%,熔点196~197℃。 上述46.4g(153.5mmo1)的5-氟尿嘧啶核苷的缩酮化物溶于250ml二甲基甲酰胺中,加入86.7g三苯磷甲基碘化合物,在室温下放置50min。加入250ml甲醇,放置30min后,蒸去溶剂。剩余的油状物用1L醋酸乙酯和1L 5%的硫代硫酸钠水溶液一起摇晃,静置分层。分出的醋酸乙酯层用2×1L水洗,无水硫酸钠干燥过夜,蒸发至干。剩余的油状物用醋酸乙酯重结晶,得52.9g的5’-去氧-5’-碘代-2’,3’-O-异丙亚基-5-氟尿嘧啶核苷,收率85%,熔点202~203.5℃。 上述得到的氟尿衍生物24g溶于800ml甲醇和15ml三乙胺中,在12g 5%钯-炭催化剂存在下,于常压、室温和剧烈搅拌下加氢还原90min。过滤除去催化剂,并用甲醇洗。洗液和滤液一起蒸发至干,剩余物和200ml醋酸乙酯搅拌1h。过滤除去形成的结晶,滤液蒸发掉一半的溶剂,放置过夜,再次过滤除去结晶。滤液减压蒸至干,得到的5'-去氧-2’,3’-O-异丙亚基-5-氟尿嘧啶核苷和200ml90%的三氟乙酸水溶液反应1h。反应蒸发至干,加入乙醇,共沸除去水和三氟乙酸,并蒸发至干。剩余物用醋酸乙酯重结晶,得11.35g的去氧氟尿苷,收率79%,熔点189~190℃。
  • Hazard Note:Irritant
  • 上游原料:乙酸乙酯 --> 碘甲烷 --> 对甲苯磺酸水合物 --> 钯炭催化剂 --> 三苯基锑 --> 2,2-二甲氧基丙烷
  • TCI Shanghai:去氧氟尿苷 5'-Deoxy-5-fluorouridine,>;98.0%(T)(3094-09-5)
  • 用途二:医药中间体。
  • 去氧氟尿苷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 D3579 5'-脱氧-5-氟尿苷 5'-Deoxy-5-fluorouridine 5G 2710元 2014/06/02 D3579 5'-脱氧-5-氟尿苷 5'-Deoxy-5-fluorouridine 1G 900元
  • 外观性质:白色结晶粉末。熔点:188-192 °C

系列性分类


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