5-Fluorouracil 5-氟尿嘧啶

CAS 51-21-8 MFCD00006018

化学结构图

51-21-8
SMILES: O=c1[nH]cc(F)c(=O)[nH]1

化学属性

Mol. FormulaC4H3FN2O2
Mol. Weight130
Melting Point282-286
TSCAT
Density1.53
Solubility12.2 G/L 20 ºC
Stability对光敏感
Appearance 50 白色或类白色结晶性粉末。Mp282-283℃(分解)，0.1mol/L盐酸溶液在 265nm波长处有最大吸收。微溶于水和乙醇，不溶于氯仿和乙醚，溶于稀盐酸和氢氧化钠液。中等毒，LD powder (小鼠，腹腔) 230mg/kg。
Boiling Point190-200°C/0.1mmHg

别名和识别编码

Chemical Name5-Fluorouracil
CAS Number51-21-8
Alfabeta NameFLUOROURACIL 5-
MDL NumberMFCD00006018
Synonym 2,4-DI 2,4-Dihydroxy-5-fluoropyrimidine 2,4-Dihydroxy-5-fluorpyrimidin 2,4-二羟基-5-氟嘧啶 3h)-pyrimidinedione,5-fluoro-4(1h 5-FLUORO-2,4(1H,3H)-PYRIMIDINEDIONE 5-FLUORO-2,4-DIHYDROXYPYRIMIDINE 5-FLUOROPYRIMIDINE-2,4(1H,3H)-DIONE 5-Fluor-2,4(1H,3H 5-Fluor-2,4(1H,3H) 5-Fluor-2,4-pyrimidindiol 5-Fluoro-1H-pyrimidine-2,4-dione 5-Fluoro-2,4-pyrimidinedione 5-Ftouracyl 5-faracil 5-fluor-2,4(1h,3h)-pyrimidindion 5-fluoro-2,4-pyrimidinedione Adrucil Arumel Carzonal Efudex Efudix Fluoroblastin Fluorouracil Fluracil Fluracilum Kecimeton U-8953 {} {} {} { {} {} {} {} {Chemicalb
EC Number200-085-6
Beilstein Registry Number127172
PubChem Substance ID87569939
Merck Number4181
Reaxys-RN127172
Chemical Name Translation5-氟尿嘧啶
Wiswesser Line NotationT6MVMVJ EF
LabNetwork Molecule IDLN00115439
InChIInChI=1S/C4H3FN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
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分类

  • {SNA} APIs & Metabolites, APIs (Act
  • Bases & Related Reagents
  • {SNA} Building Blocks, C4 to C5, Chemical Synthesis, Heterocyclic Building Blocks, Pyrimidines
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards E - F, Pharmaceutical Standards, Pharmacopeia Standards
  • {SA} Alphabetic, Analytical Standards, Analytical/Chromatography, Biochemicals and Reagents, Enzyme Inhibitors,
  • Nucleotides
  • {SNA} Analytical Standards, Chromatography, EP Standards, EP Standards E - F, Pharmaceutical Standards, Pharmacopeia Standards, 分析/色谱
  • {SNA} Core Bioreagents,
  • {SNA} Analytical/C
  • {SNA} Antitumor Agents,
  • {SNA} Apoptosis and Ce

产品应用

  • 一个强有力的抗肿瘤试剂，通过抑制胸苷酸合成酶，影响嘧啶合成从而消耗细胞内dTTP池,5- FU被代谢成核糖核苷酸和脱氧核糖核苷酸，并被注入到RNA和DNA。用5- FU处理细胞可导致细胞在S期积聚，5- FU已被证明可诱导p53依赖的细胞凋亡。
  • 核酸代谢，研究稻、麦穗子分化，遗传代谢测定，植物生长发育研究。

相关文献及参考

  • [2]. Zeng Q, et al. Knockdown of NFBD1/MDC1 enhances chemosensitivity to NSC 119875 or 5-fluorouracil in nasopharyngeal carcinoma CNE1 cells. Mol Cell Biochem. 2016 Jul;418(1-2):137-46.
  • [3]. Jones DH, et al. Ten-Year and Beyond Follow-up After Treatment With Highly Purified Liquid-Injectable Silicone for HIV-Associated Facial Lipoatrophy: A Report of 164 Patients. Dermatol Surg. 2019 Jul;45(7):941-948.
  • [4]. McQuade RM, et al. Gastrointestinal dysfunction and enteric neurotoxicity following treatment with anticancer chemotherapeutic agent 5-fluorouracil. Neurogastroenterol Motil. 2016 Jun 28.
  • [5]. Yin L, et al. Antitumor effects of oncolytic herpes simplex virus type 2 against colorectal cancer in vitro and in vivo. Ther Clin Risk Manag. 2017 Feb 7;13:117-130.
  • [6]. Snyder SM, et al. Initial Experience with Topical Fluorouracil for Treatment of HIV-Associated Anal Intraepithelial Neoplasia. J Int Assoc Physicians AIDS Care (Chic). 2011;10(2

安全信息

Warnings IRRITANT, TOXIC, CORROSIVE
Signal word Danger
GHS Symbol
WGK Germany3
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36 Wear suitable protective clothing 穿戴适当的防护服；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
Risk Statements
  • R20/21/22 Harmful by inhalation, in contact with skin and if swallowed 吸入、皮肤接触和不慎吞咽有害
  • R22 Harmful if swallowed 吞咽有害
  • R25 Toxic if swallowed 吞咽有毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R52 Harmful to aquatic organisms 对水生生物有害
Precautionary statements
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • 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。
  • P301+P310
  • P301+P310+P330
  • P302+P350
  • P302+P352+P332+P313+P362+P364
  • P305+P351+P338
  • P305+P351+P338+P337+P313
  • P332+P313
  • P337+P313
  • 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
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
RTECSYR0350000
Packing GroupIII
UN Number 2811 UN 2811 6.1/PG 3
Storage condition Light Sensitive 对光敏感 Store at 0-5
Hazard statements
  • H301 Toxic if swallowed 吞食有毒
  • H351 Suspected of causing cancer 怀疑致癌
  • H412 Harmfutoaquaticlifewithlonglastingeffects 对水生生物有害并具有长期影响。
Hazard Codes 6.1 T Xn
Hazard Class6.1 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1500 mg/kg/50W-I
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Blood - tumors
REFERENCE :
   TUMOAB Tumori.  (Casa Editrice Ambrosiana, Via G. Frua 6, 20146 Milan,
   Italy)  V.1-    1911-  Volume(issue)/page/year: 76,179,1990

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 217 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   IYKEDH Iyakuhin Kenkyu.  Study of Medical Supplies.  (Nippon Koteisho
   Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan)  V.1- 1970- 
   Volume(issue)/page/year: 4,90,1973

T

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 70 mg/kg
TOXIC EFFECTS :
   Gastrointestinal - hypermotility, diarrhea
   Gastrointestinal - nausea or vomiting
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 5,569,1971

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 230 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   IYKEDH Iyakuhin Kenkyu.  Study of Medical Supplies.  (Nippon Koteisho
   Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan)  V.1- 1970- 
   Volume(issue)/page/year: 4,90,1973

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intramuscular
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 240 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   KTUNAA K'at'ollik Taehak Uihakpu Nonmunjip.  Journal of Catholic Medical
   College.  (Catholic Medical College, Graduate School, Seoul 135, S. Korea)
   V.1-    1957-  Volume(issue)/page/year: 38,481,1985

TYPE OF TEST            : TDL

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Human Cells - not otherwise specified
DOSE/DURATION           : 1 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   42,3005,1982

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 125 mg/L
REFERENCE :
   MIBLAO Microbiology (Moscow).  (Plenum Pub. Corp., 233 Spring St., New York,
   NY 10013) V.26-    1957-  Volume(issue)/page/year: 36,773,1967

{h

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 50 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 12,349,1971

TYPE OF TEST            : Micronucleus test
ROUTE OF EXPOSURE       : Intraperitoneal
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 250 mg/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 182,309,1987

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 26 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 192,239,1987

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Mammal - species unspecified Cells - not otherwise
                          specified
DOSE/DURATION           : 100 umol/L
REFERENCE :
   MUREAV Mutation Research.

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE                    : 240 mg/kg
SEX/DURATION            : female 11-14 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   AJOGAH American Journal of Obstetrics and Gynecology.  (C.V. Mosby Co.,
   11830 Westline Industrial Dr., St. Louis, MO 63146)  V.1-    1920-
   Volume(issue)/page/year: 137,747,1980

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE                    : 150 mg/kg
SEX/DURATION            : female 20-31 week(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - other neonatal measures or effects
REFERENCE :
   JAMAAP JAMA, Journal of the American Medical Association.  (AMA, 535 N.
   Dearborn St., Chicago, IL 60610)  V.1-    1883-  Volume(issue)/page/year:
   217,214,1971

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 15 mg/kg
SEX/DURATION            : female 9 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 - fetal death
   Reproductive - Specific Developmental Abnormalities - other developmental
   abnormalities
REFERENCE :
   JPETAB Journal of Pharmacology and Experimental Therapeutics.  (Williams &
   Wilkins Co., 428 E. Preston St., Baltimore, MD 21202)  V.1-    1909/10-
   Volume(issue)/page/year: 144,429,1964

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - ra

其他信息

  • 不良反应与注意事项:氟脲嘧啶的主要毒性作用是侵犯胃肠道和血细胞生成系统。厌食、恶心和呕吐常见。口腔炎、咽食管炎和腹泻均为停药的指征，否则会出现严重的口咽部和肠道溃疡。静脉点滴给药时胃肠道毒性作用常是限制剂量的原因。相反，巨大剂量静脉注射时，白细胞减少是限制剂量的毒性作用。最低白细胞计数常出现在第1次用药后的7～ 14日。血小板减少则不太明显，可以出现在7～17日。监测血细胞计数是必须的。 其他不良反应是脱发、皮炎和色素沉着。曾遇到急性和慢性结合膜炎。可逆性小脑共济失调出现在1%的病人中，可能与剂量有关，可发生在治疗过程的任何时候(常常是几个月后)。小脑体征在停药后可持续几周。心肌缺血偶尔出现在氟脲嘧啶静脉点滴时。本药在动物是致畸形的并可能致癌。 对肝功能有损害的病人(例如广泛肝转移)应用氟脲嘧啶应减量;对营养状况差的病人用药应谨慎。 采用每天间歇静脉点滴连续4～5日可大大减低对血液的毒性作用。然而，临床研究的结果并不说明快速注射或者点滴方法在治疗上的优越性。长期点滴输药可以发生伴有疼痛、红斑和脱皮的手-足综合征。 本药归于FDA妊娠分类D。
  • 方法一:2-甲硫基-5-氟尿嘧啶在酸性条件下回流制得。
  • 5-氟脲嘧啶价格(试剂级):更新日期
  • Acros Organics:5-氟脲嘧啶 5-Fluorouracil, 99%(51-21-8)
  • {Chemic
  • TCI Shanghai:5-氟尿嘧啶 5-Fluorouracil,>;99.0%(LC)(T)(51-21-8)
  • 海关编码:29335995
  • 敏感性:Air Sensitive
  • TSCA:T
  • 用途二:生化研究，抗肿瘤药。
  • 药代动力学:由于氟脲嘧啶的吸收不稳定，因此常规不采用口服(在欧洲可获得口服制剂)。一般均静脉内给药。为了直接达到肿瘤也可以经动脉给药(例如肝转移时通过肝动脉)，并可直接注入体腔之渗液中(如卵巢癌)。静脉注入后血浆半衰期为7.5～10分钟，3小时后血浆中已查不到未改变的药物。细胞内药物水平持续更久。 氟脲嘧啶在肝中广为代谢;60～80%在8～12小时内作为呼吸的二氧化碳而排出，并有15%在6小时内原药不变从尿排出。本药可进入渗出液和脑脊液。已有血浆中氟脲嘧啶的测定方法。
  • 上游原料:甲醇钠 --> 甲酸乙酯 --> 氟乙酸乙酯 --> 不锈钢反应锅
  • 抗代谢药:5-氟脲嘧啶简称氟脲嘧啶，为嘧啶类抗代谢药，是目前临床上常用的一种化疗药物，对增殖期各期均有作用，能阻止胸腺嘧啶的形成，抑制DNA的生物合成，从而抑制癌细胞的生长。临床用于治疗消化道肿瘤，如胃癌、肠癌、肝癌等。对乳腺癌、卵巢癌、肺癌、膀胱癌、宫颈癌、胰腺癌等亦有效。瑞士生产的癌肤治为含本品5%的软膏，主要用于日光角化病和老年角化病、癌前期皮炎、单个和多发性浅表基底细胞癌、放射性皮肤病损害后的癌期及表浅基底细胞癌。 5-氟脲嘧啶在体内先转变为5-氟-2-脱氧脲嘧啶核苷酸，抑制胸腺嘧啶核苷酸合成酶，阻断脲嘧啶脱氧核苷酸转变为胸腺嘧啶脱氧核苷酸，从而影响DNA的生物合成。同时，它能掺入RNA，通过阻断脲嘧啶及乳清酸掺入RNA，达到直接抑制RNA的合成。 本药主要在肝脏中分解代谢，大部分解为二氧化碳从呼吸排出，极少由尿排出。口服后吸收差异很大;静脉给药后，其血浆浓度很快在两小时内下降;静注后于30分钟内可到达脑脊液中并维持3小时;静脉持续滴注的毒
  • Sigma Aldrich:51-21-8(sigmaaldrich)
  • F:10-23
  • color:white
  • 适应症:临床用于乳腺癌、消化道癌肿、卵巢癌及原发性支气管肺腺癌的辅助化疗和姑息治疗;也是治疗恶性葡萄胎、绒毛膜上皮癌、浆膜腔癌
  • 用途一:抗肿瘤药。对多种肿瘤如消化道肿瘤、乳腺癌、卵巢癌
  • 用途四:核酸代谢，研究稻、麦穗子分化，遗传代谢测定，植物生长发育研究。
  • 溶于水、碱溶液和DMSO，难溶于醇。溶解度:12.2 g/L 水(20°C)，2.9 g/L (20°C) 乙醇。 最大吸收波长(0.1mol/L盐酸中)265～266nm(ε7070)。中等毒，半数致

系列性分类

  1. Application Areas 应用领域分类
  2. Drug Discovery 新药研发
  3. Pharmacopoeia 药典
  4. Pharmacopoeia A-Z - Pharmacopoeia
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleoside Analogs - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleosides - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleotide Analogs - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Nucleotides - Nucleosides, Nucleotides, Oligonucleotides
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Pyrimidines 嘧啶
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Chemicals by Class 化学分类法
  4. Halogenated 卤化物 (氟氯溴碘)
  5. Fluoro 氟化物
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Chromatography - Analytical Standards
  4. Pharmaceutical Standards - Chromatography
  5. Pharmaceutical Secondary Standards - Pharmaceutical Standards
  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Enzymes, Inhibitors, and Substrates - Biochemicals and Reagents
  4. Enzyme Inhibitors - Enzymes, Inhibitors, and Substrates
  5. Enzyme Inhibitors by Type - Enzyme Inhibitors
  6. Substrate Analogs - Enzyme Inhibitors by Type
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. Cell Cycle Proteins and Antibodies - Apoptosis and Cell Cycle
  6. Cell Cycle Regulators - Cell Cycle Proteins and Antibodies
  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Heterocyclic Building Blocks 杂环合成砌块
  4. Pyrimidines 嘧啶
  5. C4 to C5 - Pyrimidines
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Apoptosis and Cell Cycle - Cell Signaling and Neuroscience
  5. Other Apoptosis Related Reagents - Apoptosis and Cell Cycle
  6. Inhibitors - Other Apoptosis Related Reagents
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Apoptosis and Cell Cycle
  5. Cell Cycle
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Enzymes, Inhibitors, and Substrates
  4. Enzyme Inhibitors
  5. Enzyme Inhibitors by Type
  6. Other
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Peptides and Proteins
  5. Apoptosis and Cell Cycle Proteins
  6. Apoptosis Inhibitors
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Proteins and Derivatives
  4. Proteins for Cell Biology
  5. Apoptosis and Cell Cycle Proteins
  6. Apoptosis Inhibitors
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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