5-Azacytidine 5-氮杂胞嘧啶核苷

CAS 320-67-2 MFCD00006539

化学结构图

320-67-2
SMILES: Nc1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c(=O)n1

化学属性

Mol. FormulaC8H12N4O5
Mol. Weight244.20
Melting Point228-230°C
Density2.08
SolubilitySoluble in DMSO, not in water
Appearance lyophilized powder white solid powder
Boiling Point534.5°C at 760 mmHg
Flash Point277°C

别名和识别编码

Chemical Name5-Azacytidine
CAS Number320-67-2
Synonym 5-Azacytidine {LY} 5-Azacytidine {} {LY} 5-Azacytidine {} {} {LY} 5-Azacytidine {} {} {} {LY} 5-Azacytidine {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 5-Azacytidine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {}
PubChem Substance ID9444
EC Number206-280-2
Beilstein Registry Number620461
MDL NumberMFCD00006539
Reaxys-RN620461
Merck Number887
Chemical Name Translation5-氮杂胞嘧啶核苷
Wiswesser Line NotationT6NVN ENJ DZ A- BT5OTJ CQ DQ E1Q
LabNetwork Molecule IDLN01327044
InChIInChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1
FormulaC8H12N4O5
IUPAC Name4-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,3,5-triazin-2(1H)-one
InChIKeyNMUSYJAQQFHJEW-KVTDHHQDSA-N
Canonical SMILESOC[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C(N=C(N)N=C2)=O)O1
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分类

  • {Chemicalbook} 生物化学品: 核酸类: 核苷及其衍生物
  • {SNA} A - K, AN-AZ, Antibacterial, Antibiotics A to Z, Antibiotics A-F, Antibiotics by Application, Antineoplastic and Immunosuppressive Antibiotics, Antiviral, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules for Epigenetic Research, Celgene, Chemical Structure Class, DNA Methyltransferase Inhibitors, Fluorination Ready Pharma-Developed Compounds, Gene Regulation, Gene Regulation and Expression, Interferes with DNA Synthesis, Mechanism of Action, Nucleoside analog inhibitors, Nucleosides, Small Molecules for Stem Cell Biology,

产品应用

  • Azacitidine is a pyrimidine nucleoside analogue of cytidine with antineoplastic activity. Azacitidine is incorporated into DNA, where it reversibly inhibits DNA methyltransferase, thereby blocking DNA methylation. Hypomethylation of DNA by azacitidine may activate tumor suppressor genes silenced by hypermethylation, resulting in an antitumor effect. This agent is also incorporated into RNA, thereby disrupting normal RNA function and impairing tRNA cytosine-5-methyltransferase activity.

相关文献及参考

  • Canova C., et al., Epigenetic control of programmed cell death: inhibition by 5-azacytidine of 1,25-dihydroxyvitamin D 3 -induced programmed cell death in C6.9 glioma cells. Mech. Ageing Dev. 101 , 153-166, (1998)
  • Merck: 14,890
  • Qian X., et al., DNA methylation regulates p27kip1 expression in rodent pituitary cell lines. Am. J. Pathol. 153 , 1475-1482, (1998) 摘要
  • Broday, L., et al.: Mol. Cell Biol., 19, 3198 (1999),
  • Qian, X., et al.: Am. J. Pathol., 153, 1475 (1999),
  • Kusaba, H., et al.: Eur. J. Biochem., 262, 924 (1999),

安全信息

GHS Symbol
WGK Germany3
Hazard Codes T
Hazard statements
  • H350 May cause cancer 可能致癌
  • H302 Harmful if swallowed 吞食有害
Personal Protective Equipment Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSXZ3017500
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。
  • 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。
  • 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+P312+P330
  • P305+P351+P338
  • P308+P313
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Signal word Danger
Storage condition 2-8°C {LY} 2-8°C <0°C <;0 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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R45 May cause cancer 可能致癌
  • R46 May cause inheritable genetic damage 可能引起遗传基因损害
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1 mg/kg
                          female 16 day(s) after conception
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Reproductive - Tumorigenic effects - transplacental tumorigenesis
   Blood - lymphoma, including Hodgkin's disease
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 32,33A,1985

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 90 mg/kg/8W-I
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   33,3069,1973

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 284 mg/kg/43W-I
TOXIC EFFECTS :
   Tumorigenic - neoplastic by RTECS cr

TYPE OF TEST            :

TYPE OF TEST            : T

TYPE OF TEST

TYPE OF TEST            : TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 1 mg/kg
                          female 12 day(s) after conception
TOXIC EFFECTS :
   Tumorigenic - Carcinogenic by RTECS criteria
   Blood - lymphoma, including Hodgkin's disease
   Reproductive - Tumorigenic effects - transplacental tumorigenesis
REFERENCE :
   CALEDQ Cancer Letters (Shannon, Irela

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 6 mg/kg/10D-I
TOXIC EFFECTS :
   Blood - leukopenia
   Blood - agranulocytosis
REFERENCE :
   CCROBU Cancer Chemotherapy Reports, Part 1.  (Washington, DC)  V.52(6)-59,
   1968-75.  For publisher information, see CTRRDO.  Volume(iss

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 500 ug/kg
TOXIC EFFECTS :
   Gastrointestinal - hypermotility, diarrhea
   Gastrointestinal - nausea or vomiting
REFERENCE :
   CCROBU Cancer Chemotherapy Reports, Part 1.  (Washington, DC)  V.52(6)-59,
   1968-75.  For publisher information, see CTRRDO.  Volume(issue)/page/year:
   56,413,1972

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 229 mg/kg
TOXIC EFFECTS :
   Behavioral - ataxia
   Gastrointestinal - hypermotility, diarrhea
   Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
   NTIS** National Technical Information Service.  (Springfield, VA 22161)
   Formerly U.S. Clearinghouse for Scientific & Technical Information.
   Volume(issue)/page/year: PB84-211432

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Bird - wild bird species
DOSE/DURATION           : 100 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   AECTCV Archives of Environmental Contamination and Toxicology.
   (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ
   070944)  V.1-    1973-  Volume(issue)/page/year: 12,355,1983

TYPE OF TEST

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Microorganism - not otherwise specified
DOSE/DURATION           : 5 mg/L
REFERENCE :
   JOVIAM Journal of Virology.  (American Soc. for Microbiology, 1913 I St.,
   NW, Washington, DC 20006) V.1-    1967-  Volume(issue)/page/year:
   2,1228,1968

TYPE OF TEST            : Mutation in microorganisms
TEST SYSTEM             : Bacteria - Salmonella typhimurium
DOSE/DURATION           : 3 ug/plate
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41 E.
   11th St., New York, NY 10003)  V.10-    1987-  Volume(issue)/page/year:
   19(Suppl 21),2,1992

TYPE OF TEST            : Mutation test systems - not otherwise specified
ROUTE OF EXPOSURE       : Subcutaneous
TEST SYSTEM             : Rodent - rat
DOSE/DURATION           : 25 mg/kg
REFERENCE :
   NEOLA4 Neoplasma.  (Karger-Libri, P.O. Box, CH-4009 Basel, Switzerland) V.4-
      1957-  Volume(issue)/page/year: 32,293,1985

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - hamster Lung
DOSE/DURATION           : 1 umol/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 212,253,1989

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Bacteria - Escherichia coli
DOSE/DURATION           : 1 mg/L
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(iss

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Embryo
DOSE/DURATION           : 5 mg/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(i

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 450 ug/kg
SEX/DURATION            : female 13 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003)  V.1-    1968-
   Volume(issue)/page/year: 35,247,1987

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 4 mg/kg
SEX/DURATION            : female 17 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - live birth index (measured after birth)
   Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight
   gain)
   Reproductive - Effects on Newborn - behavioral
REFERENCE :
   FCTOD7 Food and Chemical Toxicology.  (Pergamon Press Inc., Maxwell House,
   Fairview Park, Elmsford, NY 10523)  V.20-    1982- Volume(issue)/page/year:
   22,963,1984

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
S

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 4 mg/kg
SEX/DURATION            : female 15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Embryo or Fetus - cytological changes (including
   somatic cell genetic material)
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., New York, NY 10003

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Parenteral

其他信息

  • 储运特性:通风低温干燥; 与库房食品原料分开存放
  • TCI Shanghai:5-氮胞苷 5-Azacytidine,>;95.0%(T)(320-67-2)
  • 图谱信息:5-氮杂胞嘧啶核苷(320-67-2)质谱(MS) 5-氮杂胞嘧啶核苷(320-67-2)核磁图( 1 HNMR) 5-氮杂胞嘧啶核苷(320-67-2)红外图谱(IR1) 5-氮杂胞嘧啶核苷(320-67-2)核磁图( 13 CNMR)
  • 存储注意事项:光敏感
  • 毒性分级:高毒
  • MSDS 信息:5-Azacytidine(320-67-2).msds
  • 类别:有毒物品
  • 可燃性危险特性:可燃; 燃烧产生有毒氮氧化物烟雾; 病人用药副作用: 恶心,呕吐,腹泻,白细胞减少
  • 急性毒性:口服-小鼠 LD50: 572 毫克/公斤; 腹腔-小鼠 LD50: 68 毫克/公斤
  • MOL 文件:320-67-2.mol
  • F:10-23
  • 溶于甲醇。
  • 比旋光度:40 ° (C=1, H2O 22 °C)
  • 用途一:抗代谢药。主要适应症是对常规治疗无效的急性髓性白血病。亦用于乳腺癌、黑色素瘤、肠癌等。毒性主要表现为白细胞减少、血小板减少和贫血。恶心和呕吐为常见的不良反应，可通过长时间持续输注使症状改善，或在治病前24h至48h用止吐剂。其他毒性作用为腹泻、神经肌内障碍、发热、低血压和皮疹。制剂在用前3-4h新鲜配制。
  • 用途二:一种潜在的生长抑制因子和细胞毒素载体；抑制DNA甲基化转移酶，该酶是一种重要的调控基因表达、基因激活和基因关闭的机关。 该因子引起DNA去甲基化或半去甲基化，允许转录因子结合到DNA上，重新激活肿瘤抑制基因。
  • Sigma Aldrich:320-67-2(sigmaaldrich)
  • 5-氮杂胞嘧啶核苷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 A2033 5-氮胞苷 5-Azacytidine 1G 2490元 2014/06/02 A2033 5-氮胞苷 5-Azacytidine 100MG 491元 2010/06/21 226620010 5-氮杂胞嘧啶核苷 5-Azacytidine 99% 1 GR 3108元
  • 灭火剂:干粉,泡沫,沙土,二氧化碳, 雾状水
  • Acros Organics:5-氮包苷 5-Azacytidine, 99%(320-67-2)

系列性分类

  1. Life Science 生命科学
  2. Antibiotics 抗生素
  3. Antibiotics A to Z - Antibiotics
  4. Antibiotics A-F - Antibiotics A to Z
  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. Life Science 生命科学
  2. Cancer Research
  3. Antitumor Agents - Cancer Research
  4. Gene Regulation - Antitumor Agents
  1. Life Science 生命科学
  2. Cell Culture 细胞培养
  3. Serum-free Media - Cell Culture
  4. Hybridoma Platform - Serum-free Media
  5. Hybridoma Reagents - Hybridoma Platform
  1. Life Science 生命科学
  2. Molecular Biology 分子生物学
  3. Epigenetics - Molecular Biology
  4. Bioactive Small Molecules for Epigenetic Research - Epigenetics
  5. DNA Methyltransferase Inhibitors - Bioactive Small Molecules for Epigenetic Research
  6. Nucleoside analog inhibitors - DNA Methyltransferase Inhibitors
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Stem Cell Biology - Cell Biology
  4. General Stem Cell Biology - Stem Cell Biology
  5. Stem Cell Differentiation - General Stem Cell Biology
  6. Bioactives/Supplements - Stem Cell Differentiation
  7. Vitamins, Hormones, Misc. - Bioactives/Supplements
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Antibiotics by Application
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Chemical Structure Class
  5. Miscellaneous
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Mechanism of Action
  5. Interferes with Cell Wall Synthesis
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Spectrum of Activity
  5. Antibacterial
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Antibiotics
  4. Spectrum of Activity
  5. Antiparasitic / Antiprotozoal / Anthelminthic
  1. Life Science 生命科学
  2. Biochemicals and Reagents
  3. Cell Signaling and Neuroscience
  4. Gene Regulation and Expression
  5. DNA-RNA Transcription Regulators
  1. Medical Research Areas
  2. Epigenetics
  3. DNA Methyltransferase

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