1-Beta-D-Arabinofuranosylcytosine Hydrochloride 盐酸阿糖胞苷

CAS 69-74-9 MFCD00012839

化学结构图

69-74-9
SMILES: Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1

化学属性

Mol. FormulaC9H14ClN3O5
Mol. Weight279.68
Melting Point197-198°C
Appearance 本品为白色细小针状结晶或结晶性粉末。无臭，在水中极易溶解，略溶于甲醇及乙醇，在乙醚中微溶。mp189-195℃ (分解)。比旋度应为+127°- 133°(10 mg/m1)。酸性及碱性水溶液中水解生成阿糖尿苷，最稳定pH值为 6.9。 crystalline
TSCANo
Boiling Point545.7°C at 760 mmHg
Flash Point283.8°C

别名和识别编码

Chemical Name1-Beta-D-Arabinofuranosylcytosine Hydrochloride
Synonym Cytarabine (hydrochloride) {LY} Cytarabine (hydrochloride) Cytarabine Hydrochloride Cytonal Cytosar Cytosar U Cytosar-U Cytosine Arabinoside beta Ara C beta-Ara C {} {LY} Cytarabine (hydrochloride) {} {} {LY} Cytarabine (hydrochloride) {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine (hydrochloride) {} {} {} {} {} {} {} {} {} {} {} {} {} {
MDL NumberMFCD00012839
CAS Number69-74-9
PubChem Substance ID6252
EC Number200-713-9
Chemical Name Translation盐酸阿糖胞苷
LabNetwork Molecule IDLN01343518
InChIInChI=1S/C9H13N3O5.ClH/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);1H/t4-,6-,7+,8-;/m1./s1
Canonical SMILESO=C1N=C(C=CN1[C@H]2[C@@H](O)[C@H](O)[C@@H](CO)O2)N.Cl
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分类

  • {SNA} Antitumor Agents, Apoptosis and Cell Cycle, DNA Synthesis Inhibitors, DNA metabolism, 癌症研究, 细胞信号转导和神经科学, 细胞生物学
  • {Chemicalbook} 生物化学品: 核酸类: 核苷及其衍生物
  • {SNA} Apoptosis and Cell Cycle, DNA Synthesis Inhibitors, DNA metabolism, 抗肿瘤药物, 癌症研究, 细胞信号转导和神经科学, 细胞生物学
  • {SNA} Antitumor Agents,
  • {SNA} Antitumor Agents, Apoptosis and Cell Cycle, Bioactive Small Molecules, CI-CY, Cell Biology, Cell Signaling and Neuroscience, DNA Synthesis Inhibitors, DNA metabolism, 癌症研究
  • {SNA} Antitumor Agents, Apoptosis and Cell Cycle, Bioactive Small Molecules,

安全信息

WGK Germany3
GHS Symbol
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
  • 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。
  • P264+P265
  • 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。
  • 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+P352
  • P305+P351+P338
  • P308+P313
  • P318
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P333+P313
  • P333+P317
  • P337+P313
  • P337+P317
  • P362+P364
  • P363 Wash contaminated clothing before reuse. 被污染的衣服洗净后方可重新使用。
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • 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
  • H341 Suspected of causing genetic defects 怀疑导致遗传性缺陷
  • H361 Suspected of damaging fertility or the unborn child 怀疑对生育能力或未出生婴儿造成伤害
Signal word
RTECSUQ4975000
Hazard Codes Xn
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；
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
  • S24 Avoid contact with skin 避免皮肤接触；
  • S60 This material and its container must be disposed of as hazardous waste 该物质及其容器必须作为危险废物处置；
  • S37 Wear suitable gloves 戴适当手套；
Risk Statements
  • R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
  • R36 Irritating to eyes 刺激眼睛
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
Storage condition 2-8°C, sealed storage, away from moisture {LY} 2-8°C, sealed storage, away from moisture {} {LY} 2-8°C, sealed storage, away from moisture {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, away from moisture {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, sealed storage, 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Primate - monkey
DOSE/DURATION           : 396 mg/kg
TOXIC EFFECTS :
   Behavioral - changes in motor activity (specific assay)
   Gastrointestinal - changes in structure or function of salivary glands
   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: 8,353,1974

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 5500 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  V

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Oral
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >3200 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 6,1255,1972

TYPE OF T

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 825 mg/kg
TOXIC EFFECTS :
   Behavioral - food intake (animal)
   Behavioral - changes in motor activity (specific assay)
   Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
   OYYAA2 Oyo Yakuri.  Pharmacometrics.  (Oyo Yakuri Kenkyukai, CPO Box 180,
   Sendai 980-91, Japan) V.1-    1967-  Volume(issue)/page/year: 6,1255,1972

TYPE OF TEST            : Mutation test systems - not otherwise specified
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 10 mg/L
REFERENCE :
   EJCAAH European Journal of Cancer.  (Oxford, UK)  V.1-17(6), 1965-1981. For
   publisher information, see EJCODS.  Volume(issue)/page/year: 6,379,1970

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - mouse Leukocyte
DOSE/DURATION           : 100 umol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   29,1881,1969

TYPE OF TEST            : Mutation in mammalian somatic cells
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 5 mg/L
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:
   12,85,1988

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Lymphocyte
DOSE/DURATION           : 10 mg/L
REFERENCE :
   EJCAAH European Journal of Cancer.  (Oxford, UK)  V.1-17(6), 1965-1981. For
   publisher information, see EJCODS.  Volume(issue)/page/year: 6,379,1970

TYPE OF TEST            : Specific locus test
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Insect - Drosophila melanogaster
DOSE/DURATION           : 1000 ppm
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 211,153,1989

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Oral
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 240 mg/kg/3D (Continuous)
REFERENCE :
   EMMUEG Environmental and Molecular Mutagenesis.  (Alan R. Liss, Inc., 41 E.
   11th

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 280 mg/kg
SEX/DURATION            : female 15 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - biochemical and metabolic
REFERENCE :
   JONRA9 Journal of Neurochemistry.  (Raven Press, 1185 Ave. of the Americas,
   New York, NY 10036) V.1-    1956-  Volume(issue)/page/year: 34,950,1980

其他信息

  • 用途二:抗肿瘤药。主要治疗急性白血病及消化道癌，对多数实体瘤无效。眼部带状疱疹、单纯疱疹性结膜炎也有一定疗效。骨髓抑制、消化道反应常见，少数病人可有肝功能异常、发热、皮疹。用药期间应严格检查血象。
  • 方法一:方法一、5'-胞苷-磷酸(5'-CMP)为原料 胞嘧啶核苷盐酸盐的制备 5'-胞苷-磷酸100g悬浮于800ml蒸馏水中，加入约50ml浓氨水，调节pH值为8-9，不溶物可过滤除去，稀释至1L后加入氢氧化镧凝胶1L，升温至90℃搅拌水解(水解过程中可通过对氢氧化镧凝胶的电泳分析来确定反应终点)，当电泳纸上5'-胞苷-磷酸斑点消失并有胞嘧啶核苷的斑点出现后(约需25h)反应结束，离心得上清液，沉淀用6L蒸馏水洗两次后离心，将洗液与上清液混合。减压浓缩，浓缩中可过滤除去不溶物，浓缩至约0.2L后停止，冷却，用6mol/L盐酸调节pH为2.5-3，即有白色结晶析出，加100m1 95%乙醇，冰箱冷却过夜后过滤，用稀醇及无水乙醇洗涤，得产品。 5'-胞苷-磷酸[氨水，氢氧化镧]→[pH8-9, 90℃, 25h]胞嘧啶核苷盐酸盐 胞嘧啶阿拉伯糖苷的制备 300ml三氯氧磷先预冷20min，加预冷的蒸馏水30ml，有盐酸气体放出，5min后，将反应液置冰盐浴30min。加入乙酸乙酯2L及胞嘧啶核苷盐酸盐40g，热水浴中80℃回流，时间约为40-50min。将反应液倾入4L蒸馏水中，50℃减压蒸出乙酸乙酯。浓缩液用氢氧化钠溶液调pH为3-3.5，加浓氨水，80℃水解10min，过滤除去不溶物。滤液调pH为2.5-3，上活性炭柱，分别用pH为3的蒸馏水和60℃的50%乙醇-1%氨水洗脱，将洗脱液浓缩至20ml左右，调pH为3，加乙醇冷却结晶，过滤，得产品。 胞嘧啶核苷盐酸盐[三氯氧化磷，乙酸乙酯，水]→[0-80℃, 40-50min]2, 2'-氧桥-3',5'-二乙酰基胞嘧啶核苷盐酸盐[氨水]→[80℃,10min]阿糖胞苷 阿糖胞苷盐酸盐的制备 将阿糖胞苷22g加入2%盐酸-甲醇440ml及甲醇220ml，50℃水浴加热溶解，活性炭脱色半小时后过滤，浓缩，冰箱冷却过夜，过滤得粗品，用30倍甲醇重结晶得纯品。 阿糖胞苷[盐酸，甲醇]→[50℃, 30min]阿糖胞苷盐酸盐 方法二、以葡萄糖酸钙为原料 D-阿拉伯糖的制备 投料为葡萄糖酸钙(m)：硫酸铁(m)：无水乙酸钡 (m)：水(V)：过氧化氢(V)=1：0.077：0.14：13：1.2-1.3。葡萄糖酸钙加水加热溶解后，加入事先配好的乙酸钡溶液和硫酸铁溶液的混合液，搅拌升温至95℃，过滤除去不溶物，滤液加一半用量的过氧化氢于40-56℃反应30min，静置30min，再于40℃加入剩余的过氧化氢反应30min，加入草酸过滤除去草酸钙，滤液在50℃以下
  • 储运特性:库房通风低温干燥
  • 上游原料:乙醇 --> 氢氧化钠 --> 电泳 --> 胞苷 --> 氢氧化镧 --> 阿糖胞苷 --> 环胞啶
  • 方法二:环胞苷经水解、开环、成盐而得。
  • MOL 文件:69-74-9.mol
  • {Chemical
  • 刺激数据:眼睛-人 21 毫克/7天 轻度; 眼睛-兔子 42 毫克/14天 中度
  • 可燃性危险特性:可燃; 燃烧产生有毒氮氧化物和氯化物烟雾
  • 毒性分级:中毒
  • 参考质量标准:原料 中国药典2000年版619页 指标名称 指标 指标名称 指标 含量(C9H13N305.HCl)/% 97.0-103.0/干燥失重/% ≤0.5 注射剂 中国药典2000年版619页 指标名称 指标 指标名称 指标 含量(C9H13N305.HCl)/% 93.0-107.0/含量均匀度/符合规定 无菌 符合规定 pH值(10mg m1) 4.0-6.0 其他 符合注射剂有关规定 干燥失重/% ≤0.3
  • 用途三:抗恶性肿瘤药，是急性粒细胞白血病的首选药物。
  • 盐酸阿糖胞苷价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2010/06/21 227180050 盐酸阿糖胞苷 Cytosine beta-D-arabinofuranoside hydrochloride 99%, crystallin
  • Acros Organics:Cytosine beta-D-arabino

系列性分类

  1. Life Science 生命科学
  2. Biochemicals and Reagents 生化试剂
  3. Nucleosides, Nucleotides, Oligonucleotides - Biochemicals and Reagents
  4. Synthetic Oligonucleotides and Related Reagents - Nucleosides, Nucleotides, Oligonucleotides
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Bioactive Small Molecules - Cell Biology
  4. CI-CY - Bioactive Small Molecules
  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. DNA metabolism - Apoptosis and Cell Cycle
  6. DNA Synthesis Inhibitors - DNA metabolism

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