Cytosine-beta-D-arabinofuranoside 阿糖胞苷

CAS 147-94-4 MFCD00066487

化学结构图

147-94-4
SMILES: Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)c(=O)n1

化学属性

Mol. FormulaC9H13N3O5
Mol. Weight243.22
Density1.89
Melting Point214 °C
SolubilityH2O: 50 mg/mL, clear, colorless
Appearance crystalline
Boiling Point386.09 °C at 760 mmHg

别名和识别编码

Chemical NameCytosine-beta-D-arabinofuranoside
CAS Number147-94-4
Alfabeta NameCYTARABINE
MDL NumberMFCD00066487
Synonym Cytarabine {LY} Cytarabine Cytarabine Hydrochloride Cytonal Cytosar Cytosar U Cytosar-U Cytosine Arabinoside beta Ara C beta-Ara C {} {LY} Cytarabine {} {} {} {} {PubChem} Aracytine {} {} {} {PubChem} Aracytidine {} {} {} {} {PubChem} Arabinosylcytosine {} {} {} {} {} {PubChem} Arabinoside, Cytosine {} {} {} {} {} {} {} {} {} {} {} {} {PubChem} Arabinofuranosylcytosine {} {} {} {} {} {} {} {PubChem} Ara-C {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {PubChem} Ara C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cytarabine
EC Number205-705-9
Beilstein Registry Number89175
PubChem Substance ID6253
Reaxys-RN89175
Merck Number2784
Chemical Name Translation阿糖胞苷
Wiswesser Line NotationT6NVNJ DZ A- BT5OTJ CQ DQ E1Q
LabNetwork Molecule IDLN00238525
Canonical SMILESO=C1N=C(C=CN1[C@H]2[C@@H](O)[C@H](O)[C@@H](CO)O2)N
InChIInChI=1S/C9H13N3O5/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)/t4-,6-,7+,8-/m1/s1
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分类

  • Bases & Related Reagents
  • {SNA} Analytical Standards, Chromatography, EP Standards, EP Standards C - D, Pharmaceutical Standards, Pharmacopeia Standards, 分析/色谱
  • {SNA} Analytical Standards,
  • Nucleotides
  • {SNA} Antitumor Agents, Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, CI-CZ, DNA Synthesis Inhibitors, DNA metabolism, 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} Analytical Standards, EP Standards, EP Standards C - D, Pharmacopeia & Metrological Institutes Standards, 分析/色谱
  • {SNA} Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, CI-CZ,
  • {SNA} Apoptosis

产品应用

  • Ara-C 插入DNA，靠和拓扑异构酶I（topoisomerase I）形成络合物抑制DNA复制，导致DNA裂解。不能抑制RNA合成。抗白血病物质，用于各类急性白血病。

相关文献及参考

  • [2]. Besirli, C.G., et al. Cytosine arabinoside rapidly activates Bax-dependent apoptosis and a delayed Bax-independent death pathway in sympathetic neurons. Cell Death Differ, 2003. 10(9): p. 1045-58.
  • [3]. Yamauchi, H., et al., Involvement of p53 in 1-beta-D-arabinofuranosylcytosine-induced trophoblastic cell apoptosis and impaired proliferation in rat placenta. Biol Reprod, 2004. 70(6): p. 1762-7.
  • [4]. Richel, D.J., et al., Comparison of the antileukaemic activity of 5 aza-2-deoxycytidine and arabinofuranosyl-cytosine in rats with myelocytic leukaemia. Br J Cancer, 1988. 58(6): p. 730-3.
  • [5]. Shepshelovich D, et al. Pharmacodynamics of cytarabine induced leucopenia: a retrospective cohort study. Br J Clin Pharmacol. 2015 Apr;79(4):685-91.
  • [6]. Renis HE. Antiviral activity of cytarabine in herpesvirus-infected rats. Antimicrob Agents Chemother. 1973 Oct;4(4):439-44.
  • [7]. Gruffaz M, Zhou S, Vasan K, et al. Repurposing Cytarabine

安全信息

Warnings IRRITANT
Signal word
GHS Symbol
WGK Germany3
Safety Statements
  • S36/37 Wear suitable protective clothing and gloves 穿戴适当的防护服和手套；
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
  • R63 Possible risk of harm to the unborn child 可能危害未出生婴儿
  • R43 May cause sensitisation by skin contact 皮肤接触会产生过敏反应
Precautionary statements
  • 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+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
  • P318
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P333+P313
  • P333+P317
  • P337+P317
  • P362+P364
  • 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
  • H340 May cause genetic defects 可能导致遗传性缺陷
  • H341 Suspected of causing genetic defects 怀疑导致遗传性缺陷
  • 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
  • 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
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSHA5425000
Hazard Codes Xn
Storage condition 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 {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} { 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : 2500 mg/kg/7W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Blood - lymphoma, including Hodgkin's disease
   Skin and Appendages - tumors
REFERENCE :
   CANCAR Cancer (Philadelphia).  (Lippincott/Harper, Journal Fulfillment
   Dept., 2350 Virginia Ave., Hagerstown, MD 21740)  V.1-    1948-
   Volume(issue)/page/year: 40,1935,1977

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 4836 mg/kg/26W-I
TOXIC EFFECTS :
   Tumorigenic - equivocal tumorigenic agent by RTECS criteria
   Lungs, Thorax, or Respiration - tumors
   Blood - lymphoma, including Hodgkin's disease
REFERENCE :
   CANCAR Cancer (Philadelphia).  (Lippincott/Harper, Journal Fulfillment
   Dept., 2350 Virginia Ave., Hagerstown, MD 21740)  V.1-    1948-
   Volume(issue)/page/year: 40,1935,1977

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >5 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: 6,321,1982

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - woman
DOSE/DURATION           : 720 mg/kg/3D-I
TOXIC EFFECTS :
   Brain and Coverings - other degenerative changes
REFERENCE :
   NEURAI Neurology.  (Modern Medicine Pub., Inc., 1 E. First St., Duluth, MN
   55802)  V.1-    1951-  Volume(issue)/page/year: 35,1475,1985

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 649 mg/kg/4D-I
TOXIC EFFECTS :
   Peripheral Nerve and Sensation - fasciculations
REFERENCE :
   DICPBB Drug Intelligence and Clinical Pharmacy.  (POB 42435, Cincinnati, OH
   45242)  V.3-    1969-  Volume(issue)/page/year: 21,177,1987

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - rat
DOSE/DURATION           : >5 gm/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: 6,321,1982

TYPE OF TEST            :

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - child
DOSE/DURATION           : 33200 ug/kg/240D-I
TOXIC EFFECTS :
   Behavioral - somnolence (gene

TYPE OF TEST

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Rodent - mouse Lung
DOSE/DURATION           : 136 nmol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   36,95,1976

TYPE OF TEST            : Cytogenetic analysis
ROUTE OF EXPOSURE       : Subcutaneous
TEST SYSTEM             : Rodent - mouse
DOSE/DURATION           : 315 mg/kg
REFERENCE :
   MUREAV Mutation Research.  (Elsevier Science Pub. B.V., POB 211, 1000 AE
   Amsterdam, Netherlands) V.1-    1964-  Volume(issue)/page/year: 58,67,1978

TYPE OF TEST            : Morphological transformation
TEST SYSTEM             : Rodent - mouse Embryo
DOSE/DURATION           : 1 umol/L/24H
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-

{hazard_c

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,

{

TYPE OF TEST            : Specific locus test

TYPE OF TEST            : Cytogenetic analysis
TEST SYSTEM             : Rodent - hamster Ovary
DOSE/DURATION           : 1 mg/L
REFERENCE :
   ENMUDM Environmental Mutagenesis.  (New York, NY)  V.1-9, 1979-87.  For
   publisher information, see EMMUEG.  Volume(issue)/page/year: 2,455,1980

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 50 mg/L
REFERENCE :
   BBRCA9 Biochemical and Biophysical Research Communications.  (Academic
   Press, Inc., 1 E. First St., Duluth, MN 55802)  V.1-    1959-
   Volume(issue)/page/year: 60,96,1974

TYPE OF TEST            : Sperm M

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

TYPE OF TEST            : TDLo - Lowest publ

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Unreported
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 50 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured
   before birth)
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: 19,43A,1979

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EX

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - rat
DOSE                    : 50 mg/kg
SEX/DURATION            : female 12 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Specific Developmental Abnormalities - craniofacial
   (including nose and tongue)
   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: 4,7,1971

TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Parenteral
SPECIES OBSERVED        : Rodent - mouse
DOSE                    : 60 mg/kg
SEX/DURATION            : female 13-14 day(s) after conception
TOXIC EFFECTS :
   Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight
   gain)
REFERENCE :
   TJADAB Teratology, The International Journal of Abnormal Development. (Alan
   R. Liss, Inc., 41 E. 11th St., N

其他信息

  • {Chemicalbo
  • 图谱信息:阿糖胞苷(147-94-4)质谱(MS) 阿糖胞苷(147-94-4)红外图谱(IR1) 阿糖胞苷(147-94-4)核磁图( 1 HNMR) 阿糖胞苷(147-94-4)红外图谱(IR2) 阿糖胞苷(147-94-4)核磁图( 13 CNMR)
  • 下游产品:盐酸阿糖胞苷
  • 溶于水，部分溶于甲醇，几乎不溶于乙醚，本品以D-阿拉伯糖或5′-胞嘧啶核苷酸为原料制得。常用其盐酸盐。
  • 用法用量:成人用法： 1，急性白血病诱导治疗： 常与其他化疗药联用，每次1～3mg/kg，静滴，q 12h，连用5～7日。间隔1～2周重复。 2，中、大减量疗法： 常用于难治性或复发性急性白血病或急性白血病缓解后的强化治疗。中剂量指每次500～1000mg/m2，静滴1～3小时，q12h，2～6 日为一个疗程。大剂量指每次1000～3000mg/m2，用法同中剂量方案。由于阿糖胞苷的不良反应随剂量增大而加重，大剂量反而影响其疗效，故现多偏向用中剂量方案。 3，皮下注射： 每次10mg/m2，q12h，14～21日为一个疗程。如不缓解而病人情况允许，可于2～3周后重复一个疗程。此方案可用于原始细胞增多的骨髓增生异常综合征、低增生性白血病、老年急性非淋巴细胞白血病等。 4，鞘内注射： 脑膜白血病，每次25～75mg，加地塞米松5mg，以NS溶解后鞘内注射，每周1～2次，用至脑脊液检查正常。预防性用药则每4～8周1次。 儿童用法：急性白血病诱导治疗，100mg/(m2·d)，连用5～7日。
  • 刺激数据:皮肤-人 45 毫克/3周 中度; 眼睛-人 105 毫克/7天
  • 药动学:本药口服吸收量少，又极易在胃肠道黏膜及肝脏的胞嘧啶脱氨酶作用下脱氨而失去活性，故不宜口服。可经静脉、皮下、肌内或鞘内注射而吸收。静脉注射后能广泛分布于体液、组织及细胞内。静脉滴注后约有中等量的药物透入血—脑脊液屏障，脑脊液中药物浓度约为血药浓度的40%。本药在肝、肾等组织内代谢，被胞嘧啶脱氨酶迅速脱氨而形成无活性的尿嘧啶阿拉伯糖苷，在脑脊液内，由于该脱氨酶含量较低，故其脱氨作用较缓慢。静脉给药时，半衰期α相为10～15分钟，β相为2～2.5小时；鞘内给药时，半衰期可延至11小时。在24小时内，所给药物中，约 10%以药物原形、90%以尿嘧啶阿糖胞苷形式经肾脏排泄。
  • 给药说明:1.使用阿糖胞苷给药时，应适当增加患者的液体摄入量，使尿液保持碱性，必要时可合用别嘌醇，以防止血尿酸增高及尿酸性肾病。 2.快速静脉注射引起的恶心、呕吐反应虽较严重，但对骨髓的抑制较轻，患者一般能耐受。 3.静脉滴注液应稀释至0.5mg/ml。 4.配制好的注射液可在4℃(冰箱中)保存7日，室温下仅能保存24小时。 5.鞘内注射用药，稀释液中应不含防腐剂。 6.采用中剂量或大剂量的阿糖胞苷治疗时，部分患者可能发生严重的胃肠道及神经系统不良反应，如胃肠道溃疡、胃肠囊样积气、坏死性结肠炎、周围神经病变、大脑或小脑功能障碍如性格改变、肌张力减退、癫、嗜睡、昏迷、定向力障碍、眼球震颤、构音障碍、步态不稳;尚可发生出血性结膜炎、皮疹、脱发、脱皮、严重心肌病等。 7.如出现各种严重不良反应时，应立即停药，并立即采取各种有效措施治疗。部分患者给予肾上腺皮质激素，可能减轻中剂量或大剂量阿糖胞苷引起的不良反应。
  • 灭火剂:干粉,泡沫,沙土
  • 毒性分级:中毒
  • 不良反应:消化系统：常见食欲减退、恶心、呕吐、腹泻、胃炎、口腔炎和胃肠道溃疡等。部分病人出现肝功能异常、高胆红素及氨基转移酶升高。大剂量时可出现明显肝功能异常及黄疸，可引起肝脏中央静脉及肝小叶静脉闭塞，导致黄疸、肝大、腹水及肝性脑病。 血液系统：骨髓抑制随剂量增大而加重，表现为白细胞、血小板减少。 局部反应：静滴处疼痛和血栓性静脉炎大多在停药后消退，也有出现瘙痒和皮疹等反应;局部眼科用药时，常引起暂时性烧灼、痒等轻度刺激感，也可出现流泪、异物感、结膜充血、表浅点状角膜炎、疼痛、怕光等反应。 中枢神经系统：偶尔发生不适、乏力、震颤、头晕、幻觉、精神症状和意识模糊，其发生与剂量有关，通常停药后消退，也有出现头痛和脑病的报道，后者常难以与原发病相识别，多发生于肝、肾功能不全者。 逾量表现：每日摄入的阿糖胞苷剂量超过20mg/kg，可引起骨髓抑制;一旦
  • 急性毒性:口服-大鼠 LD5

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. Chemical Synthesis 化学合成
  2. Chemical Biology 生物化学
  3. Carbohydrate Chemistry - Chemical Biology
  4. Carbohydrate Derivatives 碳水化合物衍生物
  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
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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