Cladribine 克拉屈滨

CAS 4291-63-8 MFCD00153939

化学结构图

4291-63-8
SMILES: Nc1nc(Cl)nc2c1ncn2C1CC(O)C(CO)O1

化学属性

Mol. FormulaC10H12ClN5O3
Mol. Weight285.69
Density1.422
Appearance -18.8°(C=1，二甲基甲酰胺)。UV最大吸收(0.1mol/L氢氧化钠)：265nm：(0．1mol/L盐酸)：265nm。 D 23 从水中结晶，在210～215℃软化，固化后变为棕色；从乙醇中结晶，熔点22023(软化)，再固化，变为棕色，在＜300℃不再熔化。[α]
Melting Point181-185°C
SolubilitySoluble in DMSO ( ≥57 mg/ml), water (<1 mg/ml), ethanol (<1 mg/ml), and methanol.
Stability对热敏感
Boiling Point387.1°C at 760 mmHg

别名和识别编码

Chemical NameCladribine
CAS Number4291-63-8
Alfabeta NameCHLORODEOXYADENOSINE 22---'
MDL NumberMFCD00153939
Synonym Cladribine {LY} Cladribine Leustatin {} {LY} Cladribine {} {} {LY} Cladribine {} {} {} {LY} Cladribine {} {} {} {} {LY} Cladribine {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cladribine {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} Cladribine
EC Number250-023-7
Beilstein Registry Number624220
PubChem Substance ID20279
Reaxys-RN624220
Merck Number2337
Chemical Name Translation克拉屈滨
LabNetwork Molecule IDLN00173627
InChIInChI=1S/C10H12ClN5O3/c11-10-14-8(12)7-9(15-10)16(3-13-7)6-1-4(18)5(2-17)19-6/h3-6,17-18H,1-2H2,(H2,12,14,15)/t4-,5+,6+/m0/s1
Canonical SMILESOC[C@@H]1[C@@H](O)C[C@H](N2C=NC3=C2N=C(Cl)N=C3N)O1
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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} Bioactive Small Molecules, Biochemicals and Reagents, C-CH, Cell Biology, Nucleoside Analogs, Nucleosides, Nucleotides, Oligonucleotides
  • {SNA} Nucleoside Analogs, 核苷，核苷酸和寡核苷酸, 生化试剂
  • Nucleotides
  • {SNA} Biochemicals and Reagents, C-CH, Nucleoside Analogs, Nucleosides, Nucleotides, Oligonucleotides, 生物活性小分子, 细胞生物学
  • {Chemicalbook} 药物: 抗肿瘤药: 抗代谢物抗肿瘤药物
  • {SNA} Analytical Standards, EP Standards, EP Standards C - D,

产品应用

  • It is a chlorinated purine nucleoside with activity against lymphoproliferative disorders, such as hairy cell leukemia (HCL) and multiple myeloma (MM). 2-CdA resists ADA degradation and is phosphorylated to CdATP in lymphocytes. CdATP incorporation into DNA induces strand breaks and the activation of apoptosis. 2-CdA may also be used in studies involving the inhibition of DNA polymerase(s).
  • Cladribiane, like fludarabine, is a prodrug that is must be phosphorylated intracellularly to the monophosphate by the nuclear/cytosol enzyme deoxycytidine kinase (dCK) and possibly by the mitochondrial enzyme deoxyguanosine kinase (dGK).

相关文献及参考

  • [2]. Jian Ma, et al. Therapeutic potential of cladribine in combination with STAT3 inhibitor against multiple myeloma. BMC Cancer. 2011 Jun 16;11:255.
  • [3]. Young Seop Chang, et al. MP28-10 COMBINED EFFECTS OF MELATONIN AND CLADRIBINE ON APOPTOSIS IN ISCHEMIA/REPERFUSION INJURY IN RAT BLADDER. THE JOURNAL OF UROLOGY. April 2016. 195 (4S): e375.
  • [4]. Crystal D Hayes, et al. Chronic cladribine administration increases amyloid beta peptide generation and plaque burden in mice. PLoS One. 2012;7(10):e45841.
  • [5]. Yeung, P. K. F., et al. Pharmacokinetics of Cladribine in a Rat Model Following Subcutaneous and Intra-arterial Injections. Drug Metabol Drug Interact. 2008;23(3-4):291-8.
  • Piro, L.D., et al.: N. Engl. J. Med., 322, 1117 (1990),
  • Seto, S., et al.: J. Clin. Invest., 75, 377 (1985),
  • [1]. Linyan Xu, et al. Cladribine Induces ATF4 Mediated Apoptosis and Synergizes with SAHA in Diffuse Large B-Cell Lymphoma Cells. Int J Med Sci. 20

安全信息

Warnings IRRITANT
Signal word Danger
GHS Symbol
WGK Germany3
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • 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；
  • S36/37/39 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）；
Risk Statements
  • R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入，皮肤接触及吞食都有毒
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
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。
  • 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
  • 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。
  • 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。
  • 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+P316
  • P302+P352
  • P304+P340
  • P305+P351+P338
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • 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。
  • P316
  • P319
  • P321 Specific treatment (see … on this label). 具体治疗（见本标签上的）。
  • P322 Specific measures (see …on this label). 具体治疗（见本标签上的）。
  • P330 Rinse mouth. 漱口
  • P332+P313
  • P332+P317
  • P337+P313
  • P337+P317
  • P361 Remove/Take off immediately all contaminated clothing. 立即去除/脱掉所有被污染的衣服。
  • P361+P364
  • 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。
  • P403+P233
  • P405 Store locked up. 上锁保管。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H301 Toxic if swallowed 吞食有毒
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H315 Causes skin irritation 会刺激皮肤
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H331 Toxic if inhaled 吸入中毒
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
RTECSAU7357560
Personal Protective Equipment Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
Hazard Codes T
Storage condition 2-8°C, protect from light {LY} 2-8°C, protect from light {} {LY} 2-8°C, protect from light {} {} {LY} 2-8°C, protect from light {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {LY} 2-8°C, protect from light {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} {} 
TYPE OF TEST            : TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Human - man
DOSE/DURATION           : 700 ug/kg/7D-C
TOXIC EFFECTS :
   Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
   AJHEDD American Journal of Hematology.  (John Wiley & Sons, 605 Third
   Avenue, New York, NY 10158) V.1-    1976-  Volume(issue)/page/year:
   53,209,1996

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 150 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   LELYEA Leukemia and Lymphoma.  (Harwood Academic Publishers GmbH c/o STBS
   Ltd., POB 90 Reading, Berks, RG1 8JL, UK)  V.1-   1989-
   Volume(issue)/page/year: 5,1,1991

TYPE OF TEST            : DNA inhibition
TEST SYSTEM             : Human Lymphocyte
DOSE/DURATION           : 16 nmol/L
REFERENCE :
   CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut
   Sts., Philadelphia, PA 19106)  V.1-    1941-  Volume(issue)/page/year:
   46,2362,1986

其他信息

  • 用途一:为耐腺苷脱氨酶的脱氧腺苷类似物。用于活动性毛细胞白血病。
  • Sigma Aldrich:4291-63-8(sigmaaldrich)
  • 功能主治:主要对毛细胞白血病疗效很好，对其他淋巴瘤及白血病亦有效。
  • MSDS 信息:2-Chloro-2'-deoxyadenosine(4291-63-8).msds
  • 方法一:2，6-二氯嘌呤(I)(0.95g，5mmo1)和氢化钠(50%分散油，0.25g，5.2mmo1)悬浮于35ml无水乙腈，在室温及氮气保护下搅拌30min。在搅拌下20min内分批加入1-氯-2-去氧-3，5-二-O-对甲苯甲酰基-α-D-赤式-呋喃戊糖(Ⅱ)(1.95g，5mmo1)。加毕，再搅拌15h。滤去少量不溶物，滤液浓缩。剩余的油状物经硅胶柱层析，用甲苯-丙酮(9：1，体积比)洗脱。得到的固体再用乙醇结晶，得1.60g化合物(Ⅲ)，收率59%，熔点159-162℃。 化合物(Ⅲ)(2.50g，4.6mmo1)溶于60ml饱和氨的甲醇溶液(0℃饱和)，在100℃搅拌5h。蒸发至干，剩余物经硅胶柱层析，用氯仿-甲醇(8：2，体积比)洗脱。再乙醇结晶，得0.87g克拉屈滨，收率71%，熔点220℃(软化)。
  • Cladribine是一种腺苷脱氨酶抑制剂，作用于U266， RPMI8226，和MM1.S细胞，IC50分别约为2.43 μM， 0.75 μM，和0.18 μM。
  • MOL 文件:4291-63-8.mol
  • 上游原料:三氯甲烷 --> 硅凝胶 --> 呋喃 --> 2,6-二氯嘌呤 --> 无水乙腈 --> 氢化钠50%

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. 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. 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. Deoxynucleosides&Deoxynucleotides and their Analogs
  1. Medical Research Areas
  2. Metabolism
  3. Adenosine Deaminase  (腺苷脱氨酶)

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