CAS 4291-63-8 MFCD00153939-Cladribine 克拉屈滨 TAO{mole}

Cladribine 克拉屈滨

CAS 4291-63-8 MFCD00153939

化学结构图

SMILES: Nc1nc(Cl)nc2c1ncn2C1CC(O)C(CO)O1

化学属性

Mol. Formula	C10H12ClN5O3
Mol. Weight	285.69
Density	1.422
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 Point	181-185°C
Solubility	Soluble in DMSO ( ≥57 mg/ml), water (<1 mg/ml), ethanol (<1 mg/ml), and methanol.
Stability	对热敏感
Boiling Point	387.1°C at 760 mmHg

别名和识别编码

Chemical Name	Cladribine
CAS Number	4291-63-8
Alfabeta Name	CHLORODEOXYADENOSINE 22---'
MDL Number	MFCD00153939
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 Number	250-023-7
Beilstein Registry Number	624220
PubChem Substance ID	20279
Reaxys-RN	624220
Merck Number	2337
Chemical Name Translation	克拉屈滨
LabNetwork Molecule ID	LN00173627
InChI	InChI=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 SMILES	OC[C@@H]1[C@@H](O)C[C@H](N2C=NC3=C2N=C(Cl)N=C3N)O1

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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).

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%