Merck
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文件

安全信息

C4438

Sigma-Aldrich

2-氯-2′-脱氧腺苷

antileukemic

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别名:
CdA, Cladribine
经验公式（希尔记法）:
C10H12ClN5O3
CAS号:
4291-63-8
分子量:
285.69
MDL编号:
MFCD00153939
PubChem化学物质编号:
24892693
NACRES:
NA.51

质量水平

200

检测方案

≥98% (HPLC)

形式

powder or crystals

储存温度

2-8°C

SMILES string

Nc1nc(Cl)nc2n(cnc12)[C@H]3C[C@H](O)[C@@H](CO)O3

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

InChI key

PTOAARAWEBMLNO-KVQBGUIXSA-N

Gene Information

human ... NP(4860)
rat ... Adora1(29290) , Adora2a(25369) , Adora3(25370)

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应用

2-Chloro-2′-deoxyadenosine (2-CdA) 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).
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). Clinically used for treatment of hairy cell leukemia, chronic lymphocytic leukemia and other indolent leukemias.

生化/生理作用

Deoxyadenosine analog resistant to adenosine deaminase; antileukemic with immunosuppressive activity

象形图

Skull and crossbonesHealth hazard
GHS06,GHS08

警示用语：

Danger

危险分类

Acute Tox. 3 Oral - Muta. 2 - Repr. 2 - STOT RE 1

储存分类代码

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

法规信息

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L Bastin-Coyette et al.
Biochemical pharmacology, 81(5), 586-593 (2010-12-21)
Nucleoside analogs (NAs) represent an important class of anticancer agents that induce cell death after conversion to triphosphate derivatives. One of their most important mechanisms of action is the activation of p53, leading to apoptosis through the intrinsic pathway. Classically
D A Carson et al.
Proceedings of the National Academy of Sciences of the United States of America, 81(7), 2232-2236 (1984-04-01)
The adenosine deaminase-resistant purine deoxynucleoside 2-chloro-2'-deoxyadenosine (CdA) is markedly toxic in vitro to nondividing and proliferating normal human lymphocytes and to many leukemia cell specimens. The CdA is also effective against mouse L1210 leukemia in vivo. The present investigations have
H M Bryson et al.
Drugs, 46(5), 872-894 (1993-11-01)
Cladribine (2-chloro-2'-deoxyadenosine) is an adenosine deaminase-resistant analogue of deoxyadenosine. In the treatment of hairy cell leukaemia, cladribine has demonstrated excellent efficacy (complete response in 33 to 92% of patients) in noncomparative studies. Cladribine appears to compare favourably with other systemic
V Gandhi et al.
Blood, 87(1), 256-264 (1996-01-01)
The effectiveness of arabinosylcytosine (ara-C) for the treatment of acute myelogenous leukemia (AML) depends on the formation of its active metabolite, the triphosphate of ara-C (ara-CTP). Using biochemical modulation strategies to increase the accumulation of ara-CTP in leukemia blasts, a
Tadeusz Robak et al.
Molecules (Basel, Switzerland), 14(3), 1183-1226 (2009-03-28)
For the past few years more and more new cytotoxic agents active in the treatment of hematological malignancies have been synthesized and become available for either in vitro studies or clinical trials. Among them the class of antineoplastic drugs belonging
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