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C4438

Sigma-Aldrich

2-Chloro-2′-deoxyadenosine

antileukemic

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Synonym(s):
CdA, Cladribine
Empirical Formula (Hill Notation):
C10H12ClN5O3
CAS Number:
4291-63-8
Molecular Weight:
285.69
MDL number:
MFCD00153939
UNSPSC Code:
41106305
PubChem Substance ID:
24892693
NACRES:
NA.51

Quality Level

200

Assay

≥98% (HPLC)

form

powder or crystals

storage temp.

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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Application

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.

Biochem/physiol Actions

Deoxyadenosine analog resistant to adenosine deaminase; antileukemic with immunosuppressive activity

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H341,H361fd,H372

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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
Tomasz Bączek et al.
Journal of pharmaceutical and biomedical analysis, 70, 330-336 (2012-06-05)
Individualization of the topotecan dosing can reduce inter-patient variability, toxicity, and at the same time increases chemotherapy efficacy. Topotecan dosing based on simultaneous drug monitoring and pharmacokinetic analysis can yield more accurate and precise estimation of the topotecan systemic exposure
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
Philippa L Kohnke et al.
Journal of proteome research, 11(9), 4436-4448 (2012-07-31)
Fludarabine and cladribine are purine analogues used to treat hematological malignancies. Alone or in combination with therapeutic antibodies, they are effective in treating patients with chronic lymphocytic leukemia and non-Hodgkin's lymphoma. However, the mechanisms of action of these drugs are
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