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C4438

Sigma-Aldrich

2-Chloro-2′-deoxyadenosine

antileukemic

Sinónimos:

CdA, Cladribine

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10 MG
MXP 6,867.00
25 MG
MXP 13,777.00

MXP 6,867.00

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10 MG
MXP 6,867.00
25 MG
MXP 13,777.00

About This Item

Fórmula empírica (notación de Hill):
C10H12ClN5O3
Número de CAS:
4291-63-8
Peso molecular:
285.69
Número MDL:
MFCD00153939
Código UNSPSC:
41106305
ID de la sustancia en PubChem:
24892693
NACRES:
NA.51

MXP 6,867.00

Check Cart for Availability

Nivel de calidad

200

Ensayo

≥98% (HPLC)

Formulario

powder or crystals

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

PTOAARAWEBMLNO-KVQBGUIXSA-N

Información sobre el gen

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

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Aplicación

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.

Acciones bioquímicas o fisiológicas

Deoxyadenosine analog resistant to adenosine deaminase; antileukemic with immunosuppressive activity

Pictogramas

Skull and crossbonesHealth hazard
GHS06,GHS08

Palabra de señalización

Danger

Frases de peligro

H301,H341,H361fd,H372

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
0000160877
0000160877
0000160887
0000128104

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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
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
Joshua D Rosenberg et al.
Blood, 123(2), 177-183 (2013-11-07)
Hairy cell leukemia (HCL) is a rare, indolent B-cell disorder in which single courses of cladribine induce high rates of complete responses. We report on 88 young HCL patients (≤40 years of age at diagnosis) treated with cladribine from the
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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