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C4438 Sigma-Aldrich

2-Chloro-2′-deoxyadenosine

antileukemic

Synonym: CdA, Cladribine

  • CAS Number 4291-63-8

  • Empirical Formula (Hill Notation) C10H12ClN5O3

  • Molecular Weight 285.69

  •  MDL number MFCD00153939

  •  PubChem Substance ID 24892693

  •  NACRES NA.51

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Properties

Related Categories Biochemicals and Reagents, Nucleoside Analogs, Nucleosides, Nucleotides, Oligonucleotides More...
Quality Level   200
assay   ≥98% (TLC)
form   powder
solubility   methanol: water: 9.80-10.20 mg/mL, clear, colorless to faintly yellow (8/2 heating)
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)

Description

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.

Packaging

10 mg in poly bottle

25 mg in glass bottle

Biochem/physiol Actions

Deoxyadenosine analog resistant to adenosine deaminase; antileukemic with immunosuppressive activity

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
AU7357560
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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