C4438

2-Chloro-2′-deoxyadenosine

antileukemic

• Synonym(s): CdA, Cladribine
• Empirical Formula (Hill Notation): C₁₀H₁₂ClN₅O₃
• CAS Number: 4291-63-8
• Molecular Weight: 285.69
• NACRES: NA.51
• PubChem Substance ID: 24892693
• UNSPSC Code: 41106305
• MDL number: MFCD00153939
• Assay: ≥98% (HPLC)
• Form: powder or crystals
• Storage temp.: 2-8°C

Properties

• Quality Segment: 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)

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.

Biochem/physiol Actions

Deoxyadenosine analog resistant to adenosine deaminase; antileukemic with immunosuppressive activity

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H301,H341,H361fd,H372
• pcodes: P202 - P260 - P264 - P280 - P301 + P310 - P405
• Hazard Classifications: Acute Tox. 3 Oral - Muta. 2 - Repr. 2 - STOT RE 1
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges