2-Chloro-2′-deoxyadenosine

• Catalog No.: C4438
• CAS Number: 4291-63-8
• M. F.: C10H12ClN5O3
• M. W.: 285.68698

SYNONYMS

• IUPAC name: (2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• IUPAC Traditional name: cladribine
• Synonyms: cladribine; CdA

DATABASE IDS

• CAS Number: 4291-63-8
• PubChem SID: 24892693
• MDL Number: MFCD00153939

PROPERTIES

• Gene Information: human ... NP(4860)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335
• European Hazard Symbols: Toxic (T)
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Risk Statements: 23/24/25-36/37/38
• RTECS: AU7357560
• Safety Statements: 22-26-36-45
• Storage Temperature: 2-8°C
• German water hazard class: 3

DETAILS

Description (English)

Biochem/physiol Actions
Deoxyadenosine analog resistant to adenosine deaminase; antileukemic with immunosuppressive activity
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.