Cladribine , ≥98% , 4291-63-8

Synonym(s):
2CdA, Cladribine;2-Chloro-2ʹ-deoxyadenosine - CAS 4291-63-8 - Calbiochem;2-Chloro-2′-deoxyadenosine;CdA;Cladribine

CAS NO.：4291-63-8

Empirical Formula: C10H12ClN5O3

Molecular Weight: 285.69

MDL number: MFCD00153939

EINECS: 636-978-6

PRODUCT Properties

• Melting point: 181-185 °C(lit.)
• alpha: D25 -18.8° (c = 1 in DMF)
• Boiling point: 547.6±60.0 °C(Predicted)
• Density: 2.03±0.1 g/cm3(Predicted)
• storage temp.: -20°C
• solubility: Slightly soluble in water, soluble in dimethyl sulfoxide, slightly soluble in methanol, practically insoluble in acetonitrile. It shows polymorphism (5.9).
• pka: 13.75±0.60(Predicted)
• form: White solid
• color: White to Pale Yellow
• λmax: 265nm(EtOH aq.)(lit.)
• Merck: 14,2337
• Stability: Store in Freezer
• InChIKey: PTOAARAWEBMLNO-HSUXUTPPSA-N
• CAS DataBase Reference: 4291-63-8(CAS DataBase Reference)

Description and Uses

Cladribine, an adenosine deaminase inhibitor, was introduced in the United States as a single intravenous treatment for hairy cell leukemia. The incorporation of a chlorine atom at the 2-position of deoxyadenosine renders cladribine more resistant to enzymatic attack by adenosine deaminase, resulting in a more prolonged cytotoxic effect. Cladribine efficiently crosses lymphocyte and monocyte cell membranes and is metabolized in cells to the biologically active triphosphate, which inhibits DNA synthesis. While most antineoplastic drugs are active primarily against dividing cells, cladribine destroys both resting and proliferating cells. Its potential uses in the treatment of autoimmune hemolytic anemia, multiple sclerosis, chronic lymphocytic leukemia and various lymphomas have also been evaluated.

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).

Safety

• Symbol(GHS): GHS06,GHS08
• Signal word: Danger
• Hazard statements: H301-H341-H361fd-H372
• Precautionary statements: P201-P202-P260-P264-P270-P301+P310
• Hazard Codes: T
• Risk Statements: 36/37/38-23/24/25
• Safety Statements: 26-37/39-45-36-22
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• RTECS: AU7357560
• HS Code: 29349990
• Hazardous Substances Data: 4291-63-8(Hazardous Substances Data)
• Toxicity: LD50 intraperitoneal in mouse: 150mg/kg