Cladribine
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
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-04-28 16:56:32
What is Cladribine?
Absorption
Oral bioavailability is 34 to 48%.
Toxicity
Symptoms of overdose include irreversible neurologic toxicity (paraparesis/quadriparesis), acute nephrotoxicity, and severe bone marrow suppression resulting in neutropenia, anemia and thrombocytopenia.
Description
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.
The Uses of Cladribine
It is a substituted purine nucleoside with antileukemic activity
Indications
For the treatment of active hairy cell leukemia (leukemic reticuloendotheliosis) as defined by clinically significant anemia, neutropenia, thrombocytopenia, or disease-related symptoms. Also used as an alternative agent for the treatment of chronic lymphocytic leukemia (CLL), low-grade non-Hodgkin's lymphoma, and cutaneous T-cell lymphoma.
Background
An antineoplastic agent used in the treatment of lymphoproliferative diseases including hairy-cell leukemia.
What are the applications of Application
2-Chloro-2′-deoxyadenosine is an apoptosis inducer
Pharmacokinetics
Cladribine is a synthetic purine nucleoside that acts as an antineoplastic agent with immunosuppressive effects. Cladribine differs structurally from deoxyadenosine only by the presence of a chlorine atom at position 2 of the purine ring, which results in resistance to enzymatic degradation by adenosine deaminase. Due to this resistance, cladribine exhibits a more prolonged cytotoxic effect than deoxyadenosine against resting and proliferating lymphocytes. Cladribine is one of a group of chemotherapy drugs known as the anti-metabolites.?Anti-metabolites stop cells from making and repairing DNA, which are processes that are necessary for cancer cells to grow and multiply.
Metabolism
Metabolized in all cells with deoxycytidine kinase activity to 2-chloro-2'-deoxyadenosine-5'-triphosphate
Properties of Cladribine
Melting point: | 181-185 °C(lit.) |
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). |
form | White solid |
color | White to Pale Yellow |
Safety information for Cladribine
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 Health Hazard GHS08 |
GHS Hazard Statements |
H301:Acute toxicity,oral H341:Germ cell mutagenicity H372:Specific target organ toxicity, repeated exposure |
Precautionary Statement Codes |
P201:Obtain special instructions before use. P202:Do not handle until all safety precautions have been read and understood. P260:Do not breathe dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
Computed Descriptors for Cladribine
InChIKey | PTOAARAWEBMLNO-HSUXUTPPSA-N |
Abamectin manufacturer
Biophore India Pharmaceuticals Pvt Ltd
Mac Chem Products (India) Pvt Ltd (Naprod Group)
Aspen Biopharma Labs Pvt Ltd
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