ChemicalBook > Product Catalog >Biochemical Engineering >Nucleoside drugs >Deoxynucleotides and their analogs >Cladribine

Cladribine

Cladribine Structure
CAS No.
4291-63-8
Chemical Name:
Cladribine
Synonyms
CDA;Leustat;(2R,3S,5R)-5-(6-aMino-2-chloro-9H-purin-9-yl)-2-(hydroxyMethyl)tetrahydrofuran-3-ol;2CDA;CldAdo;2-Cl-dA;Jk 6251;CS-1392;rwj26251;Leustati
CBNumber:
CB4222723
Molecular Formula:
C10H12ClN5O3
Molecular Weight:
285.69
MOL File:
4291-63-8.mol
Modify Date:
2024/7/26 17:49:17

Cladribine 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)

SAFETY

Risk and Safety Statements

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
Toxicity LD50 intraperitoneal in mouse: 150mg/kg
NFPA 704
0
4 0

Cladribine price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) C4438 2-Chloro-2′-deoxyadenosine antileukemic 4291-63-8 10MG ₹25265.55 2022-06-14 Buy
Sigma-Aldrich(India) C4438 2-Chloro-2′-deoxyadenosine antileukemic 4291-63-8 25MG ₹57036.93 2022-06-14 Buy
Sigma-Aldrich(India) 220467 2-Chloro-2ʹ-deoxyadenosine - CAS 4291-63-8 - Calbiochem A deoxyadenosine analog that displays strong antileukemic and immunosuppressive activity. 4291-63-8 10MG ₹8210 2022-06-14 Buy
TCI Chemicals (India) C2499 Cladribine 4291-63-8 50MG ₹19800 2022-05-26 Buy
Product number Packaging Price Buy
C4438 10MG ₹25265.55 Buy
C4438 25MG ₹57036.93 Buy
220467 10MG ₹8210 Buy
C2499 50MG ₹19800 Buy

Cladribine Chemical Properties,Uses,Production

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.

Chemical Properties

White Crystalline Solid

Uses

It is a substituted purine nucleoside with antileukemic activity

Indications

Cladribine (Leustatin) is a synthetic purine nucleoside that is converted to an active cytotoxic metabolite by the enzyme deoxycytidine kinase. Like the other purine antimetabolites, it is relatively selective for both normal and malignant lymphoid cells and kills resting as well as dividing cells by mechanisms that are not completely understood.
The drug is highly active against hairy cell leukemia, producing complete remissions in more than 60% of patients treated with a single 7-day course. Activity has also been noted in other low-grade lymphoid malignancies. The major side effect is myelosuppression.

Definition

ChEBI: 2'-Deoxyadenosine in which the hydrogen at position 2 on the purine ring has been substituted by chlorine. It inhibits the synthesis and repair of DNA, particularly in lymphocytes and monocytes, and is used as an antimetabolite antineoplastic drug for the treatment of lymphoid malignancies including hairy-cell leukaemia and chronic lymphocytic leukaemia.

General Description

The drug is available in a 10-mg or 10-mL single-use vialfor IV use. Cladribine is used for chronic lymphocyticleukemia, hairy cell leukemia, and non-Hodgkin’s lymphoma.The mechanism of action of this purine deoxyadenosineanalog involves incorporation into DNA resultingin inhibition of DNA chain extension and inhibitionof DNA synthesis and function. This incorporation intoDNA occurs via the triphosphate metabolite active species.The 2-chloro group on the adenine ring produces resistanceto breakdown by adenosine deaminase. Resistance to the anticancereffects can occur because of decreased expressionof the activating enzyme or overexpression of the catabolicenzymes. Oral bioavailability is variable and averages about50%. The drug crosses the blood-brain barrier; however,CSF concentrations reach only 25% of those in plasma. Thedrug is selectively activated inside the cell, and intracellularconcentrations of phosphorylated metabolites exceed thosein plasma. Toxicities include myelosuppression, neutropenia,immunosuppression, fever, nausea, and vomiting.

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Cladribine Spectrum

2-chlorodeoxyadenosine Biodribin Cladarabine Jk 6251 NSC 105014 (2R,3S,5R)-5-(6-aMino-2-chloro-9H-purin-9-yl)-2-(hydroxyMethyl)oxolan-3-ol Cladribine API 2-Chloro-2'-deoxyadenosine 2-Chloro-9-(2-deoxy-beta-D-arabinofuranosyl)adenine CdA 2-Cl-dA (2R,3S,5R)-5-(6-Amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxalan-3-ol 2-Chloro-2′-deoxyadenosine, >=99% leustatin nsc105014-f rwj26251 2'-Deoxy-2-chloroadenosine 2-CHLORO-2'-DEOXY-D-ADENOSINE Leustati Adenosine, 2-chloro-2'-deoxy- CLADRIBINE [2-CHLORO-2''-DEOXYADENOSINE] CldAdo NSC-105014-F:Leustatin 2-CHLORO-2''-DEOXYADENOSINE (CDA: CLADRIBINE) Cladribine(Base) CdA, Cladribine 2-CHLORO-2'-DEOXYADENOSINE 2CDA 2-CL-DADO CLADRIBINE CLADRIBINE CDA LABOTEST-BB LT01147851 2-Chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine 6-Amino-2-chloro-9-(2-deoxy-β-D-arabinofuranosyl)-9H-purine Cladrivine 9-(2-Deoxy-β-D-ribofuranosyl)-2-chloro-adenine 2-Chloro-2'-cladribine Cladribine (200 mg) 2-chloro-2’-deoxy-adenosin CS-1392 2-Chloro-2-deoxyadenosine - CAS 4291-63-8 - Calbiochem Cladribine/2-Cl-deoxyadenosine Cladribine > Cladribine for peak identification CRS Cladribine CRS 2-Chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)-9H-purin-6-amine 2-Chloro-2’-deoxyadenosine, Cladribine 2-Chloro-9-(2-deoxy-beta-D-arabinofuranosyl)adenine Cladribine USP/EP/BP 2-Cl-deoxyadenosine Cladribine (1134200) Leustat (2R,3S,5R)-5-(6-aMino-2-chloro-9H-purin-9-yl)-2-(hydroxyMethyl)tetrahydrofuran-3-ol CDA Carat QuBin 2-hydroxypropane-1,2,3-tricarboxylicacidmonohydrate Clathrobin Cladribine (RWJ 26251) Cladribine-D4 4291-63-8