WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 100170
CAS#: 4291-63-8
Description: Cladribine is a purine nucleoside antimetabolite analogue. Cladribine triphosphate, a phosphorylated metabolite of cladribine, incorporates into DNA, resulting in single-strand breaks in DNA, depletion of nicotinamide adenine dinucleotide (NAD) and adenosine triphosphate (ATP), and apoptosis. Because this agent is resistant to adenosine deaminase, an enzyme that inactivates some antineoplastic agents, it is selectively toxic to lymphocytes and monocytes which exhibit little deoxynucleotide deaminase activity.
MedKoo Cat#: 100170
Name: Cladribine
CAS#: 4291-63-8
Chemical Formula: C10H12ClN5O3
Exact Mass: 285.06287
Molecular Weight: 285.69
Elemental Analysis: C, 42.04; H, 4.23; Cl, 12.41; N, 24.51; O, 16.80
Synonym: Cladribina. US brand name: Leustatin. Foreign brand names: Leustat; Leustatine. Abbreviations: 2CDA; 2CdA. Code name: RWJ26251. Chemical structure names: * 2chloro2deoxyadenosine; * 2chlorodeoxyadenosine.
IUPAC/Chemical Name: (2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol
InChi Key: PTOAARAWEBMLNO-KVQBGUIXSA-N
InChi Code: 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
SMILES Code: O[C@@H]1[C@@H](CO)O[C@@H](N2C=NC3=C(N)N=C(Cl)N=C23)C1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 285.69 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: El-Osta H, Janku F, Kurzrock R. Successful treatment of Castleman's disease with interleukin-1 receptor antagonist (Anakinra). Mol Cancer Ther. 2010 Jun;9(6):1485-8. Epub 2010 May 25. PubMed PMID: 20501803.
2: Sigal DS, Sharpe R, Burian C, Saven A. Very long-term eradication of minimal residual disease in patients with hairy cell leukemia after a single course of cladribine. Blood. 2010 Mar 11;115(10):1893-6. Epub 2010 Jan 7. PubMed PMID: 20056789.
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4: Grever MR, Zinzani PL. Long-term follow-up studies in hairy cell leukemia. Leuk Lymphoma. 2009 Oct;50 Suppl 1:23-6. Review. PubMed PMID: 19814694.
5: Arons E, Suntum T, Stetler-Stevenson M, Kreitman RJ. VH4-34+ hairy cell leukemia, a new variant with poor prognosis despite standard therapy. Blood. 2009 Nov 19;114(21):4687-95. Epub 2009 Sep 10. PubMed PMID: 19745070; PubMed Central PMCID: PMC2780305.
6: Spurgeon S, Yu M, Phillips JD, Epner EM. Cladribine: not just another purine analogue? Expert Opin Investig Drugs. 2009 Aug;18(8):1169-81. Review. PubMed PMID: 19604118.
7: Bosanquet AG, Richards SM, Wade R, Else M, Matutes E, Dyer MJ, Rassam SM, Durant J, Scadding SM, Raper SL, Dearden CE, Catovsky D. Drug cross-resistance and therapy-induced resistance in chronic lymphocytic leukaemia by an enhanced method of individualised tumour response testing. Br J Haematol. 2009 Aug;146(4):384-95. Epub 2009 Jun 22. PubMed PMID: 19552723.
8: Lech-Maranda E, Korycka A, Robak T. Clofarabine as a novel nucleoside analogue approved to treat patients with haematological malignancies: mechanism of action and clinical activity. Mini Rev Med Chem. 2009 Jun;9(7):805-12. Review. PubMed PMID: 19519505.
9: Larson ML, Venugopal P. Clofarabine: a new treatment option for patients with acute myeloid leukemia. Expert Opin Pharmacother. 2009 Jun;10(8):1353-7. Review. PubMed PMID: 19463072.
Cladribine (Leustatin) is a drug used to treat hairy cell leukemia (leukemic reticuloendotheliosis) and multiple sclerosis. Its chemical name is 2-chlorodeoxyadenosine (2CDA). As a purine analog, it is a synthetic anti-cancer agent that also suppresses the immune system. Chemically, it mimics the nucleoside adenosine and thus inhibits the enzyme adenosine deaminase, which interferes with the cell's ability to process DNA. It is easily destroyed by normal cells except for blood cells, with the result that it produces relatively few side effects and results in very little non-target cell loss.
Cladribine is indicated for the treatment of symptomatic hairy cell leukemia (HCL). It is under investigation for other B cell leukemias and lymphomas, such as mantle cell lymphoma,[2], and for use in the treatment of multiple sclerosis. In January 2010, a large clinical trial involving more than 1000 patients documented significant reduction in relapse rates in multiple sclerosis patients with use of oral cladribine and thus making its use as the first oral medication in multiple sclerosis patients, most likely in year [2011]. According to the Histiocytosis Association of America, cladribine is used to treat histiocytosis. See http://en.wikipedia.org/wiki/Cladribine.
DRUG DESCRIPTION
LEUSTATIN (cladribine) Injection (also commonly known as 2-chloro-2 -deoxy- β -D-adenosine) is a synthetic antineoplastic agent for continuous intravenous infusion. It is a clear, colorless, sterile, preservative-free, isotonic solution. LEUSTATIN Injection is available in single-use vials containing 10 mg (1 mg/mL) of cladribine, a chlorinated purine nucleoside analog. Each milliliter of LEUSTATIN Injection contains 1 mg of the active ingredient and 9 mg (0.15 mEq) of sodium chloride as an inactive ingredient. The solution has a pH range of 5.5 to 8.0. Phosphoric acid and/or dibasic sodium phosphate may have been added to adjust the pH to 6.3±0.3.
LEUSTATIN Injection is indicated for the treatment of active Hairy Cell Leukemia as defined by clinically significant anemia, neutropenia, thrombocytopenia or disease-related symptoms.
