Cladribine | CAS#4291-63-8 | antimetabolite analogue

MedKoo Cat#: 100170 | Name: Cladribine

Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Cladribine

CAS#4291-63-8

Theoretical Analysis

MedKoo Cat#: 100170

Name: Cladribine

CAS#: 4291-63-8

Chemical Formula: C10H12ClN5O3

Exact Mass: 285.0629

Molecular Weight: 285.69

Elemental Analysis: C, 42.04; H, 4.23; Cl, 12.41; N, 24.51; O, 16.80

Price and Availability

Size	Price	Availability
100mg	USD 350.00	2 Weeks
250mg	USD 650.00	2 Weeks
500mg	USD 950.00	2 Weeks
1g	USD 1,450.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Cladribina; 2-Chlorodeoxyadenosine; Jk 6251; Jk6251; Jk-6251; NSC 105014; NSC105014; NSC-105014; RWJ 26251; RWJ26251; RWJ-26251; Leustatin; 2-CDA

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

More Info

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 6.3Â±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.

Instruction

View handling instruction

Preparing Stock Solutions

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: Deeks ED. Cladribine Tablets: A Review in Relapsing MS. CNS Drugs. 2018 Aug;32(8):785-796. doi: 10.1007/s40263-018-0562-0. Erratum in: CNS Drugs. 2019 Feb;33(2):193. PMID: 30105527; PMCID: PMC6353806. 2: Hermann R, Krajcsi P, Fluck M, Seithel-Keuth A, Bytyqi A, Galazka A, Munafo A. Cladribine as a Potential Object of Nucleoside Transporter-Based Drug Interactions. Clin Pharmacokinet. 2022 Feb;61(2):167-187. doi: 10.1007/s40262-021-01089-9. Epub 2021 Dec 11. PMID: 34894346; PMCID: PMC8813788. 3: Chihara D, Arons E, Stetler-Stevenson M, Yuan CM, Wang HW, Zhou H, Raffeld M, Xi L, Steinberg SM, Feurtado J, James L, Wilson W, Braylan RC, Calvo KR, Maric I, Dulau-Florea A, Kreitman RJ. Randomized Phase II Study of First-Line Cladribine With Concurrent or Delayed Rituximab in Patients With Hairy Cell Leukemia. J Clin Oncol. 2020 May 10;38(14):1527-1538. doi: 10.1200/JCO.19.02250. Epub 2020 Feb 28. PMID: 32109194; PMCID: PMC7213585. 4: Giovannoni G, Comi G, Cook S, Rammohan K, Rieckmann P, Soelberg Sørensen P, Vermersch P, Chang P, Hamlett A, Musch B, Greenberg SJ; CLARITY Study Group. A placebo-controlled trial of oral cladribine for relapsing multiple sclerosis. N Engl J Med. 2010 Feb 4;362(5):416-26. doi: 10.1056/NEJMoa0902533. Epub 2010 Jan 20. PMID: 20089960. 5: Cladribine (Mavenclad) for multiple sclerosis. Med Lett Drugs Ther. 2019 Jul 29;61(1577):118-120. PMID: 31381552. 6: Beutler E. Cladribine (2-chlorodeoxyadenosine). Lancet. 1992 Oct 17;340(8825):952-6. doi: 10.1016/0140-6736(92)92826-2. PMID: 1357355. 7: Jacobs BM, Ammoscato F, Giovannoni G, Baker D, Schmierer K. Cladribine: mechanisms and mysteries in multiple sclerosis. J Neurol Neurosurg Psychiatry. 2018 Dec;89(12):1266-1271. doi: 10.1136/jnnp-2017-317411. Epub 2018 Jul 10. PMID: 29991490. 8: Spurgeon S, Yu M, Phillips JD, Epner EM. Cladribine: not just another purine analogue? Expert Opin Investig Drugs. 2009 Aug;18(8):1169-81. doi: 10.1517/13543780903071038. PMID: 19604118. 9: Giovannoni G. Cladribine to Treat Relapsing Forms of Multiple Sclerosis. Neurotherapeutics. 2017 Oct;14(4):874-887. doi: 10.1007/s13311-017-0573-4. PMID: 29168160; PMCID: PMC5722776. 10: Qasrawi A, Bahaj W, Qasrawi L, Abughanimeh O, Foxworth J, Gaur R. Cladribine in the remission induction of adult acute myeloid leukemia: where do we stand? Ann Hematol. 2019 Mar;98(3):561-579. doi: 10.1007/s00277-018-3562-8. Epub 2018 Nov 23. PMID: 30470874. 11: Lambe T, Duarte R, Mahon J, Nevitt S, Greenhalgh J, Boland A, Beale S, Kotas E, McEntee J, Pomeroy I. Cladribine Tablets for the First-Line Treatment of Relapsing-Remitting Multiple Sclerosis: An Evidence Review Group Perspective of a NICE Single Technology Appraisal. Pharmacoeconomics. 2019 Mar;37(3):345-357. doi: 10.1007/s40273-018-0718-2. PMID: 30328051; PMCID: PMC6380198. 12: Sigal DS, Saven A. Cladribine in indolent non-Hodgkin's lymphoma. Expert Rev Anticancer Ther. 2008 Apr;8(4):535-45. doi: 10.1586/14737140.8.4.535. PMID: 18402520. 13: Moser T, Ziemssen T, Sellner J. Real-world evidence for cladribine tablets in multiple sclerosis: further insights into efficacy and safety. Wien Med Wochenschr. 2022 Nov;172(15-16):365-372. doi: 10.1007/s10354-022-00931-4. Epub 2022 Apr 22. PMID: 35451662; PMCID: PMC9026047. 14: Brownlee WJ. Cladribine-induced liver injury: Implications for practice. Mult Scler. 2022 Nov;28(13):2146. doi: 10.1177/13524585221125370. Epub 2022 Sep 28. PMID: 36169282. 15: Rammohan K, Coyle PK, Sylvester E, Galazka A, Dangond F, Grosso M, Leist TP. The Development of Cladribine Tablets for the Treatment of Multiple Sclerosis: A Comprehensive Review. Drugs. 2020 Dec;80(18):1901-1928. doi: 10.1007/s40265-020-01422-9. PMID: 33247831; PMCID: PMC7708385. 16: Baltz JK, Montello MJ. Cladribine for the treatment of hematologic malignancies. Clin Pharm. 1993 Nov;12(11):805-13; quiz 860-2. PMID: 7903917. 17: Hermann R, Krajcsi P, Fluck M, Seithel-Keuth A, Bytyqi A, Galazka A, Munafo A. Review of Transporter Substrate, Inhibitor, and Inducer Characteristics of Cladribine. Clin Pharmacokinet. 2021 Dec;60(12):1509-1535. doi: 10.1007/s40262-021-01065-3. Epub 2021 Aug 26. PMID: 34435310; PMCID: PMC8613159. 18: Brousil JA, Roberts RJ, Schlein AL. Cladribine: an investigational immunomodulatory agent for multiple sclerosis. Ann Pharmacother. 2006 Oct;40(10):1814-21. doi: 10.1345/aph.1H037. Epub 2006 Sep 19. PMID: 16985095. 19: Sipe JC. Cladribine for multiple sclerosis: review and current status. Expert Rev Neurother. 2005 Nov;5(6):721-7. doi: 10.1586/14737175.5.6.721. PMID: 16274330. 20: Biernacki T, Sandi D, Bencsik K, Vécsei L. Medicinal Chemistry of Multiple Sclerosis: Focus on Cladribine. Mini Rev Med Chem. 2020;20(4):269-285. doi: 10.2174/1389557519666191015201755. PMID: 31644403.

View History

Clamikalant monosodium