Welcome: Chemsynlab ,carbohydrate chemistry
Language: Chinese ∷  English

4291-63-8, Cladribine, CAS:4291-63-8

4291-63-8, Cladribine,
CAS:4291-63-8
C10H12ClN5O3 / 285.69
MFCD00153939

克拉屈滨, Cladribine

2-Chloro-2'-deoxyadenosine

Cladribine is a purine nucleoside analogue that interferes with DNA synthesis by acting as a false building block in the DNA chain during replication. Cladribine is incorporated into the growing DNA chain, causing chain termination and leading to DNA damage, apoptosis (programmed cell death), and ultimately cell death. Cladribine is structurally similar to adenosine, but is partially resistant to breakdown by adenosine deaminase due to a chlorine molecule at position 2. This causes it to accumulate in cells and interfere with the targeted cell's ability to process DNA. This mechanism of action makes cladribine an effective treatment for certain types of cancer and autoimmune diseases, where it targets rapidly dividing cells.

Cladribine is part of our Bio-X ™ Range. These products are aimed at life science researchers who need high quality ready to use products for assay development, screening or other R&D work. With a solubility datasheet and convenient vials, all of our Bio-X ™ products are in stock across our global warehouses for rapid delivery and ease of use.

Nucleoside analogue that induces DNA double-strand breaks. Adenosine deaminase inhibitor. Active in vivo and in vitro. Orally active.

Cladribine is an adenosine analog which shows selective cytotoxicity against both proliferating and non-dividing lymphocytes. Resistant to adenosine deaminase, cladribine is phosphorylated by deoxycytidine kinase, resulting in its intracellular accumulation and inhibition of ribonucleotide reductase. It inhibits lymphocyte growth with an IC50 value of 45 nM. The pharmacokinetics of clabridine in humans have been published. After only a single course of treatment, clabridine eradicates hairy cell leukemia. It has potential use in a variety of hematologic malignancies, but its use in treating multiple sclerosis is compromised by serious adverse events.

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. (NCI04)

Cladribine is a purine analogue and antineoplastic agent used primarily in the therapy of hairy cell leukemia. Cladribine is typically given intravenously daily for 7 days, usually as a single course, and has not been associated with serum enzyme elevations during therapy or with instances of clinically apparent acute liver injury with jaundice.

Cladribine, also known as leustatin or 2-cda, belongs to the class of organic compounds known as purine 2'-deoxyribonucleosides. Purine 2'-deoxyribonucleosides are compounds consisting of a purine linked to a ribose which lacks a hydroxyl group at position 2. Cladribine is a drug which is used 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. Cladribine exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Cladribine has been detected in multiple biofluids, such as urine and blood. Within the cell, cladribine is primarily located in the cytoplasm. Cladribine is a potentially toxic compound.

Title: Cladribine

CAS Registry Number: 4291-63-8

CAS Name: 2-Chloro-2'-deoxyadenosine

Additional Names: 2-chloro-6-amino-9-(2-deoxy-b-D-erythro-pentofuranosyl)purine; 2-chlorodeoxyadenosine; 2-CdA; CldAdo

Manufacturers' Codes: NSC-105014-F

Trademarks: Leustatin (Ortho Biotech)

Molecular Formula: C10H12ClN5O3

Molecular Weight: 285.69

Percent Composition: C 42.04%, H 4.23%, Cl 12.41%, N 24.51%, O 16.80%

Literature References: Substituted purine nucleoside with antileukemic activity. Prepn as intermediate in synthesis of 2-deoxynucleosides: H. Venner, Ber. 93, 140 (1960); M. Ikehara, H. Tada, J. Am. Chem. Soc. 85, 2344 (1963); eidem, ibid. 87, 606 (1965). Synthesis and biological activity: L. F. Christensen et al., J. Med. Chem. 15, 735 (1972). Stereospecific synthesis: Z. Kazimierczuk et al., J. Am. Chem. Soc. 106, 6379 (1984); R. K. Robins, G. R. Revankar, EP 173059; eidem, US 4760137 (1986, 1988 both to Brigham Young Univ.). Specific toxicity to lymphocytes: D. A. Carson et al., Proc. Natl. Acad. Sci. USA 77, 6865 (1980); eidem, Blood 62, 737 (1983). Mechanism of action: S. Seto et al., J. Clin. Invest. 75, 377 (1985). Clinical evaluation in chronic lymphocytic leukemia: L. D. Piro et al., Blood 72, 1069 (1988); in hairy cell leukemia: eidem, N. Engl. J. Med. 322, 1117 (1990).

Properties: Crystals from water, softens at 210-215°, solidifies and turns brown (Christensen). Also reported as crystals from ethanol, mp 220° (softens), resolidifies, turns brown and does not melt below 300° (Kazimierczuk). [a]D25 -18.8° (c = 1 in DMF). uv max in 0.1N NaOH: 265 nm; in 0.1N HCl: 265 nm.

Melting point: mp 220° (softens), resolidifies, turns brown and does not melt below 300°

Optical Rotation: [a]D25 -18.8° (c = 1 in DMF)

Absorption maximum: uv max in 0.1N NaOH: 265 nm; in 0.1N HCl: 265 nm

Therap-Cat: Antineoplastic.

Keywords: Antineoplastic; Antimetabolites; Purine Analogs.

CAS Number4291-63-8
Product NameCladribine
IUPAC Name5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
Molecular FormulaC10H12ClN5O3
Molecular Weight285.69 g/mol
InChIInChI=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)
InChI KeyPTOAARAWEBMLNO-KVQBGUIXSA-N
SMILESC1C(C(OC1N2C=NC3=C(N=C(N=C32)Cl)N)CO)O
SolubilityIn water, 1X10+6 mg/L at 25 °C (est)
6.35e+00 g/L
SynonymsCladribina. US brand name: Leustatin. Foreign brand names: Leustat; Leustatine. Abbreviations: 2CDA; 2CdA. Code name: RWJ26251. Chemical structure names: * 2chloro2deoxyadenosine; * 2chlorodeoxyadenosine.
Canonical SMILESC1C(C(OC1N2C=NC3=C(N=C(N=C32)Cl)N)CO)O
Isomeric SMILESC1[C@@H]([C@H](O[C@H]1N2C=NC3=C(N=C(N=C32)Cl)N)CO)O
CAS No: 4291-63-8 Synonyms: CladribineLeustatin9-(2-Deoxy-b-D-ribofuranosyl)-2-chloroadenine2-Chloro-2'-deoxy-D-adenosine MDL No: MFCD00153939 Chemical Formula: C10H12ClN5O3 Molecular Weight: 285.69
References: 1. Kazimierczuk Z, Cottam HB, Revankar GR, et al., J. Am. Chem. Soc. 1984, 106, p63792. Set S, et al, J. Clin. Invest. 1985, 75, p3773. Piro LD, et al, N. Engl. J. Med 1990, 322, p1117


INQUIRY

Scan the qr codeClose
the qr code