Home Halogens (2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol

CAS No.:
4291-63-8
Catalog Number:
AG003P0J
Molecular Formula:
C10H12ClN5O3
Molecular Weight:
285.6870
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
100mg
98%
In Stock USA
United States
$138
- +
250mg
98%
In Stock USA
United States
$250
- +
1g
98%
In Stock USA
United States
$675
- +
Product Description
Catalog Number:
AG003P0J
Chemical Name:
(2R,3S,5R)-5-(6-amino-2-chloro-9H-purin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
CAS Number:
4291-63-8
Molecular Formula:
C10H12ClN5O3
Molecular Weight:
285.6870
MDL Number:
MFCD00153939
IUPAC Name:
(2R,3S,5R)-5-(6-amino-2-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
InChI:
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
InChI Key:
PTOAARAWEBMLNO-KVQBGUIXSA-N
SMILES:
OCC1OC(CC1O)n1cnc2c1nc(Cl)nc2N
UNII:
47M74X9YT5
Properties
Complexity:
338  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
285.063g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
285.688g/mol
Monoisotopic Mass:
285.063g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
119A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.8  
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Compared benefit of approved and experimental immunosuppressive therapeutic approaches in multiple sclerosis. Expert opinion on pharmacotherapy 20070601
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Membrane localization and pH-dependent transport of a newly cloned organic cation transporter (PMAT) in kidney cells. American journal of physiology. Renal physiology 20070201
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The multicenter trial SAKK 37/95 of cladribine, cyclophosphamide and prednisone in the treatment of chronic lymphocytic leukemias and low-grade non-Hodgkin's lymphomas. Acta haematologica 20070101
Langerhans cell histiocytosis of vulva in adolescent. International journal of gynecological cancer : official journal of the International Gynecological Cancer Society 20070101
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Effects of drug combinations on smooth muscle cell proliferation: an isobolographic analysis. European journal of pharmacology 20060217
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A comparison of the transportability, and its role in cytotoxicity, of clofarabine, cladribine, and fludarabine by recombinant human nucleoside transporters produced in three model expression systems. Molecular pharmacology 20060101
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PRIMA-1 induces apoptosis in acute myeloid leukaemia cells with p53 gene deletion. British journal of haematology 20060101
Early-onset autoimmune hemolytic anemia after cladribine therapy for Waldenström's macroglobulinemia. Transfusion 20060101
Hairy cell leukemia: a diagnosis by endoscopic ultrasound guided fine needle aspiration. CytoJournal 20060101
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The relation between deoxycytidine kinase activity and the radiosensitising effect of gemcitabine in eight different human tumour cell lines. BMC cancer 20060101
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Study of the efficacy of a pronucleotide of 2-chloro-2'-deoxyadenosine in deoxycytidine kinase-deficient lymphoma cells. Nucleosides, nucleotides & nucleic acids 20060101
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Asymmetries in the spatial distributions of enhancing lesions and black holes in relapsing-remitting MS. Journal of clinical neuroscience : official journal of the Neurosurgical Society of Australasia 20051101
Drug therapy for the treatment of Langerhans cell histiocytosis. Expert opinion on pharmacotherapy 20051101
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High activity and incomplete cross resistance of nucleoside analogues cladribine and fludarabine versus Ara-C on leukemic cells from patients with AML. Therapeutic drug monitoring 20051001
Comparison of cladribine plus prednisone with chlorambucil plus prednisone in patients with chronic lymphocytic leukemia. Final report of the Polish Adult Leukemia Group (PALG CLL1). Medical science monitor : international medical journal of experimental and clinical research 20051001
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Quantitation of synergism of arabinosylcytosine and cladribine against the growth of arabinosylcytosine-resistant human lymphoid cells. Journal of cancer research and clinical oncology 20050901
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Merkel cell carcinoma in a patient with B-cell chronic lymphocytic leukemia treated with cladribine and rituximab. Leukemia & lymphoma 20050601
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Therapy of chronic lymphocytic leukemia with purine analogs and monoclonal antibodies. Transfusion and apheresis science : official journal of the World Apheresis Association : official journal of the European Society for Haemapheresis 20050201
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Application of population pharmacokinetics to cladribine. BMC pharmacology 20050101
Primary progressive multiple sclerosis : current and future treatment options. CNS drugs 20050101
Cytotoxic effects of cladribine and tezacitabine toward HL-60. Acta biochimica Polonica 20050101
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Efficient chemo-enzymatic syntheses of pharmaceutically useful unnatural 2'-deoxynucleosides. Nucleosides, nucleotides & nucleic acids 20050101
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The influence of farnesyl protein transferase inhibitor R115777 (Zarnestra) alone and in combination with purine nucleoside analogs on acute myeloid leukemia progenitors in vitro. European journal of haematology 20041201
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[nhibitory effect of adenosine analogues on invasion of human ovarian cancer cell line HO-8910PM]. Ai zheng = Aizheng = Chinese journal of cancer 20041201
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Electrophysiological characterization of a recombinant human Na+-coupled nucleoside transporter (hCNT1) produced in Xenopus oocytes. The Journal of physiology 20040801
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Treatment of advanced mycosis fungoides/Sézary syndrome with fludarabine and potential adjunctive benefit to subsequent extracorporeal photochemotherapy. The British journal of dermatology 20040201
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Evidence-based evaluation of immunomodulatory therapy for the cutaneous manifestations of lupus. Advances in dermatology 20040101
The influence of 2-chlorodeoxyadenosine (2-CdA) on the adenine energy charge and glutathione content of human erythrocytes. Cell biology international 20040101
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Histomorphometry of nuclei of proximal convoluted tubules epithelium of kidney of experimental animals after Cladribine (2-CdA) administration. Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20040101
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The ultrastructure of kidney renal corpuscles of experimental animals after Cladribine (2-CdA) administration. Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20040101
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Cutaneous reactions in hairy cell leukaemia treated with 2-chlorodeoxyadenosine and allopurinol. British journal of haematology 20030901
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Phase 2 study of rituximab in the treatment of cladribine-failed patients with hairy cell leukemia. Blood 20030801
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Functional expression and characterization of a sodium-dependent nucleoside transporter hCNT2 cloned from human duodenum. Biochemical and biophysical research communications 20030801
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Increased sensitivity to gemcitabine of P-glycoprotein and multidrug resistance-associated protein-overexpressing human cancer cell lines. British journal of cancer 20030616
A key role for caspase-2 and caspase-3 in the apoptosis induced by 2-chloro-2'-deoxy-adenosine (cladribine) and 2-chloro-adenosine in human astrocytoma cells. Molecular pharmacology 20030601
Doxorubicin-resistant, MRP1-expressing U-1285 cells are sensitive to idarubicin. Therapeutic drug monitoring 20030601
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Gastrointestinal involvement in disseminated Langerhans cell histiocytosis (LCH) with durable complete response to 2-chlorodeoxyadenosine and high-dose cytarabine. Journal of pediatric hematology/oncology 20030601
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Effect of gamma-irradiation on cladribine and cladribine-containing biodegradable copolymers. Journal of controlled release : official journal of the Controlled Release Society 20030520
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Successful treatment of a patient with hairy cell leukemia and pentostatin-induced autoimmune thrombocytopenia with rituximab. American journal of hematology 20030501
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Hodgkin's type of Richter's syndrome in familial chronic lymphocytic leukemia treated with cladribine and cyclophosphamide. Leukemia & lymphoma 20030501
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Indolent neuroendocrine tumor involving the bone marrow. A case report with a 9-year follow-up. Archives of pathology & laboratory medicine 20030401
Hairy cell leukemia variant developing in a background of polycythemia vera. Archives of pathology & laboratory medicine 20030401
Impact of graft-versus-host disease in reduced-intensity stem cell transplantation (RIST) for patients with haematological malignancies. British journal of haematology 20030401
Treatment recommendations in Waldenstrom's macroglobulinemia: consensus panel recommendations from the Second International Workshop on Waldenstrom's Macroglobulinemia. Seminars in oncology 20030401
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2-Chlorodeoxyadenosine therapy for disseminated Langerhans cell histiocytosis. Mayo Clinic proceedings 20030301
Comparison of cytotoxicity of 2-chloro- 2'-arabino-fluoro-2'-deoxyadenosine (clofarabine) with cladribine in mononuclear cells from patients with acute myeloid and chronic lymphocytic leukemia. Haematologica 20030301
The variant form of hairy-cell leukaemia. Best practice & research. Clinical haematology 20030301
Splenectomy and treatments of historical interest. Best practice & research. Clinical haematology 20030301
Interferon in the treatment of hairy-cell leukemia. Best practice & research. Clinical haematology 20030301
Hairy-cell leukaemia as a model for drug development. Best practice & research. Clinical haematology 20030301
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Efficacy of 2-chlorodeoxyadenosine in refractory factor VIII inhibitors in persons without hemophilia. Blood 20030201
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A phase II study of cladribine treatment for fludarabine refractory B cell chronic lymphocytic leukemia: results from CALGB Study 9211. Leukemia 20030201
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Alkaline hydrolysis of cladribine. Die Pharmazie 20030201
CD4+ CD56+ neoplasia: clinical and biological features with emphasis on cytotoxic drug-induced apoptosis and expression of sialyl Lewis X. Leukemia & lymphoma 20030201
Synthesis and induction of apoptosis in B cell chronic leukemia by diosgenyl 2-amino-2-deoxy-beta-D-glucopyranoside hydrochloride and its derivatives. Carbohydrate research 20030120
The effects of cladribine and fludarabine on DNA methylation in K562 cells. Biochemical pharmacology 20030115
Down-regulation of deoxycytidine kinase in human leukemic cell lines resistant to cladribine and clofarabine and increased ribonucleotide reductase activity contributes to fludarabine resistance. Biochemical pharmacology 20030115
Influence of p53 and p21(WAF1) expression on sensitivity of cancer cells to cladribine. Biochemical pharmacology 20030101
Phase II study of cladribine and cyclophosphamide in patients with chronic lymphocytic leukemia and prolymphocytic leukemia. Cancer 20030101
Newer drugs for the treatment of lupus nephritis. Drugs 20030101
In AML cell lines Ara-C combined with purine analogues is able to exert synergistic as well as antagonistic effects on proliferation, apoptosis and disruption of mitochondrial membrane potential. Leukemia & lymphoma 20030101
The effect of cyclosporin A used alone and in combination with either 2-chlorodeoxyadenosine or fludarabine on normal and chronic myelogenous leukemia progenitors in vitro. Archivum immunologiae et therapiae experimentalis 20030101
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p53 status and its in vitro relationship to radiosensitivity and chemosensitivity in lung cancer. Anticancer research 20030101
Nucleotide excision repair-deficient human cells in culture exhibit decreased survival after 2-chlorodeoxyadenosine treatment. Anticancer research 20030101
2-Chloro-deoxyadenosine induces durable complete remission in Castleman's disease but may accelerate its transformation to non-Hodgkin's lymphoma. Acta oncologica (Stockholm, Sweden) 20030101
Hairy cell leukemia in father and son. Medical oncology (Northwood, London, England) 20030101
Treatment of cutaneous T-cell lymphomas with purine analogues (fludarabine and 2-chlorodeoxyadenosine). Journal of B.U.ON. : official journal of the Balkan Union of Oncology 20030101
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[Immunosuppressive medication in multiple sclerosis]. Revista de neurologia 20021201
Relationships of in vitro sensitivities tested with nine drugs and two types of irradiation in chronic lymphocytic leukemia. Leukemia research 20021101
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Cellular drug resistance in childhood acute myeloid leukemia is related to chromosomal abnormalities. Blood 20021101
Pharmacokinetics of 2-chlorodeoxyadenosine in a child undergoing hemofiltration and hemodialysis for acute renal failure. Journal of pediatric hematology/oncology 20021101
Complete remission of chronic plaque psoriasis and gastric marginal zone B-cell lymphoma of MALT type after treatment with 2-chlorodeoxyadenosine. Annals of hematology 20021101
Cladribine in the treatment of IgM paraproteinemic polyneuropathy. Neurology 20021022
Interim comparison of a continuous infusion versus a short daily infusion of cytarabine given in combination with cladribine for pediatric acute myeloid leukemia. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20021015
Role of caspases and apoptosis-inducing factor (AIF) in cladribine-induced apoptosis of B cell chronic lymphocytic leukemia. Leukemia 20021001
Successful treatment of leukaemia cutis with cladribine in a patient with B-cell chronic lymphocytic leukaemia. The British journal of dermatology 20021001
Treatment of hairy cell leukemia with cladribine (2-chlorodeoxyadenosine) by subcutaneous bolus injection: a phase II study. Annals of oncology : official journal of the European Society for Medical Oncology 20021001
[Pulmonary localization of hairy cell leukemia]. La Revue de medecine interne 20021001
Langerhans cell histiocytosis in a patient with systemic lupus erythematosus: a clonal disease responding to treatment with cladribine, and cyclophosphamide. Leukemia & lymphoma 20021001
Treatment of extranodal marginal zone B-cell lymphoma of mucosa-associated lymphoid tissue type with cladribine: a phase II study. Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020915
Adenine and deazaadenine nucleoside and deoxynucleoside analogues: inhibition of viral replication of sheep MVV (in vitro model for HIV) and bovine BHV-1. Bioorganic & medicinal chemistry 20020901
Response of idiopathic hypereosinophilic syndrome to treatment with imatinib mesylate. Leukemia research 20020901
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Cytotoxic effect of cyclosporin A alone and in combination with 2-chlorodeoxyadenosine against P388 murine leukemia in vivo. Medical science monitor : international medical journal of experimental and clinical research 20020901
[The BCTRIMS Expanded Consensus on treatment of multiple sclerosis: I. The evidences for the use of immunosuppressive agents, plasma exchange and autologous hematopoietic stem cell transplantation]. Arquivos de neuro-psiquiatria 20020901
Evaluation of apoptosis induced in vitro by cladribine (2-CdA) combined with anthracyclines in lymphocytes from patients with B-cell chronic lymphocytic leukemia. Annals of hematology 20020901
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Specificity of human and rat orthologs of the concentrative nucleoside transporter, SPNT. American journal of physiology. Renal physiology 20020801
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Bendamustine in the treatment of chronic lymphocytic leukemia: results and future perspectives. Seminars in oncology 20020801
Systemic vasculitis complicating hairy cell leukaemia treatment with cladribine. Clinical and laboratory haematology 20020801
2-chloro-2'-deoxyadenosine in the treatment of Sjögren's syndrome-associated B cell lymphoproliferation. Arthritis and rheumatism 20020801
Successful treatment with 2-chlorodeoxyadenosine of secondary lesions of the central nervous system in low-grade lymphoid malignancies. American journal of hematology 20020801
[Immunosuppressants and multiple sclerosis]. Revista de neurologia 20020801
Waldenström's macroglobulinemia: a review of therapy. Leukemia & lymphoma 20020801
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Evolving role of ribonucleoside reductase inhibitors in hematologic malignancies. Expert review of anticancer therapy 20020801
Immune response by host after allogeneic chondrocyte transplant to the cartilage. Microscopy research and technique 20020701
Exposure-disease continuum for 2-chloro-2'-deoxyadenosine (2-CdA), a prototype teratogen: induction of lumbar hernia in the rat and species comparison for the teratogenic responses. Teratology 20020701
[Successful treatment of hairy cell leukemia prolymphocytic variant with 2'-deoxycoformycin]. [Rinsho ketsueki] The Japanese journal of clinical hematology 20020701
Re-treatment with cladribine-based regimens in relapsed patients with B-cell chronic lymphocytic leukemia. Efficacy and toxicity in comparison with previous treatment. European journal of haematology 20020701
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Bax expression correlates with cellular drug sensitivity to doxorubicin, cyclophosphamide and chlorambucil but not fludarabine, cladribine or corticosteroids in B cell chronic lymphocytic leukemia. Leukemia 20020601
Treatment of late-stage Sézary syndrome with 2-Chlorodeoxyadenosine. International journal of dermatology 20020601
Myelodysplasia terminating in acute myeloid leukemia in a hairy cell leukemia patient treated with 2-deoxycoformycin. Leukemia & lymphoma 20020601
Anthracyclines potentiate activity against murine leukemias L1210 and P388 in vivo and in vitro. European journal of haematology 20020601
Aggressive growth of epithelial carcinomas following treatment with nucleoside analogues. American journal of hematology 20020501
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[Hairy cell leukemia treated with cladribine]. Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke 20020430
Therapeutic potential of a reduced-intensity preparative regimen for allogeneic transplantation with cladribine, busulfan, and antithymocyte globulin against advanced/refractory acute leukemia/lymphoma. Clinical cancer research : an official journal of the American Association for Cancer Research 20020401
The role of mitoxantrone in non-Hodgkin's lymphoma. Oncology (Williston Park, N.Y.) 20020401
Gateways to Clinical Trials. Methods and findings in experimental and clinical pharmacology 20020401
Cytotoxicity of 2-chlorodeoxyadenosine and arabinosylcytosine in leukaemic lymphoblasts from paediatric patients: significance of cellular nucleoside transporter content. British journal of haematology 20020301
Oral cladribine for B-cell chronic lymphocytic leukaemia: report of a phase II trial with a 3-d, 3-weekly schedule in untreated and pretreated patients, and a long-term follow-up of 126 previously untreated patients. British journal of haematology 20020301
Severe decrease in peripheral blood dendritic cells in hairy cell leukaemia. British journal of haematology 20020301
Treatment of children with Langerhans cell histiocytosis with 2-chlorodeoxyadenosine. American journal of hematology 20020301
Widespread skin-limited adult Langerhans cell histiocytosis: long-term follow-up with good response to interferon alpha. Clinical and experimental dermatology 20020301
Radiation therapy and combination of cladribine, cyclophosphamide, and prednisone as treatment of Bing-Neel syndrome: Case report and review of the literature. American journal of hematology 20020201
Suspected delayed immune recovery against cytomegalovirus after reduced-intensity stem cell transplantation using anti-thymocyte globulin. Bone marrow transplantation 20020201
Therapeutic approaches to secondary progressive multiple sclerosis. Multiple sclerosis (Houndmills, Basingstoke, England) 20020201
Fludarabine therapy in Waldenström's macroglobulinemia patients treated previously with 2-chlorodeoxyadenosine. Leukemia & lymphoma 20020201
Cladribine underdosing in hairy-cell leukemia: a cause for apparent response failure. Leukemia & lymphoma 20020201
Induction of apoptosis by cladribine (2-CdA), gemcitabine and other chemotherapeutic drugs on CD34+/CD38+ and CD34+/CD38- hematopoietic progenitor cells: selective effects of doxorubicin and 2-CdA with protection of immature cells. Leukemia & lymphoma 20020201
Resistance of leukemic cells to 2-chlorodeoxyadenosine is due to a lack of calcium-dependent cytochrome c release. Blood 20020115
Anti-CD20 antibody (IDEC-C2B8, rituximab) enhances efficacy of cytotoxic drugs on neoplastic lymphocytes in vitro: role of cytokines, complement, and caspases. Haematologica 20020101
Cladribine (2-chlorodeoxyadenosine) therapy in hairy cell leukemia variant. A report of three cases. Haematologica 20020101
2-Chloro-2'-deoxyadenosine inhibits DNA repair synthesis and potentiates UVC cytotoxicity in chronic lymphocytic leukemia B lymphocytes. Leukemia 20020101
Use of 2-chlorodeoxyadenosine to treat infantile myofibromatosis. Journal of pediatric hematology/oncology 20020101
Immunosuppression with limited toxicity: the characteristics of nucleoside analogs and anti-lymphocyte antibodies used in non-myeloablative hematopoietic cell transplantation. Cancer treatment and research 20020101
Cladribine decreases the level of angiogenic factors in patients with chronic lymphocytic leukemia. Neoplasma 20020101
Therapeutic approaches in multiple sclerosis: lessons from failed and interrupted treatment trials. BioDrugs : clinical immunotherapeutics, biopharmaceuticals and gene therapy 20020101
5'-Esters of 2'-deoxyadenosine and 2-chloro-2'-deoxyadenosine with cell differentiation-provoking agents. Acta biochimica Polonica 20020101
In vitro release of cytotoxic nucleoside analogs from lactide-caprolactone and lactide-glycolide copolymers. Acta biochimica Polonica 20020101
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Cladribine combined with cyclophosphamide is highly effective in the treatment of chronic lymphocytic leukemia. The hematology journal : the official journal of the European Haematology Association 20020101
The role of membrane transporters in cellular resistance to anticancer nucleoside drugs. Cancer treatment and research 20020101
Hepatosplenic gamma delta T-cell lymphoma with leukemic phase successfully treated with 2-chlorodeoxyadenosine. Haematologia 20020101
Histological examination of the extrabulbar segment of the optic nerve in experimental animals after administration of Cladribine. Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20020101
Influence of the new medicine--2-CDA (Cladribine) on the ultrastructure of the extrabulbar segment of the optic nerve in rabbits of New Zealand breed. Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20020101
Histological examination of the retinal ganglion layer in rabbits after experimental administration of the new immunosuppressive medicine--Cladribine. Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20020101
Ultrastructural changes of retinal ganglion cells in rabbits of New Zealand breed after experimental administration of 2-CDA (Cladribine). Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20020101
Histological examination of the lacrimal gland after experimental administration of Cladribine. Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20020101
Autoanti-D in a patient after cladribine treatment for lymphoplasmocytic lymphoma. Immunohematology 20020101
Hematological effects of intermittent 2-hour infusions of cladribine in multiple sclerosis patients: a comparison of 2 dosage patterns. International journal of hematology 20011201
Cladribine. Ortho Biotech Inc. Current opinion in investigational drugs (London, England : 2000) 20011201
Successful treatment of refractory Langerhans cell histiocytosis with unrelated cord blood transplantation. Journal of pediatric hematology/oncology 20011201
Treatment of hairy-cell leukemia. The New England journal of medicine 20011115
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Cladribine induces apoptosis in human leukaemia cells by caspase-dependent and -independent pathways acting on mitochondria. The Biochemical journal 20011101
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Cladribine combined with cyclophosphamide and mitoxantrone as front-line therapy in chronic lymphocytic leukemia. Leukemia 20011001
Efficacy of anti-CD20 monoclonal antibodies (Mabthera) in patients with progressed hairy cell leukemia. Haematologica 20011001
Identification and characterization of human deoxyguanosine kinase cDNA fragments. Cancer letters 20010920
Exposure-disease continuum for 2-chloro-2'-deoxyadenosine, a prototype ocular teratogen. 1. Dose-response analysis. Teratology 20010901
Impact of treatment on the outcome of acute myeloid leukemia with inversion 16: a single institution's experience. Leukemia 20010901
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