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C0253 Sigma

Chlorambucil

Synonym: 4-(4-[Bis(2-chloroethyl)amino]phenyl)butyric acid, 4-[Bis(2-chloroethyl)amino]benzenebutyric acid

  • CAS Number 305-03-3

  • Empirical Formula (Hill Notation) C14H19Cl2NO2

  • Molecular Weight 304.21

  •  Beilstein Registry Number 999011

  •  EC Number 206-162-0

  •  MDL number MFCD00021783

  •  PubChem Substance ID 24278287

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Description

Biochem/physiol Actions

Chlorambucil is an anti-cancer drug that alkylates DNA and induces apoptosis. Death of chronic lymphocytic leukemia cells occurs via a p53-dependent mechanism.

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Chlorambucil
C1100000Chlorambucil

European Pharmacopoeia (EP) Reference Standard

Chlorambucil

purum, ≥98.0% (T)

Melphalan

powder

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Hazard Codes (Europe) 
T
Risk Statements (Europe) 
Safety Statements (Europe) 
53-26-45
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
ES7525000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

DNA Damage and Repair

Damage to cellular DNA is involved in mutagenesis and the development of cancer. The DNA in a human cell undergoes several thousand to a million damaging events per day, generated by both external (e...
BioFiles 2007, 2.4, 20.
Keywords: AGE, Alkylations, Apoptosis, Applications, Biochemistry, Cancer, Carcinogens, Catalysis, Clinical, DNA replication, Deaminations, Environmental, Error, Events, Gene expression, Metabolites, Methylations, Mutagens, Oxidations, Polymorphisms, Rearrangements, Recombination, Sequences, Substitutions, Transcription, Type

Determination of Water Content in Chlorambucil Using Karl Fischer Titration

The determination of water in carboxylic acids is usually straightforward provided the substances are soluble. Strong acids must be neutralized. Acetic acid and related compounds have a tendency to u...
Keywords: Esterifications, Pharmaceutical, Titrations

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Peer-Reviewed Papers

References

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Chlorambucil drug resistance in chronic lymphocytic leukemia: the emerging role of DNA repair. Panasci, L., et al. Clin. Cancer Res. 7, 454-461, (2001)

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DNA-Dependent protein kinase activity correlates with clinical and in vitro sensitivity of chronic lymphocytic leukemia lymphocytes to nitrogen mustards. Muller, C., et al. Blood 92, 2213-2219, (1998)

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Bcl-2 protein expression and p53 gene mutation in chronic lymphocytic leukemia: correlation with in vitro sensitivity to chlorambucil and purine analogs. Morabito, F., et al. Haematologica 82, 16-20, (1997)

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Coordinated action of glutathione S-transferases (GSTs) and multidrug resistance protein 1 (MRP1) in antineoplastic drug detoxification. Morrow, C.S., et al. J. Biol. Chem. 273, 20114-20120, (1998)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Results of a randomized trial of chlorambucil versus fludarabine for patients with untreated Waldenström macroglobulinemia, marginal zone lymphoma, or lymphoplasmacytic lymphoma. Leblond V, Johnson S, Chevret S, et al. J. Clin. Oncol. 31(3), 301-7, (2013)

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Impact of age on outcomes after initial therapy with chemotherapy and different chemoimmunotherapy regimens in patients with chronic lymphocytic leukemia: results of sequential cancer and leukemia group B studies. Woyach JA, Ruppert AS, Rai K, et al. J. Clin. Oncol. 31(4), 440-7, (2013)

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Design, synthesis and antiproliferative activity of some 3-benzylidene-2,3-dihydro-1-benzopyran-4-ones which display selective toxicity for malignant cells. Pal Perjési et al Eur. J. Med. Chem. 43, 839-45, (2008)

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Synthesis and biophysical characterization of chlorambucil anticancer ether lipid prodrugs. Palle J Pedersen et al J. Med. Chem. 52, 3408-15, (2009)

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Addition of rituximab to chlorambucil produces superior event-free survival in the treatment of patients with extranodal marginal-zone B-cell lymphoma: 5-year analysis of the IELSG-19 Randomized Study. Zucca E, Conconi A, Laszlo D, et al. J. Clin. Oncol. 31(5), 565-72, (2013)

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Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. R Scott Obach et al Drug Metab. Dispos. 36, 1385-405, (2008)

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Physicochemical determinants of human renal clearance. Manthena V S Varma et al J. Med. Chem. 52, 4844-52, (2009)

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Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination. Manthena V S Varma et al J. Med. Chem. 53, 1098-108, (2010)

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Chlorambucil induced pulmonary fibrosis: report of a case and review. Carr ME Va. Med. 113(11), 677-80, (1986)

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Chlorambucil overdose: accidental ingestion of an antineoplastic drug. Vandenberg SA, Kulig K, Spoerke DG, et al. J. Emerg. Med. 6(6), 495-8, (1988)

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Deciphering the interactions between chlorambucil and calf thymus DNA: a multi-spectroscopic and molecular docking study. Rehman SU, Sarwar T, Ishqi HM, et al. Arch. Biochem. Biophys. 566, 7-14, (2015)

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Impact of active surveillance, chlorambucil, and other therapy on health-related quality of life in patients with CLL/SLL in the Netherlands. van den Broek EC, Oerlemans S, Nijziel MR, et al. Ann. Hematol. 94(1), 45-56, (2015)

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Globular intracytoplasmic inclusions in a patient with chronic lymphocytic leukaemia. Metzgeroth G, Schneider S, Hofmann WK, et al. Br. J. Haematol. 161(3), 302, (2013)

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[Prolonged release of chlorambucil and etoposide from poly-3-oxybutyrate-based microspheres]. Filatova EV, Iakovlev SG, Bonartsev AP, et al. Prikl. Biokhim. Mikrobiol. 48(6), 662-7, (2012)

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A difficult trade off for adults with membranous nephropathy. BMJ 346, f248, (2013)

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Tumor lysis syndrome following chlorambucil therapy for chronic lymphocytic leukemia: case report and review of the literature. Kosseifi SG, Vyas B, Vyas H, et al. Tenn. Med. 102(10), 33-6, (2009)

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Mortality rate in bullous pemphigoid: a retrospective monocentric cohort study. Cortés B, Khelifa E, Clivaz L, et al. Dermatology 225(4), 320-5, (2012)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Immunosuppression for progressive membranous nephropathy: a UK randomised controlled trial. Howman A, Chapman TL, Langdon MM, et al. Lancet 381(9868), 744-51, (2013)

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The clinical significance of NOTCH1 and SF3B1 mutations in the UK LRF CLL4 trial. Oscier DG, Rose-Zerilli MJ, Winkelmann N, et al. Blood 121(3), 468-75, (2013)

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Hologram QSAR model for the prediction of human oral bioavailability. Tiago L Moda et al Bioorg. Med. Chem. 15, 7738-45, (2007)

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[Delayed allergic reaction to Chlorambucil (Leukeran). Case report and literature review]. Torricelli R, Kurer SB, Kroner T, et al. Schweiz. Med. Wochenschr. 125(40), 1870-3, (1995)

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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors. Lourdes Santana et al J. Med. Chem. 51, 6740-51, (2008)

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Biallelic ATM inactivation significantly reduces survival in patients treated on the United Kingdom Leukemia Research Fund Chronic Lymphocytic Leukemia 4 trial. Skowronska A, Parker A, Ahmed G, et al. J. Clin. Oncol. 30(36), 4524-32, (2012)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Azathioprine, cyclophosphamide and chlorambucil. Luqmani RA, Palmer RG, and Bacon PA Baillieres. Clin. Rheumatol. 4(3), 595-619, (1990)

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Assessment of chemoselective neoglycosylation methods using chlorambucil as a model. Randal D Goff et al J. Med. Chem. 53, 8129-39, (2010)

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Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Jing Yuan et al Nat. Chem. Biol. 5, 765-71, (2009)

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A high-throughput pharmaceutical screen identifies compounds with specific toxicity against BRCA2-deficient tumors. Evers B Clin. Cancer Res. 16(1), 99-108, (2010)

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Synthesis and evaluation of anticancer activity of 2-arylamino-6-trifluoromethyl-3-(hydrazonocarbonyl)pyridines. Valentina Onnis et al Bioorg. Med. Chem. 17, 6158-65, (2009)

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Rituximab for the first-line treatment of stage III-IV follicular lymphoma (review of Technology Appraisal No. 110): a systematic review and economic evaluation. Papaioannou D, Rafia R, Rathbone J, et al. Health Technol. Assess. 16(37), 1-253, iii-iv, (2012)

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A comparison of chloroambucil- and xylene-containing polyamines leads to improved ligands for accessing the polyamine transport system. Navneet Kaur et al J. Med. Chem. 51, 1393-401, (2008)

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Malignancies induced by chlorambucil. Palmer RG and Denman AM Cancer Treat. Rev. 11(2), 121-9, (1984)

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A selective mitochondrial-targeted chlorambucil with remarkable cytotoxicity in breast and pancreatic cancers. Millard M, Gallagher JD, Olenyuk BZ, et al. J. Med. Chem. 56(22), 9170-9, (2013)

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Synthesis of indirubin-N'-glycosides and their anti-proliferative activity against human cancer cell lines. Stefanie Libnow et al Bioorg. Med. Chem. 16, 5570-83, (2008)

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Cutaneous necrobiotic xanthogranuloma (NXG)--successfully treated with low dose chlorambucil. Machado S, Alves R, Lima M, et al. Eur. J. Dermatol. 11(5), 458-62, (2001)

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High-frequency induction of chromosomal rearrangements in mouse germ cells by the chemotherapeutic agent chlorambucil. Rinchik EM, Flaherty L, and Russell LB Bioessays 15(12), 831-6, (1993)

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Pig-a gene mutation and micronucleated reticulocyte induction in rats exposed to tumorigenic doses of the leukemogenic agents chlorambucil, thiotepa, melphalan, and 1,3-propane sultone. Dertinger SD, Phonethepswath S, Avlasevich SL, et al. Environ. Mol. Mutagen. 55(4), 299-308, (2014)

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Design, synthesis and biological evaluation of estradiol-chlorambucil hybrids as anticancer agents. Atul Gupta et al Bioorg. Med. Chem. Lett. 20, 1614-8, (2010)

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Chlorambucil in chronic lymphocytic leukemia: mechanism of action. Begleiter A, Mowat M, Israels LG, et al. Leuk. Lymphoma 23(3-4), 187-201, (1996)

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Corticosteroids, cyclophosphamide, and chlorambucil therapy of membranous nephropathy. Passerini P and Ponticelli C Semin. Nephrol. 23(4), 355-61, (2003)

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Synthesis and cytotoxic properties of new fluorodeoxyglucose-coupled chlorambucil derivatives. Bastien Reux et al Bioorg. Med. Chem. 16, 5004-20, (2008)

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[Renal amyloidosis in rheumatoid polyarthritis stabilized for 13 years with chlorambucil]. Maugars Y, Couverchel L, Guenel Y, et al. Rev. Rhum. Mal. Osteoartic. 57(1), 41-4, (1990)

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Synthesis and biological evaluation of cyclic nitrogen mustards based on carnitine framework. Simon Leiris et al Eur. J. Med. Chem. 45, 4140-8, (2010)

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Rational design, synthesis, and in vivo evaluation of the antileukemic activity of six new alkylating steroidal esters. Anna I Koutsourea et al Bioorg. Med. Chem. 16, 5207-15, (2008)

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Thiol-inducible direct fluorescence monitoring of drug release. Wu J, Huang R, Wang C, et al. Org. Biomol. Chem. 11(4), 580-5, (2013)

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Immunosuppressive treatment for nephrotic idiopathic membranous nephropathy: a meta-analysis based on Chinese adults. Xie G, Xu J, Ye C, et al. PLoS ONE 7(9), e44330, (2012)

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Chlorambucil-induced seizures. Salloum E, Khan KK, and Cooper DL Cancer 79(5), 1009-13, (1997)

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QSPR modeling of octanol/water partition coefficient of antineoplastic agents by balance of correlations. Andrey A Toropov et al Eur. J. Med. Chem. 45, 1639-47, (2010)

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To determine the cytotoxicity of chlorambucil and one of its nitro-derivatives, conjugated to prasterone and pregnenolone, towards eight human cancer cell-lines. Shervington, L. A.; et al. Eur. J. Med. Chem. 44, 2944, (2009)

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Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data. Xiaofan Sui et al Eur. J. Med. Chem. 44, 4455-60, (2009)

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The interaction of the chemotherapeutic drug chlorambucil with human glutathione transferase A1-1: kinetic and structural analysis. Karpusas M, Axarli I, Chiniadis L, et al. PLoS ONE 8(2), e56337, (2013)

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Synthesis of D- and L-tyrosine-chlorambucil analogs active against breast cancer cell lines. Caroline Descôteaux et al Bioorg. Med. Chem. Lett. 20, 7388-92, (2010)

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Pentostatin (Nipent) and chlorambucil with granulocyte-macrophage colony-stimulating factor support for patients with previously untreated, treated, and fludarabine-refractory B-cell chronic lymphocytic leukemia. Waselenko JK, Grever MR, Beer M, et al. Semin. Oncol. 27(2 Suppl 5), 44-51, (2000)

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Treatment outcome in children and adolescents with relapsed Hodgkin lymphoma--results of the UK HD3 relapse treatment strategy. Shankar A, Hayward J, Kirkwood A, et al. Br. J. Haematol. 165(4), 534-44, (2014)

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Drug resistance to chlorambucil in murine B-cell leukemic cells is overcome by its conjugation to a targeting peptide. Gellerman G, Baskin S, Galia L, et al. Anticancer Drugs 24(2), 112-9, (2013)

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Lipophilicity of acidic compounds: impact of ion pair partitioning on drug design. Mark C Wenlock et al Bioorg. Med. Chem. Lett. 21, 3550-6, (2011)

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Bronchiolitis obliterans organizing pneumonia following chlorambucil treatment for chronic lymphocytic leukemia. Kalambokis G, Stefanou D, Arkoumani E, et al. Eur. J. Haematol. 73(2), 139-42, (2004)

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Leukaemia cutis in chronic lymphocytic leukaemia following varicella zoster virus reactivation. Hapgood G, Mooney E, Dinh HV, et al. Intern. Med. J. 42(12), 1355-8, (2012)

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Interstitial lung disease--an underdiagnosed side effect of chlorambucil? Mohr M, Kingreen D, Rühl H, et al. Ann. Hematol. 67(6), 305-7, (1993)

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Chlorambucil-induced pulmonary disease: a case report and review of the literature. Khong HT and McCarthy J Ann. Hematol. 77(1-2), 85-7, (1998)

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Treatment practice in the elderly patient with chronic lymphocytic leukemia-analysis of the combined SEER and Medicare database. Satram-Hoang S, Reyes C, Hoang KQ, et al. Ann. Hematol. 93(8), 1335-44, (2014)

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Chlorambucil lung toxicity. Giles FJ, Smith MP, and Goldstone AH Acta Haematol. 83(3), 156-8, (1990)

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Chemoimmunotherapy for chronic lymphocytic leukemia. Author reply. Goede V, Fischer K, and Hallek M N. Engl. J. Med. 370(24), 2348-9, (2014)

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Immunosuppression for membranous nephropathy - Authors' reply. Mathieson PW Lancet 381(9884), 2163, (2013)

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Immunosuppression for membranous nephropathy. Chen Z and Du X Lancet 381(9884), 2162-3, (2013)

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Immunosuppression for membranous nephropathy. Cirillo M Lancet 381(9884), 2161, (2013)

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ACP Journal Club. Prednisolone plus chlorambucil preserved renal function in membranous nephropathy. Remuzzi G and Ruggenenti P Ann. Intern. Med. 158(10), JC9, (2013)

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Idiopathic membranous nephropathy: back to the future? Ruggenenti P and Remuzzi G Lancet 381(9868), 706-8, (2013)

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Chlorambucil for patients with primary biliary cirrhosis. Li WX, Yan X, Shi CR, et al. Cochrane Database Syst. Rev. 9, CD008714, (2012)

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Chemoimmunotherapy with GA101 plus chlorambucil in patients with chronic lymphocytic leukemia and comorbidity: results of the CLL11 (BO21004) safety run-in. Goede V, Fischer K, Busch R, et al. Leukemia 27(5), 1172-4, (2013)

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Chlorambucil therapy in juvenile chronic arthritis (juvenile idiopathic arthritis) Ansell BM J. Rheumatol. 26(4), 765-6, (1999)

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Merck 14,2073

Beil. 14,IV,1715

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