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30450 Sigma

Daunorubicin hydrochloride

≥90% (HPLC)

Synonym: Daunomycin hydrochloride

  • CAS Number 23541-50-6

  • Empirical Formula (Hill Notation) C27H29NO10 · HCl

  • Molecular Weight 563.98

  •  Beilstein Registry Number 4229221

  •  EC Number 245-723-4

  •  MDL number MFCD04974507

  •  PubChem Substance ID 24858374

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Description

Biochem/physiol Actions

Potent anticancer agent. Inhibits DNA and RNA synthesis as sequence specific ds-DNA intercalating agent.4,5,6

On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. Daunomycin effectively binds to every 3 base pairs which causes unwinding.

Application

Daunorubicin hydrochloride is used in photostability1, antileukemic2, and drug metabolism studies3.

Price and Availability

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Daunorubicin hydrochloride

meets USP testing specifications

Daunorubicin hydrochloride

European Pharmacopoeia (EP) Reference Standard

Epirubicin hydrochloride

≥90% (HPLC)

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3
RTECS 
HB7878000

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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1. Photoprotection of Daunorubicin Hydrochloride with Sodium Sulfite. Mohammad S. Islam* and Ahmed F. Asker J. Pharm. Sci. 49, 122-126, (1995)

2. Synergistic effect of SU11248 with cytarabine or daunorubicin on FLT3 ITD–positive leukemic cells. Kevin W. H. Yee, Marcus Schittenhelm, et. Al Blood 104, 4202-4209, (2004)

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3. Naturally Occurring Variants of Human Aldo-Keto Reductases with Reduced In Vitro Metabolism of Daunorubicin and Doxorubicin. Onkar S. Bains, Thomas A. Grigliatti, et al. J. Pharmacol. Exp. Ther. 335, 533-545, (2010)

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4. Potent anticancer agent that has been shown to be a strong inhibitor of DNA and RNA synthesis. J.A.A. Schelling Eur. J. Biochem. 102, 409, (1979)

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5. Daunomycin inhibits the B leads to Z transition in poly d(G-C). J.B. Chaires Nucleic Acids Res. 11, 8485, (1983)

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6. R.J. White et al. Drugs Pharm. Sci. 22, 569, (1984)

A phase 3 study of gemtuzumab ozogamicin during induction and postconsolidation therapy in younger patients with acute myeloid leukemia. Petersdorf SH, Kopecky KJ, Slovak M, et al. Blood 121(24), 4854-60, (2013)

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Improved outcome in pediatric relapsed acute myeloid leukemia: results of a randomized trial on liposomal daunorubicin by the International BFM Study Group. Kaspers GJ, Zimmermann M, Reinhardt D, et al. J. Clin. Oncol. 31(5), 599-607, (2013)

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High-risk childhood acute lymphoblastic leukemia in first remission treated with novel intensive chemotherapy and allogeneic transplantation. Marshall GM, Dalla Pozza L, Sutton R, et al. Leukemia 27(7), 1497-503, (2013)

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Randomized trial comparing liposomal daunorubicin with idarubicin as induction for pediatric acute myeloid leukemia: results from Study AML-BFM 2004. Creutzig U, Zimmermann M, Bourquin JP, et al. Blood 122(1), 37-43, (2013)

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A phase Ib GOELAMS study of the mTOR inhibitor RAD001 in association with chemotherapy for AML patients in first relapse. Park S, Chapuis N, Saint Marcoux F, et al. Leukemia 27(7), 1479-86, (2013)

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Anthracyclines during induction therapy in acute myeloid leukaemia: a systematic review and meta-analysis. Teuffel O, Leibundgut K, Lehrnbecher T, et al. Br. J. Haematol. 161(2), 192-203, (2013)

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Upregulation of drug transporter expression by osteopontin in prostate cancer cells. Hsieh IS, Huang WH, Liou HC, et al. Mol. Pharmacol. 83(5), 968-77, (2013)

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EVI1 inhibits apoptosis induced by antileukemic drugs via upregulation of CDKN1A/p21/WAF in human myeloid cells. Rommer A, Steinmetz B, Herbst F, et al. PLoS ONE 8(2), e56308, (2013)

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Minimal residual disease as biomarker for optimal biologic dosing of ARA-C in patients with acute myeloid leukemia. Maurillo L, Buccisano F, Piciocchi A, et al. Am. J. Hematol. 90(2), 125-31, (2015)

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Comparison of 60 or 90 mg/m(2) of daunorubicin in induction therapy for acute myeloid leukemia with intermediate or unfavorable cytogenetics. Devillier R, Bertoli S, Prébet T, et al. Am. J. Hematol. 90(2), E29-30, (2015)

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Phase II, multicenter, randomized trial of CPX-351 (cytarabine:daunorubicin) liposome injection versus intensive salvage therapy in adults with first relapse AML. Cortes JE, Goldberg SL, Feldman EJ, et al. Cancer 121(2), 234-42, (2015)

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Efficacy of CPX-351, (cytarabine:daunorubicin) liposome injection, against acute lymphoblastic leukemia (ALL) xenograft models of the Pediatric Preclinical Testing Program. Carol H, Fan MM, Harasym TO, et al. Pediatr. Blood Cancer 62(1), 65-71, (2015)

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Augmented Berlin-Frankfurt-Münster therapy in adolescents and young adults (AYAs) with acute lymphoblastic leukemia (ALL). Rytting ME, Thomas DA, O'Brien SM, et al. Cancer 120(23), 3660-8, (2014)

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Liposomal daunorubicin, fludarabine, and cytarabine (FLAD) as bridge therapy to stem cell transplant in relapsed and refractory acute leukemia. De Astis E, Clavio M, Raiola AM, et al. Ann. Hematol. 93(12), 2011-8, (2014)

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Internal tandem duplication of the FLT3 gene confers poor overall survival in patients with acute promyelocytic leukemia treated with all-trans retinoic acid and anthracycline-based chemotherapy: an International Consortium on Acute Promyelocytic Leukemia study. Lucena-Araujo AR, Kim HT, Jacomo RH, et al. Ann. Hematol. 93(12), 2001-10, (2014)

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Liposomes modified with p-aminophenyl-α-D-mannopyranoside: a promising delivery system in targeting the brain. Peng H, Du D, and Zhang J Ther. Deliv. 4(12), 1475-7, (2013)

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Post-chemotherapeutic resolution of acute myeloid leukaemia-induced gingival enlargement: a case report. Singh-Rambiritch S and Wood NH SADJ 67(7), 344-7, (2012)

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A correlation between cytotoxicity and reductase-mediated metabolism in cell lines treated with doxorubicin and daunorubicin. Bains OS, Szeitz A, Lubieniecka JM, et al. J. Pharmacol. Exp. Ther. 347(2), 375-87, (2013)

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Decreased survival in normal karyotype AML with single-nucleotide polymorphisms in genes encoding the AraC metabolizing enzymes cytidine deaminase and 5'-nucleotidase. Falk IJ, Fyrberg A, Paul E, et al. Am. J. Hematol. 88(12), 1001-6, (2013)

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Oxidized porous silicon particles covalently grafted with daunorubicin as a sustained intraocular drug delivery system. Chhablani J, Nieto A, Hou H, et al. Invest. Ophthalmol. Vis. Sci. 54(2), 1268-79, (2013)

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Phase I clinical trial and pharmacodynamic evaluation of combination hydroxychloroquine and doxorubicin treatment in pet dogs treated for spontaneously occurring lymphoma. Barnard RA, Wittenburg LA, Amaravadi RK, et al. Autophagy 10(8), 1415-25, (2014)

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Cyclic AMP can promote APL progression and protect myeloid leukemia cells against anthracycline-induced apoptosis. Gausdal G, Wergeland A, Skavland J, et al. Cell Death Dis. 4, e516, (2013)

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Time from diagnosis to intensive chemotherapy initiation does not adversely impact the outcome of patients with acute myeloid leukemia. Bertoli S, Bérard E, Huguet F, et al. Blood 121(14), 2618-26, (2013)

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Arsenic trioxide during consolidation for patients with previously untreated low/intermediate risk acute promyelocytic leukaemia may eliminate the need for maintenance therapy. Coutre SE, Othus M, Powell B, et al. Br. J. Haematol. 165(4), 497-503, (2014)

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High-dose cytarabine-based consolidation shows superior results for older AML patients with intermediate risk cytogenetics in first complete remission. Hassanein M, Atenafu EG, Schuh AC, et al. Leuk. Res. 37(5), 556-60, (2013)

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The Src and c-Kit kinase inhibitor dasatinib enhances p53-mediated targeting of human acute myeloid leukemia stem cells by chemotherapeutic agents. Dos Santos C, McDonald T, Ho YW, et al. Blood 122(11), 1900-13, (2013)

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Impact on survival and toxicity by duration of weight extremes during treatment for pediatric acute lymphoblastic leukemia: A report from the Children's Oncology Group. Orgel E, Sposto R, Malvar J, et al. J. Clin. Oncol. 32(13), 1331-7, (2014)

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Acute myeloid leukemia in first remission: to choose transplantation or not? Stone RM J. Clin. Oncol. 31(10), 1262-6, (2013)

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2D- and 3D-QSAR studies of a series of benzopyranes and benzopyrano[3,4b][1,4]-oxazines as inhibitors of the multidrug transporter P-glycoprotein. Jabeen I, Wetwitayaklung P, Chiba P, et al. J. Comput. Aided Mol. Des. 27(2), 161-71, (2013)

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Probing the relative orientation of molecules bound to DNA through controlled interference using second-harmonic generation. Doughty B, Rao Y, Kazer SW, et al. Proc. Natl. Acad. Sci. U. S. A. 110(15), 5756-8, (2013)

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Induction mortality and resource utilization in children treated for acute myeloid leukemia at free-standing pediatric hospitals in the United States. Kavcic M, Fisher BT, Li Y, et al. Cancer 119(10), 1916-23, (2013)

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Anthracycline resistance mediated by reductive metabolism in cancer cells: the role of aldo-keto reductase 1C3. Hofman J, Malcekova B, Skarka A, et al. Toxicol. Appl. Pharmacol. 278(3), 238-48, (2014)

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Cancer cell detection based on the interaction between an anticancer drug and cell membrane components. Chandra P, Noh HB, and Shim YB Chem. Commun. (Camb.) 49(19), 1900-2, (2013)

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Adipose tissue attracts and protects acute lymphoblastic leukemia cells from chemotherapy. Pramanik R, Sheng X, Ichihara B, et al. Leuk. Res. 37(5), 503-9, (2013)

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Prediction of adverse events during intensive induction chemotherapy for acute myeloid leukemia or high-grade myelodysplastic syndromes. Buckley SA, Othus M, Vainstein V, et al. Am. J. Hematol. 89(4), 423-8, (2014)

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Early and delayed cardioprotective intervention with dexrazoxane each show different potential for prevention of chronic anthracycline cardiotoxicity in rabbits. Jirkovský E, Lenčová-Popelová O, Hroch M, et al. Toxicology 311(3), 191-204, (2013)

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Feasibility of azacitidine added to standard chemotherapy in older patients with acute myeloid leukemia--a randomised SAL pilot study. Krug U, Koschmieder A, Schwammbach D, et al. PLoS ONE 7(12), e52695, (2012)

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Fractionated gemtuzumab ozogamicin and standard dose cytarabine produced prolonged second remissions in patients over the age of 55 years with acute myeloid leukemia in late first relapse. Pilorge S, Rigaudeau S, Rabian F, et al. Am. J. Hematol. 89(4), 399-403, (2014)

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Idarubicin is superior to daunorubicin in remission induction of de novo acute myeloid leukemia patients with high MDR1 expression. Shi P, Zha J, Guo X, et al. Pharmacogenomics 14(1), 17-23, (2013)

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S-nitrosoglutathione covalently modifies cysteine residues of human carbonyl reductase 1 and affects its activity. Hartmanová T, Tambor V, Lenčo J, et al. Chem. Biol. Interact. 202(1-3), 136-45, (2013)

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Binding of the plant alkaloid aristololactam-β-d-glucoside and antitumor antibiotic daunomycin to single stranded polyribonucleotides. Das A and Kumar GS Biochim. Biophys. Acta 1830(10), 4708-18, (2013)

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Prevalence of extramedullary relapses is higher after allogeneic stem cell transplantation than after chemotherapy in adult patients with acute myeloid leukemia. Shimizu H, Saitoh T, Hatsumi N, et al. Leuk. Res. 37(11), 1477-81, (2013)

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Idarubicin appears equivalent to dose-intense daunorubicin for remission induction in patients with acute myeloid leukemia. Trifilio S, Zhou Z, Mehta J, et al. Leuk. Res. 37(8), 868-71, (2013)

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Successful treatment of pediatric histiocytic sarcoma using abbreviated high-risk leukemia chemotherapy. Heath JL, Burgett SE, Gaca AM, et al. Pediatr. Blood Cancer 61(10), 1874-6, (2014)

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Mitoxantrone as a substitute for daunorubicin during induction in newly diagnosed lymphoblastic leukemia and lymphoma. Nickel RS, Keller F, Bergsagel J, et al. Pediatr. Blood Cancer 61(5), 810-4, (2014)

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Outcomes of elderly de novo acute myeloid leukemia treated by a risk-adapted approach based on age, comorbidity, and performance status. Yoon JH, Cho BS, Kim HJ, et al. Am. J. Hematol. 88(12), 1074-81, (2013)

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Effect of microRNA-210 on prognosis and response to chemotherapeutic drugs in pediatric acute lymphoblastic leukemia. Mei Y, Gao C, Wang K, et al. Cancer Sci. 105(4), 463-72, (2014)

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Phase II trial of clofarabine and daunorubicin as induction therapy for acute myeloid leukemia patients greater than or equal to 60 years of age. Vigil CE, Tan W, Deeb G, et al. Leuk. Res. 37(11), 1468-71, (2013)

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The clinical characteristics and prognostic significance of MN1 gene and MN1-associated microRNA expression in adult patients with de novo acute myeloid leukemia. Xiang L, Li M, Liu Y, et al. Ann. Hematol. 92(8), 1063-9, (2013)

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Artesunate has its enhancement on antibacterial activity of β-lactams via increasing the antibiotic accumulation within methicillin-resistant Staphylococcus aureus (MRSA). Jiang W, Li B, Zheng X, et al. J. Antibiot. 66(6), 339-45, (2013)

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Escalated daunorubicin dosing as an induction treatment for Philadelphia-negative adult acute lymphoblastic leukemia. Lee SM, Lee WS, Shin HJ, et al. Ann. Hematol. 92(8), 1101-10, (2013)

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In vitro induction of apoptosis and necrosis by new derivatives of daunorubicin. Stojak M, Mazur L, Opydo-Chanek M, et al. Anticancer Res. 33(10), 4439-43, (2013)

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PI-103 sensitizes acute myeloid leukemia stem cells to daunorubicin-induced cytotoxicity. Ding Q, Gu R, Liang J, et al. Med. Oncol. 30(1), 395, (2013)

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Ewing sarcoma arising after treatment of diffuse large B-cell lymphoma. Hiramoto N, Kobayashi Y, Nomoto J, et al. Jpn. J. Clin. Oncol. 43(4), 417-21, (2013)

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A case report of acute myeloid leukemia after liver transplantation. Liu M, Liu J, Liu L, et al. Acta Haematol. 129(4), 225-8, (2013)

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Nasolacrimal system obstruction, ptosis and esotropia due to chemotherapy in acute lymphoblastic leukemia. Esmer O, Karadag R, Soylu E, et al. Cutan. Ocul. Toxicol. 32(4), 330-2, (2013)

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Mutant DNMT3A clone evading chemotherapy and infiltrating central nervous system in a patient with molecularly good-risk acute myeloid leukemia. Chen YY, Huang CE, Chou HJ, et al. Ann. Hematol. 93(8), 1441-2, (2014)

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Dermatic Scedosporium apiospermum infection after autologous bone marrow transplantation. Yu Z, Hu L, Jiang M, et al. Intern. Med. 52(6), 689-93, (2013)

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