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anthracycline antibiotics
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activation (1)
adjuvant therapy (1)
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apoptosis and (1)
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-induced cardiotoxicity, prevention of (1)
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Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines
Cancer: Principles & Practice of Oncology
Chapter 37. Topoisomerase-Interacting Agents >
Mechanism of Action
The anthracyclines are flat, planar molecules that are relatively hydrophobic (Fig. 37.4). They poison Top2 by intercalating DNA with high affinity and stabilize the DNA-Top2 cleavable complexes, leading to DNA ...
Cancer: Principles & Practice of Oncology
Chapter 37. Topoisomerase-Interacting Agents >
Mechanisms of Resistance
Anthracyclines are hydrophobic molecules that enter cells via passive diffusion. Anthracyclines are substrates for P-glycoprotein and Mrp-1, and drug efflux is thought to be a major affecter of drug resistance. ...
Cancer: Principles & Practice of Oncology
Chapter 37. Topoisomerase-Interacting Agents >
Cardiac Toxicity
Anthracyclines are associated with cardiac toxicities, and special considerations are necessary from the perspective of this side effect. Acute doxorubicin cardiotoxicity is reversible, and clinical signs include tachycardia, hypotension, electrocardiogram ...
Cancer: Principles & Practice of Oncology
Chapter 37. Topoisomerase-Interacting Agents >
Anthracyclines
Anthracyclines are natural products derived from Streptomyces peucetius variation caesius. Daunorubicin and doxorubicin were discovered in the 1960s and 1970s and in the 1980s were found to target Top2.55 They ...
Cancer: Principles & Practice of Oncology
Chapter 80. Cancer of the Stomach >
Treatment of Advanced Gastric Cancer: Palliative Systemic Chemotherapy
Cancer: Principles & Practice of Oncology
Chapter 163. Cardiac Toxicity >
Anthracyclines
There is both a rare but reversible acute cardiotoxicity, and a delayed but irreversible dilated cardiomyopathy with anthracycline therapy.1,3 The acute toxicity presents as a myocarditis, with or without pericarditis, ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 6. Pharmacogenetics >
Anthracyclines
The primary variant implicated in anthracycline pharmacology affects the carbonyl reductase 3 gene (CBR3), which converts doxorubicin to its alcohol metabolite, which has decreased antitumor activity but greater cardiotoxicity (see ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Membrane Perturbations
It has been appreciated for more than two decades that the anthracycline antibiotics are membrane-active compounds that produce a myriad of effects at the cell surface.233 It is now abundantly clear that events ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Enhanced Drug Efflux
P170-Glycoprotein-Mediated Anthracycline Efflux. A majority of the doxorubicin-resistant cell lines developed in the laboratory exhibit increased expression of the P170-glycoprotein, an ATP-dependent exporter of the ABC-cassette family.27,349 The evidence supporting its role in resistance ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Liposome Encapsulated Anthracyclines
In an effort to enhance tissue distribution and alter pharmacokinetics, doxorubicin has been encapsulated in a liposomal pegylated formation (Doxil) and in a non-pegylated liposome, Myocet. Pegylation (addition of multiple polyethylene glycol groups) ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
General Mechanism of Action, Cellular, and Molecular Pharmacology
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Topoisomerase II Interactions
An important advance in our understanding of anthracycline-DNA interactions occurred with the demonstration that anthracyclines cause protein-associated DNA breaks (measured by filter elution), the number of which correlate with cytotoxicity in some cell ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
One-Electron Reduction
The one-electron reduction of the anthracyclines was initially described in hepatic microsomal systems125,126–127 but was later shown to play a central role in the cardiac toxicity of this class of drugs128,129–130 and may be ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Role of Iron
Although free radical formation was originally proposed as the basis for anthracycline cardiac toxicity in 1977 and various animal model studies suggested that hydroxyl radical scavengers could blunt doxorubicin-related heart damage, free radical ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Two-Electron Reduction of the Anthracyclines
Two-electron reduction of doxorubicin (which may occur by sequential one-electron reductions or directly by strong reducing agents) results in the formation of an unstable quinone methide, which rapidly undergoes a series of reactions ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Signal Transduction and Anthracyclines
Communication between the cell surface and the nucleus plays a crucial role in growth control; important signal transduction pathways for mitogenic stimuli are initiated at the plasma membrane.248,249,250,251–252 Anthracyclines impact signaling pathways in ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Anthracyclines and Apoptosis
Anthracycline-related alterations in membrane biochemistry, signal transduction, mitochondrial metabolism, DNA damage, and free radical formation all contribute to apoptosis.281,282–283 ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Cellular Senescence, and Other Mechanisms of Antitumor Action
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Mechanisms of Resistance
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Drug Interactions
Few drug interactions have been documented for the anthracyclines. Heparin, a large polyanion, binds to the aminosugar of doxorubicin and daunorubicin, creating insoluble aggregates. Coadministration of heparin and doxorubicin can lead to an ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Clinical Pharmacology
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Secondary Leukemia
A second important late toxicity of anthracyclines, and particularly doxorubicin, is secondary leukemia. As previously discussed, this class of drugs is mutagenic. It produces single- and double-strand breaks in DNA through its inhibition ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Structure
The structures of anthracyclines in common oncologic practice are shown in Figure 18-1. They were originally discovered as products of the fungus Streptococcus paucities var. caesius, and all contain a rigid structure of four ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Transmembrane Transport
The anthracyclines move into cells by diffusion of the un-ionized drug.8,9–10 The uptake of the less polar daunorubicin is substantially faster than that of doxorubicin, which is itself substantially faster than its ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
DNA Intercalation, Topoisomerase II Interactions, and Other Effects on DNA
DNA Intercalation. There remains considerable controversy over the mechanism of action of the anthracyclines and thus over the importance of various intracellular targets. However, there is no disagreement with the observation that the ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines >
Drug Activation by One- and Two-Electron Reduction
During DNA intercalation and binding to top II, the anthracyclines act as chemically inert compounds that owe their activity to their ability to bind to key macromolecules and distort the three-dimensional geometry ...
Diseases of the Breast
Chapter 49. Adjuvant Systemic Therapy: Chemotherapy >
Role of the Anthracyclines
After demonstrating benefit in the metastatic setting, multiple randomized trials were initiated to evaluate the potential contribution of anthracyclines in adjuvant therapy. One of the first modifications of standard CMF-type ...
Diseases of the Breast
Chapter 55. Side Effects of Systemic Therapy: Neurocognitive, Cardiac, and Secondary Malignancies >
Anthracyclines
Interpretation of data related to anthracyclines relies on understanding the mechanism of action, impact of dose and schedules, and the extent of short-or long-term patient follow-up. Potential conclusions related to ...
Diseases of the Breast
Chapter 55. Side Effects of Systemic Therapy: Neurocognitive, Cardiac, and Secondary Malignancies >
Prevention of Anthracycline-induced Cardiotoxicity
No single strategy has been successful to prevent or delay cumulative anthracycline-induced cardiotoxicity and so limitation of cumulative dose and early detection remain the most effective method to deter a ...
Diseases of the Breast
Chapter 68. Breast Cancer during Pregnancy and Subsequent Pregnancy in Breast Cancer Survivors >
Anthracycline-Based Chemotherapy
Numerous case reports and case series exist regarding different chemotherapeutic agents given during pregnancy, mostly with anthracycline-based regimens. M.D. Anderson Cancer Center has the largest prospective cohort of pregnant breast ...
Diseases of the Breast
Chapter 74. Treatment of Metastatic Breast Cancer: Chemotherapy >
Anthracyclines and Anthraquinones
Diseases of the Breast
Chapter 74. Treatment of Metastatic Breast Cancer: Chemotherapy >
Drug Resistance
There are two major mechanisms for resistance. One is classic multidrug resistance related to expression of P-glycoprotein. The other is a variety of P-glycoprotein-independent mechanisms such as increased glutathione transferase ...
Diseases of the Breast
Chapter 74. Treatment of Metastatic Breast Cancer: Chemotherapy >
Drug Interactions
Doxorubicin is a major substrate of CYP2D6 and CYP3A4. Hence CYP2D6 inhibitors such as chlorpromazine, fluoxetine, and paroxetine may increase the levels of doxorubicin. Similarly, CYP3A4 inhibitors, including azole antifungals, ...
Principles and Practice of Surgical Oncology
Chapter 20. Adjuvant Therapy in Breast Cancer >
Anthracyclines Versus CMF
The absolute difference in survival between anthracycline-based regimens and CMF chemotherapy is about 3% at 5 years and 4% at 10 years, irrespective of age. Oral CMF is superior to ...
Principles and Practice of Pediatric Oncology
Chapter 10. General Principles of Chemotherapy >
Anthracyclines
The anthracyclines, doxorubicin, daunomycin (daunorubicin), and idarubicin, are highly pigmented compounds composed of a planar tetracyclic anthraquinone nucleus linked to the amino sugar daunosamine (Fig. 10.19). Doxorubicin has a wide ...
Principles and Practice of Pediatric Oncology
Chapter 10. General Principles of Chemotherapy >
Biotransformation
The principal metabolites of the anthracyclines (Fig. 10.20) are the corresponding alcohols (13-dihydroderivative), doxorubicinol, daunomycinol, and idarubicinol, formed by the action of aldoketoreductase.818,827 Doxorubicinol and daunomycinol retain cytotoxic activity but ...
Principles and Practice of Pediatric Oncology
Chapter 10. General Principles of Chemotherapy >
Pharmacokinetics
Instability of doxorubicin and daunomycin in an acid environment prevents their oral administration. Idarubicin can be administered orally and has a bioavailability of 20% to 30%.827,829–831 The severe vesicant properties ...
Principles and Practice of Pediatric Oncology
Chapter 10. General Principles of Chemotherapy >
Toxicity
The acute toxicities of the anthracyclines include myelosuppression, mucositis (less prominent with daunomycin), nausea, vomiting, diarrhea, and alopecia.859 Extravasation of these agents leads to severe local tissue damage and deep ...
Principles and Practice of Pediatric Oncology
Chapter 10. General Principles of Chemotherapy >
Drug Interactions
Doxorubicin elimination half-life may be prolonged when coadministered with cyclophosphamide or nitrosoureas, and doxorubicin clearance appears to be enhanced by coadministration with etoposide.827 The cardioprotectant, dexrazoxane, does not modify doxorubicin ...
Perry’s The Chemotherapy Source Book, 5e
Chapter 15. Hypersensitivity Reactions >
Anthracyclines
Doxorubicin has occasionally produced severe and generalized type I reactions.157–159 These HSRs are characterized by urticaria, pruritus, angioedema, dyspnea and bronchospasm, and sometimes hypotension. Such reactions have even occurred when ...
Perry’s The Chemotherapy Source Book, 5e
Chapter 17. Cardiotoxicity of Cancer Therapy >
Anthracyclines
The anthracyclines are a class of red-pigmented antibiotics (rhodomycins) isolated from a soil bacillus, actinomycete Streptomyces.1 They include daunorubicin, doxorubicin, epirubicin, and idarubicin. Anthracycline-associated cardiac toxicity may have two clinical ...
Perry’s The Chemotherapy Source Book, 5e
Chapter 25. Chemotherapy in Pregnancy >
Anthracyclines
Although doxorubicin and daunorubicin have been shown to produce congenital malformations in animals, they have not always been associated with birth defects either alone or in combination.128 Several reports describe ...
Principles and Practice of Gynecologic Oncology
Chapter 29. Breast Cancer > Breast Cancer in Pregnancy
Several prospective case series have reported on the use of ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines > Role of Iron
Although free radical formation was originally proposed as the basis ...
Cancer Chemotherapy and Biotherapy: Principles and Practice
Chapter 18. Topoisomerase II Inhibitors: Anthracyclines > Daunorubicin (Daunomycin) and Doxorubicin
As potent radiation sensitizers, the anthracyclines cannot be administered simultaneously ...
Principles and Practice of Surgical Oncology
Chapter 34. Gastric Cancer: Perioperative Adjunctive Therapy > Adjuvant Systemic Chemotherapy
In 1999, Earle and Maroun (
20
) performed a meta-analysis ...
Principles and Practice of Pediatric Oncology
Chapter 19. Acute Lymphoblastic Leukemia > Induction Therapy
Although the basic two-drug combination of vincristine and a glucocorticoid ...
Principles and Practice of Pediatric Oncology
Chapter 20. Acute Myeloid Leukemia, Myeloproliferative and Myelodysplastic Disorders > Therapy-Related Myeloid Neoplasms
As childhood cancer survival rates increase, so does the incidence ...
Principles and Practice of Pediatric Oncology
Chapter 20. Acute Myeloid Leukemia, Myeloproliferative and Myelodysplastic Disorders > Historical Perspective—Introduction of Cytarabine and the Anthracyclines
Aggressive induction therapy is an important treatment principle that improves ...
Principles and Practice of Pediatric Oncology
Chapter 20. Acute Myeloid Leukemia, Myeloproliferative and Myelodysplastic Disorders > Salvage Options in Relapsed AML
Cytarabine is one of the most active antileukemic agents and ...
Principles and Practice of Pediatric Oncology
Chapter 20. Acute Myeloid Leukemia, Myeloproliferative and Myelodysplastic Disorders > Treatment of APL
In the early 1970s, Bernard et al. demonstrated the sensitivity ...
Perry’s The Chemotherapy Source Book, 5e
Chapter 17. Cardiotoxicity of Cancer Therapy > Anthracyclines
Though not uniformly accepted by the oncology community, liposomal formulations ...
Principles of Molecular Diagnostics and Personalized Cancer Medicine
Chapter 53. Personalized Medicine and Targeted Therapy of Breast Cancer > Chemotherapeutic Regimens
There is growing controversy over the use of anthracyclines because ...
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Journal Results from PubMed
Improved outcome in pediatric relapsed acute myeloid leukemia: results of a randomized trial on liposomal daunorubicin by the International BFM Study Group.
J. Clin. Oncol. | Feb 11, 2013
Randomized, open-label, phase III study comparing patupilone (EPO906) with pegylated liposomal doxorubicin in platinum-refractory or -resistant patients with recurrent epithelial ovarian, primary fallopian tube, or primary peritoneal cancer.
J. Clin. Oncol. | Oct 31, 2012
Single nucleotide polymorphisms and anthracycline cardiotoxicity in children: potential implications for adult oncology.
J. Clin. Oncol. | Oct 1, 2012
Bortezomib induction and maintenance treatment in patients with newly diagnosed multiple myeloma: results of the randomized phase III HOVON-65/ GMMG-HD4 trial.
J. Clin. Oncol. | Aug 20, 2012
Randomized comparison of intensified six-drug versus standard three-drug chemotherapy for high-risk nonmetastatic rhabdomyosarcoma and other chemotherapy-sensitive childhood soft tissue sarcomas: long-term results from the International Society of Pediatric Oncology MMT95 study.
J. Clin. Oncol. | Jul 9, 2012
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