蒽環類藥物

來自維基學院

 醫學維基期刊(譯本) 
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原作者信息:Alison Cheong1*, Sean McGrath1*, Suzanne Cutts2
1:拉籌伯大學 澳大利亞墨爾本
2:拉籌伯大學 澳大利亞墨爾本;通訊作者,郵箱:s.cutts@latrobe.edu.au
*:對本文的貢獻相同

摘要:蒽環類藥物是一類在臨床上具有重要意義的抗腫瘤化療藥物,能治療多種實體瘤以及血液瘤。頭兩種獲得報導的蒽環類藥物是蒽環黴素和柔紅黴素,它們是從波賽鏈黴菌(Streptomyces peucetius)的菌株中分離得到的。目前,臨床上最常用的蒽環類藥物包括多柔比星和柔紅黴素,以及這兩種藥物的半合成衍生物表柔比星和伊達比星。蒽環類藥物能抑制拓撲異構酶II的活性,並插入DNA分子中,使DNA分子斷裂、DNA合成停止。蒽環類藥物最嚴重的副作用是劑量依賴的累積性心臟毒性。為避免出現這樣的副作用,需要調整給藥量,使血藥濃度峰值控制在400-450 mg/m2。一部分蒽環類藥物使用脂質體製劑,能增加藥物的半衰期,使藥物濃度能在更長時間裡維持在治療濃度之上、血漿中自由的藥物分子濃度減少。一些蒽環類藥物的納米顆粒製劑已進入臨床實驗階段。

導言[編輯 | 編輯原始碼]

參考文獻[編輯 | 編輯原始碼]

  1. 1.0 1.1 Dubost, M.; Ganter, P.; Maral, R.; Ninet, L.; Pinnert, S.; Preudhomme, J.; Werner, G. H. RUBIDOMYCIN: A NEW ANTIBIOTIC WITH CYTOSTATIC PROPERTIES. Cancer Chemotherapy Reports. September 1964, 41: 35–36. ISSN 0069-0112. PMID 14213139. 
  2. Frederick, C. A.; Williams, L. D.; Ughetto, G.; van der Marel, G. A.; van Boom, J. H.; Rich, A.; Wang, A. H. Structural comparison of anticancer drug-DNA complexes: adriamycin and daunomycin. Biochemistry. 1990-03-13, 29 (10): 2538–2549. ISSN 0006-2960. PMID 2334681. 
  3. DI MARCO, A.; GAETANI, M.; OREZZI, P.; SCARPINATO, B. M.; SILVESTRINI, R.; SOLDATI, M.; DASDIA, T.; VALENTINI, L. ‘Daunomycin’, a New Antibiotic of the Rhodomycin Group. Nature. 1964/02, 201 (4920): 706–707. ISSN 1476-4687. doi:10.1038/201706a0 (英語). 
  4. 4.0 4.1 Weiss, R. B. The anthracyclines: will we ever find a better doxorubicin?. Seminars in Oncology. December 1992, 19 (6): 670–686. ISSN 0093-7754. PMID 1462166. 
  5. Arcamone, F.; Cassinelli, G.; Fantini, G.; Grein, A.; Orezzi, P.; Pol, C.; Spalla, C. Adriamycin, 14-hydroxydaunomycin, a new antitumor antibiotic from S. peucetius var. caesius. Biotechnology and Bioengineering. November 1969, 11 (6): 1101–1110. ISSN 0006-3592. PMID 5365804. doi:10.1002/bit.260110607. 
  6. Blum, R. H.; Carter, S. K. Adriamycin. A new anticancer drug with significant clinical activity. Annals of Internal Medicine. February 1974, 80 (2): 249–259. ISSN 0003-4819. PMID 4590654. 
  7. Cancer management in man : chemotherapy, biological therapy, hyperthermia and supporting measures. Minev, Boris R. Dordrecht: Springer. 2011. ISBN 9789048197040. OCLC 704395391. 
  8. DeVita, Hellman, and Rosenberg's cancer : principles & practice of oncology. DeVita, Vincent T., Jr., 1935-, Lawrence, Theodore S., Rosenberg, Steven A. 8th ed. Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins. 2008. ISBN 9780781772075. OCLC 192027662. 
  9. Takemura, Genzou; Fujiwara, Hisayoshi. Doxorubicin-induced cardiomyopathy from the cardiotoxic mechanisms to management. Progress in Cardiovascular Diseases. March 2007, 49 (5): 330–352. ISSN 0033-0620. PMID 17329180. doi:10.1016/j.pcad.2006.10.002. 
  10. Arcamone, Federico & Penco, S & Vigevani, A. (1975). Adriamycin (NSC 123127): new chemical developments and analogs. CANCER CHEMOTHER.REP.. 6. 123-129.
  11. Arcamone, F.; Bernardi, L.; Giardino, P.; Patelli, B.; Marco, A.; Casazza, A. M.; Pratesi, G.; Reggiani, P. Synthesis and antitumor activity of 4-demethoxydaunorubicin, 4-demethoxy-7,9-diepidaunorubicin, and their beta anomers. Cancer Treatment Reports. July 1976, 60 (7): 829–834. ISSN 0361-5960. PMID 1009518. 
  12. Evison, Benny J.; Sleebs, Brad E.; Watson, Keith G.; Phillips, Don R.; Cutts, Suzanne M. Mitoxantrone, More than Just Another Topoisomerase II Poison. Medicinal Research Reviews. 2016-3, 36 (2): 248–299. ISSN 1098-1128. PMID 26286294. doi:10.1002/med.21364. 
  13. 13.0 13.1 Marinello, Jessica; Delcuratolo, Maria; Capranico, Giovanni. Anthracyclines as Topoisomerase II Poisons: From Early Studies to New Perspectives. International Journal of Molecular Sciences. 2018-11-06, 19 (11). ISSN 1422-0067. PMID 30404148. doi:10.3390/ijms19113480. 
  14. 14.0 14.1 McGowan, John V; Chung, Robin; Maulik, Angshuman; Piotrowska, Izabela; Walker, J Malcolm; Yellon, Derek M. Anthracycline Chemotherapy and Cardiotoxicity. Cardiovascular Drugs and Therapy. 2017, 31 (1): 63–75. ISSN 0920-3206. PMC 5346598可免費查閱. PMID 28185035. doi:10.1007/s10557-016-6711-0. 
  15. 15.0 15.1 Wahba, Hanan Ahmed; El-Hadaad, Hend Ahmed. Current approaches in treatment of triple-negative breast cancer. Cancer Biology & Medicine. June 2015, 12 (2): 106–116. ISSN 2095-3941. PMC 4493381可免費查閱. PMID 26175926. doi:10.7497/j.issn.2095-3941.2015.0030. 
  16. Guo, Baoqing; Tam, Adam; Santi, Stacey A.; Parissenti, Amadeo M. Role of autophagy and lysosomal drug sequestration in acquired resistance to doxorubicin in MCF-7 cells. BMC cancer. 2016-09-29, 16 (1): 762. ISSN 1471-2407. PMC 5043608可免費查閱. PMID 27687594. doi:10.1186/s12885-016-2790-3. 
  17. 17.0 17.1 17.2 17.3 Gewirtz, D. A. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochemical Pharmacology. 1999-04-01, 57 (7): 727–741. ISSN 0006-2952. PMID 10075079. 
  18. Binaschi, M.; Bigioni, M.; Cipollone, A.; Rossi, C.; Goso, C.; Maggi, C. A.; Capranico, G.; Animati, F. Anthracyclines: selected new developments. Current Medicinal Chemistry. Anti-Cancer Agents. August 2001, 1 (2): 113–130. ISSN 1568-0118. PMID 12678762. 
  19. 19.0 19.1 Minotti, Giorgio; Menna, Pierantonio; Salvatorelli, Emanuela; Cairo, Gaetano; Gianni, Luca. Anthracyclines: molecular advances and pharmacologic developments in antitumor activity and cardiotoxicity. Pharmacological Reviews. June 2004, 56 (2): 185–229. ISSN 0031-6997. PMID 15169927. doi:10.1124/pr.56.2.6. 
  20. 20.0 20.1 20.2 Angsutararux, Paweorn; Luanpitpong, Sudjit; Issaragrisil, Surapol. Chemotherapy-Induced Cardiotoxicity: Overview of the Roles of Oxidative Stress. Oxidative Medicine and Cellular Longevity. 2015, 2015: 1–13. ISSN 1942-0900. doi:10.1155/2015/795602 (英語). 
  21. 21.0 21.1 21.2 21.3 21.4 21.5 21.6 21.7 21.8 Simůnek, Tomás; Stérba, Martin; Popelová, Olga; Adamcová, Michaela; Hrdina, Radomír; Gersl, Vladimír. Anthracycline-induced cardiotoxicity: overview of studies examining the roles of oxidative stress and free cellular iron. Pharmacological reports: PR. January 2009, 61 (1): 154–171. ISSN 1734-1140. PMID 19307704. 
  22. 22.0 22.1 Cutts, Suzanne M.; Rephaeli, Ada; Nudelman, Abraham; Ugarenko, Michal; Phillips, Don R. Potential Therapeutic Advantages of Doxorubicin when Activated by Formaldehyde to Function as a DNA Adduct-Forming Agent. Current Topics in Medicinal Chemistry. 2015, 15 (14): 1409–1422. ISSN 1873-4294. PMID 25866273. 
  23. Cutts, Suzanne M.; Nudelman, Abraham; Rephaeli, Ada; Phillips, Don R. The power and potential of doxorubicin-DNA adducts. IUBMB life. February 2005, 57 (2): 73–81. ISSN 1521-6543. PMID 16036566. doi:10.1080/15216540500079093. 
  24. 24.0 24.1 Bartlett, John M. S.; McConkey, Christopher C.; Munro, Alison F.; Desmedt, Christine; Dunn, Janet A.; Larsimont, Denis P.; O'Malley, Frances P.; Cameron, David A.; Earl, Helena M. Predicting Anthracycline Benefit: TOP2A and CEP17-Not Only but Also. Journal of Clinical Oncology: Official Journal of the American Society of Clinical Oncology. 2015-05-20, 33 (15): 1680–1687. ISSN 1527-7755. PMID 25897160. doi:10.1200/JCO.2013.54.7869. 
  25. 25.0 25.1 25.2 25.3 Cagel, Maximiliano; Grotz, Estefanía; Bernabeu, Ezequiel; Moretton, Marcela A.; Chiappetta, Diego A. Doxorubicin: nanotechnological overviews from bench to bedside. Drug Discovery Today. 02 2017, 22 (2): 270–281. ISSN 1878-5832. PMID 27890669. doi:10.1016/j.drudis.2016.11.005. 
  26. Scully, Rebecca E.; Lipshultz, Steven E. Anthracycline cardiotoxicity in long-term survivors of childhood cancer. Cardiovascular Toxicology. 2007, 7 (2): 122–128. ISSN 1530-7905. PMID 17652816. doi:10.1007/s12012-007-0006-4. 
  27. 27.0 27.1 27.2 27.3 27.4 27.5 27.6 27.7 Ewer, Michael S.; Ewer, Steven M. Cardiotoxicity of anticancer treatments. Nature Reviews. Cardiology. September 2015, 12 (9): 547–558. ISSN 1759-5010. PMID 25962976. doi:10.1038/nrcardio.2015.65. 
  28. Vejpongsa, P.; Yeh, E. T. H. Topoisomerase 2β: a promising molecular target for primary prevention of anthracycline-induced cardiotoxicity. Clinical Pharmacology and Therapeutics. January 2014, 95 (1): 45–52. ISSN 1532-6535. PMID 24091715. doi:10.1038/clpt.2013.201. 
  29. 29.0 29.1 29.2 29.3 29.4 29.5 29.6 29.7 Gabizon, Alberto; Shmeeda, Hilary; Barenholz, Yechezkel. Pharmacokinetics of pegylated liposomal Doxorubicin: review of animal and human studies. Clinical Pharmacokinetics. 2003, 42 (5): 419–436. ISSN 0312-5963. PMID 12739982. doi:10.2165/00003088-200342050-00002. 
  30. 30.0 30.1 30.2 Jordan, Karin; Behlendorf, Timo; Mueller, Franziska; Schmoll, Hans-Joachim. Anthracycline extravasation injuries: management with dexrazoxane. Therapeutics and Clinical Risk Management. 2009, 5: 361–366. ISSN 1176-6336. PMC 2697522可免費查閱. PMID 19536310. 
  31. Chou, Hunghsueh; Lin, Hao; Liu, Jacqueline M. A tale of the two PEGylated liposomal doxorubicins. OncoTargets and therapy. 2015-07-13, 8: 1719–1720. ISSN 1178-6930. PMC 4508070可免費查閱. PMID 26203262. doi:10.2147/OTT.S79089. 
  32. Araujo, F. I.; Proença, F. P. P.; Ferreira, C. G.; Ventilari, S. C.; Rosado de Castro, P. H.; Moreira, R. D.; Fonseca, L. M. B.; Souza, S. a. L.; Gutfilen, B. Use of (99m)Tc-doxorubicin scintigraphy in females with breast cancer: a pilot study. The British Journal of Radiology. 2015-8, 88 (1052): 20150268. ISSN 1748-880X. PMC 4651371可免費查閱. PMID 26111270. doi:10.1259/bjr.20150268. 
  33. 33.0 33.1 Perez, Edith A. Impact, mechanisms, and novel chemotherapy strategies for overcoming resistance to anthracyclines and taxanes in metastatic breast cancer. Breast Cancer Research and Treatment. March 2009, 114 (2): 195–201. ISSN 1573-7217. PMID 18443902. doi:10.1007/s10549-008-0005-6. 
  34. 34.0 34.1 Arnason, Terra; Harkness, Troy. Development, Maintenance, and Reversal of Multiple Drug Resistance: At the Crossroads of TFPI1, ABC Transporters, and HIF1α. Cancers. 2015-10-16, 7 (4): 2063–2082. ISSN 2072-6694. PMC 4695877可免費查閱. PMID 26501324. doi:10.3390/cancers7040877. 
  35. 35.0 35.1 Sercombe, Lisa; Veerati, Tejaswi; Moheimani, Fatemeh; Wu, Sherry Y.; Sood, Anil K.; Hua, Susan. Advances and Challenges of Liposome Assisted Drug Delivery. Frontiers in Pharmacology. 2015-12-01, 6. ISSN 1663-9812. PMC 4664963可免費查閱. PMID 26648870. doi:10.3389/fphar.2015.00286. 
  36. Barenholz, Yechezkel. Doxil®--the first FDA-approved nano-drug: lessons learned. Journal of Controlled Release: Official Journal of the Controlled Release Society. 2012-06-10, 160 (2): 117–134. ISSN 1873-4995. PMID 22484195. doi:10.1016/j.jconrel.2012.03.020. 
  37. Udhrain, Ashish; Skubitz, Keith M.; Northfelt, Donald W. Pegylated liposomal doxorubicin in the treatment of AIDS-related Kaposi's sarcoma. International Journal of Nanomedicine. 2007, 2 (3): 345–352. ISSN 1176-9114. PMC 2676669可免費查閱. PMID 18019833. 
  38. 38.0 38.1 38.2 Soloman, Rebecca; Gabizon, Alberto A. Clinical pharmacology of liposomal anthracyclines: focus on pegylated liposomal Doxorubicin. Clinical Lymphoma & Myeloma. February 2008, 8 (1): 21–32. ISSN 1557-9190. PMID 18501085. 
  39. Haran, G.; Cohen, R.; Bar, L. K.; Barenholz, Y. Transmembrane ammonium sulfate gradients in liposomes produce efficient and stable entrapment of amphipathic weak bases. Biochimica Et Biophysica Acta. 1993-09-19, 1151 (2): 201–215. ISSN 0006-3002. PMID 8373796. 
  40. Maeda, Hiroshi; Nakamura, Hideaki; Fang, Jun. The EPR effect for macromolecular drug delivery to solid tumors: Improvement of tumor uptake, lowering of systemic toxicity, and distinct tumor imaging in vivo. Advanced Drug Delivery Reviews. 2013-1, 65 (1): 71–79. ISSN 1872-8294. PMID 23088862. doi:10.1016/j.addr.2012.10.002. 
  41. Batist, Gerald. Cardiac safety of liposomal anthracyclines. Cardiovascular Toxicology. 2007, 7 (2): 72–74. ISSN 1530-7905. PMID 17652807. doi:10.1007/s12012-007-0014-4. 
  42. Batist, Gerald; Barton, Jeremy; Chaikin, Philip; Swenson, Christine; Welles, Lauri. Myocet (liposome-encapsulated doxorubicin citrate): a new approach in breast cancer therapy. Expert Opinion on Pharmacotherapy. December 2002, 3 (12): 1739–1751. ISSN 1465-6566. PMID 12472371. doi:10.1517/14656566.3.12.1739. 
  43. Leonard, R. C. F.; Williams, S.; Tulpule, A.; Levine, A. M.; Oliveros, S. Improving the therapeutic index of anthracycline chemotherapy: focus on liposomal doxorubicin (Myocet). Breast (Edinburgh, Scotland). August 2009, 18 (4): 218–224. ISSN 1532-3080. PMID 19656681. doi:10.1016/j.breast.2009.05.004. 
  44. 44.0 44.1 Swenson, CE; Perkins, WR; Roberts, P; Janoff AS (2005) Liposome technology and the development of Myocet™ (liposomal doxorubicin citrate). The Breast. 2001-06-01, 10: 1–7. ISSN 0960-9776. doi:10.1016/S0960-9776(01)80001-1. 
  45. Bulbake, Upendra; Doppalapudi, Sindhu; Kommineni, Nagavendra; Khan, Wahid. Liposomal Formulations in Clinical Use: An Updated Review. Pharmaceutics. 2017-03-27, 9 (2). ISSN 1999-4923. PMC 5489929可免費查閱. PMID 28346375. doi:10.3390/pharmaceutics9020012. 
  46. Mross, Klaus; Niemann, Bernward; Massing, Ulrich; Drevs, Joachim; Unger, Clemens; Bhamra, Rupinder; Swenson, Christine E. Pharmacokinetics of liposomal doxorubicin (TLC-D99; Myocet) in patients with solid tumors: an open-label, single-dose study. Cancer Chemotherapy and Pharmacology. 2004-08-21, 54 (6): 514–524. ISSN 0344-5704. doi:10.1007/s00280-004-0825-y (英語). 
  47. Poon, Ronnie T. P.; Borys, Nicholas. Lyso-thermosensitive liposomal doxorubicin: a novel approach to enhance efficacy of thermal ablation of liver cancer. Expert Opinion on Pharmacotherapy. February 2009, 10 (2): 333–343. ISSN 1744-7666. PMID 19236203. doi:10.1517/14656560802677874. 
  48. Mukai, Hirofumi; Kogawa, Takahiro; Matsubara, Nobuaki; Naito, Yoichi; Sasaki, Masaoki; Hosono, Ako. A first-in-human Phase 1 study of epirubicin-conjugated polymer micelles (K-912/NC-6300) in patients with advanced or recurrent solid tumors. Investigational New Drugs. 06 2017, 35 (3): 307–314. ISSN 1573-0646. PMID 28054329. doi:10.1007/s10637-016-0422-z. 
  49. Nishiyama, Nobuhiro; Matsumura, Yasuhiro; Kataoka, Kazunori. Development of polymeric micelles for targeting intractable cancers. Cancer Science. July 2016, 107 (7): 867–874. ISSN 1349-7006. PMC 4946707可免費查閱. PMID 27116635. doi:10.1111/cas.12960. 
  50. Kivistö, K T; Kroemer, H K; Eichelbaum, M. The role of human cytochrome P450 enzymes in the metabolism of anticancer agents: implications for drug interactions.. British Journal of Clinical Pharmacology. December 1995, 40 (6): 523–530. ISSN 0306-5251. PMC 1365206可免費查閱. PMID 8703657. 
  51. 51.0 51.1 Bedford Laboratories (2012). Product Information: Adriamcycin (Doxorubcin HCl) for Injection, USP. In (pp. 8). Ohio (https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/062921s022lbl.pdf)
  52. Tacar, Oktay; Sriamornsak, Pornsak; Dass, Crispin R. Doxorubicin: an update on anticancer molecular action, toxicity and novel drug delivery systems. The Journal of Pharmacy and Pharmacology. February 2013, 65 (2): 157–170. ISSN 2042-7158. PMID 23278683. doi:10.1111/j.2042-7158.2012.01567.x. 
  53. Lyu, Yi Lisa; Kerrigan, John E.; Lin, Chao-Po; Azarova, Anna M.; Tsai, Yuan-Chin; Ban, Yi; Liu, Leroy F. Topoisomerase IIbeta mediated DNA double-strand breaks: implications in doxorubicin cardiotoxicity and prevention by dexrazoxane. Cancer Research. 2007-09-15, 67 (18): 8839–8846. ISSN 0008-5472. PMID 17875725. doi:10.1158/0008-5472.CAN-07-1649. 
  54. Ewer, Michael S.; Ewer, Steven M. Troponin I provides insight into cardiotoxicity and the anthracycline-trastuzumab interaction. Journal of Clinical Oncology: Official Journal of the American Society of Clinical Oncology. 2010-09-01, 28 (25): 3901–3904. ISSN 1527-7755. PMID 20679626. doi:10.1200/JCO.2010.30.6274. 
  55. Rayson, D.; Richel, D.; Chia, S.; Jackisch, C.; van der Vegt, S.; Suter, T. Anthracycline-trastuzumab regimens for HER2/neu-overexpressing breast cancer: current experience and future strategies. Annals of Oncology: Official Journal of the European Society for Medical Oncology. September 2008, 19 (9): 1530–1539. ISSN 1569-8041. PMID 18480068. doi:10.1093/annonc/mdn292. 
  56. Slamon, D. J.; Leyland-Jones, B.; Shak, S.; Fuchs, H.; Paton, V.; Bajamonde, A.; Fleming, T.; Eiermann, W.; Wolter, J. Use of chemotherapy plus a monoclonal antibody against HER2 for metastatic breast cancer that overexpresses HER2. The New England Journal of Medicine. 2001-03-15, 344 (11): 783–792. ISSN 0028-4793. PMID 11248153. doi:10.1056/NEJM200103153441101. 
  57. Gianni, L.; Viganò, L.; Locatelli, A.; Capri, G.; Giani, A.; Tarenzi, E.; Bonadonna, G. Human pharmacokinetic characterization and in vitro study of the interaction between doxorubicin and paclitaxel in patients with breast cancer. Journal of Clinical Oncology: Official Journal of the American Society of Clinical Oncology. May 1997, 15 (5): 1906–1915. ISSN 0732-183X. PMID 9164201. doi:10.1200/JCO.1997.15.5.1906.