Oral delivery of anticancer drugs II: the prodrug strategy

Drug Discovery Today - Tập 18 - Trang 93-98 - 2013
Silvia Mazzaferro1, Kawthar Bouchemal1, Gilles Ponchel1
1Université Paris-Sud, Faculté de Pharmacie, UMR CNRS 8612, Institut Galien Paris-Sud, 5, rue J.B. Clément, 92296 Châtenay-Malabry Cedex, France

Tài liệu tham khảo

Albert, 1958, Chemical aspects of selective toxicity, Nature, 182, 421, 10.1038/182421a0 Testa, 2004, Prodrug research: futile or fertile?, Biochem. Pharmacol., 68, 2097, 10.1016/j.bcp.2004.07.005 Singh, 2008, Recent trends in targeted anticancer prodrug and conjugate design, Curr. Med. Chem., 15, 1802, 10.2174/092986708785132997 Sharma, 2010, Antibody-directed enzyme prodrug therapy (ADEPT) for cancer, Vol. 4, 10.1007/978-1-4419-0507-9_11 Tietze, 2009, Antibody-directed enzyme prodrug therapy: a promising approach for a selective treatment of cancer based on prodrugs and monoclonal antibodies, Chem. Biol. Drug Des., 74, 205, 10.1111/j.1747-0285.2009.00856.x Rowland, 1975, Suppression of tumor growth in mice by a drug–antibody conjugate using a novel approach to linkage, Nature, 255, 487, 10.1038/255487a0 Fleisher, 1996, Improved oral drug delivery: solubility limitations overcome by the use of prodrugs, Adv. Drug Deliv. Rev., 19, 115, 10.1016/0169-409X(95)00103-E Heidelberger, 1957, Fluorinated pyrimidines, a new class of tumour-inhibitory compounds, Nature, 179, 663, 10.1038/179663a0 Sharma, 2000, Oral chemotherapeutic agents for colorectal cancer, Oncologist, 5, 99, 10.1634/theoncologist.5-2-99 Eng, 2001, Oral fluoropyrimidine treatment of colorectal cancer, Clin. Colorectal Cancer, 1, 95, 10.3816/CCC.2001.n.009 Malet-Martino, 2002, Clinical studies of three oral prodrugs of 5-fluorouracil (capecitabine, UFT, S-1): a review, Oncologist, 7, 288, 10.1634/theoncologist.7-4-288 Grothey, 2004, Oxaliplatin plus oral fluoropyrimidines in colorectal cancer, Clin. Colorectal Cancer, 4, S37, 10.3816/CCC.2004.s.006 Gradishar, 1990, Review: 5-fluorouracil cardiotoxicity: a critical review, Ann. Oncol., 1, 409, 10.1093/oxfordjournals.annonc.a057793 Cunningham, 2001, New options for outpatient chemotherapy – the role of oral fluoropyrimidines, Cancer Treat. Rev., 27, 211, 10.1053/ctrv.2001.0229 Fraile, 1980, Pharmacokinetics of 5-fluorouracil administered orally, by rapid intravenous and by slow infusion, Cancer Res., 40, 2223 Diasio, 1998, The role of dihydropyrimidine dehydrogenase (DPD) modulation in 5-FU pharmacology, Oncology-Huntington, 12, 23 Bajetta, 1996, A pilot safety study of capecitabine, a new oral fluoropyrimidine, in patients with advanced neoplastic disease, Tumori, 82, 450, 10.1177/030089169608200507 Haraguchi, 1994, Angiogenic activity of enzymes, Nature, 368, 198, 10.1038/368198a0 Ho, 2000, Oral uracil and ftorafur plus leucovorin: pharmacokinetics and toxicity in patients with metastatic cancer, Cancer Chemother. Pharmacol., 46, 351, 10.1007/s002800000156 Lamont, 1999, The oral fluoropyrimidines in cancer chemotherapy, Clin. Cancer Res., 5, 2289 Braun, 2011, Review: balancing the efficacy and toxicity of chemotherapy in colorectal cancer, Ther. Adv. Med. Oncol., 3, 43, 10.1177/1758834010388342 Ferguson, 2001, The role of pro-drug therapy in the treatment of cancer, Drug Resist. Updates, 4, 225, 10.1054/drup.2001.0207 Judson, 1999, A human capecitabine excretion balance and pharmacokinetic study after administration of a single oral dose of 14C-labelled drug, Invest. New Drugs, 17, 49, 10.1023/A:1006263400888 Reigner, 2001, Clinical pharmacokinetics of capecitabine, Clin. Pharmacokinet., 40, 85, 10.2165/00003088-200140020-00002 Miwa, 1998, Design of a novel oral fluoropyrimidine carbamate, capecitabine, which generates 5-fluorouracil selectively in tumours by enzymes concentrated in human liver and cancer tissue, Eur. J. Cancer, 34, 1274, 10.1016/S0959-8049(98)00058-6 Ishitsuka, 1995, Capecitabine: an orally available fluoropyrimidine with tumor selective activity, Invest. New Drugs, 18, 343, 10.1023/A:1006497231579 Koukourakis, 2008, Efficacy of the oral fluorouracil pro-drug capecitabine in cancer treatment: a review, Molecules, 13, 1897, 10.3390/molecules13081897 Mikhail, 2010, Safety of capecitabine: a review, Expert Opin. Drug Saf., 9, 831, 10.1517/14740338.2010.511610 Meropol, 1998, Oral fluoropyrimidines in the treatment of colorectal cancer, Eur. J. Cancer, 34, 1509, 10.1016/S0959-8049(98)00226-3 Fujii, 1979, Effect of coadministration of uracil or cytosine on the anti-tumor activity of clinical doses of 1-(2-tetrahydrofuryl)-5-fluorouracil and level of 5-fluorouracil in rodents, Gann, 70, 209 El-Sayed, 2002, Transepithelial transport of poly(amidoamine) dendrimers across Caco-2 cell monolayers, J. Control. Release, 8, 355, 10.1016/S0168-3659(02)00087-1 Tanaka, 1998, Advantage of post-operative oral administration of UFT (Tegafur and Uracil) for completely resected p-stage I–IIIa non-small cell lung cancer (NSCLC) 1, Eur. J. Cardio-Thorac., 14, 256, 10.1016/S1010-7940(98)00186-9 Brito, 2000, Fluoropyrimidines: a critical evaluation, Oncology, 57, 2, 10.1159/000055262 Ohyama, 1982, Antineoplastic effect of UFT therapy (uracil–FT-207 combination therapy) on experimental pancreatic cancer transplanted in the pancreas and subcutaneous region, Gan To Kagaku Ryoho/Cancer Chemother., 9, 2168 Fukui, 1980, Clinical study on the enhancement of drug delivery into tumor tissue by using UFT, Jpn. J. Cancer Chemother., 7, 2124 Tanaka, 2010, UFT and S-1 for treatment of primary lung cancer, Gen. Thorac. Cardiovasc. Surg., 58, 3, 10.1007/s11748-009-0498-x Saltz, 1995, A fixed-ratio combination of uracil and ftorafur (UFT) with low dose leucovorin. An active oral regimen for advanced colorectal cancer, Cancer, 75, 782, 10.1002/1097-0142(19950201)75:3<782::AID-CNCR2820750306>3.0.CO;2-I De la Torre, 1999, Phase II study of radiochemotherapy with UFT and low-dose oral leucovorin in patients with unresectable rectal cancer, Int. J. Radiat. Oncol., 45, 629, 10.1016/S0360-3016(99)00225-4 Borner, 2002, Patient preference and pharmacokinetics of oral modulated UFT versus intravenous fluorouracil and leucovorin: a randomised crossover trial in advanced colorectal, Eur. J. Cancer, 38, 349, 10.1016/S0959-8049(01)00371-9 Shirao, 2004, Comparison of the efficacy, toxicity, and pharmacokinetics of a uracil/tegafur (UFT) plus oral leucovorin (LV) regimen between Japanese and American patients with Advanced Colorectal Cancer: Joint United States and Japan Study of UFT/LV, J. Clin. Oncol., 22, 3466, 10.1200/JCO.2004.05.017 Shirasaka, 2000, Conceptual changes in cancer chemotherapy: from an oral fluoropyrimidine prodrug, UFT, to a novel oral fluoropyrimidine prodrug, S-1, and low-dose FP therapy in Japan, Invest. New Drugs, 18, 315, 10.1023/A:1006476730671 Schoffski, 1999, Safety, toxicity and antitumor efficacy of the modulated oral fluoropyrimidine derivative S-1 in patients with metastatic colorectal cancer: preliminary results of an early phase II study, Clin. Cancer Res., 5, S3772 Nakamura, 2006, Phase II trial of oral S-1 combined with gemcitabine in metastatic pancreatic cancer, Br. J. Cancer, 94, 1575, 10.1038/sj.bjc.6603168 Nakamura, 2005, Phase I trial of oral S-1 combined with gemcitabine in metastatic pancreatic cancer, Br. J. Cancer, 92, 2134, 10.1038/sj.bjc.6602644 Sakuramoto, 2007, Adjuvant chemotherapy for gastric cancer with S-1, an oral fluoropyrimidine, N. Engl. J. Med., 357, 1810, 10.1056/NEJMoa072252 Sakata, 1998, Late phase II study of novel oral fluoropyrimidine anticancer drug S-1 (1M tegafur–0.4M gimestat–1M otastat potassium) in advanced gastric cancer patients, Eur. J. Cancer, 34, 1715, 10.1016/S0959-8049(98)00211-1 Kawahara, 2001, Phase II study of S-1, a novel oral fluorouracil, in advanced non-small-cell lung cancer, Br. J. Cancer, 85, 939, 10.1054/bjoc.2001.2031 Cohen, 2002, Phase I and pharmacokinetic study of once daily oral administration of S-1 in patients with advanced cancer, Clin. Cancer Res., 8, 2116 Iwamoto, 2011, Metronomic S-1 chemotherapy and vandetanib: an efficacious and nontoxic treatment for hepatocellular carcinoma, Neoplasia, 13, 187, 10.1593/neo.101186 Hijioka, 2010, Eight-year survival after advanced gastric cancer treated with S-1 followed by surgery, World J. Gastroenterol., 16, 2824, 10.3748/wjg.v16.i22.2824 Yamamoto, 2010, Efficacy of S-1 in patients with capecitabine-resistant breast cancer – Japan Breast Cancer Research Network (JBCRN) 04-1 Trial, Anticancer Res., 30, 3827 Hara, 2010, Efficacy and safety of S-1 in patients with metastatic breast cancer: retrospective review in a single institution, Oncology, 79, 273, 10.1159/000322371 Seong, 2001, Preoperative chemoradiotherapy with oral doxifluridine plus low-dose oral leucovorin in unresectable primary rectal cancer, Int. J. Radiat. Oncol., 50, 435, 10.1016/S0360-3016(00)01585-6 Ninomiya, 1990, Comparative antitumor activity and intestinal toxicity of 5′-deoxy-5-fluorouridine and its prodrug trimethoxybenzoyl-5′-deoxy-5-fluorocytidine, Cancer Sci., 81, 188 Wheate, 2010, The status of platinum anticancer drugs in the clinic and in clinical trials, Dalton Trans., 39, 8097, 10.1039/c0dt00292e Choy, 2008, Current status and future prospects for satraplatin, an oral platinum analogue, Clin. Cancer Res., 14, 1633, 10.1158/1078-0432.CCR-07-2176 Kelland, 2007, The resurgence of platinum-based cancer chemotherapy, Nat. Rev. Cancer, 7, 573, 10.1038/nrc2167 Ringsdorf, 1975, Structure and properties of pharmacologically active polymers, J. Polym. Sci. Polym. Symp., 51, 135, 10.1002/polc.5070510111 Tong, 2007, Anticancer polymeric nanomedicines, Polym. Rev., 47, 345, 10.1080/15583720701455079 Greenwald, 2003, Effective drug delivery by PEGylated drug conjugates, Adv. Drug Deliv. Rev., 55, 217, 10.1016/S0169-409X(02)00180-1 Greenwald, 2001, PEG drugs: an overview, J. Control. Release, 74, 159, 10.1016/S0168-3659(01)00331-5 Maeda, 1992, Conjugates of anticancer agents and polymers: advantages of macromolecular therapeutics in vivo, Bioconjug. Chem., 3, 351, 10.1021/bc00017a001 Pasut, 2007, Polymer–drug conjugation, recent achievements and general strategies, Prog. Polym. Sci., 32, 933, 10.1016/j.progpolymsci.2007.05.008 Vicent, 2006, Polymer conjugates: nanosized medicines for treating cancer, Trends Biotechnol., 24, 39, 10.1016/j.tibtech.2005.11.006 Skwarczynski, 2006, Paclitaxel prodrugs: toward smarter delivery of anticancer agents, J. Med. Chem., 49, 7253, 10.1021/jm0602155 Choi, 2004, Enhanced paclitaxel bioavailability after oral administration of pegylated paclitaxel prodrug for oral delivery in rats, Int. J. Pharm., 280, 221, 10.1016/j.ijpharm.2004.05.014 Choi, 2004, Enhanced paclitaxel bioavailability after oral administration of paclitaxel or prodrug to rats pretreated with quercetin, Eur. J. Pharm. Biopharm., 57, 313, 10.1016/j.ejpb.2003.11.002 Choi, 2005, Enhanced oral exposure of diltiazem by the concomitant use of naringin in rats, Int. J. Pharm., 305, 122, 10.1016/j.ijpharm.2005.09.004 Lee, 2009, In vivo antitumor effects of chitosan-conjugated docetaxel after oral administration, J. Control. Release, 140, 79, 10.1016/j.jconrel.2009.08.014 Lee, 2008, Conjugated chitosan as a novel platform for oral delivery of paclitaxel, J. Med. Chem., 51, 6442, 10.1021/jm800767c Gelderblom, 1999, Oral topoisomerase 1 inhibitors in adult patients: present and future, Invest. New Drugs, 17, 401, 10.1023/A:1006394610219 Kuppens, 2004, Topoisomerase I inhibitors in the treatment of gastrointestinal cancer: from intravenous to oral administration, Clin. Colorectal Cancer, 4, 163, 10.3816/CCC.2004.n.017 Mathijssen, 2001, Clinical pharmacokinetics and metabolism of irinotecan (CPT-11), Clin. Cancer Res., 7, 2182 Soepenberg, 2005, Phase I pharmacokinetic, food effect, and pharmacogenetic study of oral irinotecan given as semisolid matrix capsules in patients with solid tumors, Clin. Cancer Res., 11, 1504, 10.1158/1078-0432.CCR-04-1758 Soepenberg, 2005, Phase I and pharmacokinetic study of oral irinotecan given once daily for 5 days every 3 weeks in combination with capecitabine in patients with solid tumors, J. Clin. Oncol., 23, 889, 10.1200/JCO.2005.01.008 Pappo, 2007, Two consecutive phase II window trials of irinotecan alone or in combination with vincristine for the treatment of metastatic rhabdomyosarcoma: The Children's Oncology Group, J. Clin. Oncol., 25, 362, 10.1200/JCO.2006.07.1720 Bajetta, 2004, Randomized multicenter Phase II trial of two different schedules of irinotecan combined with capecitabine as first-line treatment in metastatic colorectal carcinoma, Cancer, 100, 279, 10.1002/cncr.11910 Drengler, 1999, Phase I and pharmacokinetic trial of oral irinotecan administered daily for 5 days every 3 weeks in patients with solid tumors, J. Clin. Oncol., 17, 685, 10.1200/JCO.1999.17.2.685 Pitot, 2006, A phase I and pharmacokinetic study of a powder-filled capsule formulation of oral irinotecan (CPT-11) given daily for 5 days every 3 weeks in patients with advanced solid tumor, Cancer Chemother. Pharmacol., 58, 165, 10.1007/s00280-005-0138-9 Wagner, 2010, Phase I trial of two schedules of vincristine, oral irinotecan, and temozolomide (VOIT) for children with relapsed or refractory solid tumors: a Children's Oncology Group Phase I Consortium Study, Pediatr. Blood Cancer, 54, 538, 10.1002/pbc.22407 Clark, 2006, Rubitecan, Expert Opin. Investig. Drugs, 15, 71, 10.1517/13543784.15.1.71 Schöffski, 2002, Clinical phase II study and pharmacological evaluation of rubitecan in non-pretreated patients with metastatic colorectal cancer – significant effect of food intake on the bioavailability of the oral camptothecin analogue, Eur. J. Cancer, 38, 807, 10.1016/S0959-8049(02)00022-9 Caponigro, 2008, Phase II study of rubitecan in recurrent or metastatic head and neck cancer, Cancer Chemother. Pharmacol., 62, 209, 10.1007/s00280-007-0592-7 Baka, 2005, A phase II trial with RFS2000 (rubitecan) in patients with advanced non-small cell lung cancer, Eur. J. Cancer, 41, 1547, 10.1016/j.ejca.2005.03.009 Patel, 2006, Phase II study of rubitecan, an oral camptothecin in patients with advanced colorectal cancer who have failed previous 5-fluorouracil based chemotherapy, Invest. New Drugs, 24, 359, 10.1007/s10637-006-6451-2 Burris, 2005, Phase II trial of oral rubitecan in previously treated pancreatic cancer patients, Oncologist, 10, 183, 10.1634/theoncologist.10-3-183 Tedesco, 2005, A phase I study of concurrent 9-nitro-20 (s)-camptothecin (9NC/orathecin) and radiation therapy in the treatment of locally advanced adenocarcinoma of the pancreas, Radiother. Oncol., 76, 54, 10.1016/j.radonc.2005.04.005 Fracasso, 2002, Phase I study of rubitecan and gemcitabine in patients with advanced malignancies, Ann. Oncol., 13, 1819, 10.1093/annonc/mdf342 Conley, 1998, Phase I study of the orally administered butyrate prodrug, tributyrin, in patients with solid tumors, Clin. Cancer Res., 4, 629 Edelman, 2003, Clinical and pharmacologic study of tributyrin: an oral butyrate prodrug, Cancer Chemother. Pharmacol., 51, 439, 10.1007/s00280-003-0580-5