LATENTIATED PRODRUG APPROACH OF DRUGS: AN OVERVIEW
DOI:
https://doi.org/10.22159/ijap.2021v13i6.42794Keywords:
Prodrug, Carriers, Enzymes, Strategies, Specificity, ChemotherapyAbstract
Prodrugs, with their capability of declining the adverse events and elevating the bioavailability of certain drugs, have captured enormous attention throughout the world since the 20th century. The versatility of the prodrugs that are inert and after administration releasing the parent moiety for the desired effect has become a major criterion for the scientists to incorporate this to alleviate the undesired effects of a conventional drug. About 10% of the prevailing drugs are prodrugs and their usage is being amplified owing to its critical application in cancer therapy, toxicity alleviation, and specificity. The purpose of this review is to understand the prodrugs, strategies incorporated in designing the prodrugs, applications, their crucial benefits in targeted action at a specific site of the body, their advantageous effects in chemotherapy. Also, to be acknowledged with the ongoing clinical trials and researches on prodrugs and some notable marketed prodrugs in a depth manner.
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Stella VJ, Charman WN, Naringrekar VH. Prodrugs do they have advantages in clinical practice? Drugs. 1985;29(5):455-73. doi: 10.2165/00003495-198529050-00002, PMID 3891303.
Rautio J, Kumpulainen H, Heimbach T, Oliyai R, Oh D, Järvinen T, Savolainen J. Prodrugs: design and clinical applications. Nat Rev Drug Discovery. 2008;7(3):255-70. doi: 10.1038/nrd2468, PMID 18219308.
Rautio J, Meanwell NA, Di L, Hageman MJ. The expanding role of prodrugs in contemporary drug design and development. Nat Rev Drug Discovery. 2018;17(8):559-87. doi: 10.1038/nrd.2018.46, PMID 29700501.
Han HK, Amidon GL. Targeted prodrug design to optimize drug delivery. AAPS PharmSci. 2000;2(1):E6. doi: 10.1208/ps020106, PMID 11741222.
Yu LX, Straughn AB, Faustino PJ, Yang Y, Parekh A, Ciavarella AB, Asafu-Adjaye E, Mehta MU, Conner DP, Lesko LJ, Hussain AS. The effect of food on the relative bioavailability of rapidly dissolving immediate-release solid oral products containing highly soluble drugs. Mol Pharm. 2004;1(5):357-62. doi: 10.1021/mp0499407, PMID 16026005.
Surendran V, Singh A, Sampathkumar KP. Synthesis and characterization of novel amino acid prodrug of famotidine. Int J Pharm Pharm Sci. 2015;7:403-8.
Gomes P, Vale N, Moreira R. Cyclization-activated prodrugs. Molecules. 2007;12(11):2484-506. doi: 10.3390/12112484, PMID 18065953.
Zawilska JB, Wojcieszak J, Olejniczak AB. Prodrugs: a challenge for the drug development. Pharmacol Rep. 2013;65(1):1-14. doi: 10.1016/s1734-1140(13)70959-9, PMID 23563019.
Huttunen KM, Raunio H, Rautio J. Prodrugs-from serendipity to rational design. Pharmacol Rev. 2011;63(3):750-71. doi: 10.1124/pr.110.003459, PMID 21737530.
Das N, Dhanawat M, Dash B, Nagarwal RC, Shrivastava SK. Codrug: an efficient approach for drug optimization. Eur J Pharm Sci. 2010;41(5):571-88. doi: 10.1016/j.ejps.2010.09.014, PMID 20888411.
Wu KM. A new classification of prodrugs: regulatory perspectives. Pharmaceuticals (Basel). 2009;2(3):77-81. doi: 10.3390/ph2030077, PMID 27713225.
Testa B, Mayer JM, Mayer J. Hydrolysis in drug and prodrug metabolism. John Wiley & Sons; 2003.
Karaman R. Prodrugs design based on inter- and intramolecular chemical processes. Chem Biol Drug Des. 2013;82(6):643-68. doi: 10.1111/cbdd.12224, PMID 23998799.
Clas SD, Sanchez RI, Nofsinger R. Chemistry-enabled drug delivery (prodrugs): recent progress and challenges. Drug Discovery Today. 2014;19(1):79-87. doi: 10.1016/j.drudis.2013.08.014, PMID 23993918.
Lai WF. editor. Systemic delivery technologies in anti-aging medicine: methods and applications. Springer International Publishing; 2020.
Karaman R, Fattash B, Qtait A. The future of prodrugs - design by quantum mechanics methods. Expert Opin Drug Delivery. 2013;10(5):713-29. doi: 10.1517/17425247.2013.786699, PMID 23540707.
Karaman R. Prodrugs design by computation methods-a new era. Drug Designing. 2013;1:e113.
Karaman R. Prodrug Design vs drug design. Drug Des. 2013;02(2):e114. doi: 10.4172/2169-0138.1000e114.
Papot S, Tranoy I, Tillequin F, Florent JC, Gesson JP. Design of selectively activated anticancer prodrugs: elimination and cyclization strategies. Curr Med Chem Anticancer Agents. 2002;2(2):155-85. doi: 10.2174/1568011023354173, PMID 12678742.
Chen XQ, Venkatesh S. Miniature device for aqueous and non-aqueous solubility measurements during drug discovery. Pharm Res. 2004;21(10):1758-61. doi: 10.1023/b:pham.0000045225.76650.53, PMID 15553219.
Liu HF, Wan N, Huan ML, Jia YY, Yuan XF, Zhou SY, Zhang BL. Enhanced water-soluble derivative of PC407 as a novel potential COX-2 inhibitor injectable formulation. Bioorg Med Chem Lett. 2014;24(20):4794-7. doi: 10.1016/j.bmcl.2014.09.007, PMID 25248683.
Jornada DH, dos Santos Fernandes GF, Chiba DE, De Melo TR, Dos Santos JL, Chung MC. The prodrug approach: A successful tool for improving drug solubility. Molecules. 2015;21(1):42. doi: 10.3390/molecules21010042, PMID 26729077.
Draganov DI, La Du BN. Pharmacogenetics of paraoxonases: a brief review. Naunyn Schmiedebergs Arch Pharmacol. 2004;369(1):78-88. doi: 10.1007/s00210-003-0833-1, PMID 14579013.
Testa B. Prodrugs: bridging pharmacodynamic/pharmacokinetic gaps. Curr Opin Chem Biol. 2009;13(3):338-44. doi: 10.1016/j.cbpa.2009.04.620, PMID 19473869.
Glazko AJ, Edgerton WH, Dill WA, Lenz WR. Chloromycetin palmitate; a synthetic ester of chloromycetin. Antibiot Chemother (Northfield). 1952;2(5):234-42. PMID 24541898.
Sinkula AA, Morozowich W, Rowe EL. Chemical modification of clindamycin: synthesis and evaluation of selected esters. J Pharm Sci. 1973;62(7):1106-11. doi: 10.1002/jps.2600620711, PMID 4714118.
Clark Jr RK, Varner EL. New esters of erythromycin. Antibiot Chemother (Northfield). 1957;7(9):487-9. PMID 24544532.
Bundy GL. Inventor. 9-deoxy-6, 9α-nitrilo-PGF1. Upjohn Co Assignee Bioprecursors of. United States patent US; 1979 Apr 24. PMID 4151176.
Morozowich W, Lamb DJ, Karnes HA, Mackellar FA, Lewis C, Stern KF, Rowe EL. Synthesis and bioactivity of lincomycin-2-phosphate. J Pharm Sci. 1969;58(12):1485-9. doi: 10.1002/jps.2600581213, PMID 5353265.
Morozowich W, Sinkula AA, MacKellar FA, Lewis C. Synthesis and bioactivity of lincomycin 2-monoesters. J Pharm Sci. 1973;62(7):1102-5. doi: 10.1002/jps.2600620710, PMID 4714117.
Gruber Jr CM, Stephens VC, Terrill PM. Propoxyphene napsylate: chemistry and experimental design. Toxicol Appl Pharmacol. 1971;19(3):423-6. doi: 10.1016/0041-008x(71)90001-9, PMID 4936996.
Glazko AJ, Carnes HE, Kazenko A, Wolf LM, Reutner TF. Succinic acid esters of chloramphenicol. Antibiot Annu. 1957-1958;5:792-802. PMID 13521897.
Edmondson HT. Parenteral and oral clindamycin therapy in surgical infections: a preliminary report. Ann Surg. 1973;178(5):637-42. doi: 10.1097/00000658-197311000-00014, PMID 4748302.
Gray JE, Weaver RN, Moran J, Feenstra ES. The parenteral toxicity of clindamycin 2-phosphate in laboratory animals. Toxicol Appl Pharmacol. 1974;27(2):308-21. doi: 10.1016/0041-008x(74)90202-6, PMID 4137286.
DeHAAN RM, Metzler CM, Schellenberg D, Vandenbosch WD. Pharmacokinetic studies of clindamycin phosphate. J Clin Pharmacol. 1973;13(5):190-209. doi: 10.1002/j.1552-4604.1973.tb00208.x, PMID 4488654.
Bundgaard H. Spectrophotometric determination of ampicillin sodium in the presence of its degradation and polymerization products. J Pharm Pharmacol. 1974;26(6):385-92. doi: 10.1111/j.2042-7158.1974.tb09302.x, PMID 4154981.
Schwartz MA, Hayton WL. Relative stability of hetacillin and ampicillin in solution. J Pharm Sci. 1972;61(6):906-9. doi: 10.1002/jps.2600610616, PMID 4339954.
Ho NF, Park JY, Morozowich W, Higuchi WI. Physical model approach to the design of drugs with improved intestinal absorption. Des Biopharm Prop Prodrugs Analogs. 1977:136-227.
Jana S, Mandlekar S, Marathe P. Prodrug design to improve pharmacokinetic and drug delivery properties: challenges to the discovery scientists. Curr Med Chem. 2010;17(32):3874-908. doi: 10.2174/092986710793205426, PMID 20858214.
Halen PK, Murumkar PR, Giridhar R, Yadav MR. Prodrug designing of NSAIDs. Mini Rev Med Chem. 2009;9(1):124-39. doi: 10.2174/138955709787001695, PMID 19149665.
Friend DR, Chang GW. A colon-specific drug-delivery system based on drug glycosides and the glycosidases of colonic bacteria. J Med Chem. 1984;27(3):261-6. doi: 10.1021/jm00369a005, PMID 6699871.
Stella VJ, Himmelstein KJ. Critique of prodrugs and site specific delivery. In: Benzon A, editor. Optimization of drug delivery Symposium Copenhagen: Munksgaard; 1982. p. 134-55.
Wermuth CG. Designing prodrugs and bioprecursors. In: The practice of medicinal chemistry. Academic Press; 2008. p. 721-46.
Ettmayer P, Amidon GL, Clement B, Testa B. Lessons learned from marketed and investigational prodrugs. J Med Chem. 2004;47(10):2393-404. doi: 10.1021/jm0303812, PMID 15115379.
Abbott NJ, Patabendige AA, Dolman DE, Yusof SR, Begley DJ. Structure and function of the blood–brain barrier. Neurobiol Disease. 2010;37(1):13-25. doi: 10.1016/j.nbd.2009.07.030, PMID 19664713.
Anderson BD. Prodrugs for improved CNS delivery. Adv Drug Delivery Rev. 1996;19(2):171-202. doi: 10.1016/0169-409X(95)00106-H.
Pardridge WM. Brain drug development and brain drug targeting. Pharm Res. 2007;24(9):1729-32. doi: 10.1007/s11095-007-9387-0, PMID 17629776.
Patel MM, Goyal BR, Bhadada SV, Bhatt JS, Amin AF. Getting into the brain: approaches to enhance brain drug delivery. CNS Drugs. 2009;23(1):35-58. doi: 10.2165/0023210-200923010-00003, PMID 19062774.
Warren MS, Rautio J, editors. Prodrugs and targeted delivery. Wiley-VCH Verlag; 2011.
Brogden RN, Speight TM, Avery GS. Levodopa: a review of its pharmacological properties and therapeutic use with particular reference to Parkinsonism. Drugs. 1971;2(4):262-400. doi: 10.2165/00003495-197102040-00002, PMID 4340597.
Van Montfoort JE, Hagenbuch B, Groothuis GM, Koepsell H, Meier PJ, Meijer DK. Drug uptake systems in liver and kidney. Curr Drug Metabolism. 2003;4(3):185-211. doi: 10.2174/1389200033489460, PMID 12769665.
Erion MD, Bullough DA, Lin CC, Hong Z. HepDirect prodrugs for targeting nucleotide-based antiviral drugs to the liver. Curr Opinion Investigational Drugs (London, England: 2000); 2006;7(2):109-17. PMID 16499280.
Li F, Maag H, Alfredson T. Prodrugs of nucleoside analogues for improved oral absorption and tissue targeting. J Pharm Sci. 2008;97(3):1109-34. doi: 10.1002/jps.21047, PMID 17696166.
Lin CC, Yeh LT, Vitarella D, Hong Z, Erion MD. Remofovir mesylate: a prodrug of PMEA with improved liver-targeting and safety in rats and monkeys. Antiviral Chem Chemotherapy. 2004;15(6):307-17. doi: 10.1177/095632020401500603, PMID 15646644.
Reddy KR, Colby TJ, Fujitaki JM, van Poelje PD, Erion MD. Liver targeting of hepatitis-B antiviral lamivudine using the HepDirect prodrug technology. Nucleosides, Nucleotides Nucleic Acids. 2005;24(5-7):375-81. doi: 10.1081/ncn-200059781, PMID 16247954.
Sinha VR, Kumria R. Colonic drug delivery: prodrug approach. Pharm Res. 2001;18(5):557-64. doi: 10.1023/a:1011033121528, PMID 11465408.
Minami K, Hirayama F, Uekama K. Colon-specific drug delivery based on a cyclodextrin prodrug: release behavior of biphenylylacetic acid from its cyclodextrin conjugates in rat intestinal tracts after oral administration. J Pharm Sci. 1998;87(6):715-20. doi: 10.1021/js9704339, PMID 9607948.
Kumar SU, Tyagi DK, Gupta AR. Synthesis, characterization and pharmcological activity of ester prodrugs of naproxen. Asian J Pharm Clin Res. 2010;3:208-11.
Valia KH, Tojo K, Chien YW. Long-term permeation kinetics of estradiol: (III) kinetic analyses of the simultaneous skin permeation and bioconversion of estradiol esters. Drug Dev Ind Pharm. 1985;11(6-7):1133-73. doi: 10.3109/03639048509059861.
Fang JY, Leu YL. Prodrug strategy for enhancing drug delivery via skin. Curr Drug Discovery Technol. 2006;3(3):211-24. doi: 10.2174/157016306780136772, PMID 17311566.
Ar C, Gandhi PM. Synthesis and evaluation of amino acid ester conjugates of hiv protease inhibitor. Asian J Pharm Clin Res. 2019;12:342-6.
Devarajan-Ketha H, Sloan KB. N, N′-Dialkylaminoalkylcarbonyl (DAAC) prodrugs and aminoalkylcarbonyl (AAC) prodrugs of 4-hydroxyacetanilide and naltrexone with improved skin permeation properties. Bioorganic Med Chem Lett. 2011;21(13):4078-82. doi: 10.1016/j.bmcl.2011.04.118, PMID 21616664.
Mahato R, Tai W, Cheng K. Prodrugs for improving tumor targetability and efficiency. Adv Drug Delivery Rev. 2011;63(8):659-70. doi: 10.1016/j.addr.2011.02.002, PMID 21333700.
de Groot FM, Damen EW, Scheeren HW. Anticancer prodrugs for application in monotherapy: targeting hypoxia, tumor-associated enzymes, and receptors. Curr Med Chem. 2001;8(9):1093-122. doi: 10.2174/0929867013372634, PMID 11472243.
Kavanaugh WM. Antibody prodrugs for cancer. Expert Opinion Biol Ther. 2020;20(2):163-71. doi: 10.1080/14712598.2020.1699053, PMID 31779489.
Giang I, Boland EL, Poon GM. Prodrug applications for targeted cancer therapy. AAPS J. 2014;16(5):899-913. doi: 10.1208/s12248-014-9638-z, PMID 25004822.
Johnston PG, Kaye S. Capecitabine: a novel agent for the treatment of solid tumors. Anticancer Drugs. 2001;12(8):639-46. doi: 10.1097/00001813-200109000-00001, PMID 11604550.
Koukourakis GV, Kouloulias V, Koukourakis MJ, Zacharias GA, Zabatis H, Kouvaris J. Efficacy of the oral fluorouracil pro-drug capecitabine in cancer treatment: a review. Molecules. 2008;13(8):1897-922. doi: 10.3390/molecules13081897, PMID 18794792.
Miwa M, Ura M, Nishida M, Sawada N, Ishikawa T, Mori K, Shimma N, Umeda I, Ishitsuka H. 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. 1998;34(8):1274-81. doi: 10.1016/s0959-8049(98)00058-6, PMID 9849491.
Zhang JZ, Bonnitcha P, Wexselblatt E, Klein AV, Najajreh Y, Gibson D, Hambley TW. Facile preparation of mono-, di- and mixed-carboxylato platinum(IV) complexes for versatile anticancer prodrug design. Chemistry. 2013;19(5):1672-6. doi: 10.1002/chem.201203159. PMID 23255183.
Hoskins JM, Carey LA, McLeod HL. CYP2D6 and tamoxifen: DNA matters in breast cancer. Nat Rev Cancer. 2009;9(8):576-86. doi: 10.1038/nrc2683, PMID 19629072.
Sánchez Sanchez L, Cadena Nava RD, Palomares LA, Ruiz Garcia J, Koay MS, Cornelissen JJ, Vazquez Duhalt R. Chemotherapy pro-drug activation by biocatalytic virus-like nanoparticles containing cytochrome P450. Enzyme Microb Technol. 2014;60:24-31. doi: 10.1016/j.enzmictec.2014.04.003, PMID 24835096.
Xu Z, Wang D, Xu S, Liu X, Zhang X, Zhang H. Preparation of a camptothecin prodrug with glutathione‐responsive disulfide Linker for anticancer drug delivery. Chem Asian J. 2014;9(1):199-205. doi: 10.1002/asia.201301030, PMID 24136878.
Xu G, McLeod HL. Strategies for enzyme/prodrug cancer therapy. Clin Cancer Res. 2001;7(11):3314-24. PMID 11705842.
Chari RV. Targeted delivery of chemotherapeutics: tumor-activated prodrug therapy. Adv Drug Delivery Rev. 1998;31(1-2):89-104. doi: 10.1016/s0169-409x(97)00095-1, PMID 10837619.
Bagshawe KD, Sharma SK, Begent RH. Antibody-directed enzyme prodrug therapy (ADEPT) for cancer. Expert Opin Biol Ther. 2004;4(11):1777-89. doi: 10.1517/14712598.4.11.1777, PMID 15500406.
Singh PP, Joshi S, Russell PJ, Verma ND, Wang X, Khatri A. Molecular chemotherapy and chemotherapy: a new front against late-stage hormone-refractory prostate cancer. Clin Cancer Res. 2011;17(12):4006-18. doi: 10.1158/1078-0432.CCR-11-0248, PMID 21531822.
Altaner C. Prodrug cancer gene therapy. Cancer Lett. 2008;270(2):191-201. doi: 10.1016/j.canlet.2008.04.023, PMID 18502571.
Stella VJ. Prodrugs as therapeutics. Expert Opin Ther Pat. 2004;14(3):277-80. doi: 10.1517/13543776.14.3.277.
Markovic M, Ben-Shabat S, Dahan A. Prodrugs for improved drug delivery: lessons learned from recently developed and marketed products. Pharmaceutics. 2020;12(11):1031. doi: 10.3390/pharmaceutics12111031, PMID 33137942.
Hale JJ, Mills SG, MacCoss M, Dorn CP, Finke PE, Budhu RJ, Reamer RA, Huskey SE, Luffer-Atlas D, Dean BJ, McGowan EM, Feeney WP, Chiu SH, Cascieri MA, Chicchi GG, Kurtz MM, Sadowski S, Ber E, Tattersall FD, Rupniak NM, Williams AR, Rycroft W, Hargreaves R, Metzger JM, MacIntyre DE. Phosphorylated morpholine acetal human neurokinin-1 receptor antagonists as water-soluble prodrugs. J Med Chem. 2000;43(6):1234-41. doi: 10.1021/jm990617v, PMID 10737756.
Michel MC. Fesoterodine: a novel muscarinic receptor antagonist for the treatment of overactive bladder syndrome. Expert Opin Pharmacother. 2008;9(10):1787-96. doi: 10.1517/14656566.9.10.1787, PMID 18570610.
Stella VJ, Zygmunt JJ, Georg IG, Safadi MS. Inventors; University of Kansas., assignee. Water soluble prodrugs of hindered alcohols. United States patent US. PMID 6872838; 2005 Mar 29.
Kumpulainen H, Jarvinen T, Mannila A, Leppanen J, Nevalainen T, Mantyla A, Vepsalainen J, Rautio J. Synthesis, in vitro and in vivo characterization of novel ethyl dioxy phosphate prodrug of propofol. Eur J Pharm Sci. 2008;34(2-3):110-7. doi: 10.1016/j.ejps.2008.02.121, PMID 18403185.
Dobesh PP. Pharmacokinetics and pharmacodynamics of prasugrel, a thienopyridine P2Y12 inhibitor. Pharmacotherapy. 2009;29(9):1089-102. doi: 10.1592/phco.29.9.1089, PMID 19698014.
VanderMolen KM, McCulloch W, Pearce CJ, Oberlies NH. Romidepsin (Istodax, NSC 630176, FR901228, FK228, depsipeptide): a natural product recently approved for cutaneous T-cell lymphoma. J Antibiot (Tokyo). 2011;64(8):525-31. doi: 10.1038/ja.2011.35, PMID 21587264.
Adachi K, Chiba K. FTY720 story. Its discovery and the following accelerated development of sphingosine 1-phosphate receptor agonists as immunomodulators based on reverse pharmacology. Perspect Medicin Chem. 2007;1:11-23. doi: 10.1177/1177391X0700100002, PMID 19812733.
Stangier J, Rathgen K, Stahle H, Gansser D, Roth W. The pharmacokinetics, pharmacodynamics and tolerability of dabigatran etexilate, a new oral direct thrombin inhibitor, in healthy male subjects. Br J Clin Pharmacol. 2007;64(3):292-303. doi: 10.1111/j.1365-2125.2007.02899.x, PMID 17506785.
Ishikawa T, Matsunaga N, Tawada H, Kuroda N, Nakayama Y, Ishibashi Y, Tomimoto M, Ikeda Y, Tagawa Y, Iizawa Y, Okonogi K, Hashiguchi S, Miyake A. TAK-599, a novel N-phosphono type prodrug of anti-MRSA cephalosporin T-91825: synthesis, physicochemical and pharmacological properties. Bioorg Med Chem. 2003;11(11):2427-37. doi: 10.1016/s0968-0896(03)00126-3, PMID 12735989.
Kurtz TW, Kajiya T. Differential pharmacology and benefit/risk of azilsartan compared to other sartans. Vasc Health Risk Manag. 2012;8:133-43. doi: 10.2147/VHRM.S22595, PMID 22399858.
Cundy KC, Branch R, Chernov Rogan T, Dias T, Estrada T, Hold K, Koller K, Liu X, Mann A, Panuwat M, Raillard SP, Upadhyay S, Wu QQ, Xiang JN, Yan H, Zerangue N, Zhou CX, Barrett RW, Gallop MA. XP13512 [(+/-)-1-([(alpha-isobutanoyloxyethoxy)carbonyl] aminomethyl)-1-cyclohexane acetic acid], a novel gabapentin prodrug: I. Design, synthesis, enzymatic conversion to gabapentin, and transport by intestinal solute transporters. J Pharmacol Exp Ther. 2004;311(1):315-23. doi: 10.1124/jpet.104.067934, PMID 15146028.
Stappaerts J, Geboers S, Snoeys J, Brouwers J, Tack J, Annaert P, Augustijns P. Rapid conversion of the ester prodrug abiraterone acetate results in intestinal supersaturation and enhanced absorption of abiraterone: in vitro, rat in situ and human in vivo studies. Eur J Pharm Biopharm. 2015;90:1-7. doi: 10.1016/j.ejpb.2015.01.001, PMID 25592324.
Fukano Y, Kawazu K. Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats. Drug Metab Dispos. 2009;37(8):1622-34. doi: 10.1124/dmd.108.024885, PMID 19477946.
Hoy SM. Tafluprost/timolol: a review in open-angle glaucoma or ocular hypertension. Drugs. 2015;75(15):1807-13. doi: 10.1007/s40265-015-0476-9, PMID 26431840.
Linker RA, Haghikia A. Dimethyl fumarate in multiple sclerosis: latest developments, evidence and place in therapy. Ther Adv Chronic Dis. 2016;7(4):198-207. doi: 10.1177/2040622316653307, PMID 27433310.
Benes J, Parada A, Figueiredo AA, Alves PC, Freitas AP, Learmonth DA, Cunha RA, Garrett J, Soares-da-Silva P. Anticonvulsant and sodium channel-blocking properties of novel 10, 11-dihydro-5 H-dibenz [b, f] azepine-5-carboxamide derivatives. J Med Chem. 1999;42(14):2582-7. doi: 10.1021/jm980627g, PMID 10411478.
Ben-Menachem E. Eslicarbazepine acetate: a well-kept secret? Epilepsy Curr. 2010;10(1):7-8. doi: 10.1111/j.1535-7511.2009.01337.x, PMID 20126330.
Sofia MJ, Bao D, Chang W, Du J, Nagarathnam D, Rachakonda S, Reddy PG, Ross BS, Wang P, Zhang HR, Bansal S, Espiritu C, Keilman M, Lam AM, Steuer HM, Niu C, Otto MJ, Furman PA. Discovery of a β-d-2′-deoxy-2′-α-fluoro-2′-β-C-methyluridine nucleotide prodrug (PSI-7977) for the treatment of hepatitis C virus. J Med Chem. 2010;53(19):7202-18. doi: 10.1021/jm100863x, PMID 20845908.
Goldstein DS. L‐dihydroxyphenylserine (L‐DOPS): a norepinephrine prodrug. Cardiovasc Drug Rev. 2006;24(3-4):189-203. doi: 10.1111/j.1527-3466.2006.00189.x, PMID 17214596.
Vera Cabrera L, Gonzalez E, Rendon A, Ocampo Candiani J, Welsh O, Velazquez Moreno VM, Choi SH, Molina Torres C. In vitro activities of DA-7157 and DA-7218 against Mycobacterium tuberculosis and Nocardia brasiliensis. Antimicrob Agents Chemother. 2006;50(9):3170-2. doi: 10.1128/AAC.00571-06, PMID 16940121.
Ohwada J, Tsukazaki M, Hayase T, Oikawa N, Isshiki Y, Fukuda H, Mizuguchi E, Sakaitani M, Shiratori Y, Yamazaki T, Ichihara S, Umeda I, Shimma N. Design, synthesis and antifungal activity of a novel water soluble prodrug of antifungal triazole. Bioorg Med Chem Lett. 2003;13(2):191-6. doi: 10.1016/s0960-894x(02)00892-2, PMID 12482421.
Ksander GM, Ghai RD, deJesus R, Diefenbacher CG, Yuan A, Berry C, Sakane Y, Trapani A. Dicarboxylic acid dipeptide neutral endopeptidase inhibitors. J Med Chem 1995;38(10):1689-700. doi: 10.1021/jm00010a014, PMID 7752193.
Von Borstel RW, Bamat MK. Inventors; Pro-Neuron. inc, assignee. Acylated uridine and cytidine and uses thereof. Patent WO 89/03837; 1989 May 5.
Raedler LA. Aripiprazole lauroxil (Aristada): long-acting atypical antipsychotic injection approved for the treatment of patients with schizophrenia. American Health Drug Benefits. 2016;9(Spec Feature):40-3. PMID 27668044.
Ballatore C, McGuigan C, De Clercq E, Balzarini J. Synthesis and evaluation of novel aAmidate prodrugs of PMEA and PMPA. Bioorganic Med Chem Lett. 2001;11(8):1053-6. doi: 10.1016/s0960-894x(01)00128-7, PMID 11327587.
Eisenberg EJ, He GX, Lee WA. Metabolism of GS-7340, a novel phenyl monophosphoramidate intracellular prodrug of PMPA, in blood. Nucleosides Nucleotides Nucleic Acids. 2001;20(4-7):1091-8. doi: 10.1081/NCN-100002496, PMID 11562963.
Elliott EL, Ferdous AJ, Kaufman MJ, Komar SA, Mazaik DL, McCubbin QJ. Inventors. Boronate ester compounds and pharmaceutical compositions thereof. United States patent US; 2009 Dec 31. p. 12. PMID 485344.
Nakamura A, Yamada T, Asaki T. Synthesis and evaluation of N-acylsulfonamide and N-acylsulfonylurea prodrugs of a prostacyclin receptor agonist. Bioorganic Med Chem. 2007;15(24):7720-5. doi: 10.1016/j.bmc.2007.08.052, PMID 17881233.
Asaki T, Kuwano K, Morrison K, Gatfield J, Hamamoto T, Clozel M. Selexipag: an oral and selective IP prostacyclin receptor agonist for the treatment of pulmonary arterial hypertension. J Med Chem. 2015;58(18):7128-37. doi: 10.1021/acs.jmedchem.5b00698, PMID 26291199.
Mollmann H, Hochhaus G, Rohatagi S, Barth J, Derendorf H. Pharmacokinetic/pharmacodynamic evaluation of deflazacort in comparison to methylprednisolone and prednisolone. Pharm Res. 1995;12(7):1096-100. doi: 10.1023/a:1016287104656, PMID 7494809.
Liu Q, Yang Q, Sun W, Vogel P, Heydorn W, Yu XQ, Hu Z, Yu W, Jonas B, Pineda R, Calderon-Gay V, Germann M, O’Neill E, Brommage R, Cullinan E, Platt K, Wilson A, Powell D, Sands A, Zambrowicz B, Shi ZC. Discovery and characterization of novel tryptophan hydroxylase inhibitors that selectively inhibit serotonin synthesis in the gastrointestinal tract. J Pharmacol Exp Ther. 2008;325(1):47-55. doi: 10.1124/jpet.107.132670, PMID 18192499.
O'’Brien CF, Jimenez R, Hauser RA, Factor SA, Burke J, Mandri D, Castro-Gayol JC. NBI‐98854, a selective monoamine transport inhibitor for the treatment of tardive dyskinesia: a randomized, double‐blind, placebo‐controlled study. Movement Disorders. 2015;30(12):1681-7. doi: 10.1002/mds.26330, PMID 26346941.
Hall BS, Wilkinson SR. Activation of benznidazole by trypanosomal type I nitroreductases results in glyoxal formation. Antimicrobial Agents Chemotherapy. 2012;56(1):115-23. doi: 10.1128/AAC.05135-11, PMID 22037852.
Garcia GA, Ngai P, Mosaed S, Lin KY. Critical evaluation of latanoprostene bunod in the treatment of glaucoma. Clinical Ophthalmology (Auckland, NZ) Clin Ophthalmol. 2016;10:2035-50. doi: 10.2147/OPTH.S103985, PMID 27799730.
Gillis JC, Wiseman LR. Secnidazole. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic use in the management of protozoal infections and bacterial vaginosis. Drugs. 1996;51(4):621-38. doi: 10.2165/00003495-199651040-00007, PMID 8706597.
Sun X, Vilar S, Tatonetti NP. High-throughput methods for combinatorial drug discovery. Sci Transl Med. 2013;5(205);5:205rv1. doi: 10.1126/scitranslmed.3006667, PMID 24089409.
de Albuquerque Silva AT, Chung MC, Castro LF, Carvalho Guido RV, Ferreira EISilva AT, Chung MC, Castro LF, Güido RV, Ferreira EI. Advances in prodrug design. Mini Rev Med Chem. 2005;5(10):893-914. doi: 10.2174/138955705774329528, PMID 16250833.
Stella VJ, Nti-Addae KW. Prodrug strategies to overcome poor water solubility. Advanced Drug Delivery Rev. 2007;59(7):677-94. doi: 10.1016/j.addr.2007.05.013, PMID 17628203.
Stella VJ. Prodrug approaches to enhancing the oral delivery of poorly permeable drugs. In: Prodrugs. Springer; 2007. p. 37-82.
Dahan A, Khamis M, Agbaria R, Karaman R. Targeted prodrugs in oral drug delivery: the modern molecular biopharmaceutical approach. Expert Opinion Drug Delivery. 2012;9(8):1001-13. doi: 10.1517/17425247.2012.697055, PMID 22703376.
Dahan A, Markovic M, Aponick A, Zimmermann EM, Ben-Shabat S. The prospects of lipidic prodrugs: an old approach with an emerging future. Future Med Chem. 2019;11(19):2563-71. doi: 10.4155/fmc-2019-0155, PMID 31633401.
Markovic M, Ben-Shabat S, Aponick A, Zimmermann EM, Dahan A. Lipids and lipid-processing pathways in drug delivery and therapeutics. Int J Mol Sci. 2020;21(9):3248. doi: 10.3390/ijms21093248, PMID 32375338.
Markovic M, Ben‐Shabat S, Keinan S, Aponick A, Zimmermann EM, Dahan A. Lipidic prodrug approach for improved oral drug delivery and therapy. Med Res Rev. 2019;39(2):579-607. doi: 10.1002/med.21533, PMID 30320896.
Markovic M, Ben-Shabat S, Dahan A. Computational simulations to guide enzyme-mediated prodrug activation. Int J Mol Sci. 2020;21(10):3621. doi: 10.3390/ijms21103621, PMID 32443905.
Markovic M, Ben-Shabat S, Keinan S, Aponick A, Zimmermann EM, Dahan A. Molecular modeling-guided design of phospholipid-based prodrugs. Int J Mol Sci. 2019;20(9):2210. doi: 10.3390/ijms20092210, PMID 31060339.
Markovic M, Dahan A, Keinan S, Kurnikov I, Aponick A, Zimmermann EM, Ben-Shabat S. Phospholipid-based prodrugs for colon-targeted drug delivery: Experimental study and in-silico simulations. Pharmaceutics. 2019;11(4):186. doi: 10.3390/pharmaceutics11040186, PMID 30995772.
McNamara MG, Goyal L, Doherty M, Springfeld C, Cosgrove D, Sjoquist KM, Park JO, Verdaguer H, Braconi C, Ross PJ, Gramont A, Zalcberg JR, Palmer DH, Valle JW, Knox JJ. NUC-1031/cisplatin versus gemcitabine/cisplatin in untreated locally advanced/metastatic biliary tract cancer (NuTide: 121). Future Oncol. 2020;16(16):1069-81. doi: 10.2217/fon-2020-0247, PMID 32374623.
Evans K, Duan J, Pritchard T, Jones CD, McDermott L, Gu Z, Toscan CE, El-Zein N, Mayoh C, Erickson SW, Guo Y, Meng F, Jung D, Rathi KS, Roberts KG, Mullighan CG, Shia CS, Pearce T, Teicher BA, Smith MA, Lock RB. OBI-3424, a novel AKR1C3-activated prodrug, exhibits potent efficacy against preclinical models of T-ALL. Clin Cancer Res. 2019;25(14):4493-503. doi: 10.1158/1078-0432.CCR-19-0551, PMID 31015346.
Alanazi AS, James E, Mehellou Y. The ProTide prodrug technology: where next?. ACS Med Chem Lett. 2019;10(1):2-5. doi: 10.1021/acsmedchemlett.8b00586, PMID 30655934.
Arora M, Bogenberger JM, Abdelrahman A, Leiting JL, Chen X, Egan JB, Kasimsetty A, Lenkiewicz E, Malasi S, Uson PLS, Nagalo BM, Zhou Y, Salomao MA, Kosiorek HE, Braggio E, Barrett MT, Truty MJ, Borad MJ. Evaluation of NUC-1031: A first-in-class ProTide in biliary tract cancer. Cancer Chemotherapy Pharmacol. 2020;85(6):1063-78. doi: 10.1007/s00280-020-04079-z, PMID 32440762.
Mullard A. FDA drug approvals. Nat Rev Drug Discovery 2018;18:85-9.
Hendaus MA. Remdesivir in the treatment of coronavirus disease 2019 (COVID-19): a simplified summary. J Biomol Struct Dyn. 2021;39(10):3787-92. doi: 10.1080/07391102.2020.1767691. PMID 32396771.
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