Chaturvedi D. Role of organic carbamates in anticancer drug design. In: Brahmachari G, editor. Chemistry and pharmacology of naturally occurring bioactive compounds. 1st ed. Boca Raton (FL): CRC Press; 2013. p. 117–40. doi: 10.1201/b13867-6
Strzelczyk A, Mann C, Willems LM. Rosenow F, Bauer S. Cenobamate for the treatment of focal epilepsies. Expert Opin Pharmacother 2020. doi: 10.1080/14656566.2020.1803830
DeRuiter J. Amides and related functional groups. Principles of Drug Action 1, 2005 [displayed 20 April 2019]. Available at http://webhome.auburn.edu/~deruija/pda1_amides.pdf
Moraczewski AL, Banaszynski LA, From AM, White CE, Smith BD. Using hydrogen bonding to control carbamate C-N rotamer equilibria. J Org Chem 1998;63:7258–62. doi: 10.1021/jo980644d
Deetz MJ, Forbes CC, Jonas M, Malerich JP, Smith BD, Wiest O. Unusually low barrier to carbamate C-N rotation. J Org Chem 2002;67:3949–52. doi: 10.1021/jo025554u
Jung T, Do HJ, Son J, Song JH, Cha W, Kim YJ, Lee KK, Kwak K. Hindered C-N bond rotation in triazinyl dithiocarbamates. J Mol Struct 2018;1152:215–22. doi: 10.1016/j.molstruc.2017.09.063
Dugave C, Demange L. Cis-trans isomerization of organic molecules and biomolecules: implications and applications. Chem Rev 2003;103:2475–532. doi: 10.1021/cr0104375
Lauvergnat D, Hiberty PC. Role of conjugation in the stabilities and rotational barriers of formamide and thioformamide. An ab initio valence-bond study. J Am Chem Soc 1997;119:9478–82. doi: 10.1021/ja9639426
Marcovici-Mizrahi D, Gottlieb HE, Marks V, Nudelman A. On the stabilization of the syn-rotamer of amino acid carbamate derivatives by hydrogen bonding. J Org Chem 1996;61:8402–6. doi: 10.1021/jo961446u
Woolley GA, Jaikaran ASI, Zhang Z, Peng S. Design of regulated ion channels using measurements of cis-trans isomerization in single molecules. J Am Chem Soc 1995;117:4448–54. doi: 10.1021/ja00121a002
Vacondio F, Silva C, Mor M, Testa B. Qualitative structure-metabolism relationship in the hydrolysis of carbamates. Drug Metab Rev 2010;42:551–89. doi: 10.3109/03602531003745960
Reiner E, Škrinjarić-Špoljar M. Enzimska razgradnja karbamata [Carbamate metabolism, in Croatian]. Arh Hig Rada Toksikol 1968;19:251–8 [displayed 20 March 2019]. Available at https://hrcak.srce.hr/176452
Mattarei A, Azzolini M, Zoratti M, Biasutto L, Paradisi C. N-monosubstituted methoxy-oligo(ethylene glycol) carbamate ester prodrugs of resveratrol. Molecules 2015;20:16085–102. doi: 10.3390/molecules200916085
Parise Filho R, Polli MC, Garcia M, Barberato-Filho S. Prodrugs available on the Brazilian pharmaceutical market and their corresponding bioactivation pathways. Braz J Pharm Sci 2010;46:393–420. doi: 10.1590/S1984-82502010000300003
Maki T, Tsuritani T, Yasukata T. A mild method for the synthesis of carbamateprotected guanidines using the Burgess reagent. Org Lett 2014;16:1868–71. doi: 10.1021/ol5002208
Hong JY, Seo UR, Chung YK. Synthesis of carbamates from amines and N-tosylhydrazones under atmospheric pressure of carbon dioxide without an external base. Org Chem Front 2016;3:764–7. doi: 10.1039/c6qo00111d
Sogorb MA, Vilanova E. Enzymes involved in the detoxification of organophosphorus, carbamate and pyrethroid insecticides through hydrolysis. Toxicol Lett 2002;128:215–28. doi: 10.1016/s0378-4274(01)00543-4
Nunes G, Barceló D. Analysis of carbamate insecticides in foodstuffs using chromatography and immunoassay techniques. Trends Anal Chem1999;18:99–107. doi: 10.1016/S0165-9936(98)00076-4
Wang Q, Lemley AT. Competitive degradation and detoxification of carbamate insecticides by membrane anodic fenton treatment. J Agric Food Chem 2003;51:5382–90. doi: 10.1021/jf034311f
Plastics Europe. Plastics-the facts 2014/2015. An analysis of European plastics production, demand and waste data [displayed 17 May 2020]. Available at https://www.plasticseurope.org/application/files/5515/1689/9220/2014plastics_the_facts_PubFeb2015.pdf
Akindoyo JO, Beg MDH, Ghazali S, Islam MR, Jeyaratnam N, Yuvaray AR. Polyurethane types, synthesis and applications-a review. RSC Adv 2016;6;114453–82. doi: 10.1039/C6RA14525F
Dhanapal D, Rebheka G, Palanivel S, Srinivasan AK. A comparative study on modified epoxy and glycidyl carbamate coatings for corrosion and fouling prevention. Surf Innov 2015;3:127–39. doi: 10.1680/si.13.00025
Grube A, Donaldson D, Kiely T, Wu L. Pesticides industry sales and usage 2006 and 2007 market estimates [displayed 15 May 2020]. Availabile at https://www.epa.gov/pesticides/pesticides-industry-sales-and-usage-2006-and-2007-market-estimates
Sun B, Straubinger RM, Lovell JF. Current taxane formulations and emerging cabazitaxel delivery systems. Nano Res 2018;11:5193–218. doi: 10.1007/s12274-018-2171-0
Avendaño C, Menéndez JC. Anticancer drugs that interact with the DNA minor groove. In: Avendaño C, Menéndez JC, editors. Medicinal chemistry of anticancer drugs. 2nd ed. Elsevier Science, 2015. p. 243–71. doi: 10.1016/B978-0-444-62649-3.00006-5
Meanwell NA, Belema M. The discovery and development of daclatasvir: an inhibitor of the hepatitis C virus NS5A replication complex. Top Med Chem 2019;32:27–56. doi: 10.1007/7355_2018_47
Daniel-Mwambete K, Torrado S, Cuesta-Bandera C, Ponce-Gordo F, Torrado J. The effect of solubilization on the oral bioavailability of three benzimidazole carbamate drugs. Int J Pharm 2004;272:29–36. doi: 10.1016/j.ijpharm.2003.11.030
Aícua-Rapún I, André P, Rossetti AO, Ryvlin P, Hottinger AF, Decosterd LA, Buclin T, Novy J. Therapeutic drug monitoring of newer antiepileptic drugs: a randomized trial for dosage adjustment. Ann Neurol 2020;87:22–9. doi: 10.1002/ana.25641
Flynn S, Babi A. Anticonvulsants. In: Dowd F, Johnson B, Mariotti A, authors. Pharmacology and therapeutics for dentistry. 7th ed. Chapter 12. St. Louis: Elsevier Inc.; 2017. p. 176–92.
Rautio J, Meanwell N, Di L, Hageman MJ. The expanding role of prodrugs in contemporary drug design and development. Nat Rev Drug Discov 2018;17:559–87. doi: 10.1038/nrd.2018.46
Ray S, Chaturvedi D. Application of organic carbamates in drug design. Part 1: anticancer agents - recent reports. Drugs Fut 2004;29:343. doi: 10.1358/dof.2004.029.04.787236
Montero A, Fossella F, Hortobagyi G, Valero V. Docetaxel for treatment of solid tumours: a systematic review of clinical data. Lancet Oncol 2005;6:229–39. doi: 10.1016/S1470-2045(05)70094-2
Achenbach CJ, Darn KM, Murphy RL. Atazanavir/ritonavir-based combination antiretroviral therapy for treatment of HIV-1 infection in adults. Future Virol 2011;6:157–77. doi: 10.2217/fvl.10.89
Croom KF, Dhilloh S, Keam SJ. Atazanavir: a review of its use in the management of HIV-1 infection. Drugs 2009;69:1107–40. doi: 10.2165/00003495-200969080-00009
Ghosh AK, Dawson ZL, Mitsuya H. Darunavir, a conceptually new HIV-1 protease inhibitor for the treatment of drug-resistant HIV. Bioorg Med Chem 2007;15:7576–80. doi: 10.1016/j.bmc.2007.09.010
Shi LL, Dong J, Ni H, Geng J, Wu T. Felbamate as an add-on therapy for refractory partial epilepsy. Cochrane Database Syst Rev 2017;7(7):CD008295. doi: 10.1002/14651858. CD008295.pub4
Swinyard EA, Sofia RD, Kupferberg HJ. Comparative anticonvulsant activity and neurotoxicity of felbmate and four prototype antiepileptic drugs in mice and rats. Epilepsia 1986;27:27–34. doi: 10.1111/j.1528-1157.1986.tb03497.x
Rho JM, Donevan SD, Rogawski MA. Mechanism of action of the anticonvulsant felbamate: opposing effects on N-methyl-D-aspartate and γ-aminobutyric acidA receptors. Ann Neurol 1994;35:229–34. doi: 10.1002/ana.410350216
Wisden W, Laurie UJ, Monyer H, Seeburg PH. The distribution of thirteen GABAA receptor subunit mRNAs in the rat brain. I. Telencephalon, diencephalon, mesencephalon. J Neurosci 1992;12:1040–62. doi: 10.1523/JNEUROSCI.12-03-01040.1992
Wuttke TV, Seebohm G, Bail S, Maljevic S, Lerche H. The new anticonvulsant retigabine favors voltage-dependent opening of the Kv7.2 KCNQ2 channel by binding to its activation gate. Mol Pharmacol 2005;67:1009–17. doi: 10.1124/mol.104.010793
Sharma R, Nakamura M, Neupane C, Jeon BH, Shinc H, Melnick SM, Glenn KJ, Jang IS, Park JB. Positive allosteric modulation of GABAA receptors by a novel antiepileptic drug cenobamate. Eur J Pharmacol 2020:879:173117. doi: 10.1016/j.ejphar.2020.173117
Haake A, Nguyen K, Friedman L, Chakkamparambil B, Grossberg GT. An update on the utility and safety of cholinesterase inhibitors for the treatment of Alzheimer’s disease. Expert Opin Drug Saf 2020;19:147–57. doi: 10.1080/14740338.2020.1721456
Bosak A, Katalinić M, Kovarik Z. Cholinesterases: structure, role, and inhibition. Arh Hig Rada Toksikol 2011;62:175–90. doi: 10.2478/10004-1254-62-2011-2107
Plata-Salaman CR, Zhao B, Teyman RE. Carbamate compounds for use in preventing or treating neurodegenerative disorders. Unites States Patent Application Publication 2002;US 2002/0165273 A1 [displayed 23 November 2020]. Available at https://patents.google.com/patent/US20020165273A1/en
Darvesh S, Darvesh KV, McDonald RS, Mataija D, Walsh R, Mothana S, Lockridge O, Martin E. Carbamates with differential mechanism of inhibition toward acetylcholinesterase and butyrylcholinesterase. J Med Chem 2008;51:4200–12. doi: 10.1021/jm8002075
Prince M, Comas-Herrera A, Knapp M, Guerchet M, Karagiannidou M. World Alzheimer Report 2016: improving helatchare for people living with dementia: coverage, quality and costs now and in the future, Alzheimer’s disease International (ADI), 2016 [displayed 23 November 2020]. Availabile at https://www.alz.co.uk/research/WorldAlzheimerReport2016.pdf
Kovacs GG, Adle-Biassette H, Milenkovic I, Cipriani S, van Scheppingen J, Aronica E. Linking pathways in the developing and aging brain with neurodegeneration. Neuroscience 2014;269:152–72. doi: 10.1016/j. neuroscience.2014.03.045
Bitzinger DI, Gruber M, Tummler S, Malsy M, Seyfried T, Weber F, Redel A, Graf BM, Zausig YA. In vivo effects of neostigmine and physostigmine on neutrophil functions and evaluation of acetylcholinesterase and butyrylcholinesterase as inflammatory markers during experimental sepsis in rats. Mediat Inflamm 2019;4:ID8274903. doi: 10.1155/2019/8274903
Frascogna N. Physostigmine: is there a role for this antidote in pediatric poisonings? Curr Opin Pediatr 2007;19:201–5. doi: 10.1097/MOP.0b013e32802c7be1
Kamal MA, Klein P, Luo WM, Li YZ, Holloway HW, Tweedie D, Greig NH. Kinetics of human serum butyrylcholinesterase inhibition by a novel experimental Alzheimer therapeutic, dihydrobenzodioxepine cymserine. Neurochem Res 2008;33;745–53. doi: 10.1007/s11064-007-9490-y
Guo T, Gu H, Hobbs DW, Rokosz LL, Stauffer TM, Jacob B, Clader JW. Design, synthesis, and evaluation of tetrahydroquinoline and pyrrolidine sulfonamide carbamates as γ-secretase inhibitors. Bioorg Med Chem Lett 2007;17:3010–3. doi: 10.1016/j.bmcl.2007.03.055
Kamal MA, Qu X, Yu Q, Tweedie D, Holloway HW, Li Y, Tan Y, Greig NH. Tetrahydrofurobenzofuran cymserine, a potent butyrylcholinesterase inhibitor and experimental Alzheimer drug candidate, enzyme kinetic analysis. J Neural Transm (Vienna) 2008;115:889–98. doi: 10.1007/s00702-008-0022-y
Chary A, Holodniy M. Recent advances in hepatitis C virus treatment: review of HCV protease inhibitor clinical trials. Rev Recent Clin Trials 2010;5:158–73. doi: 10.2174/157488710792007293
Shi ST, Polyak SJ, Tu H, Taylor DR, Gretch DR, Lai MM. Hepatitis C virus NS5A colocalizes with the core protein on lipid droplets and interacts with apolipoproteins. Virology 2002;292:198–210. doi: 10.1006/viro.2001.1225
Belema M, Nguyen VN, Bachand C, Deon DH, Goodrich JT, James CA, Lavoie R, Lopez OD, Martel A, Romine JL, Ruediger EH, Snyder LB, St Laurent DR, Yang F, Zhu J, Wong HS, Langley DR, Adams SP, Cantor GH, Chimalakonda A, Fura A, Johnson BM, Knipe JO, Parker DD, Santone KS, Fridell RA, Lemm JA, O’Boyle DR, Colonno RJ, Gao M, Meanwell NA, Hamann LG. Hepatitis C virus NS5A replication complex inhibitors: the discovery of daclatasvir. J Med Chem 2014;57:2013–32. doi: 10.1021/jm401836p
World Health Organization. World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization [displayed 8 December 2020]. Available at: https://apps.who.int/iris/handle/10665/325771
O’Doherty DS, Shields CD. Methocarbamol-new agent in treatment of neurological and neuromuscular diseases. J Am Med Assoc 1958;167:160–3. doi: 10.1001/jama.1958.02990190014003
Giordani C, Marin GH, Perez D, Soraci A, Errecalde J. Mechanism of action of drugs with activity against multicellular parasites. Parazitologija 2017;51:294–316 [displayed 23 November 2020]. Available at http://sedici.unlp.edu.ar/bitstream/handle/10915/98772/Mechanism_of_action_of_drugs_with_activity_against_multicellular_parasites.pdf-PDFA.pdf?sequence=1&isAllowed=y
Mathijessen RH, van Alphen RJ, Verweij J, Loos WJ, Nooter K, Stoter G, Sparreboom A. Clinical pharmacokinetics and metabolism of irinotecan (CPT-11). Clin Cancer Res 2001;7:2182–94. PMID:11489791
Zhou T, Liu S, Zhao T, Zeng J, He M, Xu B, Qu S, Xu L, Tan W. Chiral analysis of bambuterol, its intermediate and active drug in human plasma by liquid chromatography-tandem mass spectrometry: application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci 2015;997:38–44. doi: 10.1016/j.jchromb.2015.05.024
Yaltho TC, Ondo WG. The use of gabapentin enacarbil in the treatment of restless legs syndrome. Ther Adv Neurol Disord 2010;3:269–75. doi: 10.1177/1756285610378059
Terranova-Barberio M, Roca M, Zotti A, Leone A, Bruzzese F, Vitagliano C, Scogliamiglio G, Russo D, D’Angelo G, Franco R, Budillon A, Gennaro E. Valproic acid potentiates the anticancer activity of capecitabine in vitro and in vivo in breast cancer models via induction of thymidine phosphorylase expression. Oncotarget 2016;7:7715–31. doi: 10.18632/oncotarget.6802