Micro and nanosystems for delivering local anesthetics

Expert Opinion on Drug Delivery

Volumn 9, Issue 12, 2012, Pages 1505-1524

  De Paula, Eneida ^a   Cereda, Cíntia Ms ^a   Fraceto, Leonardo F ^a,b   De Araújo, Daniele R ^c   Franz Montan, Michelle ^a   Tofoli, Giovana R ^d   Ranali, José ^a   Volpato, Maria C ^a   Groppo, Francisco C ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

^c UNIVERSIDADE FEDERAL DO ABC   (Brazil)

^d UNIVERSIDADE SÃO FRANCISCO   (Brazil)

Author keywords

Cyclodextrins; Liposomes; Local anesthetics; Microparticles; Nanocapsules; Nanospheres; Polymers

Indexed keywords

ADRENALIN; ARTICAINE; BENZOCAINE; BIOPOLYMER; BUPIVACAINE; BUTYLCAINE; CHLOROPROCAINE; CINCHOCAINE; CYCLODEXTRIN; ETIDOCAINE; LIDOCAINE; LIPOSOME; LOCAL ANESTHETIC AGENT; MACROGOL; MEPIVACAINE; MICROSPHERE; NANOCAPSULE; NANOCARRIER; NANOSPHERE; OXETACAINE; OXYBUPROCAINE; POLYCAPROLACTONE; POLYGLACTIN; POLYLACTIDE; PRAMOCAINE; PRILOCAINE; PROCAINE; PROXYMETACAINE; ROPIVACAINE; TETRACAINE;

CRYSTAL STRUCTURE; DRUG DELIVERY SYSTEM; DRUG EFFECT; DRUG FORMULATION; DRUG RELEASE; HUMAN; IMMUNE RESPONSE; KIDNEY TUBULE ABSORPTION; MICROCAPSULE; MICROENCAPSULATION; NANOENCAPSULATION; NEPHROTOXICITY; NONHUMAN; PARTICLE SIZE; RANDOMIZED CONTROLLED TRIAL (TOPIC); REVIEW; SURFACE CHARGE;

ADMINISTRATION, TOPICAL; ANALGESIA; ANESTHESIA, LOCAL; ANESTHETICS, LOCAL; CHEMISTRY, PHARMACEUTICAL; DRUG DELIVERY SYSTEMS; HUMANS; LIPOSOMES; MICROSPHERES; NANOCAPSULES; NANOSPHERES; PAIN;

EID: 84869786653     PISSN: 17425247     EISSN: 17447593     Source Type: Journal    
DOI: 10.1517/17425247.2012.738664     Document Type: Review

References (142)

1. McLure HA, Rubin AP. Review of local anaesthetic agents. Minerva Anestesiol 2005;71:59-74 (Pubitemid 43932949)
2. Rose JS, Neal JM, Kopacz DJ. Extended-duration analgesia: update on microspheres and liposomes. Reg Anesth Pain Med 2005;30:275-85 (Pubitemid 40718910)
3. Weiniger CF, Golovanevski M, Sokolsky-Papkov M, Domb AJ. Review of prolonged local anesthetic action. Expert Opin Drug Deliv 2010;7:737-52
4. Scholz A. Mechanisms of (local) anaesthetics on voltage-gated sodium and other ion channels. Br J Anaesth 2002;89:52-61 (Pubitemid 34778103)
5. Yanagidate F, Strichartz GR. Bupivacaine inhibits activation of neuronal spinal extracellular receptor-activated kinase through selective effects on ionotropic receptors. Anesthesiology 2006;104:805-14
6. Strichartz GR. Novel ideas of local anaesthetic actions on various ion channels to ameliorate postoperative pain. Br J Anaesth 2008;101:45-7 (Pubitemid 351881907)
7. Malamed S. What's new in local anaesthesia? SAAD Dig 2009;25:4-14
8. Wiles MD, Nathanson MH. Local anaesthetics and adjuvants-future developments. Anaesthesia 2010;65:22-37
9. Lagan G, McLure HA. Review of local anaesthetic agents. Curr Anaesth Crit Care 2004;15:247-54 (Pubitemid 39497231)
10. Columb MO, MacLennan K. Local anaesthetic agents. Anaesth Intensive Care Med 2007;8:159-62 (Pubitemid 46504844)
11. Mulroy MF, Larkin KL, Batra MS, et al. Femoral nerve block with 0.25% or 0.5% bupivacaine improves postoperative analgesia following outpatient arthroscopic anterior cruciate ligament repair. Reg Anesth Pain Med 2001;26:24-9 (Pubitemid 32062355)
12. Davidson EM, Barenholz Y, Cohen R, et al. High-dose bupivacaine remotely loaded into multivesicular liposomes demonstrates slow drug release without systemic toxic plasma concentrations after subcutaneous administration in humans. Anesth Analg 2010;110:1018-23
13. Takenami T, Wang G, Nara Y, et al. Intrathecally administered ropivacaine is less neurotoxic than procaine, bupivacaine, and levobupivacaine in a rat spinal model. Can J Anaesth 2012;59:456-65
14. Werdehausen R, Braun S, Hermanns H, et al. The influence of adjuvants used in regional anesthesia on lidocaine-induced neurotoxicity in vitro. Reg Anesth Pain Med 2011;36:436-43
15. Grant SA, Nielsen KC, Greengrass RA, et al. Continuous peripheral nerve block for ambulatory surgery. Reg Anesth Pain Med 2001;26:209-14 (Pubitemid 32476581)
16. Klein SM, Grant SA, Greengrass RA, et al. Interscalene brachial plexus block with a continuous catheter insertion system and a disposable infusion pump. Anesth Analg 2000;91:1473-8
17. Battaglia L, Gallarate M. Lipid nanoparticles: state of the art, new preparation methods and challenges in drug delivery. Expert Opin Drug Deliv 2012;9:497-508
18. Puglia C, Bonina F. Lipid nanoparticles as novel delivery systems for cosmetics and dermal pharmaceuticals. Expert Opin Drug Deliv 2012;9:429-41
19. Mura P, Maestrelli F, González-Rodríguez ML, et al. Development, characterization and in vivo evaluation of benzocaine-loaded liposomes. Eur J Pharm Biopharm 2007;67:86-95 (Pubitemid 46991345)
20. Shim J, Kim MJ, Kim HK, et al. Morphological effect of lipid carriers on permeation of lidocaine hydrochloride through lipid membranes. Int J Pharm 2010;388:251-6
21. Padula C, Fulgoni A, Santi P. In vivo stratum corneum distribution of lidocaine, assessed by tape stripping, from a new bioadhesive film. Skin Res Technol 2010;16:125-30
22. Eichenfield LF, Funk A, Fallon-Friedlander S, Cunningham BB. A clinical study to evaluate the efficacy of ELA-Max (4% liposomal lidocaine) as compared with eutectic mixture of local anesthetics cream for pain reduction of venipuncture in children. Pediatrics 2002;109:1093-9 (Pubitemid 34587436)
23. Fraceto LF, Spisni A, Schreier S, de Paula E. Differential effects of uncharged aminoamide local anesthetics on phospholipid bilayers, as monitored by 1H-NMR measurements. Biophys Chem 2005;115:11-18 (Pubitemid 40543102)
24. Malheiros SV, Pinto LM, Gottardo L, et al. A new look at the hemolytic effect of local anesthetics, considering their real membrane/water partitioning at pH 7.4. Biophys Chem 2004;110:213-21
25. de Paula E, Schreier S. Use of a novel method for determination of partition coefficients to compare the effect of local anesthetics on membrane structure. Biochim Biophys Acta 1995;1240:25-33
26. de Paula E, Cereda C, Tofoli G, et al. Drug delivery systems for local anesthetics. Recent Pat Drug Deliv Formul 2010;4:23-34
27. Rao JP, Geckeler KE. Cyclodextrin supramacromolecules: unexpected formation in aqueous phase under ambient conditions. Macromol Rapid Commun 2011;32:426-30
28. Wakiyama N, Juni K, Nakano M. Preparation and evaluation in vitro of polylactic acid microspheres containing local anesthetics. Chem Pharm Bull (Tokyo) 1981;29:3363-8 (Pubitemid 12150769)
29. Wakiyama N, Juni K, Nakano M. Preparation and evaluation in vitro and in vivo of polylactic acid microspheres containing dibucaine. Chem Pharm Bull (Tokyo) 1982;30:3719-27 (Pubitemid 13210106)
30. Estebe JP, Le Corre P, Mallédant Y, et al. Prolongation of spinal anesthesia with bupivacaine-loaded (DL-lactide) microspheres. Anesth Analg 1995;81:99-103
31. Le Corre P, Le Guevello P, Gajan V, et al. Preparation and characterization of bupivacaine-loaded polylactide and polylactide-co-glycolide microspheres. Int J Pharm 1994;107:41-9 (Pubitemid 24150376)
32. Curley J, Castillo J, Hotz J, et al. Prolonged regional nerve blockade. Injectable biodegradable bupivacaine/polyester microspheres. Anesthesiology 1996;84:1401-10 (Pubitemid 26192049)
33. Kopacz DJ, Bernards CM, Allen HW, et al. A model to evaluate the pharmacokinetic and pharmacodynamic variables of extended-release products using in vivo tissue microdialysis in humans: bupivacaine-loaded microcapsules. Anesth Analg 2003;97:124-31 (Pubitemid 36736549)
34. Pedersen JL, Lillesø J, Hammer NA, et al. Bupivacaine in microcapsules prolongs analgesia after subcutaneous infiltration in humans: a dose-finding study. Anesth Analg 2004;99:912-18 (Pubitemid 39100389)
35. Gorner T, Gref R, Michenot D, et al. Lidocaine-loaded biodegradable nanospheres. I. Optimization Of the drug incorporation into the polymer matrix. J Control Release 1999;57:259-68 (Pubitemid 29073441)
36. Polakovic M, Gorner T, Gref R, Dellacherie E. Lidocaine loaded biodegradable nanospheres. II. Modelling of drug release. J Control Release 1999;60:169-77 (Pubitemid 29335943)
37. Govender T, Stolnik S, Garnett MC, et al. PLGA nanoparticles prepared by nanoprecipitation: drug loading and release studies of a water soluble drug. J Control Release 1999;57:171-85 (Pubitemid 29062869)
38. Klose D, Siepmann F, Elkharraz K, et al. How porosity and size affect the drug release mechanisms from PLGA-based microparticles. Int J Pharm 2006;314:198-206
39. Moraes CM, de Matos AP, de Lima R, et al. Initial development and characterization of PLGA nanospheres containing ropivacaine. J Biol Phys 2007;33:455-61
40. Holgado MA, Arias JL, Cózar MJ, et al. Synthesis of lidocaine-loaded PLGA microparticles by flow focusing. Effects on drug loading and release properties. Int J Pharm 2008;358:27-35
41. Zhang H, Lu Y, Zhang G, et al. Bupivacaine-loaded biodegradable poly (lactic-co-glycolic) acid microspheres I. Optimization of the drug incorporation into the polymer matrix and modelling of drug release. Int J Pharm 2008;351:244-9 (Pubitemid 351186865)
42. Horie RT, Sakamoto T, Nakagawa T, et al. Sustained delivery of lidocaine into the cochlea using poly lactic/glycolic acid microparticles. Laryngoscope 2010;120:377-83
43. de Melo NFS, Grillo R, Rosa AH, et al. Desenvolvimento e caracterização de nanocápsulas de poli(L-lactideo) contendo benzocaína. Química Nova 2010;33:65-9
44. Moraes CM, Matos AP, de Paula E, et al. Benzocaine loaded biodegradable poly(D,L-lactide-co-glycolide) nanocapsules: factorial design and characterization. Mater Sci Eng B 2009;165:243-6
45. Moraes CM, de Paula E, Rosa AH, Fraceto LF. Physicochemical stability of poly(lactide-co-glycolide) nanocapsules containing the local anesthetic bupivacaine. J Braz Chem Soc 2010;6:995-1000
46. Moraes CM, Matos AP, de Paula E, et al. Solid state materials for advanced technology. Mater Sci Eng B 2009;165:243
47. Grillo R, de Melo NFS, de Araujo DR, et al. Polymeric alginate nanoparticles containing the local anesthetic bupivacaine. J Drug Target 2010;18:688-99
48. de Melo NFS, de Araujo DR, Grillo R, et al. Benzocaine-loaded polymeric nanocapsules: study of the anesthetic activities. J Pharm Sci 2012;101:1157-65
49. de Melo NFS, Grillo R, Guilherme VA, et al. Poly(lactide-co-glycolide) nanocapsules containing benzocaine: influence of the composition of the oily nucleus on physico-chemical properties and anesthetic activity. Pharm Res 2011;28:1984-94
50. Nel AE, Mädler L, Velegol D, et al. Understanding biophysicochemical interactions at the nano-bio interface. Nat Mater 2009;8:543-57
51. Loftsson T, Brewster ME. Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes. J Pharm Pharmacol 2011;63:1119-35
52. Davis ME, Brewster ME. Cyclodextrin-based pharmaceutics: past, present and future. Nat Rev Drug Discov 2004;3:1023-35 (Pubitemid 39642365)
53. Loftsson T, Duchêne D. Cyclodextrins and their pharmaceutical applications. Int J Pharm 2007;329:1-11 (Pubitemid 44937538)
54. Brewster ME, Loftsson T. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 2007;59:645-66 (Pubitemid 47299263)
55. Dollo G, Le Corre P, Chevanne F, Le Verge R. Inclusion complexation of amide-typed local anesthetics with b-cyclodextrin and its derivatives. I. Physicochemical characterization. Int J Pharm 1996;131:165-74 (Pubitemid 26200747)
56. Rajewski RA, Stella VJ. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J Pharm Sci 1996;85:1142-69 (Pubitemid 26372882)
57. Irie T, Uekama K. Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J Pharm Sci 1997;86:147-62 (Pubitemid 27078377)
58. Moraes CM, Abrami P, de Paula E, et al. Study of the interaction between S (-) bupivacaine and 2-hydroxypropylbeta-cyclodextrin. Int J Pharm 2007;331:99-106
59. de Araujo DR, Tsuneda SS, Cereda CM, et al. Development and pharmacological evaluation of ropivacaine-2-hydroxypropyl-beta-cyclodextrin inclusion complex. Eur J Pharm Sci 2008;33:60-71 (Pubitemid 350235192)
60. Moraes CM, Abrami P, de Araujo DR, et al. Characterization of lidocaine: hydroxypropyl-b-cyclodextrin inclusion complex. J Incl Phenom Macrocycl Chem 2007;57:313-16
61. Cabeça LF, Figueiredo IM, de Paula E, Marsaioli AJ. Prilocaine-cyclodextrin-liposome: effect of pH variations on the encapsulation and topology of a ternary complex using 1H NMR. Magn Reson Chem 2011;49:295-300
62. Pinto LM, Fraceto LF, Santana MH, et al. Physico-chemical characterization of benzocaine-beta-cyclodextrin inclusion complexes. J Pharm Biomed Anal 2005;39:956-63 (Pubitemid 41441724)
63. Cabeça LF, Fernandes SA, de Paula E, Marsaioli AJ. Topology of a ternary complex (proparacaine-beta-cyclodextrinliposome) by STD NMR. Magn Reson Chem 2008;46:832-7
64. de Lima RAF, de Jesus MB, Cereda CMS, et al. Improvement of tetracaine antinociceptive effect by inclusion in cyclodextrins. J Drug Target 2012;20:85-96
65. Meert TF, Melis W. Interactions between epidurally and intrathecally administered sufentanil and bupivacaine in hydroxypropyl-beta-cyclodextrin in the rat. Acta Anaesthesiol Belg 1992;43:79-89
66. Dollo G, Le Corre P, Chevanne F, Le Verge R. Inclusion complexation of amide-typed local anesthetics with b-cyclodextrin and its derivatives. II. Evaluation of affinity constants and in vitro transfer rate constants. Int J Pharm 1996;136:219-28
67. Dollo G, Thompson DO, Le Corre P, et al. Inclusion complexation of amide-typed local anesthetics with b-cyclodextrin and its derivatives. III. Biopharmaceutics of bupivacaine-SBE7-b-CD complex following percutaneous sciatic nerve administration in rabbits. Int J Pharm 1998;164:11-19 (Pubitemid 28160093)
68. Al-nouti Y, Bartlett MG. Comparison of local anesthetic-cyclodextrin non-covalent complexes using capillary electrophoresis and electrospray ionization mass spectrometry. J Am Soc Mass Spectrom 2002;13:928-35 (Pubitemid 36876006)
69. Fréville JC, Dollo G, Le Corre P, et al. Controlled systemic absorption and increased anesthetic effect of bupivacaine following epidural administration of bupivacaine-hydroxypropyl-betacyclodextrin complex. Pharm Res 1996;13:1576-80 (Pubitemid 26356965)
70. Estebe JP, Ecoffey C, Dollo G, et al. Bupivacaine pharmacokinetics and motor blockade following epidural administration of the bupivacaine- sulphobutylether 7-beta-cyclodextrin complex in sheep. Eur J Anaesthesiol 2002;19:308-10 (Pubitemid 34984210)
71. Araujo DR, Fraceto LF, Braga AeF, Paula E. Drug-delivery systems for racemic bupivacaine (S50-R50) and bupivacaine enantiomeric mixture (S75-R25): cyclodextrins complexation effects on sciatic nerve blockade in mice. Rev Bras Anestesiol 2005;55:316-28 (Pubitemid 40686177)
72. Araujo DR, Braga AFA, Moraes CM, et al. Complexation of 50% enantiomeric excess (S75-R25) bupivacaine with cyclodextrins and spinal block anesthesia in rats. Rev Bras Anestesiol 2006;56:495-506 (Pubitemid 44540099)
73. Karashima K, Taniguchi M, Nakamura T, et al. Prolongation of intrathecal and sciatic nerve blocks using a complex of levobupivacaine with maltosyl-beta-cyclodextrin in rats. Anesth Analg 2007;104:1121-8 (Pubitemid 46649932)
74. Suzuki R, Arai YC, Hamayasu K, et al. Complex of branched cyclodextrin and lidocaine prolonged the duration of peripheral nerve block. J Anesth 2009;23:295-7
75. Stella VJ, He Q. Cyclodextrins. Toxicol Pathol 2008;36:30-42
76. Frank DW, Gray JE, Weaver RN. Cyclodextrin nephrosis in the rat. Am J Pathol 1976;83:367-82
77. Frijlink HW, Eissens AC, Hefting NR, et al. The effect of parenterally administered cyclodextrins on cholesterol levels in the rat. Pharm Res 1991;8:9-16
78. Carpenter TO, Gerloczy A, Pitha J. Safety of parenteral hydroxypropyl beta-cyclodextrin. J Pharm Sci 1995;84:222-5
79. Gould S, Scott RC. 2-Hydroxypropylbeta-cyclodextrin (HP-beta-CD): a toxicology review. Food Chem Toxicol 2005;43:1451-9
80. Rajewski RA, Traiger G, Bresnahan J, et al. Preliminary safety evaluation of parenterally administered sulfoalkyl ether beta-cyclodextrin derivatives. J Pharm Sci 1995;84:927-32
81. Cereda CM, Tofoli GR, Maturana LG, et al. Local neurotoxicity and myotoxicity evaluation of cyclodextrin complexes of bupivacaine and ropivacaine. Anesth Analg 2012; In press
82. Kuzma PJ, Kline MD, Calkins MD, Staats PS. Progress in the development of ultra-long-acting local anesthetics. Reg Anesth 1997;22:543-51 (Pubitemid 28008142)
83. Gorfine SR, Onel E, Patou G, Krivokapic ZV. Bupivacaine extended-release liposome injection for prolonged postsurgical analgesia in patients undergoing hemorrhoidectomy: a multicenter, randomized, double-blind, placebo-controlled trial. Dis Colon Rectum 2011;54:1552-9
84. Grant SA. The holy grail: long-acting local anaesthetics and liposomes. Best Pract Res Clin Anaesthesiol 2002;16:345-52 (Pubitemid 38950033)
85. Bangham AD, Standish MM, Watkins JC. Diffusion of univalent ions across the lamellae of swollen phospholipids. J Mol Biol 1965;13:238-52
86. Lichtenberg D, Barenholz Y. Liposomes: preparation, characterization, and preservation. Methods Biochem Anal 1988;33:337-462
87. Ranade VV. Drug delivery systems. 1. site-specific drug delivery using liposomes as carriers. J Clin Pharmacol 1989;29:685-94 (Pubitemid 19222371)
88. Samad A, Sultana Y, Aqil M. Liposomal drug delivery systems: an update review. Curr Drug Deliv 2007;4:297-305 (Pubitemid 47554274)
89. Grant GJ, Bansinath M. Liposomal delivery systems for local anesthetics. Reg Anesth Pain Med 2001;26:61-3 (Pubitemid 32062362)
90. Torchilin VP. Recent advances with liposomes as pharmaceutical carriers. Nat Rev Drug Discov 2005;4:145-60 (Pubitemid 40282557)
91. Nguyen S, Alund SJ, Hiorth M, et al. Studies on pectin coating of liposomes for drug delivery. Colloids Surf B Biointerfaces 2011;88:664-73
92. Torchilin VP. Liposomes in drug delivery. In: siegel RA, Rathbone MJ, editors, Drug delivery, advances in delivery science and technology. Control Release Soc 2012;11:289-328
93. Sharata HH, Katz KH. Liposomes. Int J Dermatol 1996;35:761-9
94. Mowat JJ, Mok MJ, MacLeod BA, Madden TD. Liposomal bupivacaine. Extended duration nerve blockade using large unilamellar vesicles that exhibit a proton gradient. Anesthesiology 1996;85:635-43 (Pubitemid 26332618)
95. Grant GJ, Barenholz Y, Bolotin EM, et al. A novel liposomal bupivacaine formulation to produce ultralong-acting analgesia. Anesthesiology 2004;101:133-7 (Pubitemid 38833273)
96. Gesztes A, Mezei M. Topical anesthesia of the skin by liposome-encapsulated tetracaine. Anesth Analg 1988;67:1079-81 (Pubitemid 18260751)
97. Langerman L, Grant GJ, Zakowski M, et al. Prolongation of epidural anesthesia using a lipid drug carrier with procaine, lidocaine, and tetracaine. Anesth Analg 1992;75:900-5
98. Boogaerts JG, Lafont ND, Luo H, Legros FJ. Plasma concentrations of bupivacaine after brachial plexus administration of liposome-associated and plain solutions to rabbits. Can J Anaesth 1993;40:1201-4 (Pubitemid 24037512)
99. Boogaerts J, Declercq A, Lafont N, et al. Toxicity of bupivacaine encapsulated into liposomes and injected intravenously: comparison with plain solutions. Anesth Analg 1993;76:553-5 (Pubitemid 23077114)
100. Grant GJ, Vermeulen K, Langerman L, et al. Prolonged analgesia with liposomal bupivacaine in a mouse model. Reg Anesth 1994;19:264-9 (Pubitemid 24243478)
101. Grant GJ, Lax J, Susser L, et al. Wound infiltration with liposomal bupivacaine prolongs analgesia in rats. Acta Anaesthesiol Scand 1997;41:204-7 (Pubitemid 27084643)
102. Grant GJ, Barenholz Y, Piskoun B, et al. DRV liposomal bupivacaine: preparation, characterization, and in vivo evaluation in mice. Pharm Res 2001;18:336-43 (Pubitemid 32595822)
103. Boogaerts J, Lafont N, Donnay M, et al. Motor blockade and absence of local nerve toxicity induced by liposomal bupivacaine injected into the brachial plexus of rabbits. Acta Anaesthesiol Belg 1995;46:19-24
104. Yu HY, Li SD, Sun P. Kinetic and dynamic studies of liposomal bupivacaine and bupivacaine solution after subcutaneous injection in rats. J Pharm Pharmacol 2002;54:1221-7
105. Malinovsky JM, Bernard JM, Le Corre P, et al. Extradural bupivacaine-loaded microspheres and spinal cord blood flow in the chronically instrumented rabbit. Clin Physiol 1997;17:361-70
106. Malinovsky JM, Le Corre P, Meunier JF, et al. A dose-response study of epidural liposomal bupivacaine in rabbits. J Control Release 1999;60:111-19 (Pubitemid 29255833)
107. Malinovsky JM, Benhamou D, Alafandy M, et al. Neurotoxicological assessment after intracisternal injection of liposomal bupivacaine in rabbits. Anesth Analg 1997;85:1331-6 (Pubitemid 28130534)
108. Yu HY, Sun P, Hou WY. Prolonged local anesthetic effect of bupivacaine liposomes in rats. Int J Pharm 1998;176:133-6 (Pubitemid 28544979)
109. Mashimo T, Uchida I, Pak M, et al. Prolongation of canine epidural anesthesia by liposome encapsulation of lidocaine. Anesth Analg 1992;74:827-34
110. Cereda CM, de Araujo DR, Brunetto GB, De Paula E. Liposomal prilocaine: preparation, characterization, and in vivo evaluation. J Pharm Pharm Sci 2004;7:235-40 (Pubitemid 41528897)
111. de Araujo DR, Cereda CM, Brunetto GB, et al. Encapsulation of mepivacaine prolongs the analgesia provided by sciatic nerve blockade in mice. Can J Anaesth 2004;51:566-72 (Pubitemid 38867922)
112. Cereda CM, Brunetto GB, de Araujo DR, de Paula E. Liposomal formulations of prilocaine, lidocaine and mepivacaine prolong analgesic duration. Can J Anaesth 2006;53:1092-7 (Pubitemid 44756155)
113. de Araujo DR, Cereda CM, Brunetto GB, et al. Pharmacological and local toxicity studies of a liposomal formulation for the novel local anaesthetic ropivacaine. J Pharm Pharmacol 2008;60:1449-57
114. Boogaerts JG, Lafont ND, Declercq AG, et al. Epidural administration of liposome-associated bupivacaine for the management of postsurgical pain: a first study. J Clin Anesth 1994;6:315-20 (Pubitemid 24266947)
115. Lafont ND, Boogaerts JG, Legros FJ. Use of liposome-associated bupivacaine for the management of a chronic pain syndrome. Anesth Analg 1994;79:818 (Pubitemid 24307188)
116. Lafont ND, Legros FJ, Boogaerts JG. Use of liposome-associated bupivacaine in a cancer pain syndrome. Anaesthesia 1996;51:578-9 (Pubitemid 26175541)
117. Tofoli GR, Cereda CM, de Araujo DR, et al. Pharmacokinetic and local toxicity studies of liposome-encapsulated and plain mepivacaine solutions in rats. Drug Deliv 2010;17:68-76
118. Parnham MJ, Wetzig H. Toxicity screening of liposomes. Chem Phys Lipids 1993;64:263-74 (Pubitemid 23290878)
119. Kimelberg HK, Mayhew EG, Gregoriadis G. Properties and biological effects of liposomes and their uses in pharmacology and toxicology. Crit Rev Toxicol 1978;6:25-79
120. Cabeça LF, Figueiredo IM, de Paula E, Marsaioli AJ. Prilocaine-cyclodextrinliposome: effect of pH variations on the encapsulation and topology of a ternary complex using 1H NMR. Magn Reson Chem 2011;49:295-300
121. Bragagni M, Maestrelli F, Mennini N, et al. Liposomal formulations of prilocaine: effect of complexation with hydroxypropyl-cyclodextrin on drug anesthetic efficacy. J Liposome Res 2010;20:315-22
122. Maestrelli F, González-Rodríguez ML, Rabasco AM, et al. New "drug-in cyclodextrin-in deformable liposomes" formulations to improve the therapeutic efficacy of local anaesthetics. Int J Pharm 2010;395:222-31
123. Ullah I, Cadwallader DE. Dissolution of slightly soluble powders under sink conditions. 3. Transport of drug solution across screens and membrane barriers. J Pharm Sci 1971;60:1496-9
124. Franz-Montan M, Bergamaschi C, de Paula E, et al. Pharmacokinetic profile of liposome-encapsulated ropivacaine after maxillary infiltration anaesthesia. J Braz Chem Soc 2010;10:1945-51
125. Tofoli GR, Cereda CM, Araujo DR, et al. Pharmacokinetic study of liposome-encapsulated and plain mepivacaine formulations injected intra-orally in volunteers. J Pharm Pharmacol 2012;64:397-403
126. Kranz H, Yilmaz E, Brazeau GA, Bodmeier R. In vitro and in vivo drug release from a novel in situ forming drug delivery system. Pharm Res 2008;25:1347-54 (Pubitemid 351624356)
127. Ratajczak-Enselme M, Estebe JP, Dollo G, et al. Epidural, intrathecal and plasma pharmacokinetic study of epidural ropivacaine in PLGA-microspheres in sheep model. Eur J Pharm Biopharm 2009;72:54-61
128. Adams L. Adjuvants to local anaesthesia in ophthalmic surgery. Br J Ophthalmol 2011;95:1345-9
129. Roghani S, Duperon DF, Barcohana N. Evaluating the efficacy of commonly used topical anesthetics. Pediatr Dent 1999;21:197-200
130. McMillan AS, Walshaw D, Meechan JG. The efficacy of Emla and 5% lignocaine gel for anaesthesia of human gingival mucosa. Br J Oral Maxillofac Surg 2000;38:58-61 (Pubitemid 30182117)
131. Alqareer A, Alyahya A, Andersson L. The effect of clove and benzocaine versus placebo as topical anesthetics. J Dent 2006;34:747-50 (Pubitemid 44764934)
132. Bucalo BD, Mirikitani EJ, Moy RL. Comparison of skin anesthetic effect of liposomal lidocaine, nonliposomal lidocaine, and EMLA using 30-minute application time. Dermatol Surg 1998;24:537-41 (Pubitemid 28225956)
133. de Araujo DR, Pinto LM, Braga AF, de Paula E. Drug-delivery systems for local anesthetics: therapeutic applications. Rev Bras Anestesiol 2003;53:663-71 (Pubitemid 37138664)
134. Viscusi ER. Liposomal drug delivery for postoperative pain management. Reg Anesth Pain Med 2005;30:491-6 (Pubitemid 44437077)
135. Malamed SF. Handbook of Local Anesthesia. 5th edition. St. Louis, CV Mosby; 2004
136. Wiziack Zago PM, Baroni DB, Groppo FC, et al. Anesthetic efficacy of liposomal prilocaine in maxillary infiltration anesthesia. J Liposome Res 2011;21:81-7
137. Pérusse R, Goulet JP, Turcotte JY. Contraindications to vasoconstrictors in dentistry: part I. Cardiovascular diseases. Oral Surg Oral Med Oral Pathol 1992;74:679-86
138. Pérusse R, Goulet JP, Turcotte JY. Contraindications to vasoconstrictors in dentistry: part II. Hyperthyroidism, diabetes, sulfite sensitivity, cortico-dependent asthma, and pheochromocytoma. Oral Surg Oral Med Oral Pathol 1992;74:687-91
139. Tofoli GR, Cereda CM, Groppo FC, et al. Efficacy of liposome-encapsulated mepivacaine for infiltrative anesthesia in volunteers. J Liposome Res 2011;21:88-94
140. Franz-Montan M, de Paula E, Groppo FC, et al. Efficacy of liposome-encapsulated 0.5% ropivacaine in maxillary dental anaesthesia. Br J Oral Maxillofac Surg 2012;50:454-8
141. Cereda CM, Tófoli GR, de Brito Junior RB, et al. Stability and local toxicity evaluation of a liposomal prilocaine formulation. J Liposome Res 2008;18:329-39
142. Cohen R, Kanaan H, Grant GJ, Barenholz Y. Prolonged analgesia from bupisome and bupigel formulations: from design and fabrication to improved stability. J Control Release 2012;160:346-52