Novel oleic acid derivatives enhance buccal permeation of didanosine

Drug Development and Industrial Pharmacy

Volumn 40, Issue 5, 2014, Pages 657-668

  Ojewole, Elizabeth ^a   Kalhapure, Rahul ^a   Akamanchi, Krishnacharya ^b   Govender, Thirumala ^a  

^a UNIVERSITY OF KWAZULU NATAL   (South Africa)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Antiretroviral; Buccal; Didanosine; Oleic acid derivatives; Permeation enhancers

Indexed keywords

BICEPHALOUS DIANIONIC SURFACTANT; DICARBOXYLIC ACID DERIVATIVE; DIDANOSINE; ESTER DERIVATIVE; FATTY ACID DERIVATIVE; OLEIC ACID; PENETRATION ENHANCING AGENT; SURFACTANT; UNCLASSIFIED DRUG; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; DENDRIMER;

ARTICLE; CELL VACUOLE; CHEEK MUCOSA; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG PENETRATION; DRUG SYNTHESIS; IN VITRO STUDY; INTERCELLULAR SPACE; NONHUMAN; ANALOGS AND DERIVATIVES; ANATOMY AND HISTOLOGY; ANIMAL; BUCCAL DRUG ADMINISTRATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; GASTROINTESTINAL ABSORPTION; MEDICINAL CHEMISTRY; METABOLISM; MOUTH MUCOSA; PERMEABILITY; PIG; TRANSMISSION ELECTRON MICROSCOPY;

ADMINISTRATION, BUCCAL; ANIMALS; ANTI-HIV AGENTS; CHEMISTRY, PHARMACEUTICAL; DENDRIMERS; DIDANOSINE; DRUG DELIVERY SYSTEMS; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR STRUCTURE; MOUTH MUCOSA; OLEIC ACIDS; ORAL MUCOSAL ABSORPTION; PERMEABILITY; SUS SCROFA;

EID: 84898663917     PISSN: 03639045     EISSN: 15205762     Source Type: Journal    
DOI: 10.3109/03639045.2014.892958     Document Type: Article

References (72)

1. Dhiman MK, Dhiman A, Sawant KK. Transbuccal delivery of 5-fluorouracil: Permeation enhancement and pharmacokinetic study. AAPS PharmSciTech 2009;10:258-65
2. Li H, Yu Y, Faraji Dana S, et al. Novel engineered systems for oral, mucosal and transdermal drug delivery. J Drug Target 2013;21: 611-29
3. Morales JO, McConville JT. Manufacture and characterization of mucoadhesive buccal films. Eur J Pharm Biopharm 2011;77: 187-99
4. Singh D, Kumar PS, Sara UVS. Enhancement of intestinal absorption of poorly absorbed drugs by using various permeation enhancers: An overview. World J Pharm Pharm Sci 2013;2:179-98
5. Madhav NVS, Semwal R, Semwal DK, Semwal RB. Recent trends in oral transmucosal drug delivery systems: An emphasis on the soft palatal route. Expert Opin Drug Deliv 2012;9:629-47
6. Kaus L, Gillespie W, Hussain A, Amidon G. The effect of in vivo dissolution, gastric emptying rate, and intestinal transit time on the peak concentration and area-under-The-curve of drugs with different gastrointestinal permeabilities. Pharm Res 1999;16:272-80
7. Patel VF, Liu F, Brown MB. Advances in oral transmucosal drug delivery. J Control Release 2011;153:106-16
8. Shojaei AH, Khan M, Lim G, Khosravan R. Transbuccal permeation of a nucleoside analog, dideoxycytidine: Effects of menthol as a permeation enhancer. Int J Pharm 1999;192:139-46
9. Xiang J, Fang XL, Li XL. Transbuccal delivery of 20,30-dideoxycytidine: In vitro permeation study and histological investigation. Int J Pharm 2002;231:57-66
10. Attia MA, El-Gibaly I, Shaltout SE, Fetih GN. Transbuccal permeation, anti-inflammatory activity and clinical efficacy of piroxicam formulated in different gels. Int J Pharm 2004;276:11-28
11. Senel S, Capan Y, Sargon MF, et al. Enhancement of transbuccal permeation of morphine sulfate by sodium glycodeoxycholate in vitro. J Control Release 1997;45:153-62
12. Figueiras A, Pais A, Veiga FJB. A comprehensive development strategy in buccal drug delivery. AAPS PharmSciTech 2010;11: 1703-12
13. Xue XY, Zhou Y, Chen YY, et al. Promoting effects of chemical permeation enhancers on insulin permeation across TR146 cell model of buccal epithelium in vitro. Drug Chem Toxicol 2012;35: 199-207
14. Patel VF, Liu F, Brown MB. Modeling the oral cavity: In vitro and in vivo evaluations of buccal drug delivery systems. J Control Release 2012;161:746-56
15. Teubl BJ, Absenger M, Frohlich E, et al. The oral cavity as a biological barrier system: Design of an advanced buccal in vitro permeability model. Eur J Pharm Biopharm 2013;84: 386-93
16. Pather SI, Rathbone MJ, Senel S. Current status and the future of buccal drug delivery systems. Expert Opin Drug Deliv 2008;5: 531-42
17. Dodla S, Velmurugan S. Buccal penetration enhancers-An overview. Asian J Pharm Clin Res 2013;6:39-47
18. Kapil R, Dhawan S, Beg S, Singh B. Buccoadhesive films for oncea-day administration of rivastigmine: Systematic formulation development and pharmacokinetic evaluation. Drug Dev Ind Pharm 2013; 39:466-80
19. Aungst BJ. Absorption enhancers: Applications and advances. AAPS J 2012;14:10-8
20. Giannola LI, De Caro V, Giandalia G, et al. Release of naltrexone on buccal mucosa: Permeation studies, histological aspects and matrix system design. Eur J Pharm Biopharm 2007;67:425-33
21. Senel S, Hincal AA. Drug permeation enhancement via buccal route: Possibilities and limitations. J Control Release 2001;72: 133-44
22. Hassan N, Ahad A, Ali M, Ali J. Chemical permeation enhancers for transbuccal drug delivery. Expert Opin Drug Deliv 2010;7: 97-112
23. Sohi H, Ahuja A, Ahmad FJ, Khar RK. Critical evaluation of permeation enhancers for oral mucosal drug delivery. Drug Dev Ind Pharm 2010;36:254-82
24. Rao SS, Song YM, Peddie F, Evans AM. Particle size reduction to the nanometer range: A promising approach to improve buccal absorption of poorly water-soluble drugs. Int J Nanomed 2011;6: 1245-51
25. Hu LS, Silva SMC, Damaj BB, et al. Transdermal and transbuccal drug delivery systems: Enhancement using iontophoretic and chemical approaches. Int J Pharm 2011;421:53-62
26. Senel S, Rathbone MJ, Cansiz M, Pather I. Recent developments in buccal and sublingual delivery systems. Expert Opin Drug Deliv 2012;9:615-28
27. Wei R, Simon L, Hu LS, Michniak-Kohn B. Effects of iontophoresis and chemical enhancers on the transport of lidocaine and nicotine across the oral mucosa. Pharm Res 2012;29:961-71
28. Mrózek L, Coufalová L, Rárová L, et al. New polyfluorothiopropanoyloxy derivatives of 5b-cholan-24-oic acid designed as drug absorption modifiers. Steroids 2013;78:832-44
29. Coufalová L, Mrózek L, Rárová L, et al. New propanoyloxy derivatives of 5b-cholan-24-oic acid as drug absorption modifiers. Steroids 2013;78:435-53
30. Tsutsumi K, Obata Y, Takayama K, et al. Effect of cod-liver oil extract on the buccal permeation of ergotamine tartrate. Drug Dev Ind Pharm 1998;24:757-62
31. Bhati R, Madan-Nagrajan RK. A detailed review on oral mucosal drug delivery system. Int J Pharm Sci Res 2012;3:659-81
32. Artusi M, Nicoli S, Colombo P, et al. Effect of chemical enhancers and iontophoresis on thiocolchicoside permeation across rabbit and human skin in vitro. J Pharm Sci 2004;93:2431-8
33. Şenel S, Hincal AA. Drug permeation enhancement via buccal route: Possibilities and limitations. J Control Release 2001;72: 133-44
34. Pabla D, Akhlaghi F, Zia H. Intestinal permeability enhancement of levothyroxine sodium by straight chain fatty acids studied in MDCK epithelial cell line. Eur J Pharm Sci 2010;40:466-72
35. Ochalek M, Podhaisky H, Ruettinger HH, et al. SC lipid model membranes designed for studying impact of ceramide species on drug diffusion and permeation. Part III: Influence of penetration enhancer on diffusion and permeation of model drugs. Int J Pharm 2012;436:206-13
36. Kalhapure RS, Akamanchi KG. Oleodendrimers: A novel class of multicephalous heterolipids as chemical penetration enhancers for transdermal drug delivery. Int J Pharm 2013;454:158-66
37. Kalhapure RS, Akamanchi KG. A novel biocompatible bicephalous dianionic surfactant from oleic acid for solid lipid nanoparticles. Colloids Surf B Biointerfaces 2013;105:215-22
38. Leadbeater NE. Cleaner and greener approaches to synthetic chemistry. In: Suib SL, ed. New and future developments in catalysis: Catalysis for remediation and environmental concerns. Amsterdam: Elsevier The Netherlands; 2013:19-39
39. UNAIDS 2013. UNAIDS global report 2013. Available from: Http:// wwunaidsorg/en/resources/campaigns/globalreport2013/factsheet/ [last accessed 22 Oct 2013].
40. WHO 2013. WHO tuberculosis fact sheet 2013. Available from: Http://wwwwhoint/mediacentre/factsheets/fs104/en/indexhtml [last accessed 22 Oct 2013].
41. Li X, Chan WK. Transport, metabolism and elimination mechanisms of anti-HIV agents. Adv Drug Deliv Rev 1999;39:81-103
42. Desai PP, Date AA, Patravale VB. Overcoming poor oral bioavailability using nanoparticle formulatio9ns-opportunities and limitations. Drug Discov Today 2012;9:e87-95
43. Ojewole E, Mackraj I, Akhundov K, et al. Investigating the effect of aloe vera gel on the buccal permeability of didanosine. Planta Med 2012;78:354-61
44. Rambharose S, Ojewole E, Mackraj I, Govender T. Comparative buccal permeability enhancement of didanosine and tenofovir by potential multifunctional polymeric excipients and their effects on porcine buccal histology. Pharm Dev Technol 2014;19:82-90
45. Reddy RS, Reddy SP, Mahesh C, et al. Formulation and evaluation of buccal mucoadhesive patches of zidovudine. CIOP 2012;1:44-8
46. Kalhapure RS, Akamanchi KG. Oleic acid based heterolipid synthesis, characterization and application in self-microemulsifying drug delivery system. Int J Pharm 2012;425:9-18
47. Sudhakar Y, Kuotsu K, Bandyopadhyay AK. Buccal bioadhesive drug delivery-A promising option for orally less efficient drugs. J Control Release 2006;114:15-40
48. Shojaei AH, Zhuo SL, Li X. Transbuccal delivery of acyclovir (II): Feasibility, system design, and in vitro permeation studies. J Pharm Pharm Sci 1998;1:66-73
49. Madhav NVS, Shakya AK, Shakya P, Singh K. Orotransmucosal drug delivery systems: A review. J Control Release 2009;140:2-11
50. Hu L, Damaj BB, Martin R, Michniak-Kohn BB. Enhanced in vitro transbuccal drug delivery of ondansetron HCl. Int J Pharm 2011; 404:66-74
51. Koland M, Charyulu RN, Prabhu P. Mucoadhesive films of losartan potassium for buccal delivery: Design and characterization. Indian J Pharm Educ Res 2010;44:315-23
52. Giannola LI, Paderni C, De Caro V, et al. New prospectives in the delivery of galantamine for elderly patients using the IntelliDrug intraoral device: In vivo animal studies. Curr Pharm Design 2010; 16:653-9
53. Giannola LI, De Caro V, Giandalia G, et al. Transbuccal tablets of carbamazepine: Formulation, release and absorption pattern. Int J Immunopathol Pharm 2005;18:21-31
54. Karnovsky MJ. A formaldehyde-glutaraldehyde fixative of high osmolality for use in electron microscopy. J Cell Bio 1965; 27:137-8
55. Lee J, Kellaway IW. Buccal permeation of D-Ala(2), D-Leu(5) enkephalin from liquid crystalline phases of glyceryl monooleate. Int J Pharm 2000;195:35-8
56. Rai V, Tan HS, Michniak-Kohn B. Effect of surfactants and pH on naltrexone (NTX) permeation across buccal mucosa. Int J Pharm 2011;411:92-7
57. Mortazavi SA, Aboofazeli R. An investigation into the effect of various penetration enhancers on percutaneous absorption of piroxicam. Iranian J Pharm Res 2003;2:135-40
58. Jantharaprapap R, Stagni G. Effects of penetration enhancers on in vitro permeability of meloxicam gels. Int J Pharm 2007;343: 26-33
59. Shojaei AH, Berner B, Li XL. Transbuccal delivery of acyclovir: I. In vitro determination of routes of buccal transport. Pharm Res 1998;15:1182-8
60. Kawabata Y, Wada K, Nakatani M, et al. Formulation design for poorly water-soluble drugs based on biopharmaceutics classification system: Basic approaches and practical applications. Int J Pharm 2011;420:1-10
61. Takahashi K, Sakano H, Numata N, et al. Effect of fatty acid diesters on permeation of anti-inflammatory drugs through rat skin. Drug Dev Ind Pharm 2002;28:1285-94
62. Veuillez F, Ganem-Quintanar A, Deshusses J, et al. Comparison of the ex-vivo oral mucosal permeation of tryptophan-leucine (Trp-Leu) and its myristoyl derivative. Int J Pharm 1998;170:85-91
63. Ganem-Quintanar A, Quintanar-Guerrero D, Falson-Rieg F, Buri P. Ex vivo oral mucosal permeation of lidocaine hydrochloride with sucrose fatty acid esters as absorption enhancers. Int J Pharm 1998; 173:203-10
64. Sandri G, Poggi P, Bonferoni MC, et al. Histological evaluation of buccal penetration enhancement properties of chitosan and trimethyl chitosan. J Pharm Pharmacol 2006;58:1327-36
65. Jani GK, Shah DP, Jain VC, et al. Evaluating mucilage from Aloe barbadensis Miller as a pharmaceutical excipient for sustainedrelease matrix tablets. Pharm Technol 2007;31:90-8
66. Nicolazzo JA, Reed BL, Finnin BC. Assessment of the effects of sodium dodecyl sulfate on the buccal permeability of caffeine and estradiol. J Pharm Sci 2004;93:431-40
67. Thanou M, Verhoef JC, He J. Oral drug absorption enhancement by chitosan and its derivatives. Adv Drug Deliv Rev 2001;52:117-26
68. Figueiras A, Hombach J, Veiga F, Bernkop-Schnurch A. In vitro evaluation of natural and methylated cyclodextrins as buccal permeation enhancing system for omeprazole delivery. Eur J Pharm Biopharm 2009;71:339-45
69. Shojaei AH. Buccal mucosa as a route for systemic drug delivery: A review. J Pharm Pharm Sci 1998;1:15-30
70. Zong WX, Thompson, CB. Necrotic death as a cell fate. Genes Dev 2006;20:1-15
71. Dorr W, Jacubek A, Kummermehr J, et al. Effects of stimulated repopulation on oral mucositis during conventional radiotherapy. Radiother Oncol 1995;37:100-7
72. Veuillez F, Rieg FF, Guy RH, et al. Permeation of a myristoylated dipeptide across the buccal mucosa: Topological distribution and evaluation of tissue integrity. Int J Pharm 2002;231:1-9