Development of self emulsifying drug delivery system of itraconazole for oral delivery: formulation and pharmacokinetic consideration

Journal of Pharmaceutical Investigation

Volumn 45, Issue 3, 2015, Pages 271-283

  Chudasama, Arpan ^a   Shah, Brijesh ^a   Patel, Vineetkumar ^a   Nivsarkar, Manish ^a   Vasu, Kamala ^a   Shishoo, Chamanlal ^a  

^a B V PATEL PHARMACEUTICAL EDUCATION AND RESEARCH DEVELOPMENT PERD CENTRE   (India)

Author keywords

Antifungal; Bioavailability; Itraconazole; Lipid based formulation; Pseudo ternary phase diagram; Triglycerides

Indexed keywords

DIETHYLENE GLYCOL MONOETHYL ETHER; ITRACONAZOLE; LABRASOL; POLYSORBATE 20; SURFACTANT;

ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; BLOOD ANALYSIS; COMPARATIVE STUDY; CORRELATION COEFFICIENT; DROPLET SIZE; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG DIFFUSION; DRUG FORMULATION; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTESTINE MUCOSA PERMEABILITY; MALE; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; PHOTON CORRELATION SPECTROSCOPY; PHYSICAL PARAMETERS; PRIORITY JOURNAL; RAT; SELF EMULSIFYING DRUG DELIVERY SYSTEM; SPECTROSCOPY; STOMACH PERMEABILITY; TIME TO MAXIMUM PLASMA CONCENTRATION; TRANSMISSION ELECTRON MICROSCOPY; ZETA POTENTIAL;

EID: 84929076617     PISSN: 20935552     EISSN: 20936214     Source Type: Journal    
DOI: 10.1007/s40005-015-0172-5     Document Type: Article

References (66)

1. Akhila JS, Shyamjith M, Deepa K, Alwar MC (2007) Acute toxicity studies and determination of median lethal dose. Curr Sci 93(7):917–920
2. Anaissie E (1992) Opportunistic mycoses in the immunocompromised host: experience at a cancer center and review. Clin Infect Dis 14(Suppl 1):S43–S53
3. Araya H, Tomita M, Hayashi M (2006) The novel formulation design of self-emulsifying drug delivery systems (SEDDS) type o/w microemulsion III: the permeation mechanism of a poorly water soluble drug entrapped o/w microemulsion in rat isolated intestinal membrane by the using chamber method. Drug Metab Pharmacokinet 21(1):45–53
4. Bae SK, Park S-J, Shim E-J, Mun J-H, Kim E-Y, Shin J-G, Shon J-H (2011) Increased oral bioavailability of itraconazole and its active metabolite, 7-hydroxyitraconazole, when coadministered with a vitamin C beverage in healthy participants. J Clin Pharmacol 51:444–451
5. Balayssac D, Authier N, Cayre A, Coudore F (2005) Does inhibition of P-glycoprotein lead to drug-drug interactions? Toxicol Lett 156:319–329
6. Barone JA, Koh JG, Bierman RH, Colaizzi JL, Swanson KA, Gaffar MC, Moskovitz BL, Mechlinski W, Van de Velde V (1993) Food interaction and steady-state pharmacokinetics of itraconazole capsules in healthy male volunteers. Antimicrob Agents Chemother 37:778–784
7. Barone JA, Moskovitz BL, Guarnieri J, Hassell AE, Colaizzi JL, Bierman RH, Jessen L (1998) Enhanced bioavailability of itraconazole in hydroxypropyl-β-cyclodextrin solution versus capsules in healthy volunteers. Antimicrob Agents Chemother 42(7):1862–1865
8. Bodey GP (1992) Azole antifungal agents. Clin Infect Dis 14(Suppl 1):S161–S169
9. Cirri M, Pura P, Mora PC (2007) Liquid spray formulations of xibornol by using self-microemulsifying drug delivery systems. Int J Pharm 340:84–91
10. Craig DQM, Barker SA, Banning D, Booth SW (1995) An investigation into the mechanisms of self-emulsification using particle size analysis and low frequency dielectric spectroscopy. Int J Pharm 114:103–110
11. Dixit AR, Rajput SJ, Patel SG (2010) Preparation and bioavailability assessment of SMEDDS containing valsartan. AAPS PharmSciTech 11(1):314–321
12. Djordjevic L, Primorac M, Stupar M, Krajisnik D (2004) Characterization of caprylocaproyl macrogolglycerides basedmicroemulsion drug delivery vehicles for an amphiphilic drug. Int J Pharm 271:11–19
13. Gharzouli K, Senator A, Gharzouli A, Mustapha M, Abed S (1995) Acid secretion and fluoride absorption by the ligated stomach of the rat-Mutual influences of fluoride and luminal acidity. Fluoride 28(1):3–9
14. Ghosh PK, Majithiya RJ, Umrethia ML, Murthy RSR (2006) Design and development of microemulsion drug delivery system of acyclovir for improvement of oral bioavailability. AAPS PharmSciTech 7(3):E172–E177. doi:10.1208/pt070377
15. Gilis PMV, De Conde VF, Vandecruys RPG (1997) Beads having a core coated with an antifungal and a polymer. US Patent 5633015
16. Grant SM, Clissold SP (1989) Itraconazole. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in superficial and systemic mycoses. Drugs 37(3):310–344
17. Greiner B, Eichelbaum M, Fritz P, Kreichgauer H-P, Richter OV, Zundler J, Kroemer HK (1999) The role of intestinal P-glycoprotein in the interaction of digoxin and rifampin. J Clin Investig 104:147–153
18. Han KS, Lee MG (1999) Effect of a new chemoprotective agent, 2-(allylthio)pyrazine, on the pharmacokinetics of intravenous theophylline in rats. Int J Pharm 184:237–242
19. Hassan A, Tang Y-M, Ayres JW (2004) Itraconazole formation using supercritical carbon dioxide. Drug Dev Ind Pharm 30:1029–1035
20. Hauss DJ, Fogal SE, Ficorilli JV, Price CA, Roy T, Jayaraj AA, Keirns JJ (1998) Lipid-based delivery systems for improving the bioavailability and lymphatic transport of a poorly water-soluble LTB4 inhibitor. J Pharm Sci 87:164–169
21. Heykants J, Van Peer A, Van de Velde V, Van Rooy P, Meuldermmans W, Lavrijsen K, Woestenborghs R, Van Custem J, Cauwenbergh G (1989) The clinical pharmacokinetics of itraconazole: an overview. Mycoses 32(Suppl. s1):67–87
22. ICH (2003) Q1(A) (R2) harmonized tripartite guideline, Stability testing of new drug substances and products Q1A (R2)
23. ICH (2003) Q2(B) Guidelines: Validation of Analytical Procedure: Methodology Q2(B)
24. Jain S, Sehgal VN (2001) Itraconazole: an effective oral antifungal for onychomycosis. Int J Dermatol 2001(40):1–5
25. Janssens S, Armas HN, Roberts CJ, Mooter GV (2008) Characterization of ternary solid dispersions of itraconazole, PEG 6000 and HPMC 2910 E5. J Pharm Sci 2008(97):2110–2120
26. Julianto T, Yuen KH, Noor AM (2000) Improved bioavailability of vitamin E with a self emulsifying formulation. Int J Pharm 200:53–57
27. Jung JY, Yoo SD, Lee SH, Kim KH, Yoon DS, Lee KH (1999) Enhanced solubility and dissolution rate of itraconazole by a solid dispersion technique. Int J Pharm 187:209–218
28. Kang BK, Lee JS, Chon SK, Jeong SY, Yuk SH, Khang G, Lee HB, Cho SH (2004) Development of self-microemulsifying drug delivery systems (SMEDDS) for oral bioavailability enhancement of simvastatin in beagle dogs. Int J Pharm 274:65–73
29. Kapsi SG, Ayres JW (2001) Processing factors in development of solid solution formulation of itraconazole for enhancement of drug dissolution and bioavailability. Int J Pharm 229:193–203
30. Khoo SM, Humberstone AJ, Porter CJH, Edwards GA, Charman WN (1998) Formulation design and bioavailability assessment of lipidic selfemulsifying formulations of halofantrine. Int J Pharm 167:155–164
31. Kommuru TR, Gurley B, Khan MA, Reddy IK (2001) Self-emulsifying drug delivery systems (SEDDS) of coenzyme Q10: formulation development and bioavailability assessment. Int J Pharm 212:233–246
32. Lange D, Pavao JH, Jacqmin P, Woestenborghs R, Ding C, Klausner M (1997a) The effect of coadministration of a cola beverage on the bioavailability of itraconazole in patients with acquired immunodeficiency syndrome. Curr Ther Res 58(3):202–212
33. Lange D, Pavao JH, Wu J, Klausner M (1997b) Effect of cola beverage on the bioavailability of itraconazole in the presence of H2 blockers. J Clin Pharmacol 37:535–540
34. Lee YH, Ku YS (1999) Effects of cyclosporine on the pharmacokinetics of proparanolol after intravenous and oral administration to control rats and to rats with uranyl nitrate-induced acute renal failure. J Pharm Pharmacol 51:1149–1154
35. Lee S, Nam K, Kim MS, Jun SW, Park J-S, Woo JS, Hwang S-J (2005) Preparation and characterization of solid dispersions of itraconazole by using aerosol solvent extraction system for improvement in drug solubility and bioavailability. Arch Pharm Res 28:866–874
36. Miyake K, Irie T, Arima H, Hirayama F, Uekama K, Hirano M, Okamoto Y (1999) Characterization of itraconazole/2-hydroxypropyl-β-cyclodextrin inclusion complex in aqueous propylene glycol solution. Int J Pharm 179:237–245
37. Nakarani M, Misra A, Patel J, Vaghani S (2010) Itraconazole nanosuspension for oral delivery: formulation, characterization and in vitro comparison with marketed formulation. Acta Pharm Sci 52:305–314
38. Nazzal S, Guven N, Reddy IK, Khan MA (2002) Preparation and characterization of Coenzyme Q10-Eudragit® solid dispersion. Drug Dev Ind Pharm 28(1):49–57
39. Nielsen FS, Petersen KB, Mullertz A (2008) Bioavailability of probucol from lipid and surfactant based formulations in minipigs: influence of droplet size and dietary state. Eur J Pharm Biopharm 69:553–562
40. Paget GE, Barnes JM (1964) Evaluation of drug activities In: Pharmacometrics, vol. I. In: Laurence DR., Bacharach AL (eds.). Academic Press, London and New York, p 50
41. Peeters J, Neeskens P, Tollenaere JP, Van Remoortere P, Brewster ME (2002) Characterization of the interaction of 2-hydroxypropyl-beta-cyclodextrin with itraconazole at pH 2, 4, and 7. J Pharm Sci 91:1414–1422
42. Physician’s Desk Reference (54th edition) (2000) Medical Economics Staff, Thomson Healthcare, Montvale, pp 1457–1465
43. Porter CJH, Kaukonen AM, Boyd BJ, Edwards GA, Charman WN (2004) Susceptibility to lipase-mediated digestion reduces the oral bioavailability of danazol after administration as a medium-chain lipid-based microemulsion formulation. Pharm Res 21(8):1405–1412
44. Pouton CW (2006) Formulation of poorly water-soluble drugs for oral administration: physicochemical and physiological issues and the lipid formulation classification system. Eur J Pharm Sci 29:278–287
45. Rabinow B, Kipp J, Papadopoulos P, Wong J, Glosson J, Gass J, Sun C-S, Wielgos T, White R, Cook C, Barker K, Wood K (2007) Itraconazole IV nanosuspension enhances efficacy through altered pharmacokinetics in the rat. Int J Pharm 339:251–260
46. Richardson MD (2005) Changing patterns and trends in systemic fungal infections. J Antimicrob Chemother 56(Suppl S1):i5–i11
47. Sek L, Boyd BJ, Charman WN, Porter CJH (2006) Examination of the impact of a range of pluronic surfactants on the in vitro solubilisation behaviour and oral bioavailability of lipidic formulations of atovaquone. J Pharm Pharmacol 58:809–820
48. Shah RB, Khan MA (2004) Regional permeability of salmon calcitonin in isolated rat gastrointestinal tracts: Transport mechanism using caco-2 cell monolayer. AAPS J 6(4):34 (http://www.aapsj.org)
49. Shim SY, Ji CW, Sah H, Par ES, Lee BJ (2006) Characterization of itraconazole semisolid dosage forms prepared by hot melt technique. Arch Pharm Res 29(11):1055–1060
50. Shin JH, Choi KY, Kim YC, Lee MG (2004) Dose-dependent pharmacokinetics of itraconazole after intravenous or oral administration to rats: intestinal first-pass effect. Antimicrob Agents Chemother 48(5):1756–1762
51. Smith D, Van de Velde V, Woestenborghs R, Gazzard BG (1992) The pharmacokinetics of oral itraconazole in AIDS patients. J Pharm Pharmacol 44(7):618–619
52. Taha EI, Al-Saidan S, Samy AM, Khan MA (2004) Preparation and in vitro characterization of self-nanoemulsified drug delivery system (SNEDDS) of all-trans-retinol acetate. Int J Pharm 285:109–119
53. Trull AK, Tan KKC, Lan T, Alexander GJM, Jamieson NV (1995) Absorption of cyclosporine from conventional and new microemulsion oral formulations in liver transplant recipients with external biliary diversion. Br J Clin Pharmacol 39:627–631
54. Uch AS, Hesse U, Dressman JB (1999) Use of 1-methyl-pyrrolidone as a solubilising agent for determining the uptake of poorly soluble drugs. Pharm Res 16:968–971
55. United States Pharmacopoeia (2014) 36/NF31. US Pharmacopoeial Convention, Rockville, vol. 1, p. 807
56. Van Cauteren H, Heykants J, Coster R, Cauwenbergh G (1987) Itraconazole: pharmacologic studies in animals and humans. Rev Infect Dis 9 (Suppl 1) Jan–Feb (www.cid.oxfordjournals.org)
57. Vaughn JM, McConville JT, Burgess D, Peters JI, Johnston KP, Talbert RL, Williams RO III (2006) Single dose and multiple dose studies of itraconazole nanoparticles. Eur J Pharm Biopharm 63:95–102
58. Verreck G, Six K, Mooter GV, Baert L, Peeters J, Brewster ME (2003) Characterization of solid dispersions of itraconazole and hydroxypropylmethylcellulose prepared by melt-extrusion-part I. Int J Pharm 251:165–174
59. Vyas KS, Bradsher W (2011) Histoplasmosis can be severe for HIV-infected person in endemic areas. HIV Clin 23(2):1–3
60. Wang E-J, Lew K, Casciano CN, Clement RP, Jhonson WW (2002) Interaction of common azole antifungals with P-glycoprotein. Antimicrob Agents Chemother 46(1):160–165
61. Welage LS, Carver PL, Revankar S, Pierson C, Kauffman CA (1995) Alterations in gastric acidity in patients infected with human immunodeficiency virus. Clin Infect Dis 21(6):1431–1438
62. Yamaguchi H, Yano I, Saito H, Inui K-I (2002) Pharmacokinetic role of P-glycoprotein in oral bioavailability and intestinal secretion of grepafloxacin in vivo. J Pharmcol Exp Ther 300:1063–1069
63. Yang W, Tam J, Miller DA, Zhou J, McConville JT, Johnston KP, Williams RO III (2008) High bioavailability from nebulized itraconazole nanoparticle dispersions with biocompatible stabilizers. Int J Pharm 361:177–188
64. Yap SP, Yuen KH (2004) Influence of lipolysis and droplet size on tocotrienols absorption from self-emulsifying formulations. Int J Pharm 281:67–78
65. Yoo SD, Lee SH, Kang E, Jun J, Jung JY, Park JW, Lee KH (2000) Bioavailability of itraconazole in rats and rabbits after administration of tablets containing solid dispersion particles. Drug Dev Ind Pharm 26:27–34
66. Zhang P, Liu Y, Feng N, Xu J (2008) Preparation and evaluation of self-emulsifying drug delivery system of oridonin. Int J Pharm 355:269–276