A comparative evaluation of mono-, di- and triglyceride of medium chain fatty acids by lipid/surfactant/water phase diagram, solubility determination and dispersion testing for application in pharmaceutical dosage form development

Pharmaceutical Research

Volumn 29, Issue 1, 2012, Pages 285-305

  Prajapati, Hetal N ^a   Dalrymple, Damon M ^b   Serajuddin, Abu T M ^a  

^a ST JOHN'S UNIVERSITY   (United States)

^b AB Enzymes GmbH   (Germany)

Author keywords

Danazol; Diglyceride; Drug dispersion; Drug solubility; Lipid based drug delivery; Medium chain lipid; Monoglyceride; Phase diagram; Triglyceride

Indexed keywords

DANAZOL; DIACYLGLYCEROL; LIPID; MEDIUM CHAIN FATTY ACID; MONOACYLGLYCEROL; SURFACTANT; TRIACYLGLYCEROL; WATER; ACYLGLYCEROL; CREMOPHOR; DRUG DERIVATIVE; FATTY ACID; GLYCEROL;

ARTICLE; COMPARATIVE STUDY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DISPERSION; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG DELIVERY SYSTEM; DRUG DOSAGE FORM; DRUG SOLUBILITY; GEL; MICROEMULSION; PARTICLE SIZE; PH; PHASE SEPARATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; THERMODYNAMICS; VISCOSITY; CHEMISTRY; EMULSION; METHODOLOGY; SOLUBILITY;

CHEMISTRY, PHARMACEUTICAL; DANAZOL; DIGLYCERIDES; DOSAGE FORMS; DRUG DELIVERY SYSTEMS; EMULSIONS; FATTY ACIDS; GLYCERIDES; GLYCEROL; MONOGLYCERIDES; PARTICLE SIZE; SOLUBILITY; SURFACE-ACTIVE AGENTS; TRIGLYCERIDES; WATER;

EID: 84860573896     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-011-0541-3     Document Type: Article

References (56)

1. Lipinski CA. Drug-like properties and the causes of poor solubility and poor permeability. J Pharmacol Toxicol Meth. 2000;44 (1):235-49. (Pubitemid 32239479)
2. Serajuddin ATM, Li P, Haefele T. Development of lipid-based drug delivery systems for poorly water-soluble drugs as viable oral dosage forms-Present status and future prospects. Am Pharm Rev. 2008;11:34-42.
3. Hauss DJ, Fogal SE, Ficorilli JV, Price CA, Roy T, Jayaraj AW, et al. Lipid-based delivery systems for improving the bioavailability and lymphatic transport of a poorly water-soluble LTB4 inhibitor. J Pharm Sci. 1997;87(2):164-9. (Pubitemid 28081323)
4. Humberstone AJ, Charman WN. Lipid-based vehicles for the oral delivery of poorly water soluble drugs. Adv Drug Del Rev. 1997;25 (1):103-28.
5. Charman WN. Lipids, lipophilic drugs, and oral delivery-Some emerging concepts. J Pharm Sci. 2000;89(8):967-78.
6. Kawakami K, Yoshikawa T, Moroto Y, Kanaoka E, Takahashi K, Nishihara Y, et al. Microemulsion formulation for enhanced absorption of poorly soluble drugs. I. Prescription design. J Control Rel. 2002;81(1-2):64-74.
7. Vasanthavada M, Serajuddin ATM. Lipid-based self-emulsifying solid dispersions. In: Hauss D, editor. Lipid-based formulations for oral drug delivery: Enhancing bioavailability of poorly water-soluble drugs. New York: Informa Healthcare; 2007. p. 149-84.
8. Porter CJH, Trevaskis NL, Charman WN. Lipids and lipid-based formulations: Optimizing the oral delivery of lipophilic drugs. Nature Rev. 2007;6:231-48. (Pubitemid 46344627)
9. Porter CJH, Pouton CW, Cuine JF, Charman WN. Enhancing intestinal drug solubilization using lipid-based drug delivery systems. Adv Drug Del Rev. 2008;60(6):673-91.
10. Pouton CW, Porter JH. Formulation of lipid based delivery system for oral administration: Materials, methods and strategies. Adv Drug Del Rev. 2008;60(6):625-37.
11. Hauss DJ. Oral lipid-based formulations. Adv Drug Del Rev. 2007;59(7):667-76. (Pubitemid 47285409)
12. Chakraborty S, Shukla D, Mishra B, Singh S. Lipid-An emerging platform for oral delivery of drugs with poor bioavailability. Eur J Pharm Sci. 2009;73(1):1-15.
13. O'Driscoll CM, Griffin BT. Biopharmaceutical challenges associated with drugs low aqueous solubility-the potential impacts of lipid-based formulations. Adv Drug Del Rev. 2008;60(6):617-24.
14. Strickley RG. Currently marketed oral lipid-based dosage forms: Drug products and excipients. In: Hauss D, editor. Lipid-based formulations for oral delivery: Enhancing bioavailability of poorly water-soluble drugs. New York: Informa Healthcare; 2007. p. 1-31.
15. Gursoy RN, Benita S. Self-emulsifying drug delivery systems (SEDDS) for improved oral delivery of lipophilic drugs. Biomed Pharmacother. 2004;58(3):173-82. (Pubitemid 38479922)
16. Hauss DJ. Oral lipid-based drug delivery-A case of implementation failing to keep up with innovation? Am Pharm Rev. 2006.
17. Vonderscher J, Meinzer A. Rationale for the development of Sandimmune Neoral. Transplant Proc. 1994;26(5):2925-7. (Pubitemid 24329369)
18. Meinzer A, Mueller E, Vondersher J. Microemulsion-A suitable galenical approach for the absorption enhancement of a low soluble compound? BT Gattefosse. 1995;88:21-6.
19. Kovarik JM, Mueller EA, van Bree JB, Tetzloff W, Kutz K. Reduced inter- and intraindividual variability in cyclosporine pharmacokinetics from a microemulsion formulation. J Pharm Sci. 1994;83(3):444-6. (Pubitemid 24224228)
20. Mueller EA, Kovarik JM, van Bree JB, Grevel J, Lucker PW, Kutz K. Influence of a fat-rich meal on the pharmacokinetics of a new oral formulation of cyclosporine in a crossover comparison with the market formulation. Pharm Res. 1994;11(1):151-5. (Pubitemid 24040779)
21. Mueller EA, Kovarik JM, Kutz K. Minor influence of a fat-rich meal on the pharmacokinetics of a new oral formulation of cyclosporine. Transplant Proc. 1994;26(5):2957-8. (Pubitemid 24329378)
22. Sheen PC, Kim SI, Petillo JJ, Serajuddin ATM. Bioavailability of a poorly water-soluble drug from tablet and solid dispersion in man. J Pharm Sci. 1991;80(7):712-4.
23. Cannon JB, Long MA. Emulsions, microemulsions, and lipid-based drug delivery systems for drug solubilization and delivery-Part II: Oral applications. In: Liu R, editor. Water-insoluble drug formulation. Boca Raton: CRC; 2008. p. 227-53.
24. Pouton CW. Lipid formulations for oral administration of drugs: non-emulsifying, self-emulsifying and 'self-mcroemulsifying' drug delivery systems. Eur J Pharm Sci. 2000;11(Suppl2):S-93-S98.
25. Pouton CW. Formulation of poorly water-soluble drugs for oral administration: Physicochemical and physiological issues and the lipid formulation classification system. Eur J Pharm Sci. 2006;29 (3-4):278-87. (Pubitemid 44740131)
26. Shah NH, Carvajal MT, Patel CI, Infeld MH, Malick AW. Self-emulsifying drug delivery systems (SEDDS) with polycolized glycerides for improving in vitro dissolution and oral absorption of lipophilic drugs. Int J Pharm. 1994;106(1):15-23. (Pubitemid 24110060)
27. Nazzal S, Smalyukh II, LavrentovichOD, Khan MA. Preparation and in vitro characterization of a euticetic based semisolid self-enoemulsified drug delivery system (SNEDDS) of utiquinone: Mechanism and progress of emulstion formation. Int J Pharm. 2002;235(1-2):247-65. (Pubitemid 34185455)
28. Rao SVR, Shao J. Self-nanoemulsifying drug delivery systems (SNEDDS) for oral delivery of protein drugs. I. Formulation development. Int J Pharm. 2008;362(1-2):2-9.
29. Zhang P, Liu Y, Feng N, Xu J. Preparation and evaluation of self-microemulsifyig drug delivery system of oridin. Int J Pharm. 2008;355:269-76.
30. Elnaggar YSR, El-Massik MA, Abdallah OY. Self-nanoemulsifying drug delivery systems of tamoxifen citrate: Design and optimization. Int J Pharm. 2009;380(1-2):133-44.
31. Shafiq S, Shakeel F, Talegaonkar S, Ahmad FJ, Khar RK, Ali M. Development and bioavailability assessment of ramipril nanoemulsion formation. Eur J Pharm Biopharm. 2007;66(2):227-43. (Pubitemid 46667230)
32. Kang BK, Lee JS, Chon SK, Jeong Sy, Yuk SH, Khang G, et al. Development of self-microemulsifying drug delivery systems (SMEDDS) for oral bioavailability enhancement of simvastatin in beagle dogs. Int J Pharm. 2004;274(1-2):65-73. (Pubitemid 38457007)
33. Constantinides PP, Scalart J. Formulation and physical characterization of water-in-oil microemulsions containing long- versus medium chain glycerides. Int J Pharm. 1997;158(1):57-68. (Pubitemid 27504474)
34. Li P, Ghosh A, Wagner RF, Holinej J, Krill S, Joshi YM, et al. Effect of combined use of nonionic surfactant on oil-in-Water microemulsions. Int J Pharm. 2005;288(1):27-34. (Pubitemid 39656452)
35. Ekwall P, Mandell L, Fontell K. Ternary systems of potassium soap, alcohol and water. J Colloid Interface Sci. 1969;31(4):508-12.
36. Lo I, Madsen F, Florence AT, Treguier J-P, Seiller M, Puisieux F. The influence of surfactant HLB and the nature of the oil phase on the phase diagrams of nonionic surfactant-oil-water systems. J Colloid Interface Sci. 1977;59(2):319-25.
37. Kaukonen AM, Boyd BJ, Porter CJH, Charman WN. Drug solubilization behavior during in vitro digestion of simple triglyceride lipid solution formulations. Pharm Res. 2003;21(2):245-53. (Pubitemid 38221969)
38. Kawakami K, Yoshikawa T, Moroto Y, Kanaoka E, Takahashi K, Nishihara Y, et al. Microemulsion formation for enhanced absorption of poorly water soluble drugs I. Prescription design. J Control Rel. 2002;81(1-2):65-74. (Pubitemid 34454850)
39. Mohsin K, Long MA, Pouton CW. Design of lipid-based formulations for oral administration of poorly water-soluble drugs: Precipitation of drug after dispersion of formulations in aqueous solution. J Pharm Sci. 2009;98(10):3582-95.
40. Li P, Pudipeddi M, Hynes SR, Royce AE, Serajuddin ATM. Development and characterization of a solid microemulsion preconcentrate system for oral delivery of poorly water soluble drugs. J Pharm Sci. 2009;98(4):1750-63.
41. Ezrahi S, Aserin A, Garti N. Aggregation behavior in one-phase (Winsor IV) microemulsion systems. In: Kumar P, Mittal KL, editors. Handbook of microemulsion science and technology. New York: Informa Inc.; 1999. p. 185-246.
42. Gradzielski M, Hoffmann H. Rheological properties of microemulsions. In: Kumar P, Mittal KL, editors. Handbook of microemulsion science and technology. New York: Informa Inc.; 1999. p. 357-86.
43. Lawrence MJ, Rees GD. Microemulsion-based media as novel drug delivery systems. Adv Drug Del Rev. 2000;45(1):89-121.
44. Salager J, Anton RE, Sabatini DA, Harwell JH, Acosta EJ, Tolosa LI. Enhancing solubilization in microemulsions-State of the art and current trends. J Surfactant Detergent. 2005;8(1):3-21. (Pubitemid 41042102)
45. Sagalowicz L, Leser ME, Watzke HJ, Michel M. Monoglyceride self-assembly structures as delivery vehicles. Trends in Food Sci Technol. 2006;17(5):204-14.
46. Malmsten M. Phase transformations in self-assembly systems for drug delivery applications. J Disp Sci Technol. 2007;28(1):63-72. (Pubitemid 44869307)
47. Scherlund M, Malmsten M, Holmqvist P, Brodin A. Thermosetting microemulsions and mixed micellar solutions as drug delivery systems for periodontal anesthesia. Int J Pharm. 2000;194(1):103-16.
48. Scherlund M, Welin-Berger K, Brodin A, Malmsten M. Local anesthetic block copolymer system undergoing phase transition on dilution with water. Eur J Pharm Sci. 14:53-61.
49. Shah JC, Sadhale Y, Chilukuri DM. Cubic phase gels as drug delivery systems. Adv Drug Del Rev. 2001;47(2-3):229-50. (Pubitemid 32324116)
50. Alam MM, Varade D, Aramaki K. Solubilization of triglycerides in liquid crystals of nonionic surfactant. J Colloid Interface Sci. 2008;325(1):243-9.
51. Carvalho FC, Sarmento VHV, Chiavacci LA, Barbi MS, Gremiao MPD. Development and in vitro evaluation of surfactant systems for controlled release of zidovudine. J Pharm Sci. 2010;99(5):2367-74.
52. Prince LM. Microemulsions versus micelles. J Colloid Interface Sci. 1975;52(1):182-8.
53. Rosano HL. Introduction. In: Rosano HL, Clausse, editors. Microemulsion system. New York: Informa; 1987. p. xv-xix.
54. Shah DO. Micelles, microemulsions and monolayers: Quarter Century Progress at the University of Florida. In: Shas DO, editor. Micelles, microemulsion and monolayers: Science and technology. New York: Informa; 1999. p. 1-52.
55. Cuine JF, Charman WN, Pouton CW, Edwards GA, Porter CJH. Increasing the proportional content of surfactant (Cremophor EL) relative to lipid in self-emulsifying lipid-based formulations of danazol reduces oral bioavailability in beagle dogs. Pharm Res. 2007;24(4):248-757.
56. Larsen A, Holm R, Pedersen ML, Mullertz A. Lipid-based formulation for danazol containing a digestible surfactant, labrafill M2125CS: In vitro bioavailability and dynamic in vitro analysis. Pharm Res. 2008;25(12):2769-77.