APPLICATION OF FATTY ACID FOR PHARMACEUTICALS
DOI:
https://doi.org/10.14456/tbps.2019.1Keywords:
fatty acid, application, pharmaceuticalsAbstract
Fatty acids have been used as components in many products including food, cosmetics and medicines. Nowadays, fatty acids have also been employed in the pharmaceutical field due to their various properties. These properties include antimicrobial activities, anti-prostate growth and protection of the prostate cell structure. Some physicochemical properties of fatty acids can modify the properties of pharmaceutical products or drug molecules by, for instance, increasing the dissolution, permeability and absorption, and stability of the drug molecules or drug delivery system, improving the clinical effectiveness or controlling drug release. Factors affecting the properties of products prepared from fatty acids are fabrication techniques, product components, lipase enzymes and the melting point. Fatty acids are interesting for use in pharmaceuticals owing to their biocompatibility and low toxicity properties.
References
1. White B. Dietary fatty acids. Am Fam Physician. 2009;8:345-50.
2. Pohl CH, Kock JLF, Thibane VS. Antifungal free fatty acids: a review. In: Mendez-Vilaz A, editor. Science against microbial pathogens: communicating current research and technological advances. Badajoz: Formatex Research Center; 2011. p.61-71.
3. Yang D, Pornpattananangkul D, Nakatsuji T, Chan M, Carson D, Huang CM, et al. The antimicrobial activity of liposomal lauric acid against Propionibacterium acnes. Biomaterials. 2009;30:6035–40.
4. Loftsson T, Iliveska B, Asgrimsdottir GM, Ormarsson OT, Stefansson E. Fatty acids from marine lipids: biological activity, formulation and stability. J Drug Deliv Sci Technol. 2016;34:71-5.
5. Babu SVV, Veeresh B, Patil AA, Warke YB. Lauric acid and myristic acid prevent testosterone induced prostatic hyperplasia in rats. Eur J Pharmacol. 2010;626:262–5.
6. Imai T, Nodomi K, Shameem M, Matsumoto H, Satoh T, Otagiri M. Mutual effect of egg albumin and fatty acids on bioavailability of dl-α-tocopherol. Int J Pharm. 1997;155:45–52.
7. Kossena GA, Charman WN, Boyd BJ, Porter CJH. A novel cubic phase of medium chain lipid origin for the delivery of poorly water soluble drugs. J Control Release. 2004;99:217–29.
8. Hochman J, Artursson P. Mechanisms of absorption enhancement and tight junction regulation. J Control Release. 1994;29:253–67.
9. Raoof AA, Chiu P, Ramtoola Z, Cumming IK, Teng C, Weinbach SP, et al. Oral bioavailability and multiple dose tolerability of an antisense oligonucleotide tablet formulated with sodium caprate. J Pharm Sci. 2004;93:1431–9.
10. Lane ME. Skin penetration enhancers. Int J Pharm. 2013;447:12-21.
11. Wang MY, Yang YY, Heng PWS. Skin permeation of physostigmine from fatty acids-based formulations: evaluating the choice of solvent. Int J Pharm. 2005;290:25–36.
12. Jenning V, Gysler A, Schäfer-Korting M, Gohla SH. Vitamin A loaded solid lipid nanoparticles for topical use: occlusive and drug targeting to the upper skin. Eur J Pharm Biopharm. 2000;49:211-8.
13. Mohl S, Winter G. Continuous release of rh-interferon
-2a from triglyceride implants: storage stability of the dosage forms. Pharm Dev Technol. 2006;11:103–10.
14. Zhang Q, Yie G, Li Y, Yang Q, Nagai T. Studies on the cyclosporin A loaded stearic acid nanoparticles. Int J Pharm. 2000;200:153–9.
15. Silva CO, Rijo P, Molpeceres J, Figueiredo IV, Ascensão L, Fernandes AS, et al. Polymeric nanoparticles modified with fatty acids encapsulating betamethasone for anti-inflammatory treatment. Int J Pharm. 2015;493:271–84.
16. Grassi M, Voinovich D, Franceschinis E, Perissutti B, Grcic JF. Theoretical and experimental study on theophylline release from stearic acid cylindrical delivery systems. J Control Release. 2003;92:275–89.
17. Monteyne T, Adriaensens P, Brouckaert D, Remon JP, Vervaet C, Beer TD. Stearic acid and high molecular weight PEO as matrix for the highly water soluble metoprolol tartrate incontinuous twin-screw melt granulation. Int J Pharm. 2016;512:158–67.
18. Quintavalle U, Voinovich D, Perissutti B, Serdoz F, Grassi M. Theoretical and experimental characterization of stearic acid -based sustained release devices obtained by hot melt co-extrusion. J Drug Deliv Sci Technol. 2007;17:415-20.
19. Wang PY. The reliability of a compressed mixture of insulin and palmitic acid to sustain a reduction in hyperglycaemia in rodents. Trans Am Soc Artif Intern Organs. 1987;33:319–22.
20. Yoo HS, Choi H-K, Park TG. Protein–fatty acid complex for enhanced loading and stability within biodegradable nanoparticles. J Pharm Sci. 2001;90:194-201.
21. Li M, Zahi MR, Yuan Q, Tian F, Liang H. Preparation and stability of astaxanthin solid lipid nanoparticles based on stearic acid. Eur J Lipid Sci Technol. 2016;118:592-602.
22. Arouri A, Lauritsen KE, Nielsen HL, Mouritsen OG. Effect of fatty acids on the permeability barrier of model and biological membranes. Chem Phys Lipids. 2016;200:139–46.
23. Han HK, Amidon GL. Targeted prodrug design to optimize drug delivery. AAPS PharmSci. 2000;2(1):a6.
24. Zaro JL. Lipid-based drug delivery carriers for prodrugs to enhance drug delivery. AAPS J. 2015;17:83–92.
25. Kandula MM, KumarKB S, Palanichamy S, Rampal A. Discovery and preclinical development of a novel prodrug conjugate of mesalamine with eicosapentaenoic acid and caprylic acid for the treatment of inflammatory bowel diseases. Int Immunopharmacol. 2016;40:443–51.
26. Huan M, Cui H, Teng Z, Zhang B, Wang J, Liu X, et al. In vivo anti-tumor activity of a new doxorubicin conjugate via -Linolenic Acid. Biosci Biotechnol Biochem. 2012;76:1577-9.
27. Yuan L, Wang J, Shen WC. Reversible lipidization prolongs the pharmacological effect, plasma duration, and liver retention of octreotide. Pharm Res. 2005:22:220–7
.
28. Killen BU, Corrigan OI. Factors influencing drug release from stearic acid based compacts. Int J Pharm. 2001;228:189–98.
29. Killen BU, Corrigan OI. Effect of soluble filler on drug release from stearic acid based compacts. Int J Pharm. 2006;316:47-51.
30. Vervaeck A, Monteyne T, Siepmann F, Boone MN, Hoorebeke LV, Beer TD, et al. Fatty acids for controlled release applications: a comparison between prilling and solid lipid extrusion as manufacturing techniques. Eur J Pharm Biopharm. 2015;97:173–84.
31. Xie S, Zhu L, Dong Z, Wang X, Wang Y, Li X, et al. Preparation, characterization and pharmacokinetics of enrofloxacin-loaded solid lipid nanoparticles: Influences of fatty acids. Colloids Surf B Biointerfaces. 2011;83:382–7.
32. Reynisdottir S, Dauzats M, Thörne A, Langin D. Comparison of hormone-sensitive lipase activity in visceral and subcutaneous human adipose tissue. J Clin Endocrinol Metab. 1997;82:4162–6.
33. Ruge T, Sukonina V, Myrnäs T, Lundgren M, Eriksson JW, Olivecrona G. Lipoprotein lipase activity/mass ratio is higher in omental than in subcutaneous adipose tissue. Eur J Clin Invest. 2006;6:16–21.
34. Coppack SW, Jensen MD, Miles JM. In vivo regulation of lipolysis in humans. J Lipid Res. 1994;5:177–93.
35. Schwab M, McGoverin CM, Gordon KC, Winter G, Rades T, Myschik J, et al. Studies on the lipase-induced degradation of lipid-based drug delivery systems. Part II – Investigations on the mechanisms leading to collapse of the lipid structure. Eur J Pharm Biopharm. 2013;84:456–63.
36. Kingsbury KJ, Paul S, Crossley A, Morgan DM. The fatty acid composition of human depot fat. Biochem J. 1961;78:541-50.
37. Elmadfa I, Kornsteiner M. Fats and fatty acid requirements for adults. Ann Nutr Metab. 2009;55:56–75.
38. Phadke DS, Keeney MP, Norris DA. Evaluation of batch-to-batch and manufacturer-to-manufacturer variability in the physical properties of talc and stearic acid. Drug Dev Ind Pharm. 1994;20:859–71.
39. Burdock GA, Carabin IG. Safety assessment of myristic acid as a food ingredient. Food Chem Toxicol. 2007;45:517–29.
40. Guse C, Koennings S, Maschke A, Hacker M, Becker C, Schreiner S, et al. Biocompatibility and erosion behavior of implants made of triglycerides and blends with cholesterol and phospholipids. Int J Pharm. 2006;314:153-60.
2. Pohl CH, Kock JLF, Thibane VS. Antifungal free fatty acids: a review. In: Mendez-Vilaz A, editor. Science against microbial pathogens: communicating current research and technological advances. Badajoz: Formatex Research Center; 2011. p.61-71.
3. Yang D, Pornpattananangkul D, Nakatsuji T, Chan M, Carson D, Huang CM, et al. The antimicrobial activity of liposomal lauric acid against Propionibacterium acnes. Biomaterials. 2009;30:6035–40.
4. Loftsson T, Iliveska B, Asgrimsdottir GM, Ormarsson OT, Stefansson E. Fatty acids from marine lipids: biological activity, formulation and stability. J Drug Deliv Sci Technol. 2016;34:71-5.
5. Babu SVV, Veeresh B, Patil AA, Warke YB. Lauric acid and myristic acid prevent testosterone induced prostatic hyperplasia in rats. Eur J Pharmacol. 2010;626:262–5.
6. Imai T, Nodomi K, Shameem M, Matsumoto H, Satoh T, Otagiri M. Mutual effect of egg albumin and fatty acids on bioavailability of dl-α-tocopherol. Int J Pharm. 1997;155:45–52.
7. Kossena GA, Charman WN, Boyd BJ, Porter CJH. A novel cubic phase of medium chain lipid origin for the delivery of poorly water soluble drugs. J Control Release. 2004;99:217–29.
8. Hochman J, Artursson P. Mechanisms of absorption enhancement and tight junction regulation. J Control Release. 1994;29:253–67.
9. Raoof AA, Chiu P, Ramtoola Z, Cumming IK, Teng C, Weinbach SP, et al. Oral bioavailability and multiple dose tolerability of an antisense oligonucleotide tablet formulated with sodium caprate. J Pharm Sci. 2004;93:1431–9.
10. Lane ME. Skin penetration enhancers. Int J Pharm. 2013;447:12-21.
11. Wang MY, Yang YY, Heng PWS. Skin permeation of physostigmine from fatty acids-based formulations: evaluating the choice of solvent. Int J Pharm. 2005;290:25–36.
12. Jenning V, Gysler A, Schäfer-Korting M, Gohla SH. Vitamin A loaded solid lipid nanoparticles for topical use: occlusive and drug targeting to the upper skin. Eur J Pharm Biopharm. 2000;49:211-8.
13. Mohl S, Winter G. Continuous release of rh-interferon
-2a from triglyceride implants: storage stability of the dosage forms. Pharm Dev Technol. 2006;11:103–10.
14. Zhang Q, Yie G, Li Y, Yang Q, Nagai T. Studies on the cyclosporin A loaded stearic acid nanoparticles. Int J Pharm. 2000;200:153–9.
15. Silva CO, Rijo P, Molpeceres J, Figueiredo IV, Ascensão L, Fernandes AS, et al. Polymeric nanoparticles modified with fatty acids encapsulating betamethasone for anti-inflammatory treatment. Int J Pharm. 2015;493:271–84.
16. Grassi M, Voinovich D, Franceschinis E, Perissutti B, Grcic JF. Theoretical and experimental study on theophylline release from stearic acid cylindrical delivery systems. J Control Release. 2003;92:275–89.
17. Monteyne T, Adriaensens P, Brouckaert D, Remon JP, Vervaet C, Beer TD. Stearic acid and high molecular weight PEO as matrix for the highly water soluble metoprolol tartrate incontinuous twin-screw melt granulation. Int J Pharm. 2016;512:158–67.
18. Quintavalle U, Voinovich D, Perissutti B, Serdoz F, Grassi M. Theoretical and experimental characterization of stearic acid -based sustained release devices obtained by hot melt co-extrusion. J Drug Deliv Sci Technol. 2007;17:415-20.
19. Wang PY. The reliability of a compressed mixture of insulin and palmitic acid to sustain a reduction in hyperglycaemia in rodents. Trans Am Soc Artif Intern Organs. 1987;33:319–22.
20. Yoo HS, Choi H-K, Park TG. Protein–fatty acid complex for enhanced loading and stability within biodegradable nanoparticles. J Pharm Sci. 2001;90:194-201.
21. Li M, Zahi MR, Yuan Q, Tian F, Liang H. Preparation and stability of astaxanthin solid lipid nanoparticles based on stearic acid. Eur J Lipid Sci Technol. 2016;118:592-602.
22. Arouri A, Lauritsen KE, Nielsen HL, Mouritsen OG. Effect of fatty acids on the permeability barrier of model and biological membranes. Chem Phys Lipids. 2016;200:139–46.
23. Han HK, Amidon GL. Targeted prodrug design to optimize drug delivery. AAPS PharmSci. 2000;2(1):a6.
24. Zaro JL. Lipid-based drug delivery carriers for prodrugs to enhance drug delivery. AAPS J. 2015;17:83–92.
25. Kandula MM, KumarKB S, Palanichamy S, Rampal A. Discovery and preclinical development of a novel prodrug conjugate of mesalamine with eicosapentaenoic acid and caprylic acid for the treatment of inflammatory bowel diseases. Int Immunopharmacol. 2016;40:443–51.
26. Huan M, Cui H, Teng Z, Zhang B, Wang J, Liu X, et al. In vivo anti-tumor activity of a new doxorubicin conjugate via -Linolenic Acid. Biosci Biotechnol Biochem. 2012;76:1577-9.
27. Yuan L, Wang J, Shen WC. Reversible lipidization prolongs the pharmacological effect, plasma duration, and liver retention of octreotide. Pharm Res. 2005:22:220–7
.
28. Killen BU, Corrigan OI. Factors influencing drug release from stearic acid based compacts. Int J Pharm. 2001;228:189–98.
29. Killen BU, Corrigan OI. Effect of soluble filler on drug release from stearic acid based compacts. Int J Pharm. 2006;316:47-51.
30. Vervaeck A, Monteyne T, Siepmann F, Boone MN, Hoorebeke LV, Beer TD, et al. Fatty acids for controlled release applications: a comparison between prilling and solid lipid extrusion as manufacturing techniques. Eur J Pharm Biopharm. 2015;97:173–84.
31. Xie S, Zhu L, Dong Z, Wang X, Wang Y, Li X, et al. Preparation, characterization and pharmacokinetics of enrofloxacin-loaded solid lipid nanoparticles: Influences of fatty acids. Colloids Surf B Biointerfaces. 2011;83:382–7.
32. Reynisdottir S, Dauzats M, Thörne A, Langin D. Comparison of hormone-sensitive lipase activity in visceral and subcutaneous human adipose tissue. J Clin Endocrinol Metab. 1997;82:4162–6.
33. Ruge T, Sukonina V, Myrnäs T, Lundgren M, Eriksson JW, Olivecrona G. Lipoprotein lipase activity/mass ratio is higher in omental than in subcutaneous adipose tissue. Eur J Clin Invest. 2006;6:16–21.
34. Coppack SW, Jensen MD, Miles JM. In vivo regulation of lipolysis in humans. J Lipid Res. 1994;5:177–93.
35. Schwab M, McGoverin CM, Gordon KC, Winter G, Rades T, Myschik J, et al. Studies on the lipase-induced degradation of lipid-based drug delivery systems. Part II – Investigations on the mechanisms leading to collapse of the lipid structure. Eur J Pharm Biopharm. 2013;84:456–63.
36. Kingsbury KJ, Paul S, Crossley A, Morgan DM. The fatty acid composition of human depot fat. Biochem J. 1961;78:541-50.
37. Elmadfa I, Kornsteiner M. Fats and fatty acid requirements for adults. Ann Nutr Metab. 2009;55:56–75.
38. Phadke DS, Keeney MP, Norris DA. Evaluation of batch-to-batch and manufacturer-to-manufacturer variability in the physical properties of talc and stearic acid. Drug Dev Ind Pharm. 1994;20:859–71.
39. Burdock GA, Carabin IG. Safety assessment of myristic acid as a food ingredient. Food Chem Toxicol. 2007;45:517–29.
40. Guse C, Koennings S, Maschke A, Hacker M, Becker C, Schreiner S, et al. Biocompatibility and erosion behavior of implants made of triglycerides and blends with cholesterol and phospholipids. Int J Pharm. 2006;314:153-60.
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2018-09-19
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