Association of nicotinamide with parabens: Effect on solubility, partition and transdermal permeation

European Journal of Pharmaceutics and Biopharmaceutics

Volumn 69, Issue 2, 2008, Pages 613-621

  Nicoli, Sara ^a   Zani, Franca ^a   Bilzi, Stefania ^a   Bettini, Ruggero ^a   Santi, Patrizia ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

Nicotinamide; Parabens; Partition coefficient; Permeability coefficient; Topical formulations

Indexed keywords

BUTYL PARABEN; ETHYL PARABEN; METHYL PARABEN; NICOTINAMIDE; PROPYL PARABEN;

ANIMAL EXPERIMENT; AQUEOUS SOLUTION; ARTICLE; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STABILITY; EMULSION; IN VITRO STUDY; NONHUMAN; STRATUM CORNEUM;

ANIMALS; CALORIMETRY, DIFFERENTIAL SCANNING; CHEMISTRY, PHYSICAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COSMETICS; DERMATOLOGIC AGENTS; DIFFUSION CHAMBERS, CULTURE; EAR, EXTERNAL; EXCIPIENTS; MYRISTATES; NIACINAMIDE; PARABENS; PRESERVATIVES, PHARMACEUTICAL; RABBITS; SKIN ABSORPTION; SOLUBILITY; WATER;

EID: 43249124968     PISSN: 09396411     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejpb.2007.12.008     Document Type: Article

References (34)

1. Akomeah F., Nazir T., Martin G.P., and Brown M.B. Effect of heat on the percutaneous absorption and skin retention of three model penetrants. Eur. J. Pharm. Sci. 21 2-3 (2004) 337-345
2. Nanayakkara G.R., Bartlett A., Forbes B., Marriott C., Whitfield P.J., and Brown M.B. The effect of unsaturated fatty acids in benzyl alcohol on the percutaneous permeation of three model penetrants. Int. J. Pharm. 301 1-2 (2005) 129-139
3. El Hussein S., Muret P., Berard M., Makki S., and Humbert P. Assessment of principal parabens used in cosmetics after their passage through human epidermis-dermis layers (ex-vivo study). Exp. Dermatol. 16 (2007) 830-836
4. Soni M.G., Carabin I.G., and Burdock G.A. Safety assessment of esters of p-hydroxybenzoic acid (parabens). Food Chem. Toxicol. 43 7 (2005) 985-1015
5. Golden R., Gandy J., and Vollmer G. A review of the endocrine activity of parabens and implications for potential risks to human health. Crit. Rev. Toxicol. 35 5 (2005) 435-458
6. Harvey P.W., and Everett D.J. Regulation of endocrine-disrupting chemicals: critical overview and deficiencies in toxicology and risk assessment for human health. Best Pract. Res. Clin. Endocrinol. Metab. 20 1 (2006) 145-165
7. Harvey P.W., and Everett D.J. Significance of the detection of esters of p-hydroxybenzoic acid (parabens) in human breast tumours. J. Appl. Toxicol. 24 1 (2004) 1-4
8. Available from: http://www.cfsan.fda.gov/~dms/cos-para.html, consulted on 05-07-2007.
9. Chen J., Ahn K.C., Gee N.A., Gee S.J., Hammock B.D., and Lasley B.L. Antiandrogenic properties of parabens and other phenolic containing small molecules in personal care products. Toxicol. Appl. Pharmacol. 221 3 (2007) 278-284
10. Mirick D.K., Davis S., and Thomas D.B. Antiperspirant use and the risk of breast cancer. J. Natl. Cancer. Inst. 94 20 (2002) 1578-1580
11. FDA, Code of Federal Regulations (CFR), vol. 5, 4-1-06 Edition, p. 21CFR347.
12. Chamlin S.L., Kao J., Frieden I.J., Sheu M.Y., Fowler A.J., Fluhr J.W., Williams M.L., and Elias P.M. Ceramide-dominant barrier repair lipids alleviate childhood atopic dermatitis: changes in barrier function provide a sensitive indicator of disease activity. J. Am. Acad. Dermatol. 47 2 (2002) 198-208
13. Mao-Qiang M., Feingold K.R., Thornfeldt C.R., and Elias P.M. Optimization of physiological lipid mixtures for barrier repair. J. Invest. Dermatol. 106 5 (1996) 1096-1101
14. Hadgraft J., Peck J., Williams D.G., Pugh W.J., and Allan G. Mechanisms of action of skin penetration enhancers/retarders: azone and analogues. Int. J. Pharm. 141 1-2 (1996) 17-25
15. Williams A.C., Shatri S.R., and Barry B.W. Transdermal permeation modulation by cyclodextrins: a mechanistic study. Pharm. Dev. Technol. 3 3 (1998) 283-296
16. Tanaka M., Iwata Y., Kouzuki Y., Taniguchi K., Matsuda H., Arima H., and Tsuchiya S. Effect of 2-hydroxypropyl-beta-cyclodextrin on percutaneous absorption of methyl paraben. J. Pharm. Pharmacol. 47 11 (1995) 897-900
17. Matsuda H., Ito K., Sato Y., Yoshizawa D., Tanaka M., Taki A., Sumiyoshi H., Utsuki T., Hirayama F., and Uekama K. Inclusion complexation of p-hydroxybenzoic acid esters with 2-hydroxypropyl-beta-cyclodextrins. On changes in solubility and antimicrobial activity. Chem. Pharm. Bull. (Tokyo) 41 8 (1993) 1448-1452
18. Hasegawa T., Kim S., Tsuchida M., Issiki Y., Kondo S., and Sugibayashi K. Decrease in skin permeation and antibacterial effect of parabens by a polymeric additive, poly(2-methacryloyloxyethyl phosphorylcholine-co-butylmethacrylate). Chem. Pharm. Bull. (Tokyo) 53 3 (2005) 271-276
19. S. Nicoli, S. Montanari, V. D'Acchioli, P. Santi, The presence of niacinamide influences the in vitro skin accumulation of ethyl paraben, AAPS Annual Meeting Baltimore November 7-11, 2004.
20. Artusi M., Nicoli S., Colombo P., Bettini R., Sacchi A., and Santi P. Effect of chemical enhancers and iontophoresis on thiocolchicoside permeation across rabbit and human skin in vitro. J. Pharm. Sci. 93 10 (2004) 2431-2438
21. Nicoli S., Cappellazzi M., Colombo P., and Santi P. Characterization of the permselective properties of rabbit skin during transdermal iontophoresis. J. Pharm. Sci. 92 7 (2003) 1482-1488
22. Nicoli S., Rimondi S., Colombo P., and Santi P. Physical and chemical enhancement of transdermal delivery of triptorelin. Pharm. Res. 18 11 (2001) 1634-1637
23. Higuchi T., and Connors K. Phase-solubility techniques. Adv. Anal. Chem. Inst. 5 (1965) 117-212
24. European-Chemical-Bureau, Dir 92/69/EEC.
25. Moser K., Kriwet K., Froehlich C., Kalia Y.N., and Guy R.H. Supersaturation: enhancement of skin penetration and permeation of a lipophilic drug. Pharm. Res. 18 7 (2001) 1006-1011
26. Sanghvi R., Evans D., and Yalkowsky S.H. Stacking complexation by nicotinamide: a useful way of enhancing drug solubility. Int. J. Pharm. 336 1 (2007) 35-41
27. Suzuki H., and Sunada H. Mechanistic studies on hydrotropic solubilization of nifedipine in nicotinamide solution. Chem. Pharm. Bull. (Tokyo) 46 1 (1998) 125-130
28. Giordano F., Bettini R., Donini C., Gazzaniga A., Caira M.R., Zhang G.G., and Grant D.J. Physical properties of parabens and their mixtures: solubility in water, thermal behavior, and crystal structures. J. Pharm. Sci. 88 11 (1999) 1210-1216
29. Coffman R.E., and Kildsig D.O. Hydrotropic solubilization-mechanistic studies. Pharm. Res. 13 10 (1996) 1460-1463
30. Hussain M.A., DiLuccio R.C., and Maurin M.B. Complexation of moricizine with nicotinamide and evaluation of the complexation constants by various methods. J. Pharm. Sci. 82 1 (1993) 77-79
31. S. Nicoli, S. Bilzi, P. Santi, M. Caira, J. Li, R. Bettini, Ethyl-paraben and nicotinamide mixtures: apparent solubility, thermal behaviour and X-ray structure of the 1:1 co-crystal, J. Pharm. Sci., in press.
32. Akomeah F.K., Martin G.P., and Brown M.B. Variability in human skin permeability in vitro: comparing penetrants with different physicochemical properties. J. Pharm. Sci. 96 4 (2007) 824-834
33. Surber C., Wilhelm K.P., Hori M., Maibach H.I., and Guy R.H. Optimization of topical therapy: partitioning of drugs into stratum corneum. Pharm. Res. 7 12 (1990) 1320-1324
34. Haag T.E., and Loncrini D.F. In: Kabara J.J. (Ed). Cosmetic and Drug Preservation. Principles and Practice (1984), Marcel Dekker Inc., New York, Basel 63-77