Evaluation of hydroperoxides in common pharmaceutical excipients

Journal of Pharmaceutical Sciences

Volumn 96, Issue 1, 2007, Pages 106-116

  Wasylaschuk, Walter R ^a   Harmon, Paul A ^a   Wagner, Gabriella ^a   Harman, Amy B ^a   Templeton, Allen C ^a   Xu, Hui ^a   Reed, Robert A ^a,b  

^a MERCK RESEARCH LABORATORIES   (United States)

^b XenoPort Inc   (United States)

Author keywords

Chemical stability; Excipients; Formulation; Oxidation; Physicochemical properties

Indexed keywords

CELLULOSE; EXCIPIENT; HYDROGEN PEROXIDE; HYDROPEROXIDE; HYDROXYPROPYLCELLULOSE; LACTOSE; MACROGOL 400; MANNITOL; MEDIUM CHAIN ACYLGLYCEROL; POLOXAMER; POLYSORBATE 80; POVIDONE; SUCROSE;

ARTICLE; DEGRADATION KINETICS; DRUG MANUFACTURE; DRUG STABILITY; OXIDATION;

EID: 33846158419     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.20726     Document Type: Article

References (35)

1. Landin M, Martinez-Pacheco R, Gomez-Maoza JL, Suoto C, Concheiro A, Rowe RC. 1993. Effect of batch variation and source of pulp on the properties of microcrystalline cellulose. Int J Pharm 91:133-141.
2. Shah U, Augsburger L. 2001. Evaluation of the functional equivalence of crospovidone NF from different sources. I. Physical characterization. Pharm Dev Tech 6:39-51.
3. Hovoroka SW, Schoneich C. 2001. Oxidative degradation of pharmaceuticals: Theory, mechanisms and inhibition. J Pharm Sci 90:253-268.
4. Johnson DM, Gu LC. 1988. Autoxidation and antioxidants. In: Swarbrick J, Boylan JC, editors. Encyclopedia of pharmaceutical technology, Vol. 1. New York: Wiley. pp 415-449.
5. Sheldon RA, Kochi JK. 1976. Metal-catalyzed oxidations of organic compounds in the liquid phase: A mechanistic approach. In: Eley DD, editor. Advances in catalysis. New York: Academic Press. pp 273-413.
6. Hartauer KJ, Arbuthnot GN, Baertschi SW, Johnson RA, Luke WD, Person NG, Rickard EC, Tingle CA, Tsang PKS, Wiens RE. 2000. Influence of peroxide impurities in povidone and crospovidone on the stability of raloxifene hydrochloride in tablets: Identification and control of an oxidative degradation product. Pharm Dev Tech 5:303-310.
7. Donbrow M, Azaz E, Pillersdorf A. 1978. Autoxidation of polysorbates. J Pharm Sci 67:1676-1681.
8. Chang HW, Bock E. 1980. Pitfalls in the use of commercial nonionic detergents for the solubilization of integral membrane proteins: Sulfydryl oxidizing contaminants and their elimination. Anal Biochem 104:112-117.
9. Knepp VM, Whatley JL, Muchnik A, Calderwood TS. 1996. Identification of antioxidants for prevention of peroxide-mediated oxidation of recombinant human ciliary neurotropic factor and recombinant human nerve factor. J Pharm Sci Technol 50:163-171.
10. Mancuso JR, McClements DJ, Decker EA. 1999. Ability of iron to promote surfactant peroxide decomposition and oxidize α-tocopherol. J Agric Food Chem 47:4146-4149.
11. Ha E, Wang W, Wang J. 2002. Peroxide formation in polysorbate 80 and protein stability. J Pharm Sci 91:2252-2264.
12. McGinity JW, Patel TR, Naqvi AH. 1976. Implications of peroxide formation in lotion and ointment dosage forms containing polyethylene glycols. Drug Dev Comm 2:505-519.
13. Bindra DS, Williams TD, Stella VJ. 1994. Degradation of O6-benzylguanine in aqueous polyethylene glycol 400 (PEG 400) solutions: Concerns with formaldehyde in PEG 400. Pharm Res 11:1060-1064.
14. Huang T, Garceau ME, Gao P. 2003. Liquid chromatographic determination of residual hydrogen peroxide in pharmaceutical excipients using platinum and wired enzyme electrodes. J Pharm Bio Anal 31:1203-1210.
15. Jiang ZY, Hunt JV, Wolff SP. 1992. Ferrous ion oxidation in the presence of xylenol orange for detection of lipid hydroperoxides in low density lipoprotein. Anal Biochem 202:384-389.
16. Gay C, Collins J, Gebicki JM. 2003. Measurement of protein and lipid hydroperoxides in biological systems by the ferric-xylenol orange method. Anal Biochem 315:29-35.
17. DeLong JM, Prange RK, Hodges DM, Forney CF, Bishop MC, Quillam M. 2002. Using a modified ferrous oxidation-xylenol orange (FOX) assay for detection of lipid hydroperoxides in plant tissue. J Agric Food Chem 50:248-254.
18. Jaeger J, Sorensen K, Wolff SP. 1994. Peroxide accumulation in detergents. J Biochem Biophys Methods 29:77-81.
19. Nakamura T, Maeda H. 1991. A simple assay for lipid hydroperoxides based on triphenylphosphine oxidation and high-performance liquid chromatography. Lipids 26:765-768.
20. Rowley AG. 1979. Conversions via oxygenation. In: Cadogan JIG, editor. Organophosphorous reagents in organic synthesis. New York: Academic Press. pp 318-327.
21. Gay C, Collins J, Gebicki JM. 1999. Hydroperoxide assay with the ferric-xylenol orange complex. Anal Biochem 273:149-155.
22. Nourooz-Zadeh J, Tajaddini-Sarmadi J, Wolff SP. 1994. Measurement of plasma hydroperoxide concentrations by the ferrous oxidation-xylenol orange assay in conjunction with triphenylphosphine. Anal Biochem 220:403-409.
23. Harmon PA, Wuefling WP, Harman AB, Wasylaschuk WR, Givand J, Shelukar S, Reed RA. 2004. Role of organic hydroperoxides on process robustness and finished product quality (presented at AAPS).
24. Humberstone AJ, Charman WN. 1997. Lipid-based vehicles for the oral delivery of poorly water soluble drugs. Adv Drug Del Rev 25:103-128.
25. Poton CW. 2000. Lipid formulations for oral administration of drugs: Non-emulsifying, self-emulsifying and 'self-microemulsifying' drug delivery systems. Eur J Pharm Sci 11:S93-S98.
26. Harmon PA, Kosuda K, Nelson E, Mowery M, Reed RA. 2006. A novel peroxy radical based oxidative stressing system for ranking the oxidizability of drug substance. J Pharm Sci (in press).
27. Buhler V. 1999. Kollidon: Polyvinylpyrrolidone for the pharmaceutical industry. BASF 9-12.
28. Kroschwitz JI, Howe-Grant M, editors. 1993. Cellulose ethers. In: Kirk-Othmer encyclopedia of chemical technology, Vol. 5. New York: John Wiley & Sons. pp 541-542.
29. U.S. Patent. 2,512,338 (June 20, 1950), E.D. Klug and H.M. Spurlin (to Hercules Powder Co.).
30. U.S. Patent 3,719,663 (March 6, 1973), E.D. Klug (to Hercules Inc.).
31. Yin H, Porter NA. 2003. Specificity of the FOX assay: Analysis of autoxidation products of cholesteryl arachidonate by the TBARS and FOX assays. Anal Biochem 313:319-326.
32. Johnson DM, Taylor WF. 1984. Degradation of fenprostalene in polyethylene glycol 400 solution. J Pharm Sci 84:1414-1417.
33. Kasraian K, Kuzniar AA, Wilson GG, Wood JA. 1999. Developing an injectable formula containing an oxygen-sensitive drug: A case study of danofloxacin injectable. Pharm Dev Tech 4:475-480.
34. Dahl T, He GX, Samules G. 1998. Effect of hydrogen peroxide on the viscosity of a hydroxyethylcellulose-based gel. Pharm Res 15:1137-1140.
35. Digenis GA, Gold TB, Shah VP. 1994. Cross-linking of gelatin capsules and its relevance to their in vitro- in vivo performance. J Pharm Sci 83:915-921.