Solvent effects on the AIBN forced degradation of cumene: Implications for forced degradation practices

Journal of Pharmaceutical Sciences

Volumn 98, Issue 3, 2009, Pages 959-969

  Nelson, Eric D ^a   Thompson, Gina M ^b   Yao, Ye ^a   Flanagan, Holly M ^b   Harmon, Paul A ^b  

^a TransForm Pharmaceuticals Inc   (United States)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Chemical stability; Chromatography; High performance pressure liquid chromatography (HPLC); Preformulation; Stability

Indexed keywords

2 PHENYL 2 PROPANOL; 2, 2' AZOBISISOBUTYRONITRILE; ACETOPHENONE; BUTYRONITRILE; CUMENE; CUMENE HYDROPEROXIDE; PROPANOL; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; DRUG DEGRADATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; OXIDATIVE STRESS;

EID: 62849098503     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21489     Document Type: Article

References (33)

1. FDA. 2003. "Guidance for Industry Q1A(R2) Stability Testing of New Drug Substances and Products," Federal Register 68(225) (November 21) 65717.
2. Alsante KM, Martin L, Baertschi SW. 2003. A Stress Testing Benchmarking Study. Pharm Tech 27:60-72.
3. Reynolds DM, Facchine KL, Mullaney JF, Alsante KM, Hatajik TD, Motto MG. 2002. Available guidance and best practices for conducting forced degradation studies. Pharm Tech 26:48-54.
4. Nelson ED, Harmon PA, Szymanik RC, Teresk MG, Li L, Seburg RA, Reed RA. 2006. Evaluation of solution oxygenation requirements for azonitrile-based oxidative forced degradation studies of pharmaceutical compounds. J Pharm Sci 95:1527-1539.
5. Harmon PA, Kosuda KM, Nelson ED, Mowery MA, Reed RA. 2006. A novel peroxy radical based oxidative stressing system for predicting oxidative instability of active pharmaceutical ingredients. J Pharm Sci 95:2014-2028.
6. Boccardi G. 1994. Autoxidation of Drugs : Prediction of Degradation Impurities from Results of Reaction with Radical Chain Initiators. Il Farmaco 49:431-435.
7. Russell GA. 1957. Deuterium-isotope effects in the autoxidation of aralkyl hydrocarbons. Mechanism of the interaction of peroxy radicals. J Am Chem Soc 79:3871-3877.
8. Ingold KU. 1969. Peroxy Radicals. Acc Chem Res 2:1-9.
9. del Barrio MA, Hu J, Zhou P, Cauchon N. 2006. Simultaneous determination of formic acid and formaldehyde in pharmaceutical excipients using headspace GC/MS. J Pharm Biomed Anal 41:738-743.
10. Courtneidge JL, Bush M. 1992. Initiated, tert-butyl hydroperoxide-loaded, low-temperature autoxidation of alkenes: A chemoselective synthesis of allylic hydroperoxides, allowing analysis of the regioselectivity of hydrogen atom abstractions from some unsymmetrically substituted substrates. J Chem Soc Perkin Trans I 12:1531-1538.
11. Dixon KW. 1999. "Decomposition rates of organic free radical initiators". In: Brandrup J, Immergut EH, Grulke EA, editors. Polymer handbook, 4th edition. New York: Wiley. p. II/12.
12. McMillen DF, Golden DM. 1982. Hydrocarbon bond dissociation energies. Ann Rev Phys Chem 33:493.
13. Cadman P, Trotman-Dickenson AF, White AJ. 1971. Kinetics and pressure-dependence of the t-butoxyl radical decomposition. J Chem Soc 14:2296-2298.
14. Rauk R, Boyd RJ, Boyd SL, Henry DJ, Radom L. 2003. Alkoxy radicals in the gaseous phase: β-scission reactions and formation by radical addition to carbonyl compounds. Can J Chem 81:431-442.
15. Tsentalovich YP, Kulik LV, Gritsan NP, Yurkovskaya AV. 1998. Solvent effect on the rate of b-scission of the tert-butoxyl radical. J Phys Chem A 102:7975-7980.
16. Ilan Y, Rabani J, Henglein A. 1976. Pulse radiolytic investigations of peroxy radicals produced from 2-propanol and methanol. J Phys Chem 80:1558-1562.
17. Marklund S. 1971. The simultaneous determination of bis (hydroxymethyl)-peroxide (BHMP), hydroxymethylhydroperoxide (HMP), and H2O2 with TITANIUM (IV). Equilibria between the peroxides and the stabilities of HMP and BHMP at physiological conditions. Acta Chem Scand 25:3517.
18. Russell GA. 1955. The competetive oxidation of cumene and tetralin. J Am Chem Soc 77:4583-4590.
19. Bolland JL, Cooper HR. 1954. The Photo-sensitized oxidation of ethanol. Proc Royal Soc 225A:405.
20. Gray P, Herod AA, Jones A. 1971. Kinetic data for hydrogen and deuterium atom abstraction by methyl and trifluoromethyl radicals in the gaseous phase. Chem Rev 71:247-294.
21. Hendry DG, Mill T, Piszkiewicz L, Howard JA, Eigenmann HK. 1974. A critical review of H-atom transfer in the liquid phase: Chlorine atom, alkyl, trichloromethyl, alkoxy, and alkylperoxy radicals. J Phys Chem Ref. Data 3:937-978.
22. Karki SB, Treemaneekarn V, Kaufman MF. 2000. Oxidation of HMG-CoA reductase inhibitors by tert-botoxyl and 1,1-diphenyl-2-picrylhydrazyl radicals: Model reactions for predicting oxidatively sensitive compounds during preformulation. J Pharm Sci 89:1518-1524.
23. Kúti Z, Gál D. 1992. On the mechanism of methanol oxidation sensitized by anthraquinone. Ber Bunsenges Phys Chem 96:1843-1847.
24. Yousry MA, Naguib CS, Cohen SG, Young MA. 1987. Photoreduction of benzophenone by acetonitrile: Correlation of rates of hydrogen abstraction from RH with the ionization potentials of the radicals R. J Phys Chem 91:3033-3036.
25. Donahue NM. 2003. Reaction barriers: Origin and evolution. Chem Rev 103:4593-4604.
26. Donahue NM. 2001. Revisiting the hammond postulate: The role of reactant and product ionic states in regulating barrier heights, locations, and transition state frequencies. J Phys Chem A 105:1489-1497.
27. Donahue NM, Clarke JS, Anderson JG. 1998. Predicting radical-molecule barrier heights: The role of the ionic surface. J Phys Chem A 102:3923-3933.
28. Lias SG, Liebman JF. 2005. Ion energetics data. In: Linstrom PJ, Mallard WG, editors. NIST chemistry WebBook, NIST standard reference database number 69. Gaithersburg MD, 2089: National Institute of Standards and Technology. http://webbook. nist.gov.
29. Paul V, Roberts BP. 1987. Polarity reversal catalysis of hydrogen atom abstraction reactions. J Chem Soc Chem Commun 17:1322-1324.
30. Wang Q. 1987. Analysis for trace impurities in methanol. Shiyou Huangong 16:654-657.
31. Deshmukh BK, Coetzee JF. 1984. Characterization of reactive impurities in methanol, ethanol, and 2-propanol by monitoring the activities of added ionic probes with ion selective electrodes. Anal Chem 56:2373-2378.
32. Watkins MA, Harmon PA, Pitzenberger SM, Van Nostrand V, Bass LC, Templeton AC. Revision to the AIBN stress testing method: Identification and elimination of alkoxyradical-mediated drug degradation artifacts (in preparation).
33. Baertschi SW, Alsante KM. 2005. Stress testing: The chemistry of drug degradation. In: Baertschi SW, editor. Pharmaceutical stress testing, drugs and the pharmaceutical sciences, Vol. 153. Boca Raton: Taylor and Francis. Chapter 3.