Antioxidant-accelerated oxidative degradation: A case study of transition metal ion catalyzed oxidation in formulation

Pharmaceutical Development and Technology

Volumn 9, Issue 2, 2004, Pages 171-179

  Hong, Jinyang ^a,b   Lee, Eva ^a   Carter, Joi C ^a   Masse, Jeff A ^a   Oksanen, Darlene A ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

^b PFIZER INC   (United States)

Author keywords

Hydroxyamine; Antioxidant; Metal ion catalyzed; Oxidation

Indexed keywords

ANTIOXIDANT; ASCORBIC ACID; GLYCEROL; ION EXCHANGE RESIN; PHOTOSENSITIZING AGENT; REACTIVE OXYGEN METABOLITE; STAINLESS STEEL; TRANSITION ELEMENT; TRAXOPRODIL;

ARTICLE; ATOMIC EMISSION SPECTROMETRY; CATALYSIS; DRUG FORMULATION; DRUG OXIDATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGHT EXPOSURE; PHOTOCATALYSIS; PRIORITY JOURNAL;

ANTIOXIDANTS; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DRUG STABILITY; ION EXCHANGE RESINS; KINETICS; METALS; NEUROPROTECTIVE AGENTS; OXIDATION-REDUCTION; OXYGEN; PIPERIDINES; POLYSTYRENES; POLYVINYLS; SOLVENTS; STAINLESS STEEL;

EID: 2942718766     PISSN: 10837450     EISSN: None     Source Type: Journal    
DOI: 10.1081/PDT-120030247     Document Type: Article

References (21)

1. Akers, M.J. Antioxidants in pharmaceutical products. J. Parenter. Sci. Technol. 1982, 36 (5), 222-228.
2. Waterman, K.C.; Adami, R.C.; Alsante, K.M.; Hong, J.; Landis, M.S.; Lombardo, F.; Roberts, C.J. Stabilization of pharmaceuticals to oxidative degradation. Pharm. Dev. Technol. 2002, 7 (1), 1-32.
3. Hovorka, S.W.; Schöncich, C. Oxidative degradation of pharmaceuticals: theory, mechanisms and inhibition. J. Pharm. Sci. 2001, 90 (3), 253-269.
4. Butler, T.W.; Blake, J.F.; Bordner, J.; Butler, P.; Chenard, B.L.; Collins, M.A.; DeCosta, D.; Ducat, M.J.; Eisenhard, M.E.; Menniti, F.S.; Pagnozzi, M.J.; Sands, S.B.; Segelstein, B.E.; Volberg, W.; White, W.F.; Zhao, D. (3R,4S)-3-[4-Flurophenyl)-4-hydroxypiperidin-1-yl] chroman-4,7-diol: a conformationally restricted analogue of the NR2B subtype-selective NMDA antagonist (1S,2S)-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1- propanol. J. Med. Chem. 1998, 41, 1172-1184.
5. Wood, P.L.; Hawkinson, J.E. N-methyl-D-aspartate antagonists for stroke and head trauma. Expert Opin. Investig. Drugs 1997, 6 (4), 389-397.
6. Menniti, F.S.; Pagnozzi, M.J.; Butler, P.; Chenard, B.L.; Jaw-Tsai, S.S.; White, W.F. CP-101,606, an NR2B subunit selective NMDA receptor antagonist, inhibits NMDA and injury induced c-fos expression and cortical spreading depression in rodents. Neuropharmacology 2000, 39, 1147-1155.
7. Schowen, K.B.J. Solvent hydrogen isotope effects. In Transition States of Biochemistry Processes; Gandour, R.D., Schowen, R.L., Eds.; Plenum Press: New York, 1978.
8. Gorman, A.A.; Rodgers, M.A.J. The Handbook of Organic Photochemistry; Scaiano, J.C., Ed.; CRC Press: BocaRaton, FL, 1989; Vol. 2, 229-247.
9. Kearns, D.R. Solvent and solvent isotope effects on the lifetime of singlet oxygen. In Singlet Oxygen, Organic Chemistry a Series of Monographs - Vol. 40; Wasserman, H.H., Murray, R.W., Eds.; Academic Press: New York, 1979; 115-137.
10. Gottschalk, P.; Packzkowski, J.; Neckers, D.C. Factors influencing the quantum yield for Rose Bengal formation of singlet oxygen. J. Photochem. 1986, 35, 277-281.
11. Gorman, A.A. The bimolecular reactivity of singlet molecular oxygen. In Advances in Photochemistry; Volman, D., Hammond, G., Neckers, D., Eds.; John Wiley & Sons, 1992; 217-274.
12. Ci, X.; Kellet, M.A.; Whitten, D.G. Oxidative photofragmentation of α, β-amino alcohols via single electron transfer: cooperative reactivity of donor and acceptor ion radicals in photogenerated contact radical ion pairs. J. Am. Chem. Soc. 1991, 113, 3893-3904.
13. Haugen, C.M.; Bergmark, W.R.; Whitten, D.G. Singlet oxygen mediated fragmentation of amino alcohols, 1,2-diamines, and amino ketones. J. Am. Chem. Soc. 1992, 114, 10293-10297.
14. Burton, R.D.; Bartberger, M.D.; Zhang, Y.; Eyler, J.R.; Schanze, K.S. Carbon-carbon bond fragmentation in aminoalcohol radical cations. Kinetic, thermodynamic correlations and mechanism. J. Am. Chem. Soc. 1996, 118, 5655-5664.
15. Haugen, C.M.; Whitten, D.G. Singlet oxygen mediated photofragmentation reactions of amino alcohols: a novel oxidative fragmentation involving both superoxide and excited oxygen intermediates. J. Am. Chem. Soc. 1989, 111, 7281-7282.
16. Sakurai, T.; Uematsu, Y.; Tanaka, O.; Inoue, H. Solvent polarity control oxidizing species in the photosensitized oxidation of N,N-dibenzylhydroxylamine. J. Chem. Soc., Chem. Commun. 1991 (20), 1425-1427.
17. Földi, Z.; Földi, T.; Földi, A. Conformation of Ψ-ephedrine; copper chelates of 2-amino-alcohols. Chem. Ind. 1955, 1297-1299.
18. Beckwith, A.L.J.; Eichinger, P.H.; Mooney, B.A.; Prager, R.H. Amine autoxidation in aqueous solution. Aust. J. Chem. 1983, 36, 719-739.
19. Buettner, G.R.; Jurkiewicz, B.A. Catalytic metals, ascorbate and free radicals: combination to avoid. Radiat. Res. 1996, 145, 532-541.
20. Biaglow, J.E.; Kachur, A.V. The generation of hydroxyl radicals in the reaction of molecular oxygen with polyphosphate complexes of ferrous ion. Radiat. Res. 1997, 148, 181-187.
21. Smith, J.B.; Cusumano, J.C.; Babbs, C.F. Quantitative effects of iron chelators on hydroxyl radical production by the superoxide-driven Fenton reaction. Free Radic. Res. Commun. 1990, 8 (2), 101-106.