383
Views
28
CrossRef citations to date
0
Altmetric
Research Article

Antioxidant‐Accelerated Oxidative Degradation: A Case Study of Transition Metal Ion Catalyzed Oxidation in Formulation

, Ph.D., , , &
Pages 171-179 | Received 13 Jun 2003, Accepted 26 Jul 2003, Published online: 05 Apr 2004

References

  • Akers M. J. Antioxidants in pharmaceutical products. J. Parenter. Sci. Technol. 1982; 36(5)222–228
  • 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
  • Hovorka S. W., Schöncich C. Oxidative degradation of pharmaceuticals: theory, mechanisms and inhibition. J. Pharm. Sci. 2001; 90(3)253–269
  • 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
  • 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
  • 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
  • Schowen K. B.J. R. D. Gandour, R. L. SchowenSolvent hydrogen isotope effects. Transition States of Biochemistry Processes, . Plenum Press, New York 1978
  • Gorman A. A., Rodgers M. A.J. J. C. ScaianoThe Handbook of Organic Photochemistry, . CRC Press, BocaRaton, FL 1989; Vol. 2: 229–247
  • Kearns D. R. H. H. Wasserman, R. W. MurraySolvent and solvent isotope effects on the lifetime of singlet oxygen. Singlet Oxygen, Organic Chemistry a Series of Monographs—Vol. 40, . Academic Press, New York 1979; 115–137
  • 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
  • Gorman A. A. D. Volman, G. Hammond, D. NeckersThe bimolecular reactivity of singlet molecular oxygen. Advances in Photochemistry, . John Wiley & Sons. 1992; 217–274
  • 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
  • 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
  • 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
  • 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
  • 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
  • Földi Z., Földi T., Földi A. Conformation of ψ‐ephedrine; copper chelates of 2‐amino‐alcohols. Chem. Ind. 1955; 1297–1299
  • 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
  • Buettner G. R., Jurkiewicz B. A. Catalytic metals, ascorbate and free radicals: combination to avoid. Radiat. Res. 1996; 145: 532–541
  • 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
  • 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

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.