Abstract
This chapter summarizes results of our investigations on the oxidation of aliphatic nitrogen functions. For some time we have been studying the metabolism of arylalkylamines related to amphetamine. Our focus has been on amphetamine and phentermine and their N-hydroxy derivatives.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Caldwell, J., Koster, U., Smith, R.L. and Williams, R.T. (1975) Species variations in the N-oxidation of chlorphentermine. Biochem. Pharmacol., 24, 2225–32.
Cho, A.K. and Fukoto, J.M. (1988) Chemistry of organic nitrogen compounds, in Biotransformation of Organic Nitrogen Compounds (eds A.K. Cho and B. Lindeke), S. Karger AG, Basel.
Cho, A.K., Maynard, M.S., Matsumoto, R.M. et al., (1982) The opposing effects of N-hydroxyamphetamine and N-hydroxyphentermine on the H2O2 generated by hepatic cytochrome P-450. Mol. Pharmacol., 22, 465–70.
Duncan, J.D. and Cho, A.K. (1982) N-Oxidation of phentermine to N-hydroxy-phentermine by a reconstituted cytochrome P-450 oxidase system from rabbit liver. Mol. Pharmacol., 22, 235–8.
Duncan, J.D., Di Stefano, E.W., Miwa, G.T. and Cho, A.K. (1985) Role of superoxide in the N-oxidation of N-(2-methyl-1-phenyl-2-propyl) hydroxylamine by the rat liver cytochrome P-450 system. Biochemistry, 24, 4155–61.
Duncan, J.D., Hallstrom, G., Florence, V.M. et al. (1983) N- and’C-oxidation of’-alkyl substituted phenethylamines by a reconstituted cytochrome P-450 oxidase system from rabbit liver. Acta Pharm. Suec., 20, 331–40.
Estabrook, R.W. and Werringloer, J. (1977) Cytochrome P450 - its role in oxygen activation for drug metabolism, in Drug Metabolism Concepts (ed. D.M. Jerina), ACS symposium series No. 44, ACS, Washington, DC, pp. 1–26.
Florence, V.M. (1985) PhD Thesis, UCLA.
Fukuto, J.M., Brady, J.F., Burstyn, J.N. et al. (1985) Direct formation of complexes between cytochrome P-450 and nitrosoarenes. Biochemistry, 25, 2714–19.
Lindeke, B. and Paulsen-Sörman, U. (1988) Nitrogenous compounds as ligands to hemoporphyrins — the concept of metabolic — intermediary complexes, in Progress in Basic and Clinical Pharmacology (eds P. Lomax and E.S. Vesell), Karger, Basel, 1, 63–102.
Lotlikar, P.D. and Zaleski, K. (1975) Ring- and N-hydroxylation of 2-acetamindi-fluorene by rat liver reconstituted cytochrome P-450 enzyme system. Biochem. J., 150, 561–4.
Matsumoto, R.M. and Cho, A.K. (1982) Conversion of N-hydroxyamphetamine to phentylacetone oxime by rat liver microsomes. Biochem. Pharmacol., 31, 105–8.
Maynard, M.S. (1982) PhD Thesis, UCLA.
Maynard, M.S. and Cho, A.K. (1981) Oxidation of N-hydroxyphentermine to 2-methyl-2-nitro-1-phenylpropane by liver microsomes. Biochem. Pharmacol., 30,1115–19.
Nanni, J.E. and Sawyer, D.T. (1980) Superoxide-ion catalyzed oxidation of hydroxyphenazines, reduced flavins, hydroxylamine and related substrates via hydrogen atom transfer. J. Am. Chem. Soc., 102, 7591–3.
Rickert, D.E., Butterworth, B.P. and Popp, J.A. (1984) Dinitrotoluene: acute toxicity, oncogenicity, genotoxicity and metabolism. CRC Crit. Rev. Toxicol., 13, 217–34.
Sawyer, D.T. and Valentine, J.S. (1981) How super is superoxide? Accts. Chem. Res., 14, 393–400.
Sum, C.Y. and Cho, A.K. (1979) The metabolism of N-hydroxyphentermine by rat liver microsomes. Drug Metab. Dispos., 7, 65–9.
Udenfriend, S. (1962) Fluorescence assay in Biology and Medicine. Academic Press, New York, pp. 40–151.
Wajer, Th.A.J.W., Mackor, A. and DeBoer, Th.J. (1969) C-nitroso compounds. VII, an ESR study of alkylnitroxides. Tetrahedron, 25, 175.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1991 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Cho, A.K., Duncan, J.D., Fukuto, J.M. (1991). Studies on the N-oxidation of phentermine: evidence for an indirect pathway of N-oxidation mediated by cytochrome P-450. In: Hlavica, P., Damani, L.A. (eds) N-Oxidation of Drugs. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-3112-4_12
Download citation
DOI: https://doi.org/10.1007/978-94-011-3112-4_12
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-5378-5
Online ISBN: 978-94-011-3112-4
eBook Packages: Springer Book Archive