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Observations on the mechanism of hydroxylation of cyclophosphamide by rat liver microsomes: The metabolism of cyclophosphamide-4-d2

✍ Scribed by T. A. Connors; P. J. Cox; P. B. Farmer; A. B. Foster; M. Jarman; J. K. Macleod

Publisher
John Wiley and Sons
Year
1974
Tongue
English
Weight
600 KB
Volume
1
Category
Article
ISSN
1076-5174

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✦ Synopsis

The metabolism of cyclophosphamide-44, (2-[bis(2-chloroethyI)amino]-tetrahydro-4,4-dideuterio-2H-1,3,2-oxazaphosphorine 2-oxide), was studied. The first detectable metabolite was a hydroxy derivative which was trapped with ethanol. Mass spectrometry of the resulting two ethowy derivatives and of the deuterated acrolein 2.4-dinitrophenylhydrazones formed therefrom via reaction with acidic 2,4-dinitrophenylhydrazine, afforded evidence that the ethoxy substituents were at C-4, which was therefore the position of the original hydroxy substituent. The mass spectrum of the deuterated acrolein 2,4-dinitrophenylhydrazone obtained from the total reactive metabolites was used to estimate the ratio of 4-to 6-hydroxylation. The rate of metabolism and the antitumour activity of cyclophosphamide and its 4-d, analogue were compared.

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