Identification of cyclic metabolites of isopropylated phenyl phosphates in rabbit bile.
Some organophosphorous compounds, especially tri-o-cresylphosphate (TOCP), induce delay neuropathy. The cyclic saligenin phosphate (PSP) has been suggested to be the active metabolite of the protoxicant TOCP. The o-isopropylated triphenyl phosphates have been proven not to be neurotoxic. Studying the metabolism of these compounds we found the following cyclic metabolites: 2-phenyl-4H-4,4-dimethyl-1,1,3,2-benzodioxaphosphoran-2-oxide and 2-(o-isopropylphenyl)-4H-4,4-dimethyl-1,1,3,2-benzodioxaphospho ran-2-oxide. Additionally, monohydroxylated metabolites of the parent esters were detectable. The effect of glucuronidation on the formation of the cyclic metabolites is discussed in this paper.
Yang
S M
SM
Universitätskrankenhaus Eppendorf, Abtlg. Pharmakologie f. Pharmazeuten, Hamburg, FRG.
Thieme
R A
RA
von Meyerinck
L
L
Benthe
H F
HF
D000818:Animals; D001646:Bile / Q000737:chemistry*; D001711:Biotransformation; D002849:Chromatography, Gas; D008401:Gas Chromatography-Mass Spectrometry; D005965:Glucuronates / Q000032:analysis; D006900:Hydroxylation; D008297:Male; D010710:Phosphates / Q000032:analysis*; D011817:Rabbits; D014317:Tritolyl Phosphates / Q000378:metabolism* / Q000633:toxicity
D005965:Glucuronates; D010710:Phosphates; D014317:Tritolyl Phosphates; C025541:tri-o-cresyl phosphate