Metabolic activation of carcinogenic diethylstilbestrol in rodents and humans
- PMID: 994232
Metabolic activation of carcinogenic diethylstilbestrol in rodents and humans
Abstract
In vivo biotransformation of diethylstilbestrol (DES) was studied by radio-GLC and GLC-mass spectrometry using both radioactively and deuterium-labeled DES. Among the urinary and biliary metabolites identified in intact Wistar rat and Syrian golden hamsters are dienestrol and hydroxy and methoxy derivatives of dienestrol and DES. The identification of 4'-hydroxypropiophenone as a urinary metabolite of DES in the rat is consistent with the hypothesis that dienestrol is formed via an epoxide-diol pathway. Some of the metabolites imply electrophilic reactivity according to their chemical structure and may represent proximate carcinogens of DES. In humans, dienestrol and hydroxy dienestrol constitute the major urinary DES metabolites in men and were also identified in the urine of a woman. Considerable species differences in DES metabolism between humans and rats were found with regard to the route of excretion and the pattern of urinary metabolites.
Similar articles
-
Diethylstilbestrol: evidence for metabolic activation in man, rat, and hamster.Natl Cancer Inst Monogr. 1979 May;(51):73-6. Natl Cancer Inst Monogr. 1979. PMID: 481583
-
Dependence on exogenous metabolic activation for induction of unscheduled DNA synthesis in Syrian hamster embryo cells by diethylstilbestrol and related compounds.Cancer Res. 1984 Jan;44(1):184-9. Cancer Res. 1984. PMID: 6317168
-
Biotransformation of diethylstilbestrol in the rhesus monkey and the chimpanzee.J Toxicol Environ Health. 1977 Oct;3(3):439-50. doi: 10.1080/15287397709529577. J Toxicol Environ Health. 1977. PMID: 411947
-
The metabolism of diethylstilbestrol.CRC Crit Rev Biochem. 1981;10(3):171-212. doi: 10.3109/10409238109113599. CRC Crit Rev Biochem. 1981. PMID: 6163591 Review.
-
Diethylstilbestrol metabolic transformation in relation to organ specific tumor manifestation.Arch Toxicol Suppl. 1979;(2):275-80. doi: 10.1007/978-3-642-67265-1_23. Arch Toxicol Suppl. 1979. PMID: 380522 Review.
Cited by
-
Effects of toxic substances on female reproduction.Environ Health Perspect. 1983 Feb;48:43-52. doi: 10.1289/ehp.834843. Environ Health Perspect. 1983. PMID: 6825634 Free PMC article.
-
Upper genital tract abnormalities in the Syrian hamster as a result of in utero exposure to diethylstilbestrol. I. Uterine cystadenomatous papilloma and hypoplasia.Virchows Arch A Pathol Anat Histopathol. 1982;398(2):163-83. doi: 10.1007/BF00618867. Virchows Arch A Pathol Anat Histopathol. 1982. PMID: 6819709 Review.
-
[Transplacental induction of neurogenic tumors in rabbits (author's transl)].Z Krebsforsch Klin Onkol Cancer Res Clin Oncol. 1977 Aug 15;89(3):331-9. doi: 10.1007/BF00283787. Z Krebsforsch Klin Onkol Cancer Res Clin Oncol. 1977. PMID: 198985 German.
-
Comparison of the novel bibenzyl bifluranol with diethystilboestrol: effect of aromatic fluorine substitution on metabolism [proceedings].Br J Pharmacol. 1978 Jun;63(2):350P. Br J Pharmacol. 1978. PMID: 667433 Free PMC article. No abstract available.
-
Metabolism of stilbene estrogens and steroidal estrogens in relation to carcinogenicity.Arch Toxicol. 1984 Jul;55(2):104-9. doi: 10.1007/BF00346047. Arch Toxicol. 1984. PMID: 6383273 Review.