Prolonged oestrogenic activity in rats after single oral administration of ethinyloestradiol-3-cyclopentyl ether

Giannina, T.; Meli, A

doi:10.1111/j.2042-7158.1969.tb08247.x

Cited by 14 publications

(9 citation statements)

References 4 publications

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“…The increase in lipophilicity due to an aromatic carbamate group could cause an accumulation of the prodrug in the fatty tissues of the organism after administration, with a resulting slow release into the blood circulation upon hydrolysis of the prodrug. This compartmental accumulation has also been described for other compounds including oestradiol derivatives (Giannina & Meli 1969;Gardi et a1 1973).…”

Section: Discussionsupporting

confidence: 59%

Orally Active Carbamate Prodrugs of the Selective Dopamine Agonist N-0437: In-vivo Activities in the 6-OHDA Turning Model and In-vitro Activities

Daas

Boer

Tepper

et al. 1991

Journal of Pharmacy and Pharmacology

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The in-vivo activities of eight carbamate prodrugs of the D2-agonist N-0437 were determined by examining the effects of the prodrugs, after their oral administration in rats with unilateral 6-OHDA lesions of the striatum. The resulting contralateral turning was used as an index of the activity of the compounds. A comparison of the area under the curve of the time-effect curves of the prodrugs, revealed a significantly improved duration of action compared with N-0437 during the period 11-15 h after administration, for the propylcarbamate and the dimethoxyphenylcarbamate derivatives. The 2,4-dimethylphenylcarbamate showed a significantly enhanced turning behaviour over the whole 15 h time interval in comparison with N-0437. Three of the nine carbamates were virtually unhydrolysed in rat serum at 37 degrees C, while the other test compounds were hydrolysed relatively slowly, with t1/2 values ranging from 1.5-6 h. The test compounds differed greatly in partition coefficients, which were estimated by RP-HPLC (1-12 times more lipophilic than N-0437). The potential cholinesterase inhibiting properties of the carbamate prodrugs were assessed by a simple in-vitro incubation assay, which showed that only two carbamates were very weak cholinesterase inhibitors.

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Section: Discussionsupporting

confidence: 59%

Orally Active Carbamate Prodrugs of the Selective Dopamine Agonist N-0437: In-vivo Activities in the 6-OHDA Turning Model and In-vitro Activities

Daas

Boer

Tepper

et al. 1991

Journal of Pharmacy and Pharmacology

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“…This may be the case of bisether 30, which was found to be poorly active although the etherification at C-3 with cyclopentanol is known to endow most of the estrogens with a higher and long-lasting activity. [21][22][23] Like other lipophilic compounds,24 the labile estradiol 17-ethers are significantly absorbed and highly active after oral treatment mainly when given in oil solution. However, a too high lipophilicity may reduce the biological availability of the compound also after oral administration, as observed in the bisethers 6 and 70.…”

Section: Biology and Discussionmentioning

confidence: 99%

1,3,5(10)-Estratrien-17.beta.-yl enol ethers and acetals. New classes of orally and parenterally active estrogenic derivatives

Gardi¹,

Vitali²,

Falconi³

et al. 1973

J. Med. Chem.

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“…QUN is the 3-cyclopentyl ether of ethinyl estradiol (EE2), After oral administration, it is stored in adipose tissue where it is gradually released and metabolized principally to EE2 14 . The potent effect of QUN is approximately several times higher than EE2 with a very long biological half-life of more than 5 days 15 . The sulfate and glucuronate conjugates of QUN and EE2 are formed in the kidney and excreted by human and livestock in the urine, and they can be desulfated and deglucuronidated by corresponding enzymes in the environment and converted back into its precursors 16 .…”

Section: Introductionmentioning

confidence: 98%

Adsorption–desorption behavior of the endocrine-disrupting chemical quinestrol in soils

Guo

Lin²,

Xu³

et al. 2020

Sci Rep

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Quinestrol (QUN), a synthetic estrogen used as an oral contraceptive or emergency contraceptive component, has been shown to be an endocrine-disrupting chemical. To assess the environmental risk of QUN, batch equilibration experiments were conducted to investigate the adsorption–desorption of QUN in five contrasting soils from different areas of China. The leaching properties were also calculated based on the adsorption and degradation data from our previous study with the same soils. The Freundlich and Langmuir models were applied to the sorption–desorption data to examine the affinity towards QUN of the soils, which had varying physical and chemical properties. The K f and K f des values of QUN in the tested soils ranged from 3.72 to 20.47 mg 1−n L n kg −1 and from 1.26 to 7.8 mg 1−n L n kg −1 , respectively, and Q m ranged from 28.25 to 126.58 mg/kg. The desorption data showed that hysteresis occurred. The K f and K f des values of QUN were positively correlated with the soil total organic carbon (OC) and cation exchange capacity (CEC), and it may be due to the content of TOC and CEC exhibited a positive correlation. A low mobility potential of QUN in soils was predicted and verified the adsorption results by the groundwater ubiquity score (GUS) and retardation factor (R f ).

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Prolonged oestrogenic activity in rats after single oral administration of ethinyloestradiol-3-cyclopentyl ether

Cited by 14 publications

References 4 publications

Orally Active Carbamate Prodrugs of the Selective Dopamine Agonist N-0437: In-vivo Activities in the 6-OHDA Turning Model and In-vitro Activities

Orally Active Carbamate Prodrugs of the Selective Dopamine Agonist N-0437: In-vivo Activities in the 6-OHDA Turning Model and In-vitro Activities

1,3,5(10)-Estratrien-17.beta.-yl enol ethers and acetals. New classes of orally and parenterally active estrogenic derivatives

Adsorption–desorption behavior of the endocrine-disrupting chemical quinestrol in soils

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