�ber k�rperfremde synthetische �strogene

Wessely, F.; Bauer, A.; Chwala, Christian; Plaichinger, Ilse; Schönbeck, R.

doi:10.1007/bf00898697

Cited by 17 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…230°, and racemic-butoestrol, m.p. 139°, products similar to those reported by Wesseley, Bauer, Chwala, Plaichinger & Schönbeck [1948] and prepared from eis-and írans-dimethylstüboestrol dimethylethers.…”

supporting

confidence: 83%

Oestrogen Inhibition by Steroids and Other Substances

Emmens¹,

Cox²,

Martin³

1960

Journal of Endocrinology

View full text Add to dashboard Cite

In intravaginal tests of cornification in the spayed mouse vagina, dimethylstilboestrol, ethylstilboestrol, n-propylstilboestrol, meso-and racemic-butoestrol inhibit oestradiol. None do so when given subcutaneously. MER 25 shows very weak inhibition, but acts subcutaneously. The steroids, 19-nortestosterone, 17-ethyl-19-nortestosterone and 17-ethinyl-19-nortestosterone, inhibit oestradiol when given both intravaginally and subcutaneously.In intravaginal tests of mitosis, increase in epithelial thickness or triphenyltetrazolium reduction (a measure of metabolic activity), the stilboestrols and butoestrols inhibit oestrone. Massive doses of MER 25 partially inhibited in such tests, but actually stimulated mitosis at low levels of oestrogen administration. None of the nor-steroids showed any inhibitory potency in dose ratios of up to 1000:1, while both 19-nortestosterone and 17-ethinyl-19-nortestosterone showed oestrogenic activity at levels of only 50:1.It is concluded that both the synthetic and steroid compounds inhibit directly, not by virtue of metabolites, but that only the synthetic compounds compete with oestrogens at an early stage. Failure to show parenteral activity in these compounds may be due to their weak pro-oestrogenic potencies. It is suggested that the very weak activity found with MER 25 may reflect a species difference between mouse and rat.

show abstract

supporting

confidence: 83%

Oestrogen Inhibition by Steroids and Other Substances

Emmens¹,

Cox²,

Martin³

1960

Journal of Endocrinology

View full text Add to dashboard Cite

show abstract

“…Esters and ethers of the eis-and trans-isomers of some alkyl-stilboestrols have been reported including the dimethyl ethers of eis-and transdimethylstilboestrol [Wessely, Bauer, Chwala, Plaichinger & Schönbeck, 1948]. For the work reported in this paper, two diacetates of dimethylstilboestrol were prepared and the eis-and irons-forms identified on chemical and spectroscopic evidence [Cox, unpublished observations].…”

Section: Discussionmentioning

confidence: 99%

Oestrogen Inhibitors of the Stilboestrol Series

Emmens¹,

Cox²,

Martin³

1959

Journal of Endocrinology

View full text Add to dashboard Cite

In tests of vaginal cornification, anti-oestrogenic activity has been demonstrated in dimethylstilboestrol, ethylstilboestrol and n-propylstilboestrol. It has not been detected in some other stilboestrols.Dimethylstilboestrol, the most potent anti-oestrogen, inhibits the increase in vaginal mitosis and epithelial thickness which normally follows the administration of oestrone to the ovariectomized mouse. This contrasts with the action of substances like testosterone and progesterone, which inhibit cornification but do not inhibit mitosis in ratios of up to a million to one.Recently Emmens & Cox [1958] demonstrated that dimethylstilboestrol inhibits the response of ovariectomized mice to natural and synthetic oestrogens. Oestradiol or oestrone are more strongly inhibited in vaginal smear tests than is diethylstilboestrol, but such inhibition has so far been demonstrated only in intra vaginal tests. Since dimethylstilboestrol is a pro-oestrogen [Emmens, 1942], and detectable inhibition of oestradiol occurs with a dose of about 0-5 % or even lower of the oestrogenic median effective dose (m.e.d.), it was suggested that the untransformed molecule is the inhibitor.Emmens & Cox [1958] discussed other relevant work on oestrogen antagonists, concluding that no other inhibition described seems to be of the same nature as that seen in the case of dimethylstilboestrol. Since then, a note by Chen [1958] describing anti-oestrogenic properties of some compounds of the oestrane series ' at the 5 µg level ' and a paper by Drill & Riegel [1958] on similar properties in some other steroids have appeared. Most of the latter work is concerned with uterine responses and is related to the 'impeded' oestrogens of Huggins & Jensen [1955], the relation of which to the compounds used in the present investigations is not clear. Thus, oestrogens such as oestriol are described as oestrogen antagonists, whereas in many other tests they behave as oestrogens and exhibit little or no antagonism [cf. Claringbold, 1955]. In tests based on uterine responses it is additionally difficult to be sure that pituitary suppression is not involved, rather than direct oestrogen antagonism.In this paper, earlier results are extended to include other members of the stilboestrol series and to derivatives of dimethylstilboestrol. Another test method of high sensitivity and specificity recently developed in this laboratory [Martin & Claringbold, 1958] has also been employed to examine the inhibition of vaginal responses.

show abstract

“…The resolution of dl-dma into the pure laevoAsomtr (aD-103°, dioxan) and partly resolved dextro-isomer (aD + 66°, dioxan) was achieved via the bis-(abromocamphor-7r-sulphonate) according to the method of Wessely & Welleba (1941), and Wessely, Bauer, Chwala, Plaichinger & Schonbeck (1948). (Experimental details will be published elsewhere.)…”

Section: Preparation Of Compoundsmentioning

confidence: 99%

Anti-Oestrogenic and Antifertility Properties of Some 4,4'-Dihydroxybibenzyls

Gw¹,

Dj²,

Hobbs³

et al. 1968

Reproduction

View full text Add to dashboard Cite

A number of 4,4\m='\-dihydroxybibenzlys has been prepared, with resolution of some isomers. Most are pro-oestrogens and all are anti-oestrogens of varying potency. Dextroand l aevo-\g=a\,\g=a\\m=' \-di methyl-4,4\m=' \\x=req-\ dihydroxybibenzyl (d-and l-dma) have the same anti-oestrogenic and antifertility potencies in mice, but threo-and erythro-\g=a\-ethyl-\g=a\\m=' \-methyl \x=req-\ 4,4\m='\-dihydroxybibenzyl(threo-and erythro-mea) differ markedly in all properties examined. Erythro-mea, although a fairly potent pro-oestrogen, is highly anti-oestrogenic intravaginally and a potent antifertility agent with an med of less than 1 \g=m\g/day. dl-Hexoestrol (dl-dea) is also a potent anti-oestrogen and fairly potent antifertility agent, with an med about 10\g=m\g/day. This series of compounds contrasts with the stilbene-4,4\m='\-diols in possessing members with exceptional antifertility potency, not readily explained by their oestrogenic activities.

show abstract

�ber k�rperfremde synthetische �strogene

Cited by 17 publications

References 0 publications

Oestrogen Inhibition by Steroids and Other Substances

Oestrogen Inhibition by Steroids and Other Substances

Oestrogen Inhibitors of the Stilboestrol Series

Anti-Oestrogenic and Antifertility Properties of Some 4,4'-Dihydroxybibenzyls

Contact Info

Product

Resources

About