Esters estradiol

Katz J, Levitz M, Kadner SS, Finlay TH (1991) Estradiol esters can replace 17b-estradiol in the stimulation of DNA and esterase synthesis by MCF-7 cells a possible role for the estrogen-sensitive MCF-7 cell esterase. J Steroid Biochem Mol Biol 38 17-26... 

SAFETY PROFILE Confirmed carcinogen producing liver mmors. An experimental teratogen. A drug used in cancer treatment. When heated to decomposition it emits toxic fumes of POx. See also ESTRADIOL, ESTERS, POLYMERS, and PHOSPHORIC ACID. 

When the transdermal penetration of a drug is inadequate to achieve and maintain a plasma concentration above the minimum therapeutic concentration required to produce the desired effect, a lipophilic prodrug that will be metabolized in the epidermis to the active drug could be used in the development of a controlled-release transdermal delivery system. This approach has been applied to estradiol esters (diacetate and valerate) which are rapidly converted by esterases in the skin tissue to estradiol (Chien et al, 1985). The prodrug serves to increase the transdermal bioavailability of the active drug to which it is converted by metabolism (generally ester hydrolysis) during the percutaneous absorption process. 

Doses. The amount of substance which comprises a dose of steroid hormones, or of the steroidal synthetics varies from substance to substance—from 0.1 mg for an estradiol ester, to 50 mg for a 19-norsteroid compound. The dose is conditioned upon the order of activity of the substance, the purpose for which it is administered, as well as the patient s response. However. as additional steroids for hormonal use are synthesized—especially those with adrenocortical activity, their average dose is usually smaller than the previously available steroid. The smaller effective dose of the more recent steroid is cited as an advantage over the previously available steroid. 

Hypogonadism in girls, women Conjugated estrogens, ethinyl estradiol, estradiol esters... 

Catalytic hydrogenation of the 14—15 double bond from the face opposite to the C18 substituent yields (196). Compound (196) contains the natural steroid stereochemistry around the D-ring. A metal-ammonia reduction of (196) forms the most stable product (197) thermodynamically. When R is equal to methyl, this process comprises an efficient total synthesis of estradiol methyl ester. Birch reduction of the A-ring of (197) followed by acid hydrolysis of the resultant enol ether allows access into the 19-norsteroids (198) (204). 

Isotope labeling by derivative formation with deuterated reagents is useful for the preparation of analogs such as dg-acetonides, da-acetates, da-methyl ethers, dg-methyl esters, etc. The required reagents are either commercially available or can be easily prepared. (The preparation of da-methyl iodide is described in section IX-F. Various procedures are reported in the literature for the preparation of dg-acetone, da-diazometh-ane57.i63.i73 and da-acetyl chloride. ) These reactions can be carried out under the usual conditions and they need no further discussion. A convenient procedure has been reported for the da-methylation of sterically hindered or hydrogen bonded phenolic hydroxyl functions by using da-methyl iodide and sodium hydroxide in dimethyl sulfoxide solution. This procedure should be equally applicable to the preparation of estradiol da-methyl ether derivatives. 

Although both estrone and estradiol are available for replacement therapy, they suffer the disadvantage of poor activity on oral administration and short duration of action even when administered parenterally, because of ready metabolic disposition. In order to overcome these deficiencies, there was developed a series of esters of estradiol with long-chain fatty acids. These esters are oil-soluble and correspondingly water-insoluble compounds. 

The esters are prepared by first treating estradiol with the appropriate acid chloride. The resulting diester, 27, is then subjected to mild acid or basic hydrolysis in this way, the phenolic ester group is removed selectively. 

Therapeutic Function Estrogen Chemical Name Estradiol phosphate polymer Common Name Polymeric ester of phosphoric acid and estradiol Structural Formula r... 

Salicylate esters may be promising prodrug candidates for estrogen. 0-Estradiol has been used for treatment of various conditions such as menopausal... 

To reduce conjugative first-pass metabolism and increase the oral bioavailability of P-estradiol, estradiol-3-salicylate, and P-estradiol-3-anthranilate, ester prodrugs were synthesized and their oral bioavailabilities in dogs were evaluated... 

Yamada H, Kuwahara Y, Takamastu Y, Hayase T. 2000. A new sensitive determination method of estradiol in plasma using peroxyoxalate ester chemiluminescence combined with an HPLC system. Biomed Chromatogr 14(5) 333-337. 

Estrogen preparations. Depot preparations for i.m. injection are oily solutions of esters of estradiol (3- or 17-OH group). The hydrophobicity of the acyl moiety determines the rate of absorption, hence the duration of effect... 

One of the routes to epimestix>l begins with acylation of estradiol with benzoyl chloride to give the dibenzoate 5. Pyrolysis of the ester leads to formation of the 16,17-olefin. Hydroxylation by means of osmiiim tetroxide affords the cis-diol 7 due to the intermediacy of the cyclic osmate ester (6a)-, attack... 

Estradiol is produced in female organisms together with estrone, and if taken in the form of acid ester derivatives it exhibits strong and prolonged estrogenic action. It is used for the same indications as estradiol. Synonyms of this drug are delestrogen, estraval, retestin, deladiol, and others. 

Esters of A - hydro x y s u c c i n i in i d c are also used to carry out chemical modification of peptides, proteins, and other biological molecules by acylation of nucleophilic groups in these molecules. For example, detection of estradiol antibodies can be accomplished using... 

Estramustine is used to treat prostate cancer. It is a derivative of estradiol with an nitrogen mustard-carbamate ester moiety. 

This increased resistance of LDL to oxidation is in agreement with the findings of a number of studies with dietary soy, including the increase in lag time in a study in six young healthy male and female subjects who consumed three soy bars per day (providing 57 mg total isoflavones/day 36 mg genistein and 21 mg daidzein) for 2 weeks.Although HDL-derived 17(3-estradiol fatty acid esters have been shown to accumulate in LDL ex v/vo and esterified... 

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