Hexestrol

Chemical Name 4,4 -(1,2-diethyl-1,2-ethanediyl)bisphenol Common Name dihydrodiethylstilbestrol hexoestrol 

Trede Name Menufecturer Country Year Introduced 

50 parts by weight of p-hydroxy-propiophenone are dissolved in 200 parts by weight of a 12.5% solution of caustic soda and shaken with 350 parts by weight of 3% sodium amalgam. The sodium salt of the pinacol thereby precipitating is reacted with glacial acetic acid, whereby 

40 parts by weight of pinacolin are dissolved in ethyl alcohol and gradually treated with 80 parts by weight of sodium under reflux. The solution is decomposed with water and the pinacolin alcohol formed extractad from the neutalized solution with ether. The pinacolin alcohol is a viscous oil which is characterized by a dibenzoate of MP 172°C. The yield is 95% of the theoretical. 

Wallis, E.S. and Bernstein, S. U.S. Patent 2357385 September 12,1944 assigned to Research Corporation 

Trade Name Manufacturer Country Year Introduced 

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Synthecilline Phenethicillin potassium Synthepen Phenethicillin potassium Synthex P - Phytonadione Synthomycetin Chloramphenicol Synthovo Hexestrol... 

D Malun (Temmler)-comb. Synthrogene (Gerda) wfm Hexestrol and Phenorbital... 

F Cycloestrol (Bruneau) J Robal (Chugai as Hexestrol W/Butabarb... 

Bergmann, K.E., Carlson, K.E., and Katzenellenbogen, J.A. (1994) Hexestrol diazirine photo-affinity labeling reagent for the estrogen receptor. Bioconjugate Chem. 5, 141-150. 

Katzenellenbogen studied several steroid receptors [21,144]. Estrogen receptor is one of the most frequently investigated receptors by PAL. Hexestrol is a non-steroidal agonist, which was modified with a diazirine photophore via a sulfide linkage (52, Fig. 18). The photoprobe efficiently (30%) labeled the... 

Hexestrol Hexestrol, 4,4 -(l,2-diethylethylene)diphenol (28.1.29), is a derivative of a,j3-diphenylethane, and it is a synthetic estrogen. Hexestrol is made in a Wurtz dimerization reaction of l-bromo-l-(4-methoxyphenyl)propane (28.1.27) in the presence of sodium, magnesium, aluminum, or iron. The initial l-bromo-l-(4-methoxyphenyl)propane (28.1.27) is made in turn by addition reaction of hydrogen bromide to 4-methoxy-l-propenylbenzene. Subsequent removal of the methoxy protective groups from the resulting dimerization product (28.1.28) using hydroiodic acid gives hexestrol (28.1.29) [37-43]. 

While differing significantly from steroid estrogenic hormones in terms of structure, this drug exhibits all of the characteristic biological properties as these hormones. Hexestrol is used for the same indications as estrone. It is also used for prostate cancer or its hypertrophy in men. Synonyms of this drug are sin-estrol, cycloestrol, and others. 

Diethylstilbestrol is a derivative of stilbene, and it differs from sin-estrol by the presence of a double bond with trans-configuration of the two phenyl groups. In terms of estrogenic activity, this drug surpasses both estrone and hexestrol. Synonyms of this drug are distil-ben, menopax, stilphostrol, tilosteron, antigestil, and many others. 

In addition to estrogen agonists based on steroid structures, a variety of nonsteroidal estrogens have also been synthesized and used clinically dienestrol (5.30), diethyl-stilbestrol (5.31), benzestrol (5.32), hexestrol (5.33), methestrol (5.34), methallenestril (5.35), and chlorotrianisene (5.36). 

Of these various nonsteroidal compounds, the first were fran.y-diethylstilbestrol (DES) (5.31) and its reduced derivative hexestrol (5.33). The way in which these nonsteroidal stilbene (diphenylethylene) derivatives are usually drawn suggests a resemblance to the steroid skeleton. However, this resemblance is purely incidental, since the two ethyl groups are not indispensable for estrogenic activity. For example, four methyl groups will give comparable pharmacological activity. It seems, however, that the... 

In addition to the steroidal estrogens, a variety of nonsteroidal compounds with estrogenic activity have been synthesized and used clinically. These include dienestrol, diethylstilbestrol, benzestrol, hexestrol, methestrol, methallenestril, and chlorotrianisene (Figure 40-3). 

Zeranol and stilbene estrogens are the two major types of compounds included in this class of anabolics (Fig. 7.3). Major members of group of stilbene estrogens are diethylstilbestrol, hexestrol, and dienestrol. 

Diethylstilbestrol, hexestrol, and dienestrol are all stilbene estrogens currently banned worldwide for use in food-producing animals. They are genotoxic, not easily metabolized compounds, which are considered capable of irreversibly initiating the carcinogenic process even at small residue concentrations. 

Diethylstilbestrol and hexestrol have been legally permitted for use as anabolics for quite some time in many countries, while the use of dienestrol, which is a metabolite of diethylstilbestrol, was restricted to illegal practice. Since all stilbene estrogens have high oral activity, both oral and parenteral formulations have been in use in catde and, to a lesser extent, in sheep and swine. 

Hexestrol Synthetic Anabolic C18H22O2 270 MeOH, EtOH,... 

A preliminary investigation of SFC coupled to MS/MS for the analysis of trimethoprim, diethylstilbestrol, hexestrol, and dienestrol has demonstrated the considerable potential of this separation technique (81). Packed-column SFC has been also evaluated for the analysis of nine sulfonamides in swine kidney extracts... 

Apart from diethylstilbestrol, several other anabolics including nortestosterone, methyltestosterone, hexestrol, trenbolone, zeranol, and medroxyprogesterone have also gained importance from a regulatory point of view. Examples of immunochemical methods applied in the analysis of edible animal products for residues of these anabolics are presented in Table 28.4. 

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