hexestrol hexestrol hexestrol, sold under the brand name synestrol among others, is a nonsteroidal estrogen which was previously used for estrogen replacement therapy and in the treatment of certain hormone-dependent cancers as well as gynecological disorders but is mostly no longer marketed. it has also been used in the form of esters such as hexestrol diacetate (brand name sintestrol) and hexestrol dipropionate (brand name hexanoestrol). hexestrol and its esters are taken by mouth, held under the tongue, or via injection into muscle. hexestrolclinical datatrade namessynestrol, synoestrol, estrifar, estronalother nameshexoestrol; hexanestrol; hexanoestrol; dihydrodiethylstilbestrol; dihydrostilbestrol; 4,4'-(1,2-diethylethylene)diphenol; nsc-9894routes ofadministrationby mouth, intramuscular injection (as an ester)drug classnonsteroidal estrogenidentifiers iupac name 4-phenol cas number84-16-2pubchem cid3606iuphar/bps2823drugbankdb07931chemspider3480unii10bi795r7dkeggd01641chebichebi:31669chemblchembl6615comptox dashboard (epa)dtxsid2022381 echa infocard100.001.380 chemical and physical dataformulac18h22o2molar mass270.372 g·mol−13d model (jsmol)interactive image smiles ccc(c1=cc=c(c=c1)o)c(cc)c2=cc=c(c=c2)o inchi inchi=1s/c18h22o2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20h,3-4h2,1-2h3key:pbbgszcbwvpool-uhfffaoysa-n medical uses hexestrol has been used in estrogen replacement therapy, for the treatment of breast cancer in women and prostate cancer in men, and for the treatment of certain gynecological disorders. estrogen dosages for prostate cancer route/formestrogendosage oralestradiol1–2 mg 3x/day conjugated estrogens1.25–2.5 mg 3x/day ethinylestradiol0.15–3 mg/day ethinylestradiol sulfonate1–2 mg 1x/week diethylstilbestrol1–3 mg/day dienestrol5 mg/day hexestrol5 mg/day fosfestrol100–480 mg 1–3x/day chlorotrianisene12–48 mg/day quadrosilan900 mg/day estramustine phosphate140–1400 mg/day transdermal patchestradiol2–6x 100 μg/dayscrotal: 1x 100 μg/day im or sc injectionestradiol benzoate1.66 mg 3x/week estradiol dipropionate5 mg 1x/week estradiol valerate10–40 mg 1x/1–2 weeks estradiol undecylate100 mg 1x/4 weeks polyestradiol phosphatealone: 160–320 mg 1x/4 weekswith oral ee: 40–80 mg 1x/4 weeks estrone2–4 mg 2–3x/week iv injectionfosfestrol300–1200 mg 1–7x/week estramustine phosphate240–450 mg/day note: dosages are not necessarily equivalent. sources: see template. pharmacology pharmacodynamics hexestrol has approximately 302% and 234% of the affinity of estradiol for the estrogen receptors (ers) erα and erβ, respectively. the affinity of hexestrol for the ers is said to be similar to or slightly higher than that of estradiol. along with diethylstilbestrol, hexestrol has been said to be one of the most potent estrogens known. the total endometrial proliferation dose per cycle of different forms of hexestrol are 70 to 100 mg for oral hexestrol, 45 mg for sublingual hexestrol diacetate, and 25 mg for hexestrol dipropionate by intramuscular injection. these doses are fairly similar to those of estradiol and its esters. hexestrol induces mammary gland development in rodents similarly to other estrogens. nonsteroidal estrogens like diethylstilbestrol, which is closely related structurally to hexestrol, are known to have dramatically disproportionate estrogenic effects in the liver and on liver protein synthesis. parenteral potencies and durations of nonsteroidal estrogens estrogenformmajor brand name(s)epd (14 days)duration diethylstilbestrol (des)oil solutionmetestrol20 mg1 mg ≈ 2–3 days; 3 mg ≈ 3 days diethylstilbestrol dipropionateoil solutioncyren b12.5–15 mg2.5 mg ≈ 5 days aqueous suspension ?5 mg ? mg = 21–28 days dimestrol (des dimethyl ether)oil solutiondepot-cyren, depot-oestromon, retalon retard20–40 mg ? fosfestrol (des diphosphate)aaqueous solutionhonvan ?<1 day dienestrol diacetateaqueous suspensionfarmacyrol-kristallsuspension50 mg ? hexestrol dipropionateoil solutionhormoestrol, retalon oleosum25 mg ? hexestrol diphosphateaaqueous solutioncytostesin, pharmestrin, retalon aquosum ?very short note: all by intramuscular injection unless otherwise noted. footnotes: a = by intravenous injection. sources: see template. pharmacokinetics distribution of hexestrol radioactivity in blood and tissues after a subcutaneous injection of a physiological dose of tritium-labeled hexestrol in oil solution in five juvenile female goats. points are one animal each. with the exception of skeletal muscle, tissues with a radioactivity concentration of less than 15% of that of the endometrium are not shown. hexestrol is concentrated in target tissues such as the uterus and vagina due to binding to estrogen receptors. the pharmacokinetics and distribution of hexestrol have been studied with intravenous injection of aqueous solution in women and with subcutaneous injection of oil solution in female goats and sheep. chemistry