|Trade names||Turisteron, others|
|Synonyms||EES; Turisteron; J96; Ethinylestradiol 3-isopropylsulfonate; Ethinylestradiol 3-(2-propanesulfonate); 17α-Ethynyl-3-isopropyl-sulfonyloxyestradiol|
|Drug class||Estrogen; Estrogen ester|
|Elimination half-life||Oral: 6 days|
|Chemical and physical data|
|Molar mass||402.547 g/mol|
|3D model (JSmol)|
Ethinylestradiol sulfonate (EES), sold under the brand name Turisteron among others, is an estrogen medication which has been used in birth control in women and in the treatment of prostate cancer in men. It has also been studied in the treatment of breast cancer in women. The medication is taken by mouth once per week.
EES has been used in combination with norethisterone acetate as a once-a-week birth control pill and as a high-dose estrogen monotherapy in the treatment of prostate cancer. It has also been assessed in the treatment of breast cancer. The drug is used at a dosage of 1 to 2 mg once per week in the treatment of prostate cancer.
EES has been described as having good tolerability compared to EE, and this property has been described as "remarkable". The unique C3 sulfonate ester of EES seems to reduce its hepatic estrogenicity, which in turn reduces its adverse effects. In particular, EES is said to have considerably reduced cardiovascular side effects relative to EE when used as a form of high-dose estrogen therapy in the treatment of prostate cancer. This may in part be related to the greatly reduced oral dosing frequency of EES relative to EE, as parenteral EE, which bypasses the first pass through the liver that occurs with oral EE, has been found to have a 5-fold lower impact on liver protein synthesis than oral EE.
EES is an estrogen ester and long-acting prodrug of ethinylestradiol (EE) which is taken orally. It is more lipophilic than EE, and this results in a depot effect in which EES is taken up into fat and then slowly released from it. Following its release from fat, EES is hydrolyzed into EE. As a result of this depot effect, EES has a very long biological half-life of about 6 days. This allows it to be taken once per week.
EES is a powerful antigonadotropin, and is capable of suppressing circulating testosterone concentrations to levels comparable to those seen with castration (less than 1 to 3% of initial values). In addition, EE can strongly increase sex hormone-binding globulin (SHBG) levels, thereby additionally decreasing free testosterone levels. As such, EES is a powerful functional antiandrogen, which makes it useful for treating prostate cancer.
EES, also known as ethinylestradiol 3-isopropylsulfonate or ethinylestradiol 3-(2-propanesulfonate), is a synthetic estrane steroid and a derivative of estradiol. Specifically, it is the C3 isopropylsulfonate ester of ethinylestradiol (17α-ethynylestradiol). EES is similar to quinestrol (EE 3-cyclopentyl ether), which is a C3 ether of EE and is a long-lasting oral depot estrogen similarly.
Analogues of EES include ethinylestradiol N,N-diethylsulfamate (J271) and ethinylestradiol pyrrolidinosulfamate (J272). These analogues are rapidly taken up by erythrocytes in the blood of the hepatic portal vein during the first pass with oral administration and have been found to be much stronger oral estrogens than EE or EES. EE and EES themselves do not have affinity for erythrocytes. EES and related C3 sulfur-containing esters of EE led to the development of estrogen sulfamates like estradiol 3-sulfamate (J995), estriol 3-sulfamate (J1034), and estradiol 17β-(1-(4-(aminosulfonyl)benzoyl)-L-proline) (EC508), which are highly potent oral estradiol prodrugs that bind to erythrocytes similarly and are under investigation for potential clinical use.
Society and culture
Ethinylestradiol sulfonate is the generic name of the drug, but it is also commonly known by its brand name Turisteron. It does not appear to have an INN or other such designations. EES has also been known by its former developmental code name J96.
EES has been marketed under the brand names Turisteron and Deposiston-Oestrogen.
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