MarketEstradiol enanthate
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Estradiol enanthate

Estradiol enanthate, also spelled estradiol enantate and sold under the brand names Perlutal and Topasel among others, is an estrogen medication which is used in hormonal birth control for women. It is formulated in combination with dihydroxyprogesterone acetophenide, a progestin, and is used specifically as a combined injectable contraceptive. Estradiol enanthate is not available for medical use alone. The medication, in combination with DHPA, is given by injection into muscle once a month.

Medical uses
Estradiol enanthate is used in combination with the progestin DHPA as a once-monthly combined injectable contraceptive for women in Latin America and Hong Kong. The combination of estradiol enanthate and DHPA has likewise been used by transgender women for such purposes. Since at least the 2020s, it has grown in popularity among the transfeminine community as a means of DIY hormone therapy (without DHPA). Available forms The following forms of estradiol enanthate are or have been available for use: • Estradiol enanthate 10 mg and DHPA 150 mg (brand names Perlutal, Topasel, many others) • Estradiol enanthate 5 mg and DHPA 75 mg (brand names Anafertin, Patector NF, Yectames) • Estradiol enanthate 10 mg and DHPA 120 mg (brand names Unalmes, Yectuna) • Estradiol enanthate 10 mg and DHPA 75 mg (brand name Ova Repos; discontinued) A 6 mg estradiol enanthate and 90 mg DHPA formulation was also studied, but was never marketed. The combination of estradiol enanthate and DHPA has also been studied at other doses ranging from 5 to 50 mg estradiol enanthate and 75 to 200 mg DHPA. The combination of estradiol enanthate and DHPA is provided in ampoules at estradiol enanthate concentrations of 5 mg/mL and 10 mg/mL. ==Contraindications==
Contraindications
Contraindications of estrogens include coagulation problems, cardiovascular diseases, liver disease, and certain hormone-sensitive cancers such as breast cancer and endometrial cancer, among others. ==Side effects==
Side effects
The side effects of estradiol enanthate are the same as those of estradiol. Examples of such side effects include breast tenderness and enlargement, nausea, bloating, edema, headache, and melasma. The combination of estradiol enanthate and DHPA as a combined injectable contraceptive has shown no adverse effects on liver function, lipid metabolism, or coagulation. While DHPA was not mentioned in this instance, estradiol enanthate is normally formulated in combination with DHPA including in Brazil. ==Overdose==
Overdose
Symptoms of estrogen overdosage may include nausea, vomiting, bloating, increased weight, water retention, breast tenderness, vaginal discharge, heavy legs, and leg cramps. These side effects can be diminished by reducing the estrogen dosage. == Interactions ==
Interactions
Inhibitors and inducers of cytochrome P450 may influence the metabolism of estradiol and by extension circulating estradiol levels. ==Pharmacology==
Pharmacology
, the active form of estradiol enanthate. Pharmacodynamics Estradiol enanthate is an estradiol ester, or a prodrug of estradiol. However, it was found to significantly increase levels of triglycerides and to significantly decrease levels of total and free testosterone. The clinical estrogenic effects of estradiol enanthate and ethinylestradiol have been compared in other studies as well. Pharmacokinetics When estradiol enanthate is administered in an oil solution by intramuscular injection, a depot effect occurs, and this results in it having a long duration of action. In general, the longer the fatty acid ester chain, the more lipophilic the estradiol ester, the more slowly it is released from the depot and absorbed into the circulation, and the longer its duration of action. The pharmacokinetics of estradiol enanthate have been assessed in a number of studies.--> It has usually been studied in combination with DHPA. There were concerns about possible accumulation of estradiol enanthate and consequent estrogenic overexposure with once-monthly combined injectable contraceptives containing the medication due its long duration, and this may have limited the use of such combined injectable contraceptives. ==Chemistry==
Chemistry
Estradiol enanthate, also known as estradiol 17β-enanthate or estra-1,3,5(10)-triene-3,17β-diol 17β-heptanoate, is a synthetic estrane steroid and the C17β enanthate (heptanoate) fatty acid ester of estradiol. The experimental octanol/water partition coefficient (logP) of estradiol enanthate is 6.7. ==History==
History
Estradiol enanthate was first described, along with a variety of other estradiol esters, by Karl Junkmann of Schering AG in 1953. The first clinical study of estradiol enanthate and DHPA as a combined injectable contraceptive was conducted in 1964. The combination was marketed by the mid-1970s. ==Society and culture==
Society and culture
Generic names Estradiol enantate is the British English generic name of the medication and its and , while estradiol enanthate is its and American English generic name. Its generic names in other languages are as follows: It has been referred to as estradiol heptanoate. • EEn 10 mg / DHPA 150 mg: Acefil, Agurin†, Atrimon†, Ciclomes, Ciclovar, Ciclovular, Cicnor†, Clinomin, Cycloven, Daiva, Damix, Deprans, Deproxone, Exuna, Ginestest, Ginoplan†, Gynomes, Horprotal, Listen, Luvonal, Neogestar, Neolutin, Nomagest, Nonestrol, Normagest, Normensil, Novular, Oterol, Ovoginal, Patector, Patectro, Perludil, Perlumes, Perlutal, Perlutale, Perlutan, Perlutin, Perlutin-Unifarma, Permisil, Preg-Less, Pregnolan, Progestrol†, Protegin, Proter, Seguralmes, Synovular, Topasel, Unigalen, Uno-Ciclo, and Vagital. • EEn 10 mg / DHPA 120 mg: Anafertin†, Patector NF, and Yectames. • EEn 5 mg / DHPA 75 mg: Unalmes and Yectuna. • EEn 10 mg / DHPA 75 mg: Ova Repos†. • Unsorted: Evitas†, Femineo†, and Primyfar†. The combination of EEn 10 mg and DHPA 150 mg was developed under the developmental brand name Deladroxate, but this brand name was never used commercially. A few different preparations, with varying doses of EEn and DHPA and varying availability, have been introduced. Usage EEn/DHPA is the most widely used combined injectable contraceptive in Latin America. It was estimated in 1995 that EEn/DHPA was used as a combined injectable contraceptive in Latin America by at least 1 million women. However, combined injectable contraceptives like EEn/DHPA are unlikely to constitute a large proportion of total contraceptive use in the countries in which they are available. == See also ==
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