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Estradiol, also spelled oestradiol, is a medication and naturally occurring steroid hormone.[9][10][11] It is an estrogen and is used mainly in menopausal hormone therapy and to treat low sex hormone levels in women.[9][12] It is also used in hormonal birth control for women, in hormone therapy for transgender women, and in the treatment of hormone-sensitive cancers like prostate cancer in men and breast cancer in women, among other uses.[13][14][15][16][17] Estradiol can be taken by mouth, held and dissolved under the tongue, as a gel or patch that is applied to the skin, in through the vagina, by injection into muscle or fat, or through the use of an implant that is placed into fat, among other routes.[9]

Side effects of estradiol in women include breast tenderness, breast enlargement, headache, fluid retention, and nausea among others.[9][18] Men and children who are exposed to estradiol may develop symptoms of feminization, such as breast development and a feminine pattern of fat distribution, and men may also experience low testosterone levels and infertility.[19][20] It may increase the risk of endometrial hyperplasia and endometrial cancer in women with intact uteruses if it is not taken together with a progestogen, for instance progesterone.[9] The combination of estradiol with a progestin, though not with progesterone, may increase the risk of breast cancer.[21][22] Estradiol should not be used in women who are pregnant or breastfeeding or who have breast cancer, among other contraindications.[18]

Estradiol is a naturally occurring and bioidentical estrogen, or an agonist of the estrogen receptor, the biological target of estrogens like endogenous estradiol.[9] Due to its estrogenic activity, estradiol has antigonadotropic effects and can inhibit fertility and suppress sex hormone production in both women and men.[23][24] Estradiol differs from non-bioidentical estrogens like conjugated estrogens and ethinylestradiol in various ways, with implications for tolerability and safety.[9]

Estradiol was first isolated in 1935.[25] It first became available as a medication in the form of estradiol benzoate, a prodrug of estradiol, in 1936.[26] Micronized estradiol, which allowed estradiol to be taken by mouth, was not introduced until 1975.[27] Estradiol is also used as other prodrugs like estradiol valerate and polyestradiol phosphate.[9] Related estrogens such as ethinylestradiol, which is the most common estrogen in birth control pills, and conjugated estrogens (brand name Premarin), which is used in menopausal hormone therapy, are used as medications as well.[9]

Estradiol is available in a variety of different formulations, including oral, intranasal, transdermal/topical, vaginal, injectable, and implantable preparations.[9][68] An ester may be attached to one or both of the hydroxyl groups of estradiol to improve its oral bioavailability and/or duration of action with injection.[9] Such modifications give rise to forms such as estradiol acetate (oral and vaginal), estradiol valerate (oral and injectable), estradiol cypionate (injectable), estradiol benzoate (injectable), estradiol undecylate (injectable), and polyestradiol phosphate (injectable; a polymerized ester of estradiol), which are all prodrugs of estradiol.
Estradiol is the generic name of estradiol in American English and its INN, USAN, USP, BAN, DCF, and JAN.[143][122][121][144][145] Estradiolo is the name of estradiol in Italian and the DCIT[143] and estradiolum is its name in Latin, whereas its name remains unchanged as estradiol in Spanish, Portuguese, French, and German.[143][122] Oestradiol was the former BAN of estradiol and its name in British English,[144] but the spelling was eventually changed to estradiol.[143] When estradiol is provided in its hemihydrate form, its INN is estradiol hemihydrate.
Estradiol is marketed under a large number of brand names throughout the world.[122][143] Examples of major brand names in which estradiol has been marketed in include Climara, Climen, Dermestril, Divigel, Estrace, Natifa, Estraderm, Estraderm TTS, Estradot, Estreva, Estrimax, Estring, Estrofem, EstroGel, Evorel, Fem7 (or FemSeven), Imvexxy, Menorest, Oesclim, OestroGel, Sandrena, Systen, and Vagifem.[122][143] Estradiol valerate is marketed mainly as Progynova and Progynon-Depot, while it is marketed as Delestrogen in the U.S.[122][128] Estradiol cypionate is used mainly in the U.S. and is marketed under the brand name Depo-Estradiol.[122][128] Estradiol acetate is available as Femtrace, Femring, and Menoring.[128]

Estradiol is also widely available in combination with progestogens.[143] It is available in combination with norethisterone acetate under the major brand names Activelle, Cliane, Estalis, Eviana, Evorel Conti, Evorel Sequi, Kliogest, Novofem, Sequidot, and Trisequens; with drospirenone as Angeliq; with dydrogesterone as Femoston, Femoston Conti; and with nomegestrol acetate as Zoely.[143] Estradiol valerate is available with cyproterone acetate as Climen; with dienogest as Climodien and Qlaira; with norgestrel as Cyclo-Progynova and Progyluton; with levonorgestrel as Klimonorm; with medroxyprogesterone acetate as Divina and Indivina; and with norethisterone enantate as Mesigyna and Mesygest.[143] Estradiol cypionate is available with medroxyprogesterone acetate as Cyclo-Provera, Cyclofem, Feminena, Lunelle, and Novafem;[14] estradiol enantate with algestone acetophenide as Deladroxate and Topasel;[143][146][147] and estradiol benzoate is marketed with progesterone as Mestrolar and Nomestrol.[143]

Estradiol valerate is also widely available in combination with prasterone enantate (DHEA enantate) under the brand name Gynodian Depot.

As of November 2016, estradiol is available in the United States in the following forms:[128]

Oral tablets (Femtrace (as estradiol acetate), Gynodiol, Innofem, generics)
Transdermal patches (Alora, Climara, Esclim, Estraderm, FemPatch, Menostar, Minivelle, Vivelle, Vivelle-Dot, generics)
Topical gels (Divigel, Elestrin, EstroGel), emulsions (Estrasorb), and sprays (Evamist)
Vaginal tablets (Vagifem, generics), creams (Estrace), inserts (Imvexxy), and rings (Estring, Femring (as estradiol acetate))
Oil solution for intramuscular injection (Delestrogen (as estradiol valerate), Depo-Estradiol (as estradiol cypionate))

Oral estradiol valerate (Progynova) and other esters of estradiol that are used by injection like estradiol benzoate, estradiol enantate, and estradiol undecylate all are not marketed in the U.S.[128] Polyestradiol phosphate (Estradurin) was marketed in the U.S. previously but is no longer available.[128]

Estradiol is also available in the U.S. in combination with progestogens for the treatment of menopausal symptoms and as a combined hormonal contraceptive:[128]

Oral tablets with drospirenone (Angeliq) and norethisterone acetate (Activella, Amabelz) and as estradiol valerate with dienogest (Natazia)
Transdermal patches with levonorgestrel (Climara Pro) and norethisterone acetate (Combipatch)

A combination formulation of estradiol and progesterone micronized in oil-filled oral capsules (TX-001HR) is currently under development in the U.S. for the treatment of menopausal symptoms and endometrial hyperplasia but has not yet completed development and been approved.[150][151]

Estradiol and estradiol esters are also available in custom preparations from compounding pharmacies in the U.S.[152] This includes subcutaneous pellet implants, which are not available in the United States as FDA-approved pharmaceutical drugs.[153] In addition, topical creams that contain estradiol are generally regulated as cosmetics rather than as drugs in the U.S. and hence are also sold over-the-counter and may be purchased without a prescription on the Internet.

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