Estradiol undecylate
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Estradiol undecylate (EU, EUn, E2U), also known as estradiol undecanoate and formerly sold under the brand names Delestrec and Progynon Depot 100 among others, is an estrogen medication which has been used in the treatment of prostate cancer in men.[9][10][11][12][1] It has also been used as a part of hormone therapy for transgender women.[13][14][15] Although estradiol undecylate has been used in the past, it was discontinued [11][16].The medication has been given by injection into muscle usually once a month.[1][17][12]
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Pronunciation | /ˌɛstrəˈdaɪɒl ənˈdɛsɪleɪt/ ES-trə-DY-ol un-DESS-il-ayt |
Trade names | Delestrec, Progynon Depot 100, others |
Other names | EU; E2U; Estradiol undecanoate; Estradiol unducelate; RS-1047; SQ-9993 |
Routes of administration | Intramuscular injection[1] |
Drug class | Estrogen; Estrogen ester |
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Bioavailability | IM injection: High |
Protein binding | Estradiol: ~98% (to albumin and SHBGTooltip sex hormone-binding globulin)[2][3] |
Metabolism | Cleavage via esterases in the liver, blood, and tissues[4][5] |
Metabolites | Estradiol, undecanoic acid, estradiol metabolites[4][5] |
Elimination half-life | Unknown |
Duration of action | IM injection: • 10–12.5 mg: 1–2 months[6][7] • 25–50 mg: 2–4 months[8] |
Excretion | Urine |
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ECHA InfoCard | 100.020.616 |
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Formula | C29H44O3 |
Molar mass | 440.668 g·mol−1 |
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Side effects of estradiol undecylate in men may include breast tenderness, breast development, feminization, sexual dysfunction, infertility, fluid retention, and cardiovascular issues.[17] Estradiol undecylate is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.[5][4] It is an estrogen ester and a very long-lasting prodrug of estradiol in the body.[4][5] Because of this, it is considered to be a natural and bioidentical form of estrogen.[4][18][19] An injection of estradiol undecylate has a duration of about 1 to 4 months.[7][8][6][20]
Estradiol undecylate was first described in 1953 and was introduced for medical use by 1956.[7][21][8][22] It remained in use as late as the 2000s before being discontinued.[23][11][24] Estradiol undecylate was marketed in Europe, but does not seem to have ever been available in the United States.[14][25][11] It was used for many years as a parenteral estrogen to treat prostate cancer in men, although it was not employed as often as polyestradiol phosphate.[12]