Clinical data | |
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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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Pharmacokinetic data | |
Bioavailability | IM injection: High |
Protein binding | Estradiol: ~98% (to albumin and SHBG )[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 |
Chemical and physical data | |
Formula | C29H44O3 |
Molar mass | 440.668 g·mol−1 |
3D model (JSmol) | |
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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]
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]
Natural estrogens considered here include: [...] Esters of 17β-estradiol, such as estradiol valerate, estradiol benzoate and estradiol cypionate. Esterification aims at either better absorption after oral administration or a sustained release from the depot after intramuscular administration. During absorption, the esters are cleaved by endogenous esterases and the pharmacologically active 17β-estradiol is released; therefore, the esters are considered as natural estrogens.
Labhart2012
was invoked but never defined (see the help page).pmid13142295c
was invoked but never defined (see the help page).pmid13391788
was invoked but never defined (see the help page).Another preparation of even higher potency is Squibb's Delestrec, which at this writing is not yet on the market in the United States, but is well known in Germany and other European countries under the name of Progynon Depot (Schering). It is chemically Estradiol Undecylate in oil, likewise slowly absorbing, and containing 100 mg. to 1 cc. Injections of 1 cc. once or twice a month can be sufficient. Occasionally, however, larger doses are required to influence the patient's emotional distress.
pmid7000222a
was invoked but never defined (see the help page).Urology1973
was invoked but never defined (see the help page).WildeCoombs1959
was invoked but never defined (see the help page).pmid13345960
was invoked but never defined (see the help page).Bishop1958
was invoked but never defined (see the help page).KleemannEngel2014
was invoked but never defined (see the help page).IndexNominum2004
was invoked but never defined (see the help page).Micromedex
was invoked but never defined (see the help page).