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词条 Estradiol undecylate
释义

  1. Medical uses

     Available forms 

  2. Contraindications

  3. Side effects

  4. Overdose

  5. Interactions

  6. Pharmacology

     Pharmacodynamics  Antigonadotropic activity  Pharmacokinetics 

  7. Chemistry

  8. History

  9. Society and culture

     Generic names  Brand names  Availability 

  10. Research

  11. References

{{Drugbox
| Verifiedfields =
| Watchedfields =
| verifiedrevid =
| IUPAC_name = [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] undecanoate
| image = Estradiol undecylate.svg
| width = 250px
| image2 = Estradiol undecylate molecule ball.png
| width2 = 250px
| pronounce = {{IPAc-en|ˌ|ɛ|s|t|r|ə|ˈ|d|aɪ|ɒ|l|_|ə|n|ˈ|d|ɛ|s|ᵻ|l|eɪ|t}}
{{respell|ES|trə|DY|ol|_|un|DESS|il|ayt}}
| tradename = Delestrec, Progynon Depot 100, others
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| legal_status = Rx-only
| routes_of_administration = Intramuscular injection[1]
| class = Estrogen; Estrogen ester
| bioavailability = {{abbr|IM|Intramuscular injection}}: High
| protein_bound = Estradiol: ~98% (to albumin and {{abbrlink|SHBG|sex hormone-binding globulin}})[1][2]
| 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 = {{Resize|93%|{{abbr|IM|Intramuscular injection}} (10–12.5 mg): 1–2 months[8][9]}}
{{abbr|IM|Intramuscular injection}} (25–50 mg): 2–4 months[10]
| excretion = Urine
| CAS_number_Ref =
| CAS_number = 3571-53-7
| CAS_supplemental =
| ATC_prefix = G03
| ATC_suffix = CA03
| ATC_supplemental =
| PubChem = 19135
| IUPHAR_ligand =
| DrugBank_Ref =
| DrugBank =
| ChemSpiderID_Ref =
| ChemSpiderID = 18055
| UNII = H3N3A8MFJC
| KEGG = D04065
| ChEBI =
| ChEMBL = 1697794
| synonyms = EU; E2U; Estradiol undecanoate; Estradiol unducelate; RS-1047; SH-368; SQ-9993
| C=29 | H=44 | O=3
| molecular_weight = 440.658 g/mol
| SMILES = CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C
| StdInChI_Ref =
| StdInChI = 1S/C29H44O3/c1-3-4-5-6-7-8-9-10-11-28(31)32-27-17-16-26-25-14-12-21-20-22(30)13-15-23(21)24(25)18-19-29(26,27)2/h13,15,20,24-27,30H,3-12,14,16-19H2,1-2H3/t24-,25-,26+,27+,29+/m1/s1
| StdInChIKey_Ref =
| StdInChIKey = TXHUMRBWIWWBGW-GVGNIZHQSA-N
}}Estradiol undecylate (EU), 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.[3][4][5][6][7] It has also been used as a part of hormone therapy for transgender women.[8][9][10] Although estradiol undecylate has been used in the past, it was discontinued and hence is no longer available.[5][11] The medication has been given by injection into muscle usually once a month.[7][22][6]Side effects of estradiol undecylate in men include breast tenderness, breast development, feminization, sexual dysfunction, infertility, fluid retention, and cardiovascular issues.[22] Estradiol undecylate is a synthetic estrogen and hence is an agonist of the estrogen receptor (ER), the biological target of estrogens like estradiol.[12][4] It is an estrogen ester and a very long-lasting prodrug of estradiol in the body.[13][12] Because of this, it is considered to be a natural and bioidentical form of estrogen.[13][30][14] An injection of estradiol undecylate has a duration of about 1 to 4 months.[9][10][8][35]

Estradiol undecylate was discovered in 1954 and was introduced for medical use by 1956.[9][37][10][39] It has been used in Europe as a parenteral estrogen to treat prostate cancer in men, although not as often as polyestradiol phosphate.[5][6]

{{TOC limit|3}}

Medical uses

{{Main|Estradiol (medication)#Medical uses}}

Estradiol undecylate has been used as a form of high-dose estrogen therapy to treat prostate cancer, but has since largely been superseded for this indication by newer agents with fewer adverse effects (e.g., gynecomastia and cardiovascular complications) like {{abbr|GnRH|gonadotropin-releasing hormone}} analogues and nonsteroidal antiandrogens.[7][15] It has been assessed for this purpose in a number of clinical studies.[16][45][17][18][19] It has been used at a dosage of 100 mg every 3 to 4 weeks (or once a month) by intramuscular injection for this indication.[22][20]

Estradiol undecylate has also been used to treat breast cancer in women.[21] It has been used in menopausal hormone therapy as well, for instance in the treatment of hot flashes and other menopausal symptoms.[10] Along with estradiol valerate, estradiol cypionate, and estradiol benzoate, estradiol undecylate has been used as an intramuscular estrogen in feminizing hormone therapy for transgender women.[8][9][10] It has been used at dosages of 100 to 800 mg per month by intramuscular injection for this purpose.[9][10][8][59][60][61]

{{Estrogen dosages for breast and prostate cancer}}

Available forms

Estradiol undecylate was available as an oil solution for intramuscular injection provided in ampoules at a concentration of 100 mg/mL.[22][63]

{{Available forms of estradiol}}

Contraindications

{{See also|Estradiol (medication)#Contraindications}}

Side effects

{{Main|Estradiol (medication)#Side effects}}

Estradiol undecylate and its side effects have been evaluated for the treatment of advanced prostate cancer in a phase III comparative multicenter randomized controlled trial by Jacobi and colleagues of the Department of Urology of the University of Mainz.[23][24][25][26][27][28] The study consisted of 191 patients from 12 centers, who were treated for a short period of 6 months with either 100 mg/month estradiol undecylate (96 men) or 300 mg/week cyproterone acetate (95 men), both by intramuscular injection.[24][25][26][27][28][29][30] The findings for a subgroup of 42 men at the Urological Clinic of the Ruhr University Bochum center were initially published in 1980.[23][27][28] These men were age 51 to 84 years (mean 68 years) and had a life expectancy of less than 6 months.[6][23][82] A considerable incidence of cardiovascular complications occurred in the estradiol undecylate group (76%; 16/21 incidence total); there was a 67% (14/21) incidence of cardiovascular morbidity and 9.5% (2/21) incidence of cardiovascular mortality.[6][23][31] The cardiovascular morbidity in this group included edema and thrombophlebitis (38%; 8/21), coronary heart disease (24%; 5/21), and deep vein thrombosis (4.8%; 1/21), while the cardiovascular mortality included a myocardial infarction (4.8%; 1/21) and a pulmonary embolism (4.8%; 1/21).[23][31] Eight of the cases of cardiovascular complications in the estradiol undecylate group, including the two deaths, were described as "severe".[31][32] Conversely, no incidence of cardiovascular toxicity occurred in the cyproterone acetate comparison group (0%; 0/21).[6][23][31] Other side effects of estradiol undecylate included gynecomastia (100%; 21/21) and erectile dysfunction (90%; 19/21).[23] The findings of cardiovascular complications with estradiol undecylate in this small study are in contrast to large and high-quality clinical studies of high-dose polyestradiol phosphate and transdermal estradiol for prostate cancer, in which minimal or no cardiovascular toxicity has been observed.[33][34][35][36]

In the full report of 191 patients published in 1982,[24][30] the antitumor effectiveness of estradiol undecylate and cyproterone acectate was equivalent.[25][26][27][28] The rates of improvement, no response, and deterioration were 52%, 41%, and 7% in the estradiol undecylate group and 48%, 44%, and 8% in the cyproterone acetate group, respectively.[26] However, the incidence of side effects in the cyproterone acetate group was significantly lower than in the estradiol undecylate group (37% and 94%, respectively).[25][26] Gynecomastia specifically occurred in 13% of the patients in the cyproterone acetate group and 77% of the patients in the estradiol undecylate group.[25] The differences in the side-effect profiles of the medications were mainly due to gynecomastia, breast tenderness, and edema.[26][37] Erectile dysfunction occurred in "essentially all" patients in both groups.[30]

After the completion of the initial full study report, a 5-year extension study of the Ruhr University Bochum center subgroup was conducted.[25][27][29][28] In this long-term study, the cyproterone acetate group was changed from intramuscular injections to 100 mg/day oral cyproterone acetate.[25] Of a remaining 39 patients, the global 5-year survival rate was not significantly different between the estradiol undecylate and cyproterone acetate groups (24% and 26%, respectively).[25][26][27][29][28] The incidence of thrombosis was 4.2% in the estradiol undecylate group and 5.3% in the cyproterone acetate group.[29][30] Two patients in each of the two treatment groups died due to cardiovascular disease.[26][30] This similar rate of cardiovascular mortality is in contrast to the case of other estrogens, such as diethylstilbestrol and estramustine phosphate, compared to which cyproterone acetate has significantly lower cardiovascular toxicity.[25] On the basis of their findings, the researchers concluded that cyproterone acetate was an "acceptable alternative" to estrogen therapy with estradiol undecylate but with a more favorable side-effect profile.[26]

Like other estrogens, estradiol undecylate has been found to produce testicular abnormalities and disturbances of spermatogenesis.[38]

{{Side effects of cyproterone acetate versus estradiol undecylate in men}}

Overdose

{{See also|Estradiol (medication)#Overdose}}

Estrogens are relatively safe in the event of acute overdose. Estradiol undecylate has been used clinically at extremely high doses of up to 800 mg per month by intramuscular injection, given in divided doses of 100 mg injections twice per week.[10][39][40][41] For purposes of comparison, a single 100 mg intramuscular injection of estradiol undecylate has been found to produce maximal estradiol levels of about 500 pg/mL.

Interactions

{{See also|Estradiol (medication)#Interactions}}

Pharmacology

Pharmacodynamics

{{See also|Pharmacodynamics of estradiol}}

Esters of estradiol like estradiol undecylate are readily hydrolyzed prodrugs of estradiol, but have an extended duration when administered in oil via intramuscular injection due to a depot effect afforded by their fatty acid ester moiety.[12] As prodrugs of estradiol, estradiol undecylate and other estradiol esters are estrogens.[13][12] Estradiol undecylate is of about 62% higher molecular weight than estradiol due to the presence of its C17β undecylate ester.[3][5] Because estradiol undecylate is a prodrug of estradiol, it is considered to be a natural and bioidentical form of estrogen.[13][30][14]

The effects of estradiol undecylate on cortisol, dehydroepiandrosterone sulfate, testosterone, and prolactin levels as well as on the hypothalamic–pituitary–adrenal axis have been studied in men with prostate cancer and compared with those of high-dose cyproterone acetate therapy.[42][43][44][45][46][23][47][48][49] The effects of estradiol undecylate on serum lipids and ceruloplasmin levels have been studied as well.[50][51][52]

{{Parenteral potencies and durations of estrogens}}

Antigonadotropic activity

A phase III clinical trial comparing high-dose intramuscular cyproterone acetate (300 mg/week) and high-dose intramuscular estradiol undecylate (100 mg/month) in the treatment of prostate cancer found that estradiol undecylate suppressed testosterone levels into the castrate range (< 50 ng/dL)[53] within at least 3 months whereas testosterone levels with cyproterone acetate were significantly higher and above the castrate range even after 6 months of treatment.[23] With estradiol undecylate, testosterone levels fell from 416 ng/dL to 38 ng/mL (-91%) after 3 months and to 29.6 ng/dL (-93%) after 6 months, whereas with cyproterone acetate, testosterone levels fell from 434 ng/dL to 107 ng/mL (-75%) at 3 months and to 102 ng/mL (-76%) at 6 months.[23] In another study using the same dosages, estradiol undecylate suppressed testosterone levels by 97% while CPA suppressed them by 70%.[46] In accordance, whereas estrogens are well-established as able to suppress testosterone levels into the castrate range at sufficiently high dosages,[54] progestogens like cyproterone acetate on their own are able to decrease testosterone levels only up to an apparent maximum of around 70 to 80%.[55][56]

{{Antigonadotropic effects of estradiol undecylate}}

Pharmacokinetics

{{See also|Pharmacokinetics of estradiol}}

The pharmacokinetics of estradiol undecylate have been assessed in a few studies.[57][58][59][44][60][9][10] Following a single intramuscular injection of 100 mg estradiol undecylate in oil, mean levels of estradiol were about 500 pg/mL a day after injection and about 340 pg/mL 14 days after injection.[57] Levels of estradiol with intramuscular estradiol undecylate were reported to be very irregular and to vary by as much as 10-fold between individuals.[57] In another study, following a single intramuscular injection of 32.2 mg estradiol undecylate, levels of estradiol peaked at around 400 pg/mL after 3 days and decreased from this peak to around 200 pg/mL after 6 days.[58] In a continuous administration study of 100 mg/month estradiol undecylate, estradiol levels were about 560 pg/mL at 3 months and about 540 pg/mL at 6 months of therapy.[44] Due to its more protracted duration, doses of estradiol undecylate that are typical of other estradiol esters produce only "subthreshold" estradiol levels, and for this reason, higher single doses of estradiol undecylate are necessary for similar effects.[61][57][58] However, the relatively low levels of estradiol produced by lower doses of estradiol undecylate are favorable for menopausal replacement therapy.[61]

The duration of estradiol undecylate is markedly prolonged relative to that of estradiol benzoate, estradiol valerate, and many other estradiol esters.[62][63][64] A single intramuscular injection of 10 to 12.5 mg estradiol undecylate has a duration of 40 to 60 days (~1–2 months) and of 25 to 50 mg estradiol undecylate has an estimated duration of effect of 2 to 4 months in postmenopausal women.[9][10][62][63] A single intramuscular injection of 20 to 30 mg estradiol undecylate has been found to inhibit ovulation when used as an estrogen-only injectable contraceptive in premenopausal women for 1 to 3 months (mean 1.7 months) as well.[183] When used at a higher dose of 100 mg per injection in men with prostate cancer, estradiol undecylate has been given usually once a month.[23][20] After a single subcutaneous injection of estradiol undecylate in rats, its duration of effect was 80 days (about 2.5 months).[65][66][67] Due to its very prolonged duration, estradiol undecylate has been described in general as a favorable alternative to estradiol implants.[10]

The excretion of estradiol undecylate has been studied as well.[59]

Estradiol undecylate has not been used via oral administration. However, a closely related estradiol ester, estradiol decanoate (estradiol decylate), has been studied via the oral route, and has been found to possess significant oral bioavailability, to produce relatively high estradiol levels of about 100 pg/mL after a single 0.5 mg oral dose and about 100 to 150 pg/mL with continuous 0.25 mg/day oral therapy, and to have a much higher estradiol-to-estrone ratio than oral estradiol of about 2:1.[68][69][70] It is thought that this is due to absorption of estradiol decanoate by the lymphatic system and a consequent partial bypass of first-pass metabolism in the liver and intestines,[68][69][70] which is similarly known to occur with oral testosterone undecanoate.[71][72]

{{Hormone levels with intramuscular estradiol undecylate}}

Chemistry

{{See also|Estrogen ester|List of estrogen esters}}

Estradiol undecylate is a synthetic estrane steroid and the C17β undecylate (undecanoate) ester of estradiol.[3][4][5] It is also known as estradiol 17β-undecylate or as estra-1,3,5(10)-triene-3,17β-diol 17β-undecanoate.[4][5] A few related estradiol esters include estradiol decanoate, estradiol diundecylate, and estradiol diundecylenate.[3][4]

Estradiol undecylate is a relatively long-chain ester of estradiol. Its ester chain contains 11 carbon atoms. For comparison, the ester chains of estradiol acetate, estradiol valerate, and estradiol enantate have 2, 5, and 7 carbon atoms, respectively. As a result of its long ester chain, estradiol undecylate has by far the longest duration of all of these estradiol esters when administered via intramuscular injection.[73][74]

Estradiol undecylate shares the same undecylate ester as testosterone undecanoate, an androgen/anabolic steroid and very long-lasting testosterone ester.[3][4]

{{Structural properties of major estradiol esters}}

History

Estradiol undecylate was first described in the scientific literature, along with estradiol valerate and a variety of other estradiol esters, by Karl Junkmann of Schering AG in 1953.[75][76] It was introduced for medical use by 1956.[77][78][39] Syntex applied for a patent for estradiol undecylate in 1958, which was granted in 1961 and was given a priority date of 1957.[22][79] Estradiol undecylate was introduced for medical use and was employed for decades, but was eventually discontinued.[5][219][63] It remained in use in France and Japan as late as 2009.[22][5]

Harry Benjamin reported on the use of estradiol undecylate in transgender women in his book The Transsexual Phenomenon in 1966.[9]

Society and culture

Generic names

Estradiol undecylate is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|USAN|United States Adopted Name}}.[3][4][5][11] It is also spelled in some publications as estradiol unducelate and is also known as estradiol undecanoate.[3][4][5][11] In German, it is known under a variety of spellings including as estradiolundecylat, östradiolundecylat, östradiolundezylat, oestradiolundecylat, oestradiolundezylat, and others.[80] Estradiol undecylate is known by its former developmental code names RS-1047 and SQ-9993 as well.[3][4][5][11]

Brand names

The major brand name of estradiol undecylate is Progynon Depot 100.[3][4][5] It has also been marketed under a variety of other brand names including Delestrec, Depogin, Oestradiol-Retard Theramex, Primogyn Depot, and Progynon Depot, among others.[3][4][5][22]

Availability

Estradiol undecylate was available in the Europe (including in France, Germany, Great Britain, Monaco, the Netherlands, Switzerland, and Monaco), and Japan.[5][22][81] However, it has been discontinued and is no longer available.[82][83]

Research

Estradiol undecylate was studied by Schering alone as an estrogen-only injectable contraceptive at a dose of 20 to 30 mg once a month.[84][85][252] It was effective, lacked breast and thromboembolic complications, lacked other side effects besides amenorrhea, and prevented ovulation for 1 to 3 months (mean 1.7 months) following a single dose.[84] However, endometrial hyperplasia was occasionally encountered, and the preparation was not further developed for this purpose due to the risks of endometrial hyperplasia and cancer associated with long-term unopposed estrogen therapy.[84]

Estradiol undecylate, in combination with norethisterone enantate (at doses of 5 to 10 mg and 50 to 70 mg, respectively), was studied by Schering as a combined injectable contraceptive and was found to be effective and well-tolerated, but ultimately was not marketed for this use.[86][87][84][88][89]

References

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9. ^1 2 3 {{cite book|author1=Harry Benjamin|author2=Gobind Behari Lal|author3=Richard Green|author4=Robert E. L. Masters|title=The Transsexual Phenomenon|url=https://books.google.com/books?id=hArbAAAAMAAJ|year=1966|publisher=Ace Publishing Company|quote=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.|page=107}}
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23. ^1 2 3 4 5 6 7 8 9 10 11 12 13 {{cite journal | vauthors = Jacobi GH, Altwein JE, Kurth KH, Basting R, Hohenfellner R | title = Treatment of advanced prostatic cancer with parenteral cyproterone acetate: a phase III randomised trial | journal = Br J Urol | volume = 52 | issue = 3 | pages = 208–15 | year = 1980 | pmid = 7000222 | doi = 10.1111/j.1464-410x.1980.tb02961.x| url = }}
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28. ^1 2 3 4 5 {{cite book|author1=R. Ackermann|author2=Jens E. Altwein|author3=Peter Faul|title=Aktuelle Therapie des Prostatakarzinoms|url=https://books.google.com/books?id=mVeqBgAAQBAJ&pg=PA276|date=13 March 2013|publisher=Springer-Verlag|isbn=978-3-642-84264-1|pages=276–277}}
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30. ^1 2 3 4 {{cite book|last1=Jacobi|first1=GR|last2=Tunn|first2=UW|last3=Senge|first3=TH|chapter=Clinical experience with cyproterone acetate for palliation of inoperable prostate cancer|editor1-last=Jacobi|editor1-first=Günther H|editor2-last=Hohenfellner|editor2-first=Rudolf|title=Prostate Cancer|chapter-url=https://books.google.com/books?id=4HNrAAAAMAAJ|date=1 December 1982|publisher=Williams & Wilkins|isbn=978-0-683-04354-9|pages=305–319}}
31. ^1 2 3 4 {{cite journal|last1=Wenderoth|first1=U. K.|last2=Jacobi|first2=G. H.|title=Gonadotropin-releasing hormone analogues for palliation of carcinoma of the prostate|journal=World Journal of Urology|volume=1|issue=1|year=1983|pages=40–48|issn=0724-4983|doi=10.1007/BF00326861}}
32. ^{{cite journal|last1=Jacobi|first1=Günther H. |last2=Wenderoth|first2=Ulrich K.|title=Gonadotropin-Releasing Hormone Analogues for Prostate Cancer: Untoward Side Effects of High-Dose Regimens Acquire a Therapeutical Dimension|journal=European Urology|volume=8|issue=3|year=1982|pages=129–134|issn=0302-2838|doi=10.1159/000473499}}
33. ^{{cite journal | vauthors = Ockrim J, Lalani EN, Abel P | title = Therapy Insight: parenteral estrogen treatment for prostate cancer--a new dawn for an old therapy | journal = Nat Clin Pract Oncol | volume = 3 | issue = 10 | pages = 552–63 | date = October 2006 | pmid = 17019433 | doi = 10.1038/ncponc0602 | url = }}
34. ^{{cite journal | vauthors = Lycette JL, Bland LB, Garzotto M, Beer TM | title = Parenteral estrogens for prostate cancer: can a new route of administration overcome old toxicities? | journal = Clin Genitourin Cancer | volume = 5 | issue = 3 | pages = 198–205 | date = December 2006 | pmid = 17239273 | doi = 10.3816/CGC.2006.n.037 | url = }}
35. ^{{cite journal | vauthors = Russell N, Cheung A, Grossmann M | title = Estradiol for the mitigation of adverse effects of androgen deprivation therapy | journal = Endocr. Relat. Cancer | volume = 24 | issue = 8 | pages = R297–R313 | date = August 2017 | pmid = 28667081 | doi = 10.1530/ERC-17-0153 | url = }}
36. ^{{cite journal | vauthors = Langley RE, Cafferty FH, Alhasso AA, Rosen SD, Sundaram SK, Freeman SC, Pollock P, Jinks RC, Godsland IF, Kockelbergh R, Clarke NW, Kynaston HG, Parmar MK, Abel PD | title = Cardiovascular outcomes in patients with locally advanced and metastatic prostate cancer treated with luteinising-hormone-releasing-hormone agonists or transdermal oestrogen: the randomised, phase 2 MRC PATCH trial (PR09) | journal = Lancet Oncol. | volume = 14 | issue = 4 | pages = 306–16 | date = April 2013 | pmid = 23465742 | pmc = 3620898 | doi = 10.1016/S1470-2045(13)70025-1 | url = }}
37. ^{{cite book|last1=Schröder|first1=Fritz H.|title=Antiandrogens in Prostate Cancer|year=1996|pages=45–51|doi=10.1007/978-3-642-45745-6_4|isbn=978-3-642-45747-0|chapter=Cyproterone Acetate — Results of Clinical Trials and Indications for Use in Human Prostate Cancer}}
38. ^{{cite journal | vauthors = Schulze C | title = Response of the human testis to long-term estrogen treatment: morphology of Sertoli cells, Leydig cells and spermatogonial stem cells | journal = Cell Tissue Res. | volume = 251 | issue = 1 | pages = 31–43 | date = January 1988 | pmid = 3342442 | doi = 10.1007/BF00215444 | url = }}
39. ^1 {{cite journal | vauthors = Asscheman H, Gooren LJ, Assies J, Smits JP, de Slegte R | title = Prolactin levels and pituitary enlargement in hormone-treated male-to-female transsexuals | journal = Clin. Endocrinol. (Oxf) | volume = 28 | issue = 6 | pages = 583–8 | date = June 1988 | pmid = 2978262 | doi = 10.1111/j.1365-2265.1988.tb03849.x | url = }}
40. ^1 {{cite journal | vauthors = Asscheman H, Gooren LJ, Eklund PL | title = Mortality and morbidity in transsexual patients with cross-gender hormone treatment | journal = Metab. Clin. Exp. | volume = 38 | issue = 9 | pages = 869–73 | date = September 1989 | pmid = 2528051 | doi = 10.1016/0026-0495(89)90233-3 | url = http://www.hemingways.org/GIDinfo/Mortality_Study.pdf}}
41. ^1 {{cite journal | vauthors = Gazzeri R, Galarza M, Gazzeri G | title = Growth of a meningioma in a transsexual patient after estrogen-progestin therapy | journal = N. Engl. J. Med. | volume = 357 | issue = 23 | pages = 2411–2 | date = December 2007 | pmid = 18057351 | doi = 10.1056/NEJMc071938 | url = }}
42. ^{{cite journal | vauthors = Schürmeyer T, Graff J, Senge T, Nieschlag E | title = Effect of oestrogen or cyproterone acetate treatment on adrenocortical function in prostate carcinoma patients | journal = Acta Endocrinol. | volume = 111 | issue = 3 | pages = 360–7 | date = March 1986 | pmid = 2421511 | doi = 10.1530/acta.0.1110360 | url = }}
43. ^{{cite book | vauthors = Spona J, Lunglmayr G | title = Prolaktin-Serumspiegel unter Behandlung des Prostatakarzinoms mit Östradiol-17 beta-undezylat und Cyproteronazetat | trans-title = Serum Prolactin Levels During Therapy of Prostatic Cancer with Estradiol-17 beta-undecylate and Cyproterone Acetate | language = German | journal = Wien. Klin. Wochenschr. | volume = 92 | issue = 14 | pages = 494–7 | date = July 1980 | issn = 0043-5325 | pmid = 6933738 | doi = 10.1007/978-3-642-81706-9_120 | url = | series = Verhandlungsbericht der Deutschen Gesellschaft für Urologie | isbn = 978-3-540-11017-0 }}
44. ^1 2 {{cite journal|last1=Jacobi|first1=G.H.|last2=Altwein|first2=J.E.|title=Bromocriptin als Palliativtherapie beim fortgeschrittenen Prostatakarzinom:Experimentelles und klinisches Profil eines Medikamentes|journal=Urologia Internationalis|trans-title=Bromocriptine as Palliative Therapy in Advanced Prostate Cancer: Experimental and Clinical Profile of a Drugjournal=Urologia Internationalis|volume=34 |issue=4|year=1979 |pages=266–290|doi=10.1159/000280272|pmid=89747}}
45. ^{{cite book |last1=Schulze|first1=H. |title=Konservative Therapie des Prostatakarzinoms|last2=Senge|first2=Th.|year=1987|pages=89–98|doi=10.1007/978-3-642-72613-2_8|isbn=978-3-540-17724-1}}
46. ^1 {{cite book|last1=Neumann|first1=F.|title=Konservative Therapie des Prostatakarzinoms|last2=El Etreby |first2=M. F. |last3=Habenicht |first3=U.-F.|last4=Radlmaier|first4=A.|last5=Bormacher|first5=K.|trans-title=Options for androgen withdrawal and total blockage |year=1987 |pages=61–86|doi=10.1007/978-3-642-72613-2_6|isbn=978-3-540-17724-1}}
47. ^{{cite book|last1=Tunn|first1=U. W.|title=Verhandlungsbericht der Deutschen Gesellschaft für Urologie|last2=Senge|first2=Th. |last3=Neumann |first3=F. |trans-title=Serum concentrations of testosterone and prolactin after surgical and medical castration-A long-term study in prostate cancer patients |volume=32|year=1981|pages=419–421|issn=0070-413X|doi=10.1007/978-3-642-81706-9_123|isbn=978-3-540-11017-0}}
48. ^{{cite book|last1=Baba|first1=S.|title=Verhandlungsbericht der Deutschen Gesellschaft für Urologie|last2=Janetschek |first2=G.|last3=Wenderoth |first3=U.|last4=Jacobi|first4=G. H.|trans-title=Influence of intraprostatic testosterone metabolism by cyproterone acetate and estradiol undecylate in patients with prostate cancer: in vivo studies |volume=32|year=1981|pages=464–466 |issn=0070-413X|doi=10.1007/978-3-642-81706-9_138 |isbn=978-3-540-11017-0}}
49. ^{{cite | last1 = Derra | first1 = | title = Hormonprofile unter Östrogen-und Antiandrogentherapie bei Patienten mit Prostatakarzinom: Östradiolundecylat versus Cyproteronacetat | trans-title = Hormone profiles under estrogen and antiandrogen therapy in patients with prostate cancer: estradiol undecylate versus cyproterone acetate | publisher = Mainz, Universiẗat, Diss | year = 1981 | url = https://books.google.com/books?id=reVtGwAACAAJ}}
50. ^{{cite book|last1=Nagel|first1=R.|title=24. Tagung vom 13. Bis 16. September 1972 in Hannover |last2=Schillinger|first2=E.|last3=Kölln|first3=C.-P.|last4=Pochhammer|first4=K.|trans-title=The behavior of serum lipids in patients with prostate cancer after treatment with estradiol undecylate|volume=24|year=1973|pages=298–301|issn=0070-413X|doi=10.1007/978-3-642-80738-1_75 |series=Verhandlungsbericht der Deutschen Gesellschaft für Urologie|isbn=978-3-540-06186-1}}
51. ^{{cite journal |last1=Taupitz|first1=Artur|last2=Otaguro|first2=K.|title=前立腺癌に対する抗男性ホルモン療法の各種血清成分に及ぼす影響について: 臨床的並びに実験的観察|trans-title=Quantitative Examination of Serum Components after Antiandrogenic Therapy Against Prostatic Cancer: Clinical and Experimental Observation |journal=The Japanese Journal of Urology|volume=50|issue=3|year=1959|pages=153–162|issn=0021-5287|doi=10.5980/jpnjurol1928.50.3_153}}
52. ^{{cite journal|last1=Götz|first1=H.|last2=Ehrmeier|first2=H.|title=Oestrogene und Coeruloplasminspiegel|trans-title=Estrogens and ceruloplasmin levels|journal=Archiv für Gynäkologie|volume=211|issue=1–2|year=1971|pages=204–206|issn=0003-9128|doi=10.1007/BF00682878}}
53. ^{{cite book|author=Fabian M. Saleh|title=Sex Offenders: Identification, Risk Assessment, Treatment, and Legal Issues|url=https://books.google.com/books?id=df0RDAAAQBAJ&pg=PA176|date=11 February 2009|publisher=Oxford University Press, USA|isbn=978-0-19-517704-6|pages=176–}}
54. ^{{cite book|author=Muhammad A. Salam|title=Principles & Practice of Urology: A Comprehensive Text|url=https://books.google.com/books?id=y50kTcCCfEcC&pg=PA684|year=2003|publisher=Universal-Publishers|isbn=978-1-58112-412-5|pages=684–}}
55. ^{{cite book| first1 = Alan J. | last1 = Wein | first2 = Louis R. | last2 = Kavoussi | first3 = Andrew C. | last3 = Novick | first4 = Alan W. | last4 = Partin | first5 = Craig A. | last5 = Peters | name-list-format = vanc | title = Campbell-Walsh Urology: Expert Consult Premium Edition: Enhanced Online Features and Print, 4-Volume Set|url=https://books.google.com/books?id=fu3BBwAAQBAJ&pg=PA2938|date=25 August 2011|publisher=Elsevier Health Sciences|isbn=978-1-4160-6911-9|pages=2938–}}
56. ^{{cite journal | vauthors = Kjeld JM, Puah CM, Kaufman B, Loizou S, Vlotides J, Gwee HM, Kahn F, Sood R, Joplin GF | title = Effects of norgestrel and ethinyloestradiol ingestion on serum levels of sex hormones and gonadotrophins in men | journal = Clinical Endocrinology | volume = 11 | issue = 5 | pages = 497–504 | year = 1979 | pmid = 519881 | doi = 10.1111/j.1365-2265.1979.tb03102.x| url = }}
57. ^1 2 3 {{cite journal | vauthors = Vermeulen A | title = Longacting steroid preparations | journal = Acta Clin Belg | volume = 30 | issue = 1 | pages = 48–55 | year = 1975 | pmid = 1231448 | doi = 10.1080/17843286.1975.11716973| url = }}
58. ^1 2 {{cite journal | vauthors = Leyendecker G, Geppert G, Nocke W, Ufer J | title = Untersuchungen zur Pharmakokinetik von Östradiol-17β, Östradiol-benzoat, Östradiol-Valerianat un Östradiol-Undezylat bei der Frau: Der Verlauf der Konzentration von Östradiol-17β, Östron, LH und FSH im Serum | trans-title = Estradiol 17β, estrone, LH and FSH in serum after administration of estradiol 17β, estradiol benzoate, estradiol valeriate and estradiol undecylate in the female | language = German | journal = Geburtshilfe Frauenheilkd | volume = 35 | issue = 5 | pages = 370–4 | date = May 1975 | pmid = 1150068 | doi = | issn = 0016-5751 | url = https://books.google.com/books?id=YN4EAQAAIAAJ&q=%22Untersuchungen+zur+Pharmakokinetik+von+%C3%96stradiol-17P%2C+Ostradiol-Benzoat%2C+%C3%96stradiol-Valerianat+und+Dstradiol+Undezylat+bei+der+Frau%3A+Der+Verlauf+der+Konzentrationen+von+%C3%96stradiol-17%C3%9F%2C+%C3%96stron%2C+LH+und+FSH+im+Serum%22 | quote = Estradiol 17β, estradiol benzoate, estradiol valerianate, and estradiol undecylate were injected intravenously and intramuscularly to postmenopausal woman and to female castrates. Equal doses were used corresponding to 20 mg of free estradiol 17β. Estradiol 17β, estrone, FSH and LH were measured in serum by radioimmunoassay before and after application of the hormone and the estradiol esters. Thus the depot effect of the different esters could be compared.}}
59. ^1 {{cite journal | vauthors = Zimmermann W, Buescher HK, Taupitz A, Thewalt K | title = Steroidhormonausscheidung bei patienten mit Erkrankungen der Prostata unter Behandlung mit natürlichen und synthetischen oestrogenen | trans-title = Steroid Hormone Excretion of Patients with Diseases of the Prostate under Treatment with Natural and Synthetic Estrogens | language = German | journal = Acta Endocrinol. | volume = 45 | issue = 4 Suppl 90 | pages = S211–25 | date = 1964 | pmid = 14111328 | doi = 10.1530/acta.0.045S211 | issn = 0804-4643 | url = }}
60. ^{{cite journal | vauthors = Oriowo MA, Landgren BM, Stenström B, Diczfalusy E | title = A comparison of the pharmacokinetic properties of three estradiol esters | journal = Contraception | volume = 21 | issue = 4 | pages = 415–24 | date = April 1980 | pmid = 7389356 | doi = 10.1016/S0010-7824(80)80018-7 | url = }}
61. ^1 {{cite book|author=JUCKER|title=Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques|url=https://books.google.com/books?id=AYH1BwAAQBAJ&pg=PA243|date=8 March 2013|publisher=Birkhäuser|isbn=978-3-0348-7044-3|pages=243–|quote=Estradiol undecylenate has a more protracted effect but it releases only subthreshold doses of steroid (advantage may be taken of this for the treatment of menopause).}}
62. ^1 2 3 {{cite book|author=A. Labhart|title=Clinical Endocrinology: Theory and Practice|url=https://books.google.com/books?id=DAgJCAAAQBAJ&pg=PA551|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-96158-8|pages=551–553}}
63. ^1 2 {{cite book|author1=Percy Roberts Wilde|author2=Carey Franklin Coombs|author3=Arthur J. Rendle Short|title=The Medical Annual: A Year Book of Treatment and Practitioner's Index ... |url=https://books.google.com/books?id=Y1REAQAAIAAJ|year=1959|publisher=Publishing Science Group | quote = As in the case of progestogens the esters of oestradiol vary in the duration of their effect. Oestradiol benzoate is short-acting (three days to a week). Oestradiol valerianate is somewhat longer-acting, and oestradiol enanthate and undecylate have considerably more prolonged duration of effectiveness. The undecylate may remain effective for some months, and should not be employed, [...]}}
64. ^1 2 {{cite book|author=International Society of Urology|title=Reports of the Congress|url=https://books.google.com/books?id=WLowAAAAIAAJ|year=1973|publisher=Livingstone|page=252|quote=Progynon-Depot ist eine Oestrogenpräparat mit einem Depoteffekt von 4-6 Wochen. 1 ml Progynon Depot 100 mg enthält 100 mg Oestra- diolundecylat in öliger Lösung. Oestradiolundecylat ist ein Ester des natürlichen Oestrogens Oestradiol.}}
65. ^{{cite journal | vauthors = Kuhl H, Taubert HD | title = A new class of long-acting hormonal steroid preparation: synthesis of oligomeric estradiol derivatives | journal = Steroids | volume = 22 | issue = 1 | pages = 73–87 | date = July 1973 | pmid = 4737545 | doi = 10.1016/0039-128X(73)90072-X | url = }}
66. ^{{cite journal |last1=Kuhl|first1=H.|last2=Taubert|first2=H. D.|title=Ein neuer Typ lang-wirksamer Steroid-Präparate: Synthese und biologische Wirksamkeit |journal=Archiv für Gynäkologie|volume=214|issue=1–4|year=1973|pages=127–128|issn=0003-9128|doi=10.1007/BF00671087}}
67. ^{{cite journal | vauthors = Kuhl H, Auerhammer W, Taubert HD | title = Oligomeric oestradiol esters: a new class of long-acting oestrogens | journal = Acta Endocrinol. | volume = 83 | issue = 2 | pages = 439–48 | date = October 1976 | pmid = 989671 | doi = 10.1530/acta.0.0830439 | url = }}
68. ^1 {{cite journal | vauthors = Kicovic PM, Luisi M, Franchi F, Alicicco E | title = Effects of orally administered oestradiol decanoate on plasma oestradiol, oestrone and gonadotrophin levels, vaginal cytology, cervical mucus and endometrium in ovariectomized women | journal = Clin. Endocrinol. (Oxf) | volume = 7 | issue = 1 | pages = 73–7 | date = July 1977 | pmid = 880735 | doi = 10.1111/j.1365-2265.1977.tb02941.x | url = }}
69. ^1 {{cite journal | vauthors = Luisi M, Kicovic PM, Alicicco E, Franchi F | title = Effects of estradiol decanoate in ovariectomized women | journal = J. Endocrinol. Invest. | volume = 1 | issue = 2 | pages = 101–6 | year = 1978 | pmid = 755846 | doi = 10.1007/BF03350355 | url = }}
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71. ^{{cite book|author1=J. Larry Jameson|author2=Leslie J. De Groot |title=Endocrinology: Adult and Pediatric E-Book|url=https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2387|date=25 February 2015 |publisher=Elsevier Health Sciences|isbn=978-0-323-32195-2|pages=2387–}}
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76. ^1 2 3 4 5 {{cite journal | author = Wied GL | title = Östradiol-valerianat und Östradiol-undecylat; zwei neue protrahiert wirkende Östrogene. Wirkungsvergleich mit Östradiol-benzoat | trans-title = Estradiol valerate and estradiol undecylate, two new estrogens with prolonged action; comparison with estradiol benzoate | language = German | journal = Geburtshilfe und Frauenheilkunde | volume = 14 | issue = 1 | pages = 45–52 | date = January 1954 | issn = 0016-5751 | pmid = 13142295 | doi = | url = }}
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79. ^{{Cite web | url=https://patents.google.com/patent/US2990414A/en | title=17-undecenoate of estradiol}}
80. ^{{cite book|author1=Franz v. Bruchhausen|author2=Gerd Dannhardt|author3=Siegfried Ebel|author4=August W. Frahm, Eberhard Hackenthal, Ulrike Holzgrabe|title=Hagers Handbuch der Pharmazeutischen Praxis: Band 8: Stoffe E-O|url=https://books.google.com/books?id=8vSjBgAAQBAJ&pg=PA84|date=2 July 2013|publisher=Springer-Verlag|isbn=978-3-642-57994-3|pages=84–}}
81. ^1 2 Bishop, P. M. F. (1958). Endocrine Treatment of Gynaecological Disorders. Modern Trends in Endocrinology, 231. p. 232
82. ^1 {{Cite web | url=http://www.micromedexsolutions.com/micromedex2/librarian/ | title=Micromedex Products: Please Login}}
83. ^1 2 {{cite book |editor=Sweetman, Sean C. |chapter=Sex hormones and their modulators |title=Martindale: The Complete Drug Reference |edition=36th |year=2009 |page=2098 |publisher=Pharmaceutical Press |location=London|isbn=978-0-85369-840-1}}
84. ^1 2 3 4 {{cite journal | vauthors = Toppozada M | title = The clinical use of monthly injectable contraceptive preparations | journal = Obstet Gynecol Surv | volume = 32 | issue = 6 | pages = 335–47 | date = June 1977 | pmid = 865726 | doi = 10.1097/00006254-197706000-00001 | url = }}
85. ^{{cite journal | vauthors = el-Mahgoub S, Karim M | title = Depot estrogen as a monthly contraceptive in nulliparous women with mild uterine hypoplasia | journal = Am. J. Obstet. Gynecol. | volume = 112 | issue = 4 | pages = 575–6 | date = February 1972 | pmid = 5008627 | doi = 10.1016/0002-9378(72)90319-5 | url = }}
86. ^{{cite journal | vauthors = Toppozada MK | title = Existing once-a-month combined injectable contraceptives | journal = Contraception | volume = 49 | issue = 4 | pages = 293–301 | year = 1994 | pmid = 8013216 | doi = 10.1016/0010-7824(94)90029-9 | url = }}
87. ^1 Goldsmith, A., & Toppozada, M. (1983). Long-acting contraception. pp. 94-95 https://www.popline.org/node/423289
88. ^{{cite book|author=Dr. S. S. Kadam|title=Principles of Medicinal Chemistry Volume 2|url=https://books.google.com/books?id=Z7Pb3lJuRksC&pg=PA381|date=July 2007|publisher=Pragati Books Pvt. Ltd.|isbn=978-81-85790-03-9|pages=381–}}
89. ^{{cite journal | vauthors = Karim M, el-Mahgoub S | title = Conception control by cyclic injections of norethisterone enanthate and estradiol unducelate | journal = Am. J. Obstet. Gynecol. | volume = 110 | issue = 5 | pages = 740–2 | date = July 1971 | pmid = 5563241 | doi = 10.1016/0002-9378(71)90268-7 | url = }}
{{Estradiol}}{{Estrogens and antiestrogens}}{{Estrogen receptor modulators}}

10 : Abandoned drugs|Alcohols|Antigonadotropins|Carboxylate esters|Estradiol esters|Estranes|Hormonal antineoplastic drugs|Prodrugs|Prostate cancer|Synthetic estrogens
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