Estradiol undecylate

Not to be confused with Estradiol undecylenate.
Estradiol undecylate
Clinical data
Pronunciation/ˌɛstrəˈdaɪɒl ənˈdɛsɪleɪt/
ES-trə-DY-ol un-DESS-il-ayt
Trade namesDelestrec, Progynon Depot 100, others
Other namesEU; E2U; Estradiol undecanoate; Estradiol unducelate; RS-1047; SQ-9993
Routes of
administration		Intramuscular injection[1]
Drug classEstrogen; Estrogen ester
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityIM injection: High
Protein bindingEstradiol: ~98% (to albumin and SHBGTooltip sex hormone-binding globulin)[2][3]
MetabolismCleavage via esterases in the liver, blood, and tissues[4][5]
MetabolitesEstradiol, undecanoic acid, estradiol metabolites[4][5]
Elimination half-lifeUnknown
Duration of actionIM injection:
• 10–12.5 mg: 1–2 months[6][7]
• 25–50 mg: 2–4 months[8]
ExcretionUrine
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.616
Chemical and physical data
FormulaC29H44O3
Molar mass440.668 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C3C=CC(=C4)O)C
InChI
  • InChI=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
  • Key:TXHUMRBWIWWBGW-GVGNIZHQSA-N

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]

  1. ^ a b c Zink C (1 January 1988). Dictionary of Obstetrics and Gynecology. Walter de Gruyter. p. 85. ISBN 978-3-11-085727-6.
  2. ^ Stanczyk FZ, Archer DF, Bhavnani BR (June 2013). "Ethinyl estradiol and 17β-estradiol in combined oral contraceptives: pharmacokinetics, pharmacodynamics and risk assessment". Contraception. 87 (6): 706–727. doi:10.1016/j.contraception.2012.12.011. PMID 23375353.
  3. ^ Falcone T, Hurd WW (2007). Clinical Reproductive Medicine and Surgery. Elsevier Health Sciences. pp. 22, 362, 388. ISBN 978-0-323-03309-1.
  4. ^ a b c d e Oettel M, Schillinger E (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. p. 261,544. ISBN 978-3-642-60107-1. 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.
  5. ^ a b c d Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
  6. ^ a b Cite error: The named reference Labhart2012 was invoked but never defined (see the help page).
  7. ^ a b c Cite error: The named reference pmid13142295c was invoked but never defined (see the help page).
  8. ^ a b c Cite error: The named reference pmid13391788 was invoked but never defined (see the help page).
  9. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 898–. ISBN 978-1-4757-2085-3.
  10. ^ Roberts AD (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 415. ISBN 978-0-412-27060-4. Retrieved 20 May 2012.
  11. ^ a b c d Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. Retrieved 20 May 2012.
  12. ^ a b c Norman G, Dean ME, Langley RE, Hodges ZC, Ritchie G, Parmar MK, et al. (February 2008). "Parenteral oestrogen in the treatment of prostate cancer: a systematic review". British Journal of Cancer. 98 (4): 697–707. doi:10.1038/sj.bjc.6604230. PMC 2259178. PMID 18268497.
  13. ^ Schlatterer K, von Werder K, Stalla GK (1996). "Multistep treatment concept of transsexual patients". Experimental and Clinical Endocrinology & Diabetes. 104 (6): 413–419. doi:10.1055/s-0029-1211479. PMID 9021341. S2CID 25099676.
  14. ^ a b Benjamin H, Lal GB, Green R, Masters RE (1966). The Transsexual Phenomenon. Ace Publishing Company. p. 107. 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.
  15. ^ Israel GE (March 2001). Transgender Care: Recommended Guidelines, Practical Information, and Personal Accounts. Temple University Press. pp. 64–. ISBN 978-1-56639-852-7.
  16. ^ "Estradiol".
  17. ^ a b Cite error: The named reference pmid7000222a was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference Urology1973 was invoked but never defined (see the help page).
  19. ^ Lembeck F, Sewing KF (7 March 2013). Pharmakologie-Fibel: Tafeln zur Pharmakologie-Vorlesung. Springer-Verlag. pp. 113–. ISBN 978-3-642-65621-7.
  20. ^ Cite error: The named reference WildeCoombs1959 was invoked but never defined (see the help page).
  21. ^ Cite error: The named reference pmid13345960 was invoked but never defined (see the help page).
  22. ^ Cite error: The named reference Bishop1958 was invoked but never defined (see the help page).
  23. ^ Cite error: The named reference KleemannEngel2014 was invoked but never defined (see the help page).
  24. ^ Cite error: The named reference IndexNominum2004 was invoked but never defined (see the help page).
  25. ^ Cite error: The named reference Micromedex was invoked but never defined (see the help page).
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