Estradiol cypionate

Estradiol cypionate
Clinical data
Pronunciation/ˌɛstrəˈdaɪoʊl sɪˈpaɪoʊneɪt/
ES-trə-DY-ohl sih-PY-oh-nate[1]
Trade namesDepo-Estradiol, Depofemin, Estradep, many others
Other namesEC; E2C; Estradiol cipionate; Estradiol cyclopentylpropionate; ECP; Estradiol 17β-cyclopentylpropionate; Estradiol 17β-cyclopentanepropionate
Routes of
administration		Intramuscular injection, subcutaneous injection[2]
Drug classEstrogen; Estrogen ester
ATC code
Legal status
Legal status
  • US: WARNING[3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityIM: High[4]
Protein bindingEstradiol: ~98% (to albumin and SHBGTooltip sex hormone-binding globulin)[5][6]
MetabolismCleavage via esterases in the liver, blood, and tissues[7][8]
MetabolitesEstradiol, cypionic acid, and metabolites of estradiol[7][8]
Elimination half-lifeIM (aqueous suspension): 8–10 days[9][10]
Duration of actionIM (oil): 5 mg ≈ 11–14 days[11]
IM (aqueous suspension): 5 mg ≈ 14–24 days[9][12][13]
ExcretionUrine
Identifiers
  • [(8R,9S,13S,14S,17S)-3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] 3-cyclopentylpropanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.672 Edit this at Wikidata
Chemical and physical data
FormulaC26H36O3
Molar mass396.571 g·mol−1
3D model (JSmol)
Melting point151 to 152 °C (304 to 306 °F)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC(=O)CCC4CCCC4)CCC5=C3C=CC(=C5)O
  • InChI=1S/C26H36O3/c1-26-15-14-21-20-10-8-19(27)16-18(20)7-9-22(21)23(26)11-12-24(26)29-25(28)13-6-17-4-2-3-5-17/h8,10,16-17,21-24,27H,2-7,9,11-15H2,1H3/t21-,22-,23+,24+,26+/m1/s1
  • Key:UOACKFBJUYNSLK-XRKIENNPSA-N

Estradiol cypionate (EC), sold under the brand name Depo-Estradiol among others, is an estrogen medication which is used in hormone therapy for menopausal symptoms and low estrogen levels in women, in hormone therapy for trans women, and in hormonal birth control for women.[14][8][15][16] It is given by injection into muscle once every 1 to 4 weeks.[14][17]

Side effects of estradiol cypionate include breast tenderness, breast enlargement, nausea, headache, and fluid retention.[14][8] Estradiol cypionate is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.[8][7] Estradiol cypionate is an estrogen ester and a long-lasting prodrug of estradiol in the body.[14][8][7] Because of this, it is considered to be a natural and bioidentical form of estrogen.[7][18][12]

Estradiol cypionate was first described as well as introduced for medical use in 1952.[19][20] Along with estradiol valerate, it is one of the most commonly used esters of estradiol.[21] Estradiol cypionate has mostly been used in the United States, but is also marketed in a few other countries.[22][23][24] The medication is not available in Europe.[25] It is not currently available as a generic medication in the United States.[26]

  1. ^ "Estradiol: Uses, Dosage & Side Effects". Drugs.com. Retrieved 21 April 2023.
  2. ^ Cite error: The named reference pmid22078184 was invoked but never defined (see the help page).
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
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  5. ^ 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.
  6. ^ Gupta MK, Chia SY (2007). "Ovarian Hormones: Structure, Biosynthesis, Function, Mechanism of Action, and Laboratory Diagnosis". In Falcone T, Hurd WW (eds.). Clinical Reproductive Medicine and Surgery. Elsevier Health Sciences. p. 22. ISBN 978-0-323-03309-1.; Arredondo F, Liu JH (2007). "Menopause". In Falcone T, Hurd WW (eds.). Clinical Reproductive Medicine and Surgery. Elsevier Health Sciences. pp. 362, 388. ISBN 978-0-323-03309-1.
  7. ^ 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. 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.
  8. ^ a b c d e f Cite error: The named reference pmid16112947 was invoked but never defined (see the help page).
  9. ^ a b Thurman A, Kimble T, Hall P, Schwartz JL, Archer DF (June 2013). "Medroxyprogesterone acetate and estradiol cypionate injectable suspension (Cyclofem) monthly contraceptive injection: steady-state pharmacokinetics". Contraception. 87 (6): 738–43. doi:10.1016/j.contraception.2012.11.010. PMID 23265980.
  10. ^ Cite error: The named reference Lunelle-Label was invoked but never defined (see the help page).
  11. ^ Oriowo MA, Landgren BM, Stenström B, Diczfalusy E (April 1980). "A comparison of the pharmacokinetic properties of three estradiol esters". Contraception. 21 (4): 415–24. doi:10.1016/S0010-7824(80)80018-7. PMID 7389356.
  12. ^ a b Cite error: The named reference ArunNarendra2012 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference RahimyRyan1999 was invoked but never defined (see the help page).
  14. ^ a b c d "Estradiol cypionate injection, USP" (PDF). accessdata.fda.gov. 2005. Retrieved 21 April 2023.
  15. ^ Newton JR, D'arcangues C, Hall PE (1994). "A review of "once-a-month" combined injectable contraceptives". J Obstet Gynaecol (Lahore). 4 (Suppl 1): S1–34. doi:10.3109/01443619409027641. PMID 12290848.
  16. ^ Bagade O, Pawar V, Patel R, Patel B, Awasarkar V, Diwate S (2014). "Increasing use of long-acting reversible contraception: safe, reliable, and cost-effective birth control" (PDF). World J Pharm Pharm Sci. 3 (10): 364–392. ISSN 2278-4357.
  17. ^ Cite error: The named reference pmid25220381 was invoked but never defined (see the help page).
  18. ^ Cirigliano M (June 2007). "Bioidentical hormone therapy: a review of the evidence". J Womens Health (Larchmt). 16 (5): 600–31. doi:10.1089/jwh.2006.0311. PMID 17627398.
  19. ^ Cite error: The named reference Sittig1988 was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference Publishing2013 was invoked but never defined (see the help page).
  21. ^ Yen SS (1991). Reproductive endocrinology: physiology, pathophysiology, and clinical management. Saunders. ISBN 978-0-7216-3206-3. Retrieved 20 May 2012.
  22. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. Retrieved 20 May 2012.
  23. ^ "Estradiol". Drugs.com.
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  25. ^ Cite error: The named reference BruniBucciantini2017 was invoked but never defined (see the help page).
  26. ^ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 31 December 2017.