Estradiol cypionate

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Estradiol cypionate
Estradiol 17 beta-cypionate.svg
Systematic (IUPAC) name
(17β)-3-hydroxyestra-1,3,5(10)-trien-17-yl 3-cyclopentylpropanoate
Clinical data
Legal status
  • ℞ (Prescription only)
Routes of
administration		 Oral, IM
Identifiers
CAS Number 313-06-4
ATC code None
PubChem CID: 9403
ChemSpider 9033
Synonyms 17β-Estradiol-17-cypionate
Chemical data
Formula C26H36O3
Molecular mass 396.562 g/mol
  • O=C(O[C@H]3CC[C@H]4[C@H]2[C@@H](c1ccc(O)cc1CC2)CC[C@]34C)CCC5CCCC5
  • 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 (INN, USAN) (brand names Depo-Estradiol, Depofemin, Estradep, and many others), or estradiol cipionate, is a synthetic ester, specifically the 3-cyclopentylpropanoyl ester, of the natural estrogen, estradiol.[1][2] It was first introduced in 1952 by Upjohn in the United States,[3] and has been in widespread use since. Estradiol cypionate behaves as a sustained-release prodrug to estradiol, and therefore is considered to be natural estrogen.[4]

Estradiol cypionate is absorbed more slowly than estradiol itself, and for that reason, can be administered less often.[5] Compared to other commonly used estradiol esters, via the intramuscular route, estradiol cypionate was found to have the longest duration of action with a duration of ~11 days, while estradiol benzoate and estradiol valerate were found to last for 4–5 days and 7–8 days, respectively.[6] Estradiol cypionate, as a depot injection, has been found to have equivalent effectiveness and pharmacokinetics (e.g., duration) via subcutaneous and intramuscular routes.[7] However, subcutaneous injection is generally regarded as easier and less painful relative to intramuscular injection, and for these reasons, may result in comparatively greater patient compliance.[7]

Lunelle and Cyclofem are combination formulations of 4 mg estradiol cypionate and 25 mg medroxyprogesterone acetate for intramuscular use as long-lasting (once-monthly) contraceptives.[8][9] With these formulations, estradiol levels peak 2 days post-administration at mean serum levels of 247 pg/mL.[9][8] The terminal half-life of estradiol with these formulations is approximately 8 days, and plasma estradiol levels return to baseline (typically about 100 pg/mL) by 14 days post-administration.[9][8] At 28 days post-administration, estradiol levels reach a low of 40 to 55 pg/mL.[9][8]

See also

References

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  8. ↑ 8.0 8.1 8.2 8.3 Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ 9.0 9.1 9.2 9.3 Lua error in package.lua at line 80: module 'strict' not found.



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