Estradiol cypionate
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| Systematic (IUPAC) name | |
|---|---|
|
(17β)-3-hydroxyestra-1,3,5(10)-trien-17-yl 3-cyclopentylpropanoate | |
| Clinical data | |
| Routes of administration | Oral, IM |
| Legal status |
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| Identifiers | |
| CAS Number | 313-06-4 |
| ATC code | None |
| PubChem | CID 9403 |
| ChemSpider | 9033 |
| Synonyms | 17β-Estradiol-17-cypionate |
| Chemical data | |
| Formula | C26H36O3 |
| Molar mass | 396.562 g/mol |
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| |
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.[8][9] 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.[8][9] At 28 days post-administration, estradiol levels reach a low of 40 to 55 pg/mL.[8][9]
See also
References
- ↑ A. D. Roberts (1991). Dictionary of Steroids: Chemical Data, Structures, and Bibliographies. CRC Press. p. 415. ISBN 978-0-412-27060-4. Retrieved 20 May 2012.
- ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 405. ISBN 978-3-88763-075-1. Retrieved 20 May 2012.
- ↑ Marshall Sittig (1 January 1988). Pharmaceutical Manufacturing Encyclopedia. William Andrew. pp. 575–576. ISBN 978-0-8155-1144-1. Retrieved 20 May 2012.
- ↑ Michael Oettel; Ekkehard Schillinger (6 December 2012). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Springer Science & Business Media. pp. 261–. ISBN 978-3-642-60107-1.
- ↑ Sriram (2008). Medicinal Chemistry. Pearson Education India. p. 427. ISBN 978-81-317-0031-0. Retrieved 20 May 2012.
- ↑ 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.
- 1 2 Sierra-Ramírez JA, Lara-Ricalde R, Lujan M, Velázquez-Ramírez N, Godínez-Victoria M, Hernádez-Munguía IA, et al. (2011). "Comparative pharmacokinetics and pharmacodynamics after subcutaneous and intramuscular administration of medroxyprogesterone acetate (25 mg) and estradiol cypionate (5 mg)". Contraception 84 (6): 565–70. doi:10.1016/j.contraception.2011.03.014. PMID 22078184.
- 1 2 3 4 Nagrath Arun; Malhotra Narendra; Seth Shikha (15 December 2012). Progress in Obstetrics and Gynecology--3. Jaypee Brothers Medical Publishers Pvt. Ltd. pp. 416–418. ISBN 978-93-5090-575-3.
- 1 2 3 4 Rahimy, Mohamad H; Ryan, Kristi K; Hopkins, Nancy K (1999). "Lunelle™ monthly contraceptive injection (medroxyprogesterone acetate and estradiol cypionate injectable suspension): steady-state pharmacokinetics of MPA and E2 in surgically sterile women". Contraception 60 (4): 209–214. doi:10.1016/S0010-7824(99)00086-4. ISSN 0010-7824.
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