Estrogen ester
An estrogen ester is an ester of an endogenous, steroidal estrogen, generally estradiol but also estrone or estriol.[1] Esterification renders these drugs into metabolically-resistant prohormones of their respective parent estrogen, improving oral bioavailability, increasing lipophilicity, and extending half-life (which necessitates less frequent administration).[2] In addition, with intramuscular injection, they are absorbed more slowly into the body, further improving half-life.[1]
Estrogen esters are used in hormone replacement therapy and as hormonal contraceptives, among other indications.
The first estrogen ester to be marketed was estradiol benzoate in 1936,[3][4] which was quickly followed by many more.
List of estrogen esters
Many esters of estradiol have been marketed, including the following:[5][6]
- Cloxestradiol acetate (Genovul)
- Estradiol acetate (Femring, Femtrace, Menoring)
- Estradiol benzoate (Agofollin, Diffolisterol, Progynon-B)
- Estradiol butyrylacetate (Follikoside)
- Estradiol cypionate (Depo-Estradiol, Depofemin, Estradep)
- Estradiol dipropionate (Agofollin, Diovocyclin, Progynon-DP)
- Estradiol diundecylate (Estrolent, Etrosteron, Theramex)
- Estradiol enanthate (Anafertin, Deladroxate, Perlutan, Topasel, all in combination with dihydroxyprogesterone acetophenide)
- Estradiol furoate (Di-folliculine)
- Estradiol hemihydrate
- Estradiol hemisuccinate (Eutocol)
- Estradiol hexahydrobenzoate (Benzo-Ginoestril, Ginestryl-15-depot, Menodin, Tardoginestryl)
- Estradiol monopropionate (Acrofollin, Akrofollin, Follhormon)
- Estradiol palmitate (Esmopal)
- Estradiol propoxyphenylpropionate (Durovex)
- Estradiol stearate (Depofollan)
- Estradiol undecylate (Delestrec, Depogin, Primogyn Depot, Progynon Depot)
- Estradiol valerate (Altadiol, Climaval, Deladiol, Delestrogen, Estraval, Progynova, Valergen)
- Estramustine (Emcyt, Estracit)
- Trimethyl estradiol acetate (Estrotate)
As well as the following esters of other estrogens:[5][6]
- Estriol diacetate benzoate (Holin-Depot)
- Estriol sodium succinate (Pausan, Styptanon)
- Estriol succinate (Sinapause, Styptanon, Synapause)
- Estriol tripropionate (Estriel)
- Estrone acetate (Hovigal)
- Estrone sulfate (as the primary component of Premarin)
- Estrone tetraacetylglucoside (Glucovex, Glycovex)
- Estropipate (Ogen, Ortho-Est)
A few other estrogen esters which are notable but have not been marketed include atrimustine (bestrabucil), estrapronicate, orestrate, which are estradiol esters.[6]
See also
References
- 1 2 R. S. Satoskar; S. D. Bhandarkar &nirmala N. Rege (1969). Pharmacology And Pharmacotherapeutics (New Revised 21 St Ed.). Popular Prakashan. p. 24. ISBN 978-81-7991-527-1. Retrieved 29 May 2012.
- ↑ Gordon L. Amidon; Ping I. Lee; Elizabeth M. Topp (2000). Transport Processes in Pharmaceutical Systems. CRC Press. p. 188-189. ISBN 978-0-8247-6610-8. Retrieved 29 May 2012.
- ↑ Enrique Raviña; Hugo Kubinyi (16 May 2011). The Evolution of Drug Discovery: From Traditional Medicines to Modern Drugs. John Wiley & Sons. p. 175. ISBN 978-3-527-32669-3. Retrieved 20 May 2012.
- ↑ Folley SJ (December 1936). "The effect of oestrogenic hormones on lactation and on the phosphatase of the blood and milk of the lactating cow" (PDF). The Biochemical Journal 30 (12): 2262–72. PMC 1263335. PMID 16746289.
- 1 2 Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 404. ISBN 978-3-88763-075-1. Retrieved 29 May 2012.
- 1 2 3 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.
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