Estrogen ester

Estradiol, the base estrogen of most estrogen esters.

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.[2] In addition, with intramuscular injection, they have improved lipophilicity, which results in a longer duration when given as a depot in oil.[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 followed by many more. The most widely used estrogen ester is estradiol valerate, which was first introduced in 1954.[5]

Estradiol esters

Many esters of estradiol have been marketed, including the following major esters:[6][7]

And the following less commonly used esters:[6][7]

A few other estradiol esters which are notable but have not been marketed include:[7]

Nitrogen mustard esters

The following nitrogen mustard ester of estradiol is an alkylating antineoplastic agent and has been marketed:[6][7]

The following alkylating antineoplastic nitrogen mustard esters of estradiol have not been marketed:[7]

Estrone esters

Esters of estrone that have been marketed include:[6][7]

Other estrone esters which are notable but have not been marketed include:

Estriol esters

Esters of estriol that have been marketed include:[6][7]

The following ester of estriol was never marketed:

Esters of other estrogens

The following esters of other estrogens exist and have been marketed:[6]

Estrogen ethers

A number of estrogen ethers also exist and have been marketed, including:[10][6]

A few other estrogen ethers which are notable but have not been marketed include:[10]

See also

References

  1. 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.
  2. ↑ Gordon L. Amidon; Ping I. Lee; Elizabeth M. Topp (2000). Transport Processes in Pharmaceutical Systems. CRC Press. pp. 188–189. ISBN 978-0-8247-6610-8. Retrieved 29 May 2012.
  3. ↑ 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.
  4. ↑ 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 1263335Freely accessible. PMID 16746289.
  5. ↑ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1477–. ISBN 978-0-8155-1856-3.
  6. 1 2 3 4 5 6 7 Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 404. ISBN 978-3-88763-075-1. Retrieved 29 May 2012.
  7. 1 2 3 4 5 6 7 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.
  8. ↑ Dahlgren E, Crona N, Janson PO, Samsioe G (1985). "Oral replacement with estradiol-cyclooctyl acetate: a new estradiol analogue. Effects on serum lipids, proteins, gonadotrophins, estrogens and uterine endometrial morphology". Gynecol. Obstet. Invest. 20 (2): 84–90. PMID 3932144.
  9. ↑ Luisi M, Kicovic PM, Alicicco E, Franchi F (1978). "Effects of estradiol decanoate in ovariectomized women". J. Endocrinol. Invest. 1 (2): 101–6. doi:10.1007/BF03350355. PMID 755846.
  10. 1 2 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3.
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