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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