Chemistry:Emmenin

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Emmenin
Emmenin tablets.jpg
Combination of
Estriol glucuronideEstrogen
Estriol sulfateEstrogen
Estriol sulfate glucuronideEstrogen
Clinical data
Trade namesEmmenin
Routes of
administration		By mouth
Identifiers
ChemSpider
  • none

Emmenin was an orally active formulation of estrogen that was developed by James Collip at Ayerst and introduced in Canada in 1930 and the United States in 1934.[1][2] It was originally an extract obtained from human placentae.[3][4][5][6] At some point, it seems to have been changed to an extract of the urine of women who were in late pregnancy, which was equivalent in composition but was less expensive to source,[7] and was essentially the same product as Progynon, a related estrogen developed by Adolf Butenandt at Schering and introduced in Germany .[1][2][8][9][10][11] These estrogen products were the first orally active estrogens to be marketed for medical use.[2][11][12][13]

To reduce the costs of manufacturing Emmenin and Progynon, Ayerst and Schering eventually switched to using the urine of pregnant mares (which contains conjugated equine estrogens, primarily estrone sulfate)[14] and called their new products Premarin and Progynon 2, respectively.[1][2][15] Premarin was introduced by Ayerst in 1941[2] and has become not only a very widely used estrogen, but one of the most widely prescribed drugs in North America.[16]

Both Emmenin and Progynon contained a mixture of water-soluble conjugated estrogens, later determined to be mostly estriol glucuronide.[2][17] Conjugates of estriol like estriol glucuronide and estriol sulfate constitute more than 90% of the estrogens in the urine of pregnant women.[18] Of these conjugates, 35 to 46% are estriol glucuronide and 15 to 22% are estriol sulfate in late pregnancy; the double conjugate estriol sulfate glucuronide also occurs.[19][20] Unlike unconjugated estrogens like estradiol and estrone, these estrogens were orally active.[2][11][12][13]

See also

References

  1. ↑ 1.0 1.1 1.2 Barbara Seaman (4 January 2011). The Greatest Experiment Ever Performed on Women: Exploding the Estrogen Myth. Seven Stories Press. pp. 22–. ISBN 978-1-60980-062-8. https://books.google.com/books?id=HHm1qkcgFSUC&pg=PA22. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 Thom Rooke (1 January 2012). The Quest for Cortisone. MSU Press. pp. 54–. ISBN 978-1-60917-326-5. https://books.google.com/books?id=70vvFrtpePoC&pg=PT54. 
  3. ↑ Collip, J. B.; Browne, J. S. L.; Thomson, D. L. (1934). "THE CHEMICAL NATURE OF EMMENIN". Endocrinology 18 (1): 71–74. doi:10.1210/endo-18-1-71. ISSN 0013-7227. 
  4. ↑ Macfarlane, Catharine (1936). "Observations on the use of Collip's emmenin in the menopause". American Journal of Obstetrics and Gynecology 31 (4): 663–666. doi:10.1016/S0002-9378(36)90468-4. ISSN 0002-9378. 
  5. ↑ Campbell, A. D. (1933). "Concerning Placental Hormones and Menstrual Disorders". Annals of Internal Medicine 7 (3): 330. doi:10.7326/0003-4819-7-3-330. ISSN 0003-4819. 
  6. ↑ Campbell, A. D., & Collip, J. B. (1930). Treatment of menopausal symptoms and menstrual disorders with extracts of human placenta and pregnancy urine. Canadian Medical Association Journal, 23, 633-641.
  7. ↑ "Pregnant Mares' Urine and Oestrogens". Can J Comp Med Vet Sci 9 (11): 293–301. 1945. PMID 17648157. 
  8. ↑ http://www.jbc.org/content/87/2/357.short
  9. ↑ Christopher Kobrak (7 October 2002). National Cultures and International Competition: The Experience of Schering AG, 1851-1950. Cambridge University Press. pp. 119–. ISBN 978-0-521-81481-2. https://books.google.com/books?id=Z3iTsU6_mHsC&pg=PA119. 
  10. ↑ Streck, Arnulf (1928). ""Progynon"-Schering, ein Neues Zyklus-Hormonpräparat". Klinische Wochenschrift 7 (25): 1172–1178. doi:10.1007/BF01738283. ISSN 0023-2173. 
  11. ↑ 11.0 11.1 11.2 Vera Regitz-Zagrosek (2 October 2012). Sex and Gender Differences in Pharmacology. Springer Science & Business Media. pp. 549–. ISBN 978-3-642-30725-6. https://books.google.com/books?id=J3VxihGDh9wC&pg=PA549. "The first sex steroid used as pharmacological agent was Progynon, first sold by Schering AG in 1928. [...]" 
  12. ↑ 12.0 12.1 Alison Li (27 October 2003). J.B. Collip and the Development of Medical Research in Canada: Extracts and Enterprise. McGill-Queen's Press - MQUP. pp. 86–. ISBN 978-0-7735-2609-9. https://books.google.com/books?id=cUcZQ2l1E7wC&pg=PA86. 
  13. ↑ 13.0 13.1 Marion Gluck (1 February 2010). It Must Be My Hormones. Penguin Books Limited. pp. 25–. ISBN 978-0-85796-510-3. https://books.google.com/books?id=z6jBB0kD1nYC&pg=PT25. 
  14. ↑ "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 Suppl 1: 3–63. 2005. doi:10.1080/13697130500148875. PMID 16112947. 
  15. ↑ H. K. Chopra; Navin C. Nanda (15 December 2013). Textbook of Cardiology: A Clinical and Historical Perspective. Jaypee Brothers Medical Publishers Pvt. Ltd.. pp. 326–. ISBN 978-93-5090-803-7. https://books.google.com/books?id=3UPHBAAAQBAJ&pg=PA326. 
  16. ↑ Advances in Molecular Toxicology. Elsevier. 13 October 2006. pp. 4–. ISBN 978-0-08-046538-8. https://books.google.com/books?id=W-mN1jfBIIwC&pg=PA4. 
  17. ↑ Gregory Pincus (22 October 2013). Recent Progress in Hormone Research: The Proceedings of the Laurentian Hormone Conference. Elsevier Science. pp. 307–. ISBN 978-1-4832-1945-5. https://books.google.com/books?id=jgTgBAAAQBAJ&pg=PA307. 
  18. ↑ Robert K. Creasy; Robert Resnik; Charles J. Lockwood; Jay D. Iams; Michael F. Greene; Thomas Moore (2013). Creasy and Resnik's Maternal-Fetal Medicine: Principles and Practice. Elsevier Health Sciences. pp. 104–. ISBN 978-1-4557-1137-6. https://books.google.com/books?id=AbMKAQAAQBAJ&pg=PA104. 
  19. ↑ N. S. Assali (3 September 2013). The Maternal Organism. Elsevier. pp. 339–. ISBN 978-1-4832-6380-9. https://books.google.com/books?id=mSzLBAAAQBAJ&pg=PA339. 
  20. ↑ Helmut Sies; Lester Packer (2005). Phase II Conjugation Enzymes and Transport Systems. Gulf Professional Publishing. pp. 294–. ISBN 978-0-12-182805-9. https://books.google.com/books?id=tlm-C-H3DtIC&pg=PA294. 





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