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| image = Estrone sulfate.svg
| image = Estrone sulfate.svg
| width = 225px
| width = 225px
| caption = [[Estrone sulfate]], the primary active agent of esterified estrogen products.
| caption = [[Estrone sulfate]], the primary active component in esterified estrogens (constitutes about 80% of total content).
| image2 = Equilin sulfate.svg
| width2 = 225px
| caption2 = [[Equilin sulfate]], the second most major active component in esterified estrogens (constitutes about 11% of total content).


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| legal_US =
| legal_US =
| routes_of_administration = [[Oral administration|By mouth]]
| routes_of_administration = [[Oral administration|By mouth]]<ref name="Sherif2013" />
| class = [[Estrogen (medication)|Estrogen]]
| class = [[Estrogen (medication)|Estrogen]]


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'''Esterified estrogens''' ('''EEs''') (brand names '''Amnestrogen''', '''Estratab''', '''Evex''', '''Femogen''', '''Menest''') are an [[estrogen (medication)|estrogen]] product that contain [[synthetic compound|synthetic]], [[plant]]-based estrogens and are manufactured from [[soybean]]s and [[yam (vegetable)|yam]]s.<ref name="MDRope2013">{{cite book|author1=Carl P. Weiner, MD|author2=Kate Rope|title=The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby|url=https://books.google.com/books?id=6gdqbSanaXIC&pg=PA179|date=2 April 2013|publisher=St. Martin's Press|isbn=978-0-312-67646-9|pages=179–}}</ref><ref name="SmithHeckbert2006">{{cite journal|last1=Smith|first1=N. L.|last2=Heckbert|first2=S. R.|last3=Lemaitre|first3=R. N.|last4=Reiner|first4=A. P.|last5=Lumley|first5=T.|last6=Rosendaal|first6=F. R.|last7=Psaty|first7=B. M.|title=Conjugated Equine Estrogen, Esterified Estrogen, Prothrombotic Variants, and the Risk of Venous Thrombosis in Postmenopausal Women|journal=Arteriosclerosis, Thrombosis, and Vascular Biology|volume=26|issue=12|year=2006|pages=2807–2812|issn=1079-5642|doi=10.1161/01.ATV.0000245792.62517.3b}}</ref> They are used in [[hormone replacement therapy|hormone therapy]] for [[menopause|menopausal symptom]]s, female [[hypogonadism]], [[ovariectomy]], and [[primary ovarian failure]] and in the treatment of [[prostate cancer]].<ref name="Ebadi2007">{{cite book|author=Manuchair Ebadi|title=Desk Reference of Clinical Pharmacology, Second Edition|url=https://books.google.com/books?id=ihxyHbnj3qYC&pg=PA249|date=31 October 2007|publisher=CRC Press|isbn=978-1-4200-4744-8|pages=249–}}</ref>
'''Esterified estrogens''' ('''EEs''') (brand names '''Amnestrogen''', '''Estratab''', '''Evex''', '''Femogen''', '''Menest''') is an [[estrogen (medication)|estrogen]] medication which is used [[hormone therapy]] for [[menopausal symptom]]s and [[hypogonadism|low sex hormone levels]] in women and to treat [[prostate cancer]] in men.<ref name="MDRope2013">{{cite book|author1=Carl P. Weiner, MD|author2=Kate Rope|title=The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby|url=https://books.google.com/books?id=6gdqbSanaXIC&pg=PA179|date=2 April 2013|publisher=St. Martin's Press|isbn=978-0-312-67646-9|pages=179–}}</ref><ref name="SmithHeckbert2006">{{cite journal|last1=Smith|first1=N. L.|last2=Heckbert|first2=S. R.|last3=Lemaitre|first3=R. N.|last4=Reiner|first4=A. P.|last5=Lumley|first5=T.|last6=Rosendaal|first6=F. R.|last7=Psaty|first7=B. M.|title=Conjugated Equine Estrogen, Esterified Estrogen, Prothrombotic Variants, and the Risk of Venous Thrombosis in Postmenopausal Women|journal=Arteriosclerosis, Thrombosis, and Vascular Biology|volume=26|issue=12|year=2006|pages=2807–2812|issn=1079-5642|doi=10.1161/01.ATV.0000245792.62517.3b}}</ref> It is taken [[oral administration|by mouth]].<ref name="Sherif2013">{{cite book|author=Katherine Sherif|title=Hormone Therapy: A Clinical Handbook|url=https://books.google.com/books?id=RmmzJ8MYpUAC&pg=PA120|date=14 May 2013|publisher=Springer Science & Business Media|isbn=978-1-4614-6268-2|pages=120–}}</ref>


==Medical uses==
⚫
EEs consist primarily of [[sodium estrone sulfate]] and [[sodium equilin sulfate]], and are very similar to [[conjugated estrogens]] (CEEs; brand name Premarin).<ref name="SmithHeckbert2006" /><ref name="FritzSperoff2012">{{cite book|author1=Marc A. Fritz|author2=Leon Speroff|title=Clinical Gynecologic Endocrinology and Infertility|url=https://books.google.com/books?id=KZLubBxJEwEC&pg=PA752|date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4847-3|pages=752–}}</ref><ref name="Parker-Pope2007">{{cite book|author=Tara Parker-Pope|title=The Hormone Decision: Untangle the Controversy, Understand Your Options, Make Your Own Choices|url=https://books.google.com/books?id=3SNAAQAAQBAJ&pg=PA157|date=9 January 2007|publisher=Rodale|isbn=978-1-59486-927-3|pages=157–}}</ref> However, EEs and CEEs differ in the sources of their contents and in the percentages of their constituents; CEEs consist of approximately 53% sodium estrone sulfate and 25% sodium equilin sulfate, while EEs contain approximately 80% sodium estrone sulfate and 11% sodium equilin sulfate.<ref name="FritzSperoff2012" /><ref name="Smith2004">{{cite journal|last1=Smith|first1=Nicholas L.|title=Esterified Estrogens and Conjugated Equine Estrogens and the Risk of Venous Thrombosis|journal=JAMA|volume=292|issue=13|year=2004|pages=1581|issn=0098-7484|doi=10.1001/jama.292.13.1581}}</ref><ref name="Ebadi2007" /> EEs and CEEs have been found to produce similar serum levels of [[estrone]] and [[estradiol (medication)|estradiol]].<ref name="LemaitreWeiss2006">{{cite journal|last1=Lemaitre|first1=Rozenn N.|last2=Weiss|first2=Noel S.|last3=Smith|first3=Nicholas L.|last4=Psaty|first4=Bruce M.|last5=Lumley|first5=Thomas|last6=Larson|first6=Eric B.|last7=Heckbert|first7=Susan R.|title=Esterified Estrogen and Conjugated Equine Estrogen and the Risk of Incident Myocardial Infarction and Stroke|journal=Archives of Internal Medicine|volume=166|issue=4|year=2006|pages=399|issn=0003-9926|doi=10.1001/archinte.166.4.399|pmid=16505258}}</ref> One study found that the risk of [[venous thrombosis]] may be less with EEs relative to CEEs.<ref name="Smith2004" /><ref name="SmithHeckbert2006" />
EEs are used in [[hormone replacement therapy|hormone therapy]] for [[menopause|menopausal symptom]]s, female [[hypogonadism]], [[ovariectomy]], and [[primary ovarian failure]] and in the treatment of [[prostate cancer]].<ref name="Ebadi2007">{{cite book|author=Manuchair Ebadi|title=Desk Reference of Clinical Pharmacology, Second Edition|url=https://books.google.com/books?id=ihxyHbnj3qYC&pg=PA249|date=31 October 2007|publisher=CRC Press|isbn=978-1-4200-4744-8|pages=249–}}</ref>


===Available forms===
[[Estratest]] is a [[combination drug|combination formulation]] of 1.25&nbsp;mg EEs with 2.5&nbsp;mg [[methyltestosterone]].<ref name="MorleyBerg1999">{{cite book|author1=John E. Morley|author2=Lucretia van den Berg|title=Endocrinology of Aging|url=https://books.google.com/books?id=hGD0BwAAQBAJ&pg=PA172|date=5 November 1999|publisher=Springer Science & Business Media|isbn=978-1-59259-715-4|pages=172–}}</ref>
[[Estratest]] is a [[combination drug|combination formulation]] of 1.25&nbsp;mg EEs with 2.5&nbsp;mg [[methyltestosterone]].<ref name="MorleyBerg1999">{{cite book|author1=John E. Morley|author2=Lucretia van den Berg|title=Endocrinology of Aging|url=https://books.google.com/books?id=hGD0BwAAQBAJ&pg=PA172|date=5 November 1999|publisher=Springer Science & Business Media|isbn=978-1-59259-715-4|pages=172–}}</ref>


==Pharmacology==
⚫
Esterified estrogens were introduced for medical use by 1970.<ref name="Northwest1970">{{cite book|title=Northwest Medicine|url=https://books.google.com/books?id=2sJLAQAAIAAJ|year=1970|publisher=Northwest Medical Pub. Association.}}</ref>
⚫
EEs consist primarily of [[sodium estrone sulfate]] and [[sodium equilin sulfate]], and are very similar to [[conjugated estrogens]] (CEEs; brand name Premarin).<ref name="SmithHeckbert2006" /><ref name="FritzSperoff2012">{{cite book|author1=Marc A. Fritz|author2=Leon Speroff|title=Clinical Gynecologic Endocrinology and Infertility|url=https://books.google.com/books?id=KZLubBxJEwEC&pg=PA752|date=28 March 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-4511-4847-3|pages=752–}}</ref><ref name="Parker-Pope2007">{{cite book|author=Tara Parker-Pope|title=The Hormone Decision: Untangle the Controversy, Understand Your Options, Make Your Own Choices|url=https://books.google.com/books?id=3SNAAQAAQBAJ&pg=PA157|date=9 January 2007|publisher=Rodale|isbn=978-1-59486-927-3|pages=157–}}</ref> However, EEs and CEEs differ in the sources of their contents and in the percentages of their constituents; CEEs consist of approximately 53% sodium estrone sulfate and 25% sodium equilin sulfate, while EEs contain approximately 80% sodium estrone sulfate and 11% sodium equilin sulfate.<ref name="FritzSperoff2012" /><ref name="Smith2004">{{cite journal|last1=Smith|first1=Nicholas L.|title=Esterified Estrogens and Conjugated Equine Estrogens and the Risk of Venous Thrombosis|journal=JAMA|volume=292|issue=13|year=2004|pages=1581|issn=0098-7484|doi=10.1001/jama.292.13.1581}}</ref><ref name="Ebadi2007" /> EEs and CEEs have been found to produce similar serum levels of [[estrone]] and [[estradiol (medication)|estradiol]].<ref name="LemaitreWeiss2006">{{cite journal|last1=Lemaitre|first1=Rozenn N.|last2=Weiss|first2=Noel S.|last3=Smith|first3=Nicholas L.|last4=Psaty|first4=Bruce M.|last5=Lumley|first5=Thomas|last6=Larson|first6=Eric B.|last7=Heckbert|first7=Susan R.|title=Esterified Estrogen and Conjugated Equine Estrogen and the Risk of Incident Myocardial Infarction and Stroke|journal=Archives of Internal Medicine|volume=166|issue=4|year=2006|pages=399|issn=0003-9926|doi=10.1001/archinte.166.4.399|pmid=16505258}}</ref> One study found that the risk of [[venous thrombosis]] may be less with EEs relative to CEEs.<ref name="Smith2004" /><ref name="SmithHeckbert2006" />


==See also==
==Chemistry==
{{See also|List of estrogens|Estrogen ester|List of estrogen esters}}
* [[Conjugated estrogens]]

* [[Estrogen ester]]
EEs contain [[synthetic compound|synthetic]], [[plant]]-derived estrogens and are manufactured from [[soybean]]s and [[yam (vegetable)|yam]]s.<ref name="MDRope2013" /><ref name="SmithHeckbert2006" />
* [[List of estrogens]]

==History==
⚫
EEs were introduced for medical use by 1970.<ref name="Northwest1970">{{cite book|title=Northwest Medicine|url=https://books.google.com/books?id=2sJLAQAAIAAJ|year=1970|publisher=Northwest Medical Pub. Association.}}</ref>

==Society and culture==

===Brand names===
EEs are marketed under a variety of brand names including Amnestrogen, Estratab, Estratest (with [[methyltestosterone]]), Evex, Femogen, and Menest.<ref name="MDRope2013" />


==References==
==References==
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[[Category:Estranes]]
[[Category:Estranes]]
[[Category:Estrogens]]
[[Category:Estrogens]]


{{Steroid-stub}}
{{Genito-urinary-drug-stub}}

Revision as of 02:08, 31 March 2018

Not to be confused with Estrogen ester or Conjugated estrogens.
Esterified estrogens
Estrone sulfate, the primary active component in esterified estrogens (constitutes about 80% of total content).
Equilin sulfate, the second most major active component in esterified estrogens (constitutes about 11% of total content).
Combination of
Sodium estrone sulfateEstrogen
Sodium equilin sulfateEstrogen
Clinical data
Trade namesAmnestrogen, Estratab, Estratest (with methyltestosterone), Evex, Femogen, Menest
Routes of
administration		By mouth[1]
Drug classEstrogen
Legal status
Legal status

Esterified estrogens (EEs) (brand names Amnestrogen, Estratab, Evex, Femogen, Menest) is an estrogen medication which is used hormone therapy for menopausal symptoms and low sex hormone levels in women and to treat prostate cancer in men.[3][4] It is taken by mouth.[1]

Medical uses

EEs are used in hormone therapy for menopausal symptoms, female hypogonadism, ovariectomy, and primary ovarian failure and in the treatment of prostate cancer.[5]

Available forms

Estratest is a combination formulation of 1.25 mg EEs with 2.5 mg methyltestosterone.[6]

Pharmacology

EEs consist primarily of sodium estrone sulfate and sodium equilin sulfate, and are very similar to conjugated estrogens (CEEs; brand name Premarin).[4][7][8] However, EEs and CEEs differ in the sources of their contents and in the percentages of their constituents; CEEs consist of approximately 53% sodium estrone sulfate and 25% sodium equilin sulfate, while EEs contain approximately 80% sodium estrone sulfate and 11% sodium equilin sulfate.[7][9][5] EEs and CEEs have been found to produce similar serum levels of estrone and estradiol.[10] One study found that the risk of venous thrombosis may be less with EEs relative to CEEs.[9][4]

Chemistry

See also: List of estrogens, Estrogen ester, and List of estrogen esters

EEs contain synthetic, plant-derived estrogens and are manufactured from soybeans and yams.[3][4]

History

EEs were introduced for medical use by 1970.[11]

Society and culture

Brand names

EEs are marketed under a variety of brand names including Amnestrogen, Estratab, Estratest (with methyltestosterone), Evex, Femogen, and Menest.[3]

References

  1. ^ a b Katherine Sherif (14 May 2013). Hormone Therapy: A Clinical Handbook. Springer Science & Business Media. pp. 120–. ISBN 978-1-4614-6268-2.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  3. ^ a b c Carl P. Weiner, MD; Kate Rope (2 April 2013). The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby. St. Martin's Press. pp. 179–. ISBN 978-0-312-67646-9.
  4. ^ a b c d Smith, N. L.; Heckbert, S. R.; Lemaitre, R. N.; Reiner, A. P.; Lumley, T.; Rosendaal, F. R.; Psaty, B. M. (2006). "Conjugated Equine Estrogen, Esterified Estrogen, Prothrombotic Variants, and the Risk of Venous Thrombosis in Postmenopausal Women". Arteriosclerosis, Thrombosis, and Vascular Biology. 26 (12): 2807–2812. doi:10.1161/01.ATV.0000245792.62517.3b. ISSN 1079-5642.
  5. ^ a b Manuchair Ebadi (31 October 2007). Desk Reference of Clinical Pharmacology, Second Edition. CRC Press. pp. 249–. ISBN 978-1-4200-4744-8.
  6. ^ John E. Morley; Lucretia van den Berg (5 November 1999). Endocrinology of Aging. Springer Science & Business Media. pp. 172–. ISBN 978-1-59259-715-4.
  7. ^ a b Marc A. Fritz; Leon Speroff (28 March 2012). Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. pp. 752–. ISBN 978-1-4511-4847-3.
  8. ^ Tara Parker-Pope (9 January 2007). The Hormone Decision: Untangle the Controversy, Understand Your Options, Make Your Own Choices. Rodale. pp. 157–. ISBN 978-1-59486-927-3.
  9. ^ a b Smith, Nicholas L. (2004). "Esterified Estrogens and Conjugated Equine Estrogens and the Risk of Venous Thrombosis". JAMA. 292 (13): 1581. doi:10.1001/jama.292.13.1581. ISSN 0098-7484.
  10. ^ Lemaitre, Rozenn N.; Weiss, Noel S.; Smith, Nicholas L.; Psaty, Bruce M.; Lumley, Thomas; Larson, Eric B.; Heckbert, Susan R. (2006). "Esterified Estrogen and Conjugated Equine Estrogen and the Risk of Incident Myocardial Infarction and Stroke". Archives of Internal Medicine. 166 (4): 399. doi:10.1001/archinte.166.4.399. ISSN 0003-9926. PMID 16505258.
  11. ^ Northwest Medicine. Northwest Medical Pub. Association. 1970.


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