Chemistry:Esterified estrogens

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Short description: Pharmaceutical drug
Esterified estrogens
Estrone sulfate.svg
Estrone sulfate, the primary active component in esterified estrogens (constitutes about 75 to 85% of total content).
Equilin sulfate.svg
Equilin sulfate, the second most major active component in esterified estrogens (constitutes about 6 to 16% of total content).
Combination of
Sodium estrone sulfateEstrogen
Sodium equilin sulfateEstrogen
Clinical data
Trade namesEstratab, Menest, others
Other namesEsterified oestrogens; EEs; Esterified equine estrogens; Esterified equine oestrogens; EEEs
Routes of
administration		By mouth[1]
Drug classEstrogen
ATC code
  • None
Identifiers
PubChem SID
DrugBank
UNII

Esterified estrogens (EEs), sold under the brand names Estratab and Menest among others, is an estrogen medication which is used hormone therapy for menopausal symptoms and low sex hormone levels in women, to treat breast cancer in both women and men, and to treat prostate cancer in men.[2][3][4][5][6] It is formulated alone or in combination with methyltestosterone.[2][3] It is taken by mouth.[1]

Side effects of EEs include nausea, breast tension, edema, and breakthrough bleeding among others.[7] It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol.[4][2][3] EEs are a prodrug mainly of estradiol and to a lesser extent of equilin.[4]

EEs were introduced for medical use by 1970.[8] They are available in only a few countries, such as Chile and the United States .[2] They have also been marketed in Argentina and Switzerland in the past.[2]

Medical uses

EEs are used in hormone therapy for menopausal symptoms, female hypogonadism, ovariectomy, and primary ovarian failure and in the treatment of breast cancer and prostate cancer.[3][9]


Available forms

EEs are available in the form of 0.3 mg, 0.625 mg, 1.25 mg, and 2.5 mg oral tablets.[10] Estratest is a combination formulation of 1.25 mg EEs with 2.5 mg methyltestosterone.[11]

Side effects

Pharmacology

EEs consist primarily of sodium estrone sulfate and sodium equilin sulfate, and are very similar to conjugated estrogens (CEEs, conjugated equine estrogens; brand name Premarin).[4][6][12][13] 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 about 75 to 85% sodium estrone sulfate and 6 to 11% sodium equilin sulfate.[4][2][12][14][9] EEs have been found to produce similar serum levels of estrone and estradiol relative to CEEs, although with higher levels of estrone and lower levels of equilin.[4][15] One study found that the risk of venous thrombosis may be less with EEs relative to CEEs.[14][6]


v · d · e Protein binding and metabolic clearance rates of estrogens
Compound RBA to
SHBG (%)		 Bound to
SHBG (%)		 Bound to
albumin (%)		 Total
bound (%)		 MCR
(L/day/m2)
17β-Estradiol 50 37 61 98 580
Estrone 12 16 80 96 1050
Estriol 0.3 1 91 92 1110
Estrone sulfate 0 0 99 99 80
17β-Dihydroequilin 30 ? ? ? 1250
Equilin 8 26 13 ? 2640
17β-Dihydroequilin sulfate 0 ? ? ? 375
Equilin sulfate 0 ? ? ? 175
Δ8-Estrone ? ? ? ? 1710
Notes: RBA for SHBG (%) is compared to 100% for testosterone. Sources: See template.

Chemistry

EEs contain synthetic, plant-derived estrogens and are manufactured from soybeans and yams.[5][6]

History

EEs were introduced for medical use by 1970.[8]

Society and culture

Generic names

Estrogens, esterified is the generic name of the drug and its USP.[16] It is also known as esterified estrogens.[3]

Brand names

EEs are marketed under a variety of brand names including Amnestrogen, Estragyn, Estratab, Evex, Femibel, Femogen, Menest, Neo Estrone Tab, and Oestro-Feminal alone, and, in combination with methyltestosterone, under the brand names Covaryx, Delitan, Eemt, Essian, Estratest, Feminova-T, Menogen, and Syntest.[2][5][3]

Availability

EEs are or have been marketed in Argentina , Chile , Switzerland , and the United States .[2] Both EEs and the combination of EEs and methyltestosterone are listed as being marketed only in Chile and the United States as of present.[2]

See also

References

  1. ↑ 1.0 1.1 Hormone Therapy: A Clinical Handbook. Springer Science & Business Media. 14 May 2013. pp. 120–. ISBN 978-1-4614-6268-2. https://books.google.com/books?id=RmmzJ8MYpUAC&pg=PA120. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. 2009. p. 2097. ISBN 978-0-85369-840-1. https://www.medicinescomplete.com/. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 "Esterified estrogens". https://www.drugbank.ca/drugs/DB09381. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric 8 (Suppl 1): 3–63. August 2005. doi:10.1080/13697130500148875. PMID 16112947. 
  5. ↑ 5.0 5.1 5.2 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. 2 April 2013. pp. 179–. ISBN 978-0-312-67646-9. https://archive.org/details/completeguidetom0000wein_t9k5. 
  6. ↑ 6.0 6.1 6.2 6.3 "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. December 2006. doi:10.1161/01.ATV.0000245792.62517.3b. PMID 16973976. 
  7. ↑ "Clinical Effects of Estrogens". Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones. Springer. 1980. pp. 67–71. doi:10.1007/978-3-642-67568-3_10. ISBN 978-3-642-67570-6. 
  8. ↑ 8.0 8.1 Northwest Medicine. 69. Northwest Medical Pub. Association. 1970. https://books.google.com/books?id=2sJLAQAAIAAJ. 
  9. ↑ 9.0 9.1 Desk Reference of Clinical Pharmacology, Second Edition. CRC Press. 31 October 2007. pp. 249–. ISBN 978-1-4200-4744-8. https://books.google.com/books?id=ihxyHbnj3qYC&pg=PA249. 
  10. ↑ "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. http://www.accessdata.fda.gov/scripts/cder/daf/. 
  11. ↑ Endocrinology of Aging. Springer Science & Business Media. 5 November 1999. pp. 172–. ISBN 978-1-59259-715-4. https://books.google.com/books?id=hGD0BwAAQBAJ&pg=PA172. 
  12. ↑ 12.0 12.1 Clinical Gynecologic Endocrinology and Infertility. Lippincott Williams & Wilkins. 28 March 2012. pp. 752–. ISBN 978-1-4511-4847-3. https://books.google.com/books?id=KZLubBxJEwEC&pg=PA752. 
  13. ↑ The Hormone Decision: Untangle the Controversy, Understand Your Options, Make Your Own Choices. Rodale. 9 January 2007. pp. 157–. ISBN 978-1-59486-927-3. https://books.google.com/books?id=3SNAAQAAQBAJ&pg=PA157. 
  14. ↑ 14.0 14.1 "Esterified estrogens and conjugated equine estrogens and the risk of venous thrombosis". JAMA 292 (13): 1581–1587. October 2004. doi:10.1001/jama.292.13.1581. PMID 15467060. 
  15. ↑ "Esterified estrogen and conjugated equine estrogen and the risk of incident myocardial infarction and stroke". Archives of Internal Medicine 166 (4): 399–404. February 2006. doi:10.1001/archinte.166.4.399. PMID 16505258. 
  16. ↑ "Estrogens, Esterified (USP) - Searchable synonyms, formulas, resource links, and other chemical information". ChemIDplus. U.S. Library of Medicine. https://chem.nlm.nih.gov/chemidplus/sid/d042724000. 



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