Esterified estrogens explained

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.[1] [2] [3] [4] It is formulated alone or in combination with methyltestosterone. It is taken by mouth.[5]

Side effects of EEs include nausea, breast tension, edema, and breakthrough bleeding among others.[6] It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol. EEs are a prodrug mainly of estradiol and to a lesser extent of equilin.

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

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.[7]

Available forms

EEs are available in the form of 0.3 mg, 0.625 mg, 1.25 mg, and 2.5 mg oral tablets.[8] Estratest is a combination formulation of 1.25 mg EEs with 2.5 mg methyltestosterone.[9]

Pharmacology

See also: Pharmacodynamics of estradiol and Pharmacokinetics of estradiol.

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).[10] [11] 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.[12] 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.[13] One study found that the risk of venous thrombosis may be less with EEs relative to CEEs.

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.

History

EEs were introduced for medical use by 1970.[14]

Society and culture

Generic names

Estrogens, esterified is the generic name of the drug and its .[15] It is also known as esterified estrogens.[16]

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.

Availability

See also: List of estrogens available in the United States.

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

See also

Notes and References

  1. Book: Sweetman SC . Sex hormones and their modulators . Martindale: The Complete Drug Reference . 36th . 2009 . 2097 . Pharmaceutical Press . London. 978-0-85369-840-1. https://www.medicinescomplete.com/ .
  2. Kuhl H . Pharmacology of estrogens and progestogens: influence of different routes of administration . Climacteric . 8 . Suppl 1 . 3–63 . August 2005 . 16112947 . 10.1080/13697130500148875 . 24616324 .
  3. Book: Weiner CP, Rope K . The Complete Guide to Medications During Pregnancy and Breastfeeding: Everything You Need to Know to Make the Best Choices for You and Your Baby . registration . 2 April 2013. St. Martin's Press. 978-0-312-67646-9. 179–.
  4. Smith NL, Heckbert SR, Lemaitre RN, Reiner AP, Lumley T, Rosendaal FR, Psaty BM . 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 . 16973976 . 10.1161/01.ATV.0000245792.62517.3b . 23850792 .
  5. Book: Sherif K . Hormone Therapy: A Clinical Handbook. 14 May 2013. Springer Science & Business Media. 978-1-4614-6268-2. 120–.
  6. Book: Wittlinger H . Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones. Clinical Effects of Estrogens. 1980. 67–71. Springer . 10.1007/978-3-642-67568-3_10. 978-3-642-67570-6.
  7. Book: Ebadi M . Desk Reference of Clinical Pharmacology, Second Edition. 31 October 2007. CRC Press. 978-1-4200-4744-8. 249–.
  8. Web site: Drugs@FDA: FDA Approved Drug Products . United States Food and Drug Administration . 30 March 2018 .
  9. Book: Morley JE, van den Berg L . Endocrinology of Aging. 5 November 1999. Springer Science & Business Media. 978-1-59259-715-4. 172–.
  10. Book: Fritz MA, Speroff L . Clinical Gynecologic Endocrinology and Infertility. 28 March 2012. Lippincott Williams & Wilkins. 978-1-4511-4847-3. 752–.
  11. Book: Parker-Pope T . The Hormone Decision: Untangle the Controversy, Understand Your Options, Make Your Own Choices. 9 January 2007. Rodale. 978-1-59486-927-3. 157–.
  12. Smith NL, Heckbert SR, Lemaitre RN, Reiner AP, Lumley T, Weiss NS, Larson EB, Rosendaal FR, Psaty BM . 6 . Esterified estrogens and conjugated equine estrogens and the risk of venous thrombosis . JAMA . 292 . 13 . 1581–1587 . October 2004 . 15467060 . 10.1001/jama.292.13.1581 . free . 1887/5083 . free .
  13. Lemaitre RN, Weiss NS, Smith NL, Psaty BM, Lumley T, Larson EB, Heckbert SR . 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 . 16505258 . 10.1001/archinte.166.4.399 .
  14. Book: Northwest Medicine. 69 . 1970. Northwest Medical Pub. Association.
  15. Web site: Estrogens, Esterified (USP) - Searchable synonyms, formulas, resource links, and other chemical information . ChemIDplus . D042724000 . U.S. Library of Medicine .
  16. Web site: Esterified estrogens.

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