esterified estrogens
{{Short description|Pharmaceutical drug}}
{{Distinguish|Estrogen ester|Conjugated estrogens}}
{{Drugbox
| image = Estrone sulfate.svg
| width = 225px
| caption = Estrone sulfate, the primary active component in esterified estrogens (constitutes about 75 to 85% of total content).
| image2 = Equilin sulfate.svg
| width2 = 225px
| caption2 = Equilin sulfate, the second most major active component in esterified estrogens (constitutes about 6 to 16% of total content).
| type = combo
| drug_name =
| component1 = Sodium estrone sulfate
| class1 = Estrogen
| component2 = Sodium equilin sulfate
| class2 = Estrogen
| tradename = Estratab, Menest, others
| Drugs.com =
| MedlinePlus =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU =
| legal_CA =
| legal_UK =
| legal_US =
| routes_of_administration = By mouth
| class = Estrogen
| CAS_number =
| ATC_prefix = None
| ATC_suffix =
| PubChemSubstance = 347910451
| DrugBank = DB09381
| UNII = 3ASP8Q3768
| synonyms = Esterified oestrogens; EEs; Esterified equine estrogens; Esterified equine oestrogens; EEEs
}}
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.{{cite book | veditors = Sweetman SC |chapter=Sex hormones and their modulators |title=Martindale: The Complete Drug Reference |edition=36th |year=2009 |page=2097 |publisher=Pharmaceutical Press |location=London|isbn=978-0-85369-840-1|chapter-url=https://www.medicinescomplete.com/ }}{{cite journal | vauthors = Kuhl H | title = Pharmacology of estrogens and progestogens: influence of different routes of administration | journal = Climacteric | volume = 8 | issue = Suppl 1 | pages = 3–63 | date = August 2005 | pmid = 16112947 | doi = 10.1080/13697130500148875 | s2cid = 24616324 }}{{cite book| vauthors = Weiner CP, Rope K |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://archive.org/details/completeguidetom0000wein_t9k5 |url-access=registration |date=2 April 2013|publisher=St. Martin's Press|isbn=978-0-312-67646-9|pages=[https://archive.org/details/completeguidetom0000wein_t9k5/page/179 179]–}}{{cite journal | vauthors = Smith NL, Heckbert SR, Lemaitre RN, Reiner AP, Lumley T, Rosendaal FR, Psaty BM | 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 | pages = 2807–2812 | date = December 2006 | pmid = 16973976 | doi = 10.1161/01.ATV.0000245792.62517.3b | s2cid = 23850792 | doi-access = }} It is formulated alone or in combination with methyltestosterone. It is taken by mouth.{{cite book| vauthors = Sherif K |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–}}
Side effects of EEs include nausea, breast tension, edema, and breakthrough bleeding among others.{{cite book| vauthors = Wittlinger H |title=Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones|chapter=Clinical Effects of Estrogens|year=1980|pages=67–71|publisher=Springer |doi=10.1007/978-3-642-67568-3_10|isbn=978-3-642-67570-6}} 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.{{cite book| vauthors = Ebadi M |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–}}
{{Estrogen dosages for menopausal hormone therapy}}
=Available forms=
EEs are available in the form of 0.3 mg, 0.625 mg, 1.25 mg, and 2.5 mg oral tablets.{{cite web | title = Drugs@FDA: FDA Approved Drug Products | publisher = United States Food and Drug Administration | access-date = 30 March 2018 | url = http://www.accessdata.fda.gov/scripts/cder/daf/}} Estratest is a combination formulation of 1.25 mg EEs with 2.5 mg methyltestosterone.{{cite book| vauthors = Morley JE, van den Berg L |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–}}
Side effects
{{See also|Conjugated estrogens#Side effects|Estrogen (medication)#Side effects}}
Pharmacology
{{See also|Pharmacodynamics of estradiol|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).{{cite book| vauthors = Fritz MA, Speroff L |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–}}{{cite book| vauthors = Parker-Pope T |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–}} 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.{{cite journal | vauthors = Smith NL, Heckbert SR, Lemaitre RN, Reiner AP, Lumley T, Weiss NS, Larson EB, Rosendaal FR, Psaty BM | display-authors = 6 | title = Esterified estrogens and conjugated equine estrogens and the risk of venous thrombosis | journal = JAMA | volume = 292 | issue = 13 | pages = 1581–1587 | date = October 2004 | pmid = 15467060 | doi = 10.1001/jama.292.13.1581 | doi-access = free | hdl = 1887/5083 | hdl-access = free }} 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.{{cite journal | vauthors = Lemaitre RN, Weiss NS, Smith NL, Psaty BM, Lumley T, Larson EB, Heckbert SR | 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 | pages = 399–404 | date = February 2006 | pmid = 16505258 | doi = 10.1001/archinte.166.4.399 | doi-access = }} One study found that the risk of venous thrombosis may be less with EEs relative to CEEs.
{{Relative oral potencies of estrogens}}
{{Protein binding and metabolic clearance rates of estrogens}}
Chemistry
History
EEs were introduced for medical use by 1970.{{cite book|title=Northwest Medicine|url=https://books.google.com/books?id=2sJLAQAAIAAJ | volume = 69 |year=1970|publisher=Northwest Medical Pub. Association}}
Society and culture
=Generic names=
Estrogens, esterified is the generic name of the drug and its {{abbrlink|USP|United States Pharmacopeia}}.{{Cite web|url=https://chem.nlm.nih.gov/chemidplus/sid/d042724000| work = ChemIDplus | id = D042724000 | title = Estrogens, Esterified (USP) - Searchable synonyms, formulas, resource links, and other chemical information | publisher = U.S. Library of Medicine }} It is also known as esterified estrogens.{{Cite web|url=https://www.drugbank.ca/drugs/DB09381|title = Esterified estrogens}}
=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
References
{{Reflist}}
{{Estradiol}}
{{Estrogens and antiestrogens}}
{{Estrogen receptor modulators}}
Category:Combination sex hormone drugs