Estradiol acetate

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Chemical compound

title: "Estradiol acetate" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["acetate-esters", "estradiol-esters", "secondary-alcohols", "synthetic-estrogens"] description: "Chemical compound" topic_path: "general/acetate-esters" source: "https://en.wikipedia.org/wiki/Estradiol_acetate" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = [(8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl] acetate | image = Estradiol 3-acetate.svg | image_class = skin-invert-image | width = 250px | image2 = Estradiol acetate molecule ball.png | image_class2 = bg-transparent | width2 = 250px

| pronounce =

| tradename = Femtrace, Femring, Menoring | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = Rx-only | routes_of_administration = By mouth, vaginal (ring) | class = Estrogen; Estrogen ester

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 4245-41-4 | CAS_supplemental = | ATC_prefix = G03 | ATC_suffix = CA03 | ATC_supplemental = | PubChem = 9818306 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = DB13952 | ChemSpiderID_Ref = | ChemSpiderID = 7994056 | UNII = 5R97F5H93P | KEGG = D04061 | ChEBI = | ChEMBL = 1200430 | synonyms = EA; E2A; E3A; Estradiol 3-acetate

| C=20 | H=26 | O=3 | SMILES = CC(=O)OC1=CC2=C(C=C1)[C@H]3CC[C@]4(C@HCC[C@@H]4O)C | StdInChI_Ref = | StdInChI = 1S/C20H26O3/c1-12(21)23-14-4-6-15-13(11-14)3-5-17-16(15)9-10-20(2)18(17)7-8-19(20)22/h4,6,11,16-19,22H,3,5,7-10H2,1-2H3/t16-,17-,18+,19+,20+/m1/s1 | StdInChIKey_Ref = | StdInChIKey = FHXBMXJMKMWVRG-SLHNCBLASA-N Estradiol acetate (EA), sold under the brand names Femtrace, Femring, and Menoring, is an estrogen medication which is used in hormone therapy for the treatment of menopausal symptoms in women.{{cite web |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021633s005lbl.pdf|archive-url=https://web.archive.org/web/20160804054615/http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021633s005lbl.pdf|url-status=dead|archive-date=4 August 2016|access-date=21 April 2023|website=accessdata.fda.gov |title=Highlights of prescribing information|year=2014}}{{cite web|title=FEMRING |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=86b90d68-bfb6-47f6-aa5b-a6642391ff13#i4i_clinical_studies_id_2a230567-d4b8-4161-9dd0-fb082cd301e5|website=DailyMed|publisher=U.S. National Library of Medicine}} It is taken by mouth once daily or given as a vaginal ring once every three months.

Side effects of estradiol acetate include breast tenderness, breast enlargement, nausea, headache, and fluid retention. Estradiol acetate is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol. It is an estrogen ester and a prodrug of estradiol in the body. Because of this, it is considered to be a natural and bioidentical form of estrogen.

Estradiol acetate was introduced for medical use in 2001. It is available in the United States and the United Kingdom. The formulation for use by mouth has been discontinued in the United States.

Medical uses

Estradiol acetate is used as a component of menopausal hormone therapy to treat and prevent menopausal symptoms such as hot flashes and osteoporosis in women.

The Women's Health Initiative studies report increased health risks for menopausal women when using unopposed estrogens. Estrogens with or without progestins should be prescribed at the lowest effective doses and for the shortest duration consistent with treatment goals and risks for the individual woman.

Available forms

Estradiol acetate comes in the form of 0.45, 0.9, and 1.8 mg oral tablets (Femtrace) and in the form of 12.4 or 24.8 mg vaginal rings that release 50 or 100 μg/day estradiol for 3 months (Femring, Menoring). However, the Femtrace product was discontinued in the United States.

Contraindications

Contraindications of estrogens include coagulation problems, cardiovascular diseases, liver disease, and certain hormone-sensitive cancers such as breast cancer and endometrial cancer, among others.

Side effects

The side effects of estradiol acetate are the same as those of estradiol. Examples of such side effects include breast tenderness and enlargement, nausea, bloating, edema, headache, and melasma.

Overdose

Symptoms of estrogen overdosage may include nausea, vomiting, bloating, increased weight, water retention, breast tenderness, vaginal discharge, heavy legs, and leg cramps. These side effects can be diminished by reducing the estrogen dosage.

Interactions

Inhibitors and inducers of cytochrome P450 may influence the metabolism of estradiol and by extension circulating estradiol levels.

Pharmacology

::figure[src="https://upload.wikimedia.org/wikipedia/commons/0/00/Estradiol.svg" caption="active form]] of estradiol acetate."] ::

Pharmacodynamics

Estradiol acetate is an estradiol ester, or a prodrug of estradiol. As such, it is an estrogen, or an agonist of the estrogen receptors. Estradiol acetate is of about 15% higher molecular weight than estradiol due to the presence of its C3 acetate ester. Because estradiol acetate is a prodrug of estradiol, it is considered to be a natural and bioidentical form of estrogen.

Pharmacokinetics

Estradiol acetate is converted into estradiol in the body.

Chemistry

Estradiol acetate is a synthetic estrane steroid and the C3 acetate ester of estradiol. It is also known as estradiol 3-acetate or as estra-1,3,5(10)-triene-3,17β-diol 3-acetate. Another common ester of estradiol in use for oral administration is estradiol valerate, which is a C17β ester of estradiol.

The experimental octanol/water partition coefficient (logP) of estradiol acetate is 4.2.

History

Estradiol acetate is relatively recent to the market, having been first approved in a vaginal ring formulation as Menoring in the United Kingdom in 2001, followed by a vaginal ring formulation as Femring in the United States in 2002, and finally as an oral preparation as Femtrace in the United States in 2004.

Society and culture

Generic names

Estradiol acetate is the generic name of the drug and its .

Brand names

Estradiol acetate is marketed under the brand names Femtrace, Femring, and Menoring.

Availability

Estradiol acetate is available in the United States and the United Kingdom.

References

References

  1. "Estradiol: Uses, Dosage & Side Effects".
  2. "Estradiol Monograph for Professionals".
  3. (August 2003). "The effect of a novel vaginal ring delivering oestradiol acetate on climacteric symptoms in postmenopausal women". BJOG.
  4. (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric.
  5. (6 December 2012). "Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen". Springer Science & Business Media.
  6. (June 2007). "Bioidentical hormone therapy: a review of the evidence". Journal of Women's Health.
  7. (2005). "Bone mineral density in postmenopausal women treated with a vaginal ring delivering systemic doses of estradiol acetate". Menopause.
  8. (2005). "Comparative controlled trial of a novel oral estrogen therapy, estradiol acetate, for relief of menopause symptoms". Menopause.
  9. (2006). "Efficacy of a new, oral estradiol acetate formulation for relief of menopause symptoms". Menopause.
  10. (18 December 2014). "Maternity and Women's Health Care - E-Book". Elsevier Health Sciences.
  11. "Drugs@FDA: FDA-Approved Drugs".
  12. (22 June 2005). "Current Management of the Menopause". CRC Press.
  13. (2001). "Menopause – Andropause: Hormone Replacement Therapy Through the Ages". Krause & Pachernegg: Gablitz.
  14. (1976). "The Management of the Menopause & Post-Menopausal Years: The Proceedings of the International Symposium held in London 24–26 November 1975 Arranged by the Institute of Obstetrics and Gynaecology, The University of London". MTP Press Limited.
  15. (23 September 2010). "Mayo Clinic Internal Medicine Board Review". OUP USA.
  16. (September 1990). "Clinical use of oestrogens and progestogens". Maturitas.
  17. (February 2001). "Role of cytochrome P450 in estradiol metabolism in vitro". Acta Pharmacologica Sinica.
  18. (December 1982). "Pharmacokinetic and pharmacological features of oestradiol valerate". Maturitas.
  19. "Estradiol acetate | C20H26O3 | ChemSpider".
  20. (October 2003). "Efficacy and tolerability of a novel estradiol vaginal ring for relief of menopausal symptoms". Obstetrics and Gynecology.
  21. (May 2007). "Newer hormonal therapies: lower doses; oral, transdermal, and vaginal formulations". Cleveland Clinic Journal of Medicine.
  22. (2004). "Vaginal rings for menopausal symptom relief". Drugs & Aging.
  23. U.S. Food and Drug Administration. (2009). "Menopause - Medicines to Help You". GPO FCIC.
  24. (28 March 2012). "Clinical Gynecologic Endocrinology and Infertility". Lippincott Williams & Wilkins.

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acetate-estersestradiol-esterssecondary-alcoholssynthetic-estrogens