Estradiol acetate

Estradiol acetate
Clinical data
Pronunciation	/ˌɛstrəˈdaɪoʊl ˈæsəteɪt/; ES-trə-DY-ohl ASS-ə-tayt
Trade names	Femtrace, Femring, Menoring
Other names	EA; E2A; E3A; Estradiol 3-acetate
Routes of; administration	By mouth, vaginal (ring)
Drug class	Estrogen; Estrogen ester
ATC code	G03CA03 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	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;
CAS Number	4245-41-4;
PubChem CID	9818306;
DrugBank	DB13952;
ChemSpider	7994056;
UNII	5R97F5H93P;
KEGG	D04061;
ChEMBL	ChEMBL1200430;
CompTox Dashboard (EPA)	DTXSID7045867 ;
ECHA InfoCard	100.167.088
Chemical and physical data
Formula	C20H26O3
Molar mass	314.425 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)OC1=CC2=C(C=C1)[C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4O)C;
	InChI InChI=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; Key: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.^[3]^[4]^[5]^[6] It is taken by mouth once daily or given as a vaginal ring once every three months.^[2]

Side effects of estradiol acetate include breast tenderness, breast enlargement, nausea, headache, and fluid retention.^[7]^[5]^[6] Estradiol acetate is an estrogen and hence is an agonist of the estrogen receptor, the biological target of estrogens like estradiol.^[8]^[9] It is an estrogen ester and a prodrug of estradiol in the body.^[9]^[8] Because of this, it is considered to be a natural and bioidentical form of estrogen.^[9]^[10]

Estradiol acetate was introduced for medical use in 2001.^[11] It is available in the United States and the United Kingdom.^[11]^[3] The formulation for use by mouth has been discontinued in the United States.^[12]

^ "Estradiol: Uses, Dosage & Side Effects". Drugs.com. Retrieved 21 April 2023.
^ ^a ^b Cite error: The named reference pmid17506242 was invoked but never defined (see the help page).
^ ^a ^b "Estradiol Monograph for Professionals".
^ Buckler H, Al-Azzawi F (August 2003). "The effect of a novel vaginal ring delivering oestradiol acetate on climacteric symptoms in postmenopausal women". BJOG. 110 (8): 753–759. doi:10.1016/s1470-0328(03)02908-2. PMID 12892687.
^ ^a ^b "Highlights of prescribing information" (PDF). accessdata.fda.gov. 2014. Archived from the original (PDF) on 4 August 2016. Retrieved 21 April 2023.
^ ^a ^b "FEMRING". DailyMed. U.S. National Library of Medicine.
^ Cite error: The named reference Ghosh2010 was invoked but never defined (see the help page).
^ ^a ^b Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
^ ^a ^b ^c Kuhnz W, Blode H, Zimmermann H (6 December 2012). "Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Science & Business Media. p. 261. doi:10.1007/978-3-642-60107-1_15. ISBN 978-3-642-60107-1. Natural estrogens considered here include: [...] Esters of 17β-estradiol, such as estradiol valerate, estradiol benzoate and estradiol cypionate. Esterification aims at either better absorption after oral administration or a sustained release from the depot after intramuscular administration. During absorption, the esters are cleaved by endogenous esterases and the pharmacologically active 17β-estradiol is released; therefore, the esters are considered as natural estrogens.
^ Cirigliano M (June 2007). "Bioidentical hormone therapy: a review of the evidence". Journal of Women's Health. 16 (5): 600–631. doi:10.1089/jwh.2006.0311. PMID 17627398.
^ ^a ^b Cite error: The named reference pmid15382956 was invoked but never defined (see the help page).
^ Cite error: The named reference Femtrace-FDA was invoked but never defined (see the help page).

[Drugs.com-2-1] "Estradiol: Uses, Dosage & Side Effects". Drugs.com. Retrieved 21 April 2023.

[pmid17506242-2] Cite error: The named reference pmid17506242 was invoked but never defined (see the help page).

[Drugs.com4-3] "Estradiol Monograph for Professionals".

[pmid12892687-4] Buckler H, Al-Azzawi F (August 2003). "The effect of a novel vaginal ring delivering oestradiol acetate on climacteric symptoms in postmenopausal women". BJOG. 110 (8): 753–759. doi:10.1016/s1470-0328(03)02908-2. PMID 12892687.

[FemtraceLabel-5] "Highlights of prescribing information" (PDF). accessdata.fda.gov. 2014. Archived from the original (PDF) on 4 August 2016. Retrieved 21 April 2023.

[FemringLabel-6] "FEMRING". DailyMed. U.S. National Library of Medicine.

[Ghosh2010-7] Cite error: The named reference Ghosh2010 was invoked but never defined (see the help page).

[pmid16112947-8] Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.

[OettelSchillinger2012-9] Kuhnz W, Blode H, Zimmermann H (6 December 2012). "Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens". In Oettel M, Schillinger E (eds.). Estrogens and Antiestrogens II: Pharmacology and Clinical Application of Estrogens and Antiestrogen. Handbook of Experimental Pharmacology. Vol. 135 / 2. Springer Science & Business Media. p. 261. doi:10.1007/978-3-642-60107-1_15. ISBN 978-3-642-60107-1. Natural estrogens considered here include: [...] Esters of 17β-estradiol, such as estradiol valerate, estradiol benzoate and estradiol cypionate. Esterification aims at either better absorption after oral administration or a sustained release from the depot after intramuscular administration. During absorption, the esters are cleaved by endogenous esterases and the pharmacologically active 17β-estradiol is released; therefore, the esters are considered as natural estrogens.

[pmid17627398-10] Cirigliano M (June 2007). "Bioidentical hormone therapy: a review of the evidence". Journal of Women's Health. 16 (5): 600–631. doi:10.1089/jwh.2006.0311. PMID 17627398.

[pmid15382956-11] Cite error: The named reference pmid15382956 was invoked but never defined (see the help page).

[Femtrace-FDA-12] Cite error: The named reference Femtrace-FDA was invoked but never defined (see the help page).

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